Grgurić-Šipka, Sanja

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Authority KeyName Variants
orcid::0000-0003-1906-535X
  • Grgurić-Šipka, Sanja (105)
Projects
Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors
Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200168 (University of Belgrade, Faculty of Chemistry)
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200288 (Innovation Center of the Faculty of Chemistry) Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology
Strengthening of the MagBioVin Research and Innovation Team for Development of Novel Approaches for Tumour Therapy based on Nanostructured Materials Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds
Structure-properties relationships of natural and synthetic molecules and their metal complexes Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200043 (Institute of Oncology and Radiology of Serbia, Belgrade)
Modulation of intracellular energy balance-controlling signalling pathways in therapy of cancer and neuro-immuno-endocrine disorders COST Action [CM1105]
Austrian-Serbian mobility grant New potential anticancer drugs based on organoruthenium compounds with organic co-ligands [451-03-01039/2015-09/03, SRB-08/2016-2017] FoodEnTwin-Twinning of research activities for the frontier research in the fields of food, nutrition and environmental omics
Molecular properties and modifications of some respiratory and nutritional allergens Molecular mechanisms of physiological and pharmacological control of inflammation and cancer
Study of structure-function relationships in the plant cell wall and modifications of the wall structure by enzyme engineering Sinteza, analiza i aktivnost novih organskih polidentatnih liganada i njihovih kompleksa sa d-metalima
Farmakodinamska i farmakogenetska istraživanja novih lekova i prediktivna/prognostička vrednost farmakoterapije u onkologiji Novartis Jubilee Foundation
Stiftung fur wissenschaftliche Forschung of the University of Zurich Swiss Government Excellence Scholarship for Postdoctoral Researcher [2014.0942/India/OP]
Swiss National Science Foundation (SNSF) [PP00P2_133568, PP00P2_157545] UBS Promedica Stiftung
University of Zurich General Secretariat for Research and Technology (GSRT)
Hellenic Foundation for Research and Innovation (HFRI), Greek Ministry of Education, Research and Religion Hercules Foundation (3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence) [AUGE/11/029]
Hungarian Academy of Sciences The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors

Author's Bibliography

Interaction of organoruthenium(II)-polypyridyl complexes with DNA and BSA

Margetić, Aleksandra; Nikolić, Stefan; Grgurić-Šipka, Sanja; Vujčić, Miroslava

(2022)

TY  - JOUR
AU  - Margetić, Aleksandra
AU  - Nikolić, Stefan
AU  - Grgurić-Šipka, Sanja
AU  - Vujčić, Miroslava
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5859
AB  - The interaction of four arene ruthenium
complexes [(η6-p-cymene)Ru(Me2dppz)Cl]PF6 (1)
with Me2dppz
= 11,12-dimethyldipyrido[3,2-a:2′,3′-c]
phenazine, [(η6-p-cymene)Ru(aip)Cl]PF6 (2) with
aip = 2-(9-anthryl)-1H-imidazo[4,5-f][1,10] phenanthroline),
([(ƞ6-toluene)Ru(ppf)Cl]PF6) (3) and ([(ƞ6-pcymene)
Ru(ppf)Cl]PF6) (4) with ppf = pyrido[2′,3′:5,6]
pyrazino[2,3-f][1,10]phenanthroline with calf thymus
DNA were investigated. All of four complexes exhibit
DNA-binding activity. UV–Vis spectroscopic studies
revealed the intrinsic binding constants of the order
104
M−
1 of magnitude, indicating non-intercalative
mode. Fluorescence quenching analysis showed that all
complexes interfere with intercalator ethidium bromide
and minor groove binder Hoechst 33258 by a singular
non-intercalative mode with extent that differs by two
orders of magnitude. Gel electrophoresis results on DNA cleavage assay demonstrated that all complexes
produced conformational changes of supercoiled
circular plasmid pUC19 in concentration dependent
way. The results of fluorescence titration bovine
serum albumin by 1, 2, 3 and 4 showed that all complexes
significantly quench tryptophan residues fluorescence
through a static quenching mechanism. The
antimicrobial activity against both Gram-positive and
Gram-negative bacteria analyzed. Complex 1 was most
active, even on Escherichia coli was more active than
positive control compound.
T2  - Biometals
T1  - Interaction of organoruthenium(II)-polypyridyl complexes with DNA and BSA
VL  - 35
SP  - 813
EP  - 829
DO  - 10.1007/s10534-022-00404-6
ER  - 
@article{
author = "Margetić, Aleksandra and Nikolić, Stefan and Grgurić-Šipka, Sanja and Vujčić, Miroslava",
year = "2022",
abstract = "The interaction of four arene ruthenium
complexes [(η6-p-cymene)Ru(Me2dppz)Cl]PF6 (1)
with Me2dppz
= 11,12-dimethyldipyrido[3,2-a:2′,3′-c]
phenazine, [(η6-p-cymene)Ru(aip)Cl]PF6 (2) with
aip = 2-(9-anthryl)-1H-imidazo[4,5-f][1,10] phenanthroline),
([(ƞ6-toluene)Ru(ppf)Cl]PF6) (3) and ([(ƞ6-pcymene)
Ru(ppf)Cl]PF6) (4) with ppf = pyrido[2′,3′:5,6]
pyrazino[2,3-f][1,10]phenanthroline with calf thymus
DNA were investigated. All of four complexes exhibit
DNA-binding activity. UV–Vis spectroscopic studies
revealed the intrinsic binding constants of the order
104
M−
1 of magnitude, indicating non-intercalative
mode. Fluorescence quenching analysis showed that all
complexes interfere with intercalator ethidium bromide
and minor groove binder Hoechst 33258 by a singular
non-intercalative mode with extent that differs by two
orders of magnitude. Gel electrophoresis results on DNA cleavage assay demonstrated that all complexes
produced conformational changes of supercoiled
circular plasmid pUC19 in concentration dependent
way. The results of fluorescence titration bovine
serum albumin by 1, 2, 3 and 4 showed that all complexes
significantly quench tryptophan residues fluorescence
through a static quenching mechanism. The
antimicrobial activity against both Gram-positive and
Gram-negative bacteria analyzed. Complex 1 was most
active, even on Escherichia coli was more active than
positive control compound.",
journal = "Biometals",
title = "Interaction of organoruthenium(II)-polypyridyl complexes with DNA and BSA",
volume = "35",
pages = "813-829",
doi = "10.1007/s10534-022-00404-6"
}
Margetić, A., Nikolić, S., Grgurić-Šipka, S.,& Vujčić, M.. (2022). Interaction of organoruthenium(II)-polypyridyl complexes with DNA and BSA. in Biometals, 35, 813-829.
https://doi.org/10.1007/s10534-022-00404-6
Margetić A, Nikolić S, Grgurić-Šipka S, Vujčić M. Interaction of organoruthenium(II)-polypyridyl complexes with DNA and BSA. in Biometals. 2022;35:813-829.
doi:10.1007/s10534-022-00404-6 .
Margetić, Aleksandra, Nikolić, Stefan, Grgurić-Šipka, Sanja, Vujčić, Miroslava, "Interaction of organoruthenium(II)-polypyridyl complexes with DNA and BSA" in Biometals, 35 (2022):813-829,
https://doi.org/10.1007/s10534-022-00404-6 . .

Drug combination study of novel oxorhenium(V) complexes

Petrović, Tamara; Gligorijević, Nevenka; Belaj, Ferdinand; Aranđelović, Sandra; Mihajlović-Lalić, Ljiljana E.; Grgurić-Šipka, Sanja; Poljarević, Jelena

(Elsevier, 2022)

TY  - JOUR
AU  - Petrović, Tamara
AU  - Gligorijević, Nevenka
AU  - Belaj, Ferdinand
AU  - Aranđelović, Sandra
AU  - Mihajlović-Lalić, Ljiljana E.
AU  - Grgurić-Šipka, Sanja
AU  - Poljarević, Jelena
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5046
AB  - Three Re(V) complexes of structural formulas [ReOCl2L(PPh3)], where L is pyridine-2-carboxylic acid (C1), 3-
methyl-pyridine-2-carboxylic acid (C2) and 6-methyl-pyridine-2-carboxylic acid (C3) were synthesized and
characterized using NMR, IR spectroscopy and mass spectrometry. Crystal structures of all three complexes have
been additionally confirmed by X-ray analysis. The biological activity has been investigated in the panel of tumor
cell lines A549, PANC-1, MDA-MB-231, MCF-7, LS-174, EAhy.926 and one in non-tumor cell line MRC-5. Only
C1 showed dose-dependent cytotoxic potential, particularly toward triple-negative breast adenocarcinoma cells
MDA-MB-231 with IC50 68.90 ± 1.73 μM and pancreatic adenocarcinoma cells PANC-1 with IC50 69.84 ± 2.3
μM. Both cell lines are characterized by a highly invasive and resistant phenotype. Drug combination studies in
PANC-1 cells with C1 and Verapamil hydrochloride (VRP), which is the established inhibitor of efflux transporter
P-glycoprotein (Pgp), revealed enhancement of antiproliferative action of the complex in a dose-dependent
manner, and slight arrest of cell cycle in the S phase. Also, a depletion of the glutathione (GSH) level by Lbuthionine-sulfoximine (L-BSO) at sub-toxic concentrations (100 μM) caused an increase of activity of C1 to the
IC50 57.67 ± 6.51 (μM). A morphological analysis in PANC-1 cells by dual acridine orange/ethidium bromide
staining, revealed apoptotic potential of complex C1 and a slower kinetic of cell death induction, suggesting a
different mechanism of action compared to cisplatin.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Drug combination study of novel oxorhenium(V) complexes
VL  - 231
SP  - 111807
DO  - 10.1016/j.jinorgbio.2022.111807
ER  - 
@article{
author = "Petrović, Tamara and Gligorijević, Nevenka and Belaj, Ferdinand and Aranđelović, Sandra and Mihajlović-Lalić, Ljiljana E. and Grgurić-Šipka, Sanja and Poljarević, Jelena",
year = "2022",
abstract = "Three Re(V) complexes of structural formulas [ReOCl2L(PPh3)], where L is pyridine-2-carboxylic acid (C1), 3-
methyl-pyridine-2-carboxylic acid (C2) and 6-methyl-pyridine-2-carboxylic acid (C3) were synthesized and
characterized using NMR, IR spectroscopy and mass spectrometry. Crystal structures of all three complexes have
been additionally confirmed by X-ray analysis. The biological activity has been investigated in the panel of tumor
cell lines A549, PANC-1, MDA-MB-231, MCF-7, LS-174, EAhy.926 and one in non-tumor cell line MRC-5. Only
C1 showed dose-dependent cytotoxic potential, particularly toward triple-negative breast adenocarcinoma cells
MDA-MB-231 with IC50 68.90 ± 1.73 μM and pancreatic adenocarcinoma cells PANC-1 with IC50 69.84 ± 2.3
μM. Both cell lines are characterized by a highly invasive and resistant phenotype. Drug combination studies in
PANC-1 cells with C1 and Verapamil hydrochloride (VRP), which is the established inhibitor of efflux transporter
P-glycoprotein (Pgp), revealed enhancement of antiproliferative action of the complex in a dose-dependent
manner, and slight arrest of cell cycle in the S phase. Also, a depletion of the glutathione (GSH) level by Lbuthionine-sulfoximine (L-BSO) at sub-toxic concentrations (100 μM) caused an increase of activity of C1 to the
IC50 57.67 ± 6.51 (μM). A morphological analysis in PANC-1 cells by dual acridine orange/ethidium bromide
staining, revealed apoptotic potential of complex C1 and a slower kinetic of cell death induction, suggesting a
different mechanism of action compared to cisplatin.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Drug combination study of novel oxorhenium(V) complexes",
volume = "231",
pages = "111807",
doi = "10.1016/j.jinorgbio.2022.111807"
}
Petrović, T., Gligorijević, N., Belaj, F., Aranđelović, S., Mihajlović-Lalić, L. E., Grgurić-Šipka, S.,& Poljarević, J.. (2022). Drug combination study of novel oxorhenium(V) complexes. in Journal of Inorganic Biochemistry
Elsevier., 231, 111807.
https://doi.org/10.1016/j.jinorgbio.2022.111807
Petrović T, Gligorijević N, Belaj F, Aranđelović S, Mihajlović-Lalić LE, Grgurić-Šipka S, Poljarević J. Drug combination study of novel oxorhenium(V) complexes. in Journal of Inorganic Biochemistry. 2022;231:111807.
doi:10.1016/j.jinorgbio.2022.111807 .
Petrović, Tamara, Gligorijević, Nevenka, Belaj, Ferdinand, Aranđelović, Sandra, Mihajlović-Lalić, Ljiljana E., Grgurić-Šipka, Sanja, Poljarević, Jelena, "Drug combination study of novel oxorhenium(V) complexes" in Journal of Inorganic Biochemistry, 231 (2022):111807,
https://doi.org/10.1016/j.jinorgbio.2022.111807 . .
2
1
1

Drug combination study of novel oxorhenium(V) complexes

Petrović, Tamara; Gligorijević, Nevenka; Belaj, Ferdinand; Aranđelović, Sandra; Mihajlović-Lalić, Ljiljana E.; Grgurić-Šipka, Sanja; Poljarević, Jelena

(Elsevier, 2022)

TY  - JOUR
AU  - Petrović, Tamara
AU  - Gligorijević, Nevenka
AU  - Belaj, Ferdinand
AU  - Aranđelović, Sandra
AU  - Mihajlović-Lalić, Ljiljana E.
AU  - Grgurić-Šipka, Sanja
AU  - Poljarević, Jelena
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5047
AB  - Three Re(V) complexes of structural formulas [ReOCl2L(PPh3)], where L is pyridine-2-carboxylic acid (C1), 3-methyl-pyridine-2-carboxylic acid (C2) and 6-methyl-pyridine-2-carboxylic acid (C3) were synthesized andcharacterized using NMR, IR spectroscopy and mass spectrometry. Crystal structures of all three complexes havebeen additionally confirmed by X-ray analysis. The biological activity has been investigated in the panel of tumorcell lines A549, PANC-1, MDA-MB-231, MCF-7, LS-174, EAhy.926 and one in non-tumor cell line MRC-5. OnlyC1 showed dose-dependent cytotoxic potential, particularly toward triple-negative breast adenocarcinoma cellsMDA-MB-231 with IC50 68.90 ± 1.73 μM and pancreatic adenocarcinoma cells PANC-1 with IC50 69.84 ± 2.3μM. Both cell lines are characterized by a highly invasive and resistant phenotype. Drug combination studies inPANC-1 cells with C1 and Verapamil hydrochloride (VRP), which is the established inhibitor of efflux transporterP-glycoprotein (Pgp), revealed enhancement of antiproliferative action of the complex in a dose-dependentmanner, and slight arrest of cell cycle in the S phase. Also, a depletion of the glutathione (GSH) level by Lbuthionine-sulfoximine (L-BSO) at sub-toxic concentrations (100 μM) caused an increase of activity of C1 to theIC50 57.67 ± 6.51 (μM). A morphological analysis in PANC-1 cells by dual acridine orange/ethidium bromidestaining, revealed apoptotic potential of complex C1 and a slower kinetic of cell death induction, suggesting adifferent mechanism of action compared to cisplatin.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Drug combination study of novel oxorhenium(V) complexes
VL  - 231
SP  - 111807
DO  - 10.1016/j.jinorgbio.2022.111807
ER  - 
@article{
author = "Petrović, Tamara and Gligorijević, Nevenka and Belaj, Ferdinand and Aranđelović, Sandra and Mihajlović-Lalić, Ljiljana E. and Grgurić-Šipka, Sanja and Poljarević, Jelena",
year = "2022",
abstract = "Three Re(V) complexes of structural formulas [ReOCl2L(PPh3)], where L is pyridine-2-carboxylic acid (C1), 3-methyl-pyridine-2-carboxylic acid (C2) and 6-methyl-pyridine-2-carboxylic acid (C3) were synthesized andcharacterized using NMR, IR spectroscopy and mass spectrometry. Crystal structures of all three complexes havebeen additionally confirmed by X-ray analysis. The biological activity has been investigated in the panel of tumorcell lines A549, PANC-1, MDA-MB-231, MCF-7, LS-174, EAhy.926 and one in non-tumor cell line MRC-5. OnlyC1 showed dose-dependent cytotoxic potential, particularly toward triple-negative breast adenocarcinoma cellsMDA-MB-231 with IC50 68.90 ± 1.73 μM and pancreatic adenocarcinoma cells PANC-1 with IC50 69.84 ± 2.3μM. Both cell lines are characterized by a highly invasive and resistant phenotype. Drug combination studies inPANC-1 cells with C1 and Verapamil hydrochloride (VRP), which is the established inhibitor of efflux transporterP-glycoprotein (Pgp), revealed enhancement of antiproliferative action of the complex in a dose-dependentmanner, and slight arrest of cell cycle in the S phase. Also, a depletion of the glutathione (GSH) level by Lbuthionine-sulfoximine (L-BSO) at sub-toxic concentrations (100 μM) caused an increase of activity of C1 to theIC50 57.67 ± 6.51 (μM). A morphological analysis in PANC-1 cells by dual acridine orange/ethidium bromidestaining, revealed apoptotic potential of complex C1 and a slower kinetic of cell death induction, suggesting adifferent mechanism of action compared to cisplatin.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Drug combination study of novel oxorhenium(V) complexes",
volume = "231",
pages = "111807",
doi = "10.1016/j.jinorgbio.2022.111807"
}
Petrović, T., Gligorijević, N., Belaj, F., Aranđelović, S., Mihajlović-Lalić, L. E., Grgurić-Šipka, S.,& Poljarević, J.. (2022). Drug combination study of novel oxorhenium(V) complexes. in Journal of Inorganic Biochemistry
Elsevier., 231, 111807.
https://doi.org/10.1016/j.jinorgbio.2022.111807
Petrović T, Gligorijević N, Belaj F, Aranđelović S, Mihajlović-Lalić LE, Grgurić-Šipka S, Poljarević J. Drug combination study of novel oxorhenium(V) complexes. in Journal of Inorganic Biochemistry. 2022;231:111807.
doi:10.1016/j.jinorgbio.2022.111807 .
Petrović, Tamara, Gligorijević, Nevenka, Belaj, Ferdinand, Aranđelović, Sandra, Mihajlović-Lalić, Ljiljana E., Grgurić-Šipka, Sanja, Poljarević, Jelena, "Drug combination study of novel oxorhenium(V) complexes" in Journal of Inorganic Biochemistry, 231 (2022):111807,
https://doi.org/10.1016/j.jinorgbio.2022.111807 . .
2
1
1

Antimicrobial potency of Ru(II) arene based pyridil complexes

Nikolić, Stefan; Dimitrijević, Marija; Poljarević, Jelena; Mihajlović-Lalić, Ljiljana; Grgurić-Šipka, Sanja

(Belgrade : Faculty of Chemistry, 2022)

TY  - CONF
AU  - Nikolić, Stefan
AU  - Dimitrijević, Marija
AU  - Poljarević, Jelena
AU  - Mihajlović-Lalić, Ljiljana
AU  - Grgurić-Šipka, Sanja
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5821
AB  - Discover a new class of ruthenium-based complexes that were investigated as potential antimicrobial agents: dinuclear polypyridil ruthenium(II) complexes exhibited excellent growth inhibition, and Ru(II) arene complexes with acetyl pyridine ligands exhibited moderate antimicrobial activity in the panel of bacteria1. Here we have synthesized 14 new Ru(II) arene complexes with pyridine-based ligands and examined their antimicrobial potency, trying to correlate their structure and biological activity. Reported complexes were obtained in a reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with halogen derivatives of picolinic acid or pyridine dicarboxylic acids in a 1:2 molar ratio in ethanol. The complexes were soluble in DMSO and water. Their structural characterization included IR and NMR spectroscopy and MS spectrometry, and purity was confirmed by elemental analysis. In this report, we demonstrate the activities of these novel compounds against six typical gram-negative and two gram-positive bacteria. A micro-well dilution assay was used to determine the minimum inhibitory concentration (MIC), and minimum bactericidal concentration. Streptomycin and chloramphenicol, commercial antibiotics, were used as a positive control. The best activity of all tested bacteria was observed against E. coli, with a MIC value of 1.25 mg/mL, for C3, C6, and C10 complexes. Also, all synthesized complexes showed the same activity against C. albicans.
PB  - Belgrade : Faculty of Chemistry
C3  - Serbian Biochemical Society Eleventh Conference “Amazing Biochemistry”, September 22nd and 23rd, 2022, Novi Sad, Serbia
T1  - Antimicrobial potency of Ru(II) arene based pyridil complexes
SP  - 110
EP  - 110
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5821
ER  - 
@conference{
author = "Nikolić, Stefan and Dimitrijević, Marija and Poljarević, Jelena and Mihajlović-Lalić, Ljiljana and Grgurić-Šipka, Sanja",
year = "2022",
abstract = "Discover a new class of ruthenium-based complexes that were investigated as potential antimicrobial agents: dinuclear polypyridil ruthenium(II) complexes exhibited excellent growth inhibition, and Ru(II) arene complexes with acetyl pyridine ligands exhibited moderate antimicrobial activity in the panel of bacteria1. Here we have synthesized 14 new Ru(II) arene complexes with pyridine-based ligands and examined their antimicrobial potency, trying to correlate their structure and biological activity. Reported complexes were obtained in a reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with halogen derivatives of picolinic acid or pyridine dicarboxylic acids in a 1:2 molar ratio in ethanol. The complexes were soluble in DMSO and water. Their structural characterization included IR and NMR spectroscopy and MS spectrometry, and purity was confirmed by elemental analysis. In this report, we demonstrate the activities of these novel compounds against six typical gram-negative and two gram-positive bacteria. A micro-well dilution assay was used to determine the minimum inhibitory concentration (MIC), and minimum bactericidal concentration. Streptomycin and chloramphenicol, commercial antibiotics, were used as a positive control. The best activity of all tested bacteria was observed against E. coli, with a MIC value of 1.25 mg/mL, for C3, C6, and C10 complexes. Also, all synthesized complexes showed the same activity against C. albicans.",
publisher = "Belgrade : Faculty of Chemistry",
journal = "Serbian Biochemical Society Eleventh Conference “Amazing Biochemistry”, September 22nd and 23rd, 2022, Novi Sad, Serbia",
title = "Antimicrobial potency of Ru(II) arene based pyridil complexes",
pages = "110-110",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5821"
}
Nikolić, S., Dimitrijević, M., Poljarević, J., Mihajlović-Lalić, L.,& Grgurić-Šipka, S.. (2022). Antimicrobial potency of Ru(II) arene based pyridil complexes. in Serbian Biochemical Society Eleventh Conference “Amazing Biochemistry”, September 22nd and 23rd, 2022, Novi Sad, Serbia
Belgrade : Faculty of Chemistry., 110-110.
https://hdl.handle.net/21.15107/rcub_cherry_5821
Nikolić S, Dimitrijević M, Poljarević J, Mihajlović-Lalić L, Grgurić-Šipka S. Antimicrobial potency of Ru(II) arene based pyridil complexes. in Serbian Biochemical Society Eleventh Conference “Amazing Biochemistry”, September 22nd and 23rd, 2022, Novi Sad, Serbia. 2022;:110-110.
https://hdl.handle.net/21.15107/rcub_cherry_5821 .
Nikolić, Stefan, Dimitrijević, Marija, Poljarević, Jelena, Mihajlović-Lalić, Ljiljana, Grgurić-Šipka, Sanja, "Antimicrobial potency of Ru(II) arene based pyridil complexes" in Serbian Biochemical Society Eleventh Conference “Amazing Biochemistry”, September 22nd and 23rd, 2022, Novi Sad, Serbia (2022):110-110,
https://hdl.handle.net/21.15107/rcub_cherry_5821 .

Ru(II) bipyridine complexes with acetylpyridine analogues spectral and electrochemical characterization

Mihajlović-Lalić, Ljiljana; Poljarević, Jelena; Nikolić, Stefan; Petrović, Tamara; Stanković, Dalibor; Grgurić-Šipka, Sanja

(Belgrade : Serbian Chemical Society, 2022)

TY  - CONF
AU  - Mihajlović-Lalić, Ljiljana
AU  - Poljarević, Jelena
AU  - Nikolić, Stefan
AU  - Petrović, Tamara
AU  - Stanković, Dalibor
AU  - Grgurić-Šipka, Sanja
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5822
AB  - The versatile chemistry of ruthenium complexes involves thousands of compounds aimed
for different applications related to e.g. homogenous catalysis, cancer therapy, tumor
diagnosis, and advanced materials.1 Thus, the synthesis and full (electro)chemical
characterization of three new Ru(II) complexes carrying acetylpyridine (acpy) ligand unitis
is described. The complexes were obtained via reaction of three ligand equivalents (2-, 3-,
and 4-acpy) with an equimolar amount of metal precursor, [RuCl2(bpy)2] in methanol.
After the overnight reflux, the reaction mixture was left to cool when equimolar amount of
NH4PF6 was added. The products were isolated in a form of dark red powder. The
complexes were characterized by IR, NMR and MS revealing bidentate coordination of 2-
acpy and monodentate binding of 3- and 4-acpy. Their electrochemical profile was studied
by cyclic voltammetry which confirmed rich redox chemistry.
AB  - Raznovrsna hemija kompleksa rutenijuma obuhvata hiljade jedinjenja namenjenih za
različite primene, npr. homogenu katalizu, terapiju kancera, dijagnozu tumora i moderne
materijale.1
 S tim u vezi se opisuje sinteza i kompletna (elektro)hemijska karakterizacija tri
nova Ru(II) kompleksa sa acetilpiridinskim ligandom (acpy). Kompleksi su dobijeni
reakcijom tri ekvivalenta liganda (2-, 3-, i 4-acpy) sa ekvimolarnom količinom prekursora
metala, [RuCl2(bpy)2] u metanolu. Nakon refluksa preko noći, reakciona smeša je
ostavljena da se ohladi kad je dodata ekvimolarna količina NH4PF6. Produkti su izolovani
u obliku tamnocrvenog praha. Kompleksi su okarakterisani IC, NMR i MS pokazujući
bidentatnu koordinaciju 2-acpy i monodentatno vezivanje 3- i 4-acpy. Njihov
elektrohemijski profil je ispitan cikličnom voltametrijom koja je potvrdila bogatu redoks
hemiju.
PB  - Belgrade : Serbian Chemical Society
C3  - 58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022
T1  - Ru(II) bipyridine complexes with acetylpyridine analogues spectral and electrochemical characterization
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5822
ER  - 
@conference{
author = "Mihajlović-Lalić, Ljiljana and Poljarević, Jelena and Nikolić, Stefan and Petrović, Tamara and Stanković, Dalibor and Grgurić-Šipka, Sanja",
year = "2022",
abstract = "The versatile chemistry of ruthenium complexes involves thousands of compounds aimed
for different applications related to e.g. homogenous catalysis, cancer therapy, tumor
diagnosis, and advanced materials.1 Thus, the synthesis and full (electro)chemical
characterization of three new Ru(II) complexes carrying acetylpyridine (acpy) ligand unitis
is described. The complexes were obtained via reaction of three ligand equivalents (2-, 3-,
and 4-acpy) with an equimolar amount of metal precursor, [RuCl2(bpy)2] in methanol.
After the overnight reflux, the reaction mixture was left to cool when equimolar amount of
NH4PF6 was added. The products were isolated in a form of dark red powder. The
complexes were characterized by IR, NMR and MS revealing bidentate coordination of 2-
acpy and monodentate binding of 3- and 4-acpy. Their electrochemical profile was studied
by cyclic voltammetry which confirmed rich redox chemistry., Raznovrsna hemija kompleksa rutenijuma obuhvata hiljade jedinjenja namenjenih za
različite primene, npr. homogenu katalizu, terapiju kancera, dijagnozu tumora i moderne
materijale.1
 S tim u vezi se opisuje sinteza i kompletna (elektro)hemijska karakterizacija tri
nova Ru(II) kompleksa sa acetilpiridinskim ligandom (acpy). Kompleksi su dobijeni
reakcijom tri ekvivalenta liganda (2-, 3-, i 4-acpy) sa ekvimolarnom količinom prekursora
metala, [RuCl2(bpy)2] u metanolu. Nakon refluksa preko noći, reakciona smeša je
ostavljena da se ohladi kad je dodata ekvimolarna količina NH4PF6. Produkti su izolovani
u obliku tamnocrvenog praha. Kompleksi su okarakterisani IC, NMR i MS pokazujući
bidentatnu koordinaciju 2-acpy i monodentatno vezivanje 3- i 4-acpy. Njihov
elektrohemijski profil je ispitan cikličnom voltametrijom koja je potvrdila bogatu redoks
hemiju.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022",
title = "Ru(II) bipyridine complexes with acetylpyridine analogues spectral and electrochemical characterization",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5822"
}
Mihajlović-Lalić, L., Poljarević, J., Nikolić, S., Petrović, T., Stanković, D.,& Grgurić-Šipka, S.. (2022). Ru(II) bipyridine complexes with acetylpyridine analogues spectral and electrochemical characterization. in 58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022
Belgrade : Serbian Chemical Society..
https://hdl.handle.net/21.15107/rcub_cherry_5822
Mihajlović-Lalić L, Poljarević J, Nikolić S, Petrović T, Stanković D, Grgurić-Šipka S. Ru(II) bipyridine complexes with acetylpyridine analogues spectral and electrochemical characterization. in 58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022. 2022;.
https://hdl.handle.net/21.15107/rcub_cherry_5822 .
Mihajlović-Lalić, Ljiljana, Poljarević, Jelena, Nikolić, Stefan, Petrović, Tamara, Stanković, Dalibor, Grgurić-Šipka, Sanja, "Ru(II) bipyridine complexes with acetylpyridine analogues spectral and electrochemical characterization" in 58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022 (2022),
https://hdl.handle.net/21.15107/rcub_cherry_5822 .

Influence of Ru(II) complex on possible pathways of apoptosis in K562 leukemia cells

Krstić, Milena; Santibanez, J; Poljarević, Jelena; Nikolić, Stefan; Grgurić-Šipka, Sanja; Borozan, Sunčica

(Belgrade : Serbian Chemical Society, 2022)

TY  - CONF
AU  - Krstić, Milena
AU  - Santibanez, J
AU  - Poljarević, Jelena
AU  - Nikolić, Stefan
AU  - Grgurić-Šipka, Sanja
AU  - Borozan, Sunčica
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5823
AB  - Ruthenium complexes are of significant interest in the treatment of malignancies. Ru(II)
complexes with N-alkylphenothiazines (chlorpromazine, trifluoperazine, and thioridazine)
were used in the study of possible apoptosis pathways in K562 cells.
Spectrophotometrically extracellular LDH was quantified and immunochemical expression
of COX-2, t-JNK, p-JNK and -actin after SDS electrophoresis was determined. The
Ru(II) complex with trifluoperazine at a concentration of 10 μM reduced t-JNK
expression, inhibited COX-2 by about 42%, significantly increased the amount of
extracellular LDH compared to the untreated K562 cells and thus confirmed apoptosis.
AB  - U cilju pronalaženja adekvatne terapije u lečenju maligniteta kompleksi rutenijuma
pokazali su zavidan potencijal. Kompleksi Ru(II) sa N-alkilfenotiazinima,
hlorpromazinom, trifluoperazinom i tioridazinom, korišćeni su u ispitivanju mogućih
puteva apoptoze u K562 ćelijama. Ispitivana je spektrofotometrijski ekstracelularna LDH,
ekspresija COX-2, t-JNK, p-JNK i β-aktina imunohemijski nakon SDS elektroforeze.
Kompleks Ru(II) sa trifluoperazinom u koncentraciji od 10 µM smanjuje ekspresiju t-JNK,
inhibira COX-2 oko 42%, značajno povećava količinu ekstracelularne LDH u odnosu na
netretirane K562 ćelije i time potvrdjuje apoptozu ovih ćelija.
PB  - Belgrade : Serbian Chemical Society
C3  - 58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022
T1  - Influence of Ru(II) complex on possible pathways of apoptosis in K562 leukemia cells
T1  - Uticaj kompleksa Ru(II) na moguće puteve apoptoze u K562 ćelijama leukemije
SP  - 89
EP  - 89
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5823
ER  - 
@conference{
author = "Krstić, Milena and Santibanez, J and Poljarević, Jelena and Nikolić, Stefan and Grgurić-Šipka, Sanja and Borozan, Sunčica",
year = "2022",
abstract = "Ruthenium complexes are of significant interest in the treatment of malignancies. Ru(II)
complexes with N-alkylphenothiazines (chlorpromazine, trifluoperazine, and thioridazine)
were used in the study of possible apoptosis pathways in K562 cells.
Spectrophotometrically extracellular LDH was quantified and immunochemical expression
of COX-2, t-JNK, p-JNK and -actin after SDS electrophoresis was determined. The
Ru(II) complex with trifluoperazine at a concentration of 10 μM reduced t-JNK
expression, inhibited COX-2 by about 42%, significantly increased the amount of
extracellular LDH compared to the untreated K562 cells and thus confirmed apoptosis., U cilju pronalaženja adekvatne terapije u lečenju maligniteta kompleksi rutenijuma
pokazali su zavidan potencijal. Kompleksi Ru(II) sa N-alkilfenotiazinima,
hlorpromazinom, trifluoperazinom i tioridazinom, korišćeni su u ispitivanju mogućih
puteva apoptoze u K562 ćelijama. Ispitivana je spektrofotometrijski ekstracelularna LDH,
ekspresija COX-2, t-JNK, p-JNK i β-aktina imunohemijski nakon SDS elektroforeze.
Kompleks Ru(II) sa trifluoperazinom u koncentraciji od 10 µM smanjuje ekspresiju t-JNK,
inhibira COX-2 oko 42%, značajno povećava količinu ekstracelularne LDH u odnosu na
netretirane K562 ćelije i time potvrdjuje apoptozu ovih ćelija.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022",
title = "Influence of Ru(II) complex on possible pathways of apoptosis in K562 leukemia cells, Uticaj kompleksa Ru(II) na moguće puteve apoptoze u K562 ćelijama leukemije",
pages = "89-89",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5823"
}
Krstić, M., Santibanez, J., Poljarević, J., Nikolić, S., Grgurić-Šipka, S.,& Borozan, S.. (2022). Influence of Ru(II) complex on possible pathways of apoptosis in K562 leukemia cells. in 58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022
Belgrade : Serbian Chemical Society., 89-89.
https://hdl.handle.net/21.15107/rcub_cherry_5823
Krstić M, Santibanez J, Poljarević J, Nikolić S, Grgurić-Šipka S, Borozan S. Influence of Ru(II) complex on possible pathways of apoptosis in K562 leukemia cells. in 58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022. 2022;:89-89.
https://hdl.handle.net/21.15107/rcub_cherry_5823 .
Krstić, Milena, Santibanez, J, Poljarević, Jelena, Nikolić, Stefan, Grgurić-Šipka, Sanja, Borozan, Sunčica, "Influence of Ru(II) complex on possible pathways of apoptosis in K562 leukemia cells" in 58th Meeting of the Serbian Chemical Society, Belgrade, June 9-10, 2022 (2022):89-89,
https://hdl.handle.net/21.15107/rcub_cherry_5823 .

Oxorhenium(V) complexes in the drug combination study

Petrović, Tamara; Gligorijević, Nevenka; Belaj, Ferdinand; Grgurić-Šipka, Sanja; Nikolić, Stefan; Krstić, Milena; Poljarević, Jelena; Mihajlović-Lalić, Ljiljana

(Belgrade : Serbian Chemical Society, 2022)

TY  - CONF
AU  - Petrović, Tamara
AU  - Gligorijević, Nevenka
AU  - Belaj, Ferdinand
AU  - Grgurić-Šipka, Sanja
AU  - Nikolić, Stefan
AU  - Krstić, Milena
AU  - Poljarević, Jelena
AU  - Mihajlović-Lalić, Ljiljana
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5824
AB  - Rhenium complexes merit particular attention in the area of metallodrug design due to rhenium’s broad spectrum of oxidation states and consequently, the possibility to design compounds of a great structural diversity. Thus, the synthesis, chemical characterization and antitumor activity in vitro of the three Re(V) complexes is described. Novel compounds were obtained via reaction of [ReOCl3(PPh3)2] with corresponding ligands (pyridine-2-carboxylic acid, 3-methylpyridine-2-carboxylic acid and 6-methylpyridine-2-carboxylic acid) in acetonitrile at 78 °C for 3h. The complexes were fully characterized using NMR, IR, MS and elemental analysis. Their octahedral geometry with bidentate NO ligand was confirmed by X-ray diffraction analysis. Antiproliferative effect was determined by MTT assay and only the complex with pyridine-2-carboxylic acid (1) showed dose-dependent cytotoxic potential, particularly toward triple-negative breast adenocarcinoma cells MDA-MB-231 with IC50 68.90 ± 1.73 µM and pancreatic adenocarcinoma cells PANC-1 with IC50 69.8 ± 2.3 µM. Drug combination studies in PANC-1 cells with 1 and Verapamil hydrochloride (VRP) showed slight arrest of cell cycle in the S phase and also it increase its antiproliferative potential to IC50 51.4 ± 2.8 μM. Part of the research included a depletion of the glutathione (GSH) level by L-buthionine-sulfoximine (L-BSO) at sub-toxic concentrations (100 μM) in PANC-1 cells which caused an increase of activity of 1 to the IC50 57.67 ± 6.51 μM.
PB  - Belgrade : Serbian Chemical Society
PB  - Belgrade : Serbian Young Chemists’ Club
C3  - 8 th Conference of Young Chemists of Serbia Belgrade, 29th October 2022
T1  - Oxorhenium(V) complexes in the drug combination study
SP  - 81
EP  - 81
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5824
ER  - 
@conference{
author = "Petrović, Tamara and Gligorijević, Nevenka and Belaj, Ferdinand and Grgurić-Šipka, Sanja and Nikolić, Stefan and Krstić, Milena and Poljarević, Jelena and Mihajlović-Lalić, Ljiljana",
year = "2022",
abstract = "Rhenium complexes merit particular attention in the area of metallodrug design due to rhenium’s broad spectrum of oxidation states and consequently, the possibility to design compounds of a great structural diversity. Thus, the synthesis, chemical characterization and antitumor activity in vitro of the three Re(V) complexes is described. Novel compounds were obtained via reaction of [ReOCl3(PPh3)2] with corresponding ligands (pyridine-2-carboxylic acid, 3-methylpyridine-2-carboxylic acid and 6-methylpyridine-2-carboxylic acid) in acetonitrile at 78 °C for 3h. The complexes were fully characterized using NMR, IR, MS and elemental analysis. Their octahedral geometry with bidentate NO ligand was confirmed by X-ray diffraction analysis. Antiproliferative effect was determined by MTT assay and only the complex with pyridine-2-carboxylic acid (1) showed dose-dependent cytotoxic potential, particularly toward triple-negative breast adenocarcinoma cells MDA-MB-231 with IC50 68.90 ± 1.73 µM and pancreatic adenocarcinoma cells PANC-1 with IC50 69.8 ± 2.3 µM. Drug combination studies in PANC-1 cells with 1 and Verapamil hydrochloride (VRP) showed slight arrest of cell cycle in the S phase and also it increase its antiproliferative potential to IC50 51.4 ± 2.8 μM. Part of the research included a depletion of the glutathione (GSH) level by L-buthionine-sulfoximine (L-BSO) at sub-toxic concentrations (100 μM) in PANC-1 cells which caused an increase of activity of 1 to the IC50 57.67 ± 6.51 μM.",
publisher = "Belgrade : Serbian Chemical Society, Belgrade : Serbian Young Chemists’ Club",
journal = "8 th Conference of Young Chemists of Serbia Belgrade, 29th October 2022",
title = "Oxorhenium(V) complexes in the drug combination study",
pages = "81-81",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5824"
}
Petrović, T., Gligorijević, N., Belaj, F., Grgurić-Šipka, S., Nikolić, S., Krstić, M., Poljarević, J.,& Mihajlović-Lalić, L.. (2022). Oxorhenium(V) complexes in the drug combination study. in 8 th Conference of Young Chemists of Serbia Belgrade, 29th October 2022
Belgrade : Serbian Chemical Society., 81-81.
https://hdl.handle.net/21.15107/rcub_cherry_5824
Petrović T, Gligorijević N, Belaj F, Grgurić-Šipka S, Nikolić S, Krstić M, Poljarević J, Mihajlović-Lalić L. Oxorhenium(V) complexes in the drug combination study. in 8 th Conference of Young Chemists of Serbia Belgrade, 29th October 2022. 2022;:81-81.
https://hdl.handle.net/21.15107/rcub_cherry_5824 .
Petrović, Tamara, Gligorijević, Nevenka, Belaj, Ferdinand, Grgurić-Šipka, Sanja, Nikolić, Stefan, Krstić, Milena, Poljarević, Jelena, Mihajlović-Lalić, Ljiljana, "Oxorhenium(V) complexes in the drug combination study" in 8 th Conference of Young Chemists of Serbia Belgrade, 29th October 2022 (2022):81-81,
https://hdl.handle.net/21.15107/rcub_cherry_5824 .

Editorial: The Golden Future in Medicinal Chemistry: Perspectives and Resources From Old and New Gold-Based Drug Candidates

Massai, Lara; Grgurić-Šipka, Sanja; Liu, Wukun; Bertrand, Benoît; Pratesi, Alessandro

(Frontiers, 2021)

TY  - JOUR
AU  - Massai, Lara
AU  - Grgurić-Šipka, Sanja
AU  - Liu, Wukun
AU  - Bertrand, Benoît
AU  - Pratesi, Alessandro
PY  - 2021
UR  - https://www.frontiersin.org/articles/10.3389/fchem.2021.665244/full
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4478
AB  - Editorial: The Golden Future in Medicinal Chemistry: Perspectives and Resources From Old and New Gold-Based Drug Candidates
PB  - Frontiers
T2  - Frontiers in Chemistry
T1  - Editorial: The Golden Future in Medicinal Chemistry: Perspectives and Resources From Old and New Gold-Based Drug Candidates
VL  - 9
SP  - 665244
DO  - 10.3389/fchem.2021.665244
ER  - 
@article{
author = "Massai, Lara and Grgurić-Šipka, Sanja and Liu, Wukun and Bertrand, Benoît and Pratesi, Alessandro",
year = "2021",
abstract = "Editorial: The Golden Future in Medicinal Chemistry: Perspectives and Resources From Old and New Gold-Based Drug Candidates",
publisher = "Frontiers",
journal = "Frontiers in Chemistry",
title = "Editorial: The Golden Future in Medicinal Chemistry: Perspectives and Resources From Old and New Gold-Based Drug Candidates",
volume = "9",
pages = "665244",
doi = "10.3389/fchem.2021.665244"
}
Massai, L., Grgurić-Šipka, S., Liu, W., Bertrand, B.,& Pratesi, A.. (2021). Editorial: The Golden Future in Medicinal Chemistry: Perspectives and Resources From Old and New Gold-Based Drug Candidates. in Frontiers in Chemistry
Frontiers., 9, 665244.
https://doi.org/10.3389/fchem.2021.665244
Massai L, Grgurić-Šipka S, Liu W, Bertrand B, Pratesi A. Editorial: The Golden Future in Medicinal Chemistry: Perspectives and Resources From Old and New Gold-Based Drug Candidates. in Frontiers in Chemistry. 2021;9:665244.
doi:10.3389/fchem.2021.665244 .
Massai, Lara, Grgurić-Šipka, Sanja, Liu, Wukun, Bertrand, Benoît, Pratesi, Alessandro, "Editorial: The Golden Future in Medicinal Chemistry: Perspectives and Resources From Old and New Gold-Based Drug Candidates" in Frontiers in Chemistry, 9 (2021):665244,
https://doi.org/10.3389/fchem.2021.665244 . .
1
4
1
3

Metal complexes with α-picolinic acid frameworks and their antitumor activity

Mihajlović-Lalić, Ljiljana; Poljarević, Jelena; Grgurić-Šipka, Sanja

(Elsevier, 2021)

TY  - JOUR
AU  - Mihajlović-Lalić, Ljiljana
AU  - Poljarević, Jelena
AU  - Grgurić-Šipka, Sanja
PY  - 2021
UR  - https://www.sciencedirect.com/science/article/pii/S0020169321003388
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4662
AB  - Pyridine (carboxylate) type of molecules has been intensively studied since early 2000s as it provides diverse design capabilities in terms of coordination to metal ions. Several structural motifs featuring mono-, bi-, and pentadentate binding modes are discussed in a combination with a variety of different substituents with the pyridine unit. In this context, the current review underlines a brief summary of advances on metal complexes with pyridine-based ligands aimed for further development as metallodrug. In line with this, we also highlight their key properties, different synthetic strategies employed in the preparation, and possible structure–property correlations, indicating advantages and limitations of the applied methods used within documented studies.
PB  - Elsevier
T2  - Inorganica Chimica Acta
T1  - Metal complexes with α-picolinic acid frameworks and their antitumor activity
VL  - 527
SP  - 120582
DO  - 10.1016/j.ica.2021.120582
ER  - 
@article{
author = "Mihajlović-Lalić, Ljiljana and Poljarević, Jelena and Grgurić-Šipka, Sanja",
year = "2021",
abstract = "Pyridine (carboxylate) type of molecules has been intensively studied since early 2000s as it provides diverse design capabilities in terms of coordination to metal ions. Several structural motifs featuring mono-, bi-, and pentadentate binding modes are discussed in a combination with a variety of different substituents with the pyridine unit. In this context, the current review underlines a brief summary of advances on metal complexes with pyridine-based ligands aimed for further development as metallodrug. In line with this, we also highlight their key properties, different synthetic strategies employed in the preparation, and possible structure–property correlations, indicating advantages and limitations of the applied methods used within documented studies.",
publisher = "Elsevier",
journal = "Inorganica Chimica Acta",
title = "Metal complexes with α-picolinic acid frameworks and their antitumor activity",
volume = "527",
pages = "120582",
doi = "10.1016/j.ica.2021.120582"
}
Mihajlović-Lalić, L., Poljarević, J.,& Grgurić-Šipka, S.. (2021). Metal complexes with α-picolinic acid frameworks and their antitumor activity. in Inorganica Chimica Acta
Elsevier., 527, 120582.
https://doi.org/10.1016/j.ica.2021.120582
Mihajlović-Lalić L, Poljarević J, Grgurić-Šipka S. Metal complexes with α-picolinic acid frameworks and their antitumor activity. in Inorganica Chimica Acta. 2021;527:120582.
doi:10.1016/j.ica.2021.120582 .
Mihajlović-Lalić, Ljiljana, Poljarević, Jelena, Grgurić-Šipka, Sanja, "Metal complexes with α-picolinic acid frameworks and their antitumor activity" in Inorganica Chimica Acta, 527 (2021):120582,
https://doi.org/10.1016/j.ica.2021.120582 . .
7
1
4

Ferrous iron binding to epinephrine promotes the oxidation of iron and impedes activation of adrenergic receptors

Korać Jačić, Jelena; Nikolić, Ljiljana; Stanković, Dalibor; Opačić, Miloš; Dimitrijević, Milena; Savić, Danijela; Grgurić-Šipka, Sanja; Spasojević, Ivan; Bogdanović Pristov, Jelena

(Elsevier, 2020)

TY  - JOUR
AU  - Korać Jačić, Jelena
AU  - Nikolić, Ljiljana
AU  - Stanković, Dalibor
AU  - Opačić, Miloš
AU  - Dimitrijević, Milena
AU  - Savić, Danijela
AU  - Grgurić-Šipka, Sanja
AU  - Spasojević, Ivan
AU  - Bogdanović Pristov, Jelena
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3809
AB  - Upon release in response to stress, epinephrine (Epi) may interact with labile iron pool in human plasma with potentially important (patho)physiological consequences. We have shown that Epi and Fe3+ build stable 1:1 high-spin bidentate complex at physiological pH, and that Epi does not undergo degradation in the presence of iron. However, the interactions of Epi with the more soluble Fe2+, and the impact of iron on biological activity of Epi are still not known. Herein we showed that Epi and Fe2+ build colorless complex which is stable under anaerobic conditions. In the presence of O2, Epi promoted the oxidation of Fe2+ and the formation of Epi-Fe3+ complex. Cyclic voltammetry showed that mid-point potential of Epi-Fe2+ complex is very low (−582 mV vs. standard hydrogen electrode), which explains catalyzed oxidation of Fe2+. Next, we examined the impact of iron binding on biological performance of Epi using patch clamping in cell culture with constitutive expression of adrenergic receptors. Epi alone evoked an increase of outward currents, whereas Epi in the complex with Fe3+ did not. This implies that the binding of Epi to adrenergic receptors and their activation is prevented by the formation of complex with iron. Pro-oxidative activity of Epi-Fe2+ complex may represent a link between chronic stress and cardiovascular problems. On the other hand, labile iron could serve as a modulator of biological activity of ligands. Such interactions may be important in human pathologies that are related to iron overload or deficiency.
PB  - Elsevier
T2  - Free Radical Biology and Medicine
T1  - Ferrous iron binding to epinephrine promotes the oxidation of iron and impedes activation of adrenergic receptors
VL  - 148
SP  - 123
EP  - 127
DO  - 10.1016/j.freeradbiomed.2020.01.001
ER  - 
@article{
author = "Korać Jačić, Jelena and Nikolić, Ljiljana and Stanković, Dalibor and Opačić, Miloš and Dimitrijević, Milena and Savić, Danijela and Grgurić-Šipka, Sanja and Spasojević, Ivan and Bogdanović Pristov, Jelena",
year = "2020",
abstract = "Upon release in response to stress, epinephrine (Epi) may interact with labile iron pool in human plasma with potentially important (patho)physiological consequences. We have shown that Epi and Fe3+ build stable 1:1 high-spin bidentate complex at physiological pH, and that Epi does not undergo degradation in the presence of iron. However, the interactions of Epi with the more soluble Fe2+, and the impact of iron on biological activity of Epi are still not known. Herein we showed that Epi and Fe2+ build colorless complex which is stable under anaerobic conditions. In the presence of O2, Epi promoted the oxidation of Fe2+ and the formation of Epi-Fe3+ complex. Cyclic voltammetry showed that mid-point potential of Epi-Fe2+ complex is very low (−582 mV vs. standard hydrogen electrode), which explains catalyzed oxidation of Fe2+. Next, we examined the impact of iron binding on biological performance of Epi using patch clamping in cell culture with constitutive expression of adrenergic receptors. Epi alone evoked an increase of outward currents, whereas Epi in the complex with Fe3+ did not. This implies that the binding of Epi to adrenergic receptors and their activation is prevented by the formation of complex with iron. Pro-oxidative activity of Epi-Fe2+ complex may represent a link between chronic stress and cardiovascular problems. On the other hand, labile iron could serve as a modulator of biological activity of ligands. Such interactions may be important in human pathologies that are related to iron overload or deficiency.",
publisher = "Elsevier",
journal = "Free Radical Biology and Medicine",
title = "Ferrous iron binding to epinephrine promotes the oxidation of iron and impedes activation of adrenergic receptors",
volume = "148",
pages = "123-127",
doi = "10.1016/j.freeradbiomed.2020.01.001"
}
Korać Jačić, J., Nikolić, L., Stanković, D., Opačić, M., Dimitrijević, M., Savić, D., Grgurić-Šipka, S., Spasojević, I.,& Bogdanović Pristov, J.. (2020). Ferrous iron binding to epinephrine promotes the oxidation of iron and impedes activation of adrenergic receptors. in Free Radical Biology and Medicine
Elsevier., 148, 123-127.
https://doi.org/10.1016/j.freeradbiomed.2020.01.001
Korać Jačić J, Nikolić L, Stanković D, Opačić M, Dimitrijević M, Savić D, Grgurić-Šipka S, Spasojević I, Bogdanović Pristov J. Ferrous iron binding to epinephrine promotes the oxidation of iron and impedes activation of adrenergic receptors. in Free Radical Biology and Medicine. 2020;148:123-127.
doi:10.1016/j.freeradbiomed.2020.01.001 .
Korać Jačić, Jelena, Nikolić, Ljiljana, Stanković, Dalibor, Opačić, Miloš, Dimitrijević, Milena, Savić, Danijela, Grgurić-Šipka, Sanja, Spasojević, Ivan, Bogdanović Pristov, Jelena, "Ferrous iron binding to epinephrine promotes the oxidation of iron and impedes activation of adrenergic receptors" in Free Radical Biology and Medicine, 148 (2020):123-127,
https://doi.org/10.1016/j.freeradbiomed.2020.01.001 . .

The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c

Stanić-Vučinić, Dragana; Nikolić, Stefan; Vlajić, Katarina; Radomirović, Mirjana Ž.; Mihailović, Jelena; Ćirković-Veličković, Tanja; Grgurić-Šipka, Sanja

(Springer, 2020)

TY  - JOUR
AU  - Stanić-Vučinić, Dragana
AU  - Nikolić, Stefan
AU  - Vlajić, Katarina
AU  - Radomirović, Mirjana Ž.
AU  - Mihailović, Jelena
AU  - Ćirković-Veličković, Tanja
AU  - Grgurić-Šipka, Sanja
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3859
AB  - The reactions of four cymene-capped ruthenium(II) compounds with pro-apaptotic protein, cytochrome c (Cyt), and anti-proliferating protein lysozyme (Ly) in carbonate buffer were investigated by ESI-MS, UV–Vis absorption and CD spectroscopy. The complexes with two chloride ligands (C2 and C3) were more reactive toward proteins than those with only one (C1 and C4), and the complex with S,N-chelating ligand (C4) was less reactive than one with O,N-chelating ligand (C1). Dehalogenated complexes are most likely species initially coordinating proteins for all tested complexes. During the time, protein adducts vividly exchanged non-arene organic ligand L with CO32- and OH-, while cymene moiety was retained. In water, only dehalogenated adducts were identified suggesting that in vivo, in the presence of various anions, dynamic ligand exchange could generate different intermediate protein species. Although all complexes reduced Cyt, the reduction was not dependent on their reactivity to protein, implying that initially noncovalent binding to Cyt occures, causing its reduction, followed by coordination to protein. Cyt reduction was accompanied with rupture of ferro-Met 80 and occupation of this hem coordination site by a histidine His-33/26. Therefore, in Cyt with C2 and C3 less intensive reduction of hem iron leave more unoccupied target residues for Ru coordination, leading to more efficient formation of covalent adducts, in comparison to C1 and C4. This study contribute to development of new protein-targeted Ru(II) cymene complexes, and to design of new cancer therapies based on targeted delivery of Ru(II) arene complexes bound on pro-apoptotic/anti-proliferating proteins as vehicles.
PB  - Springer
T2  - Journal of Biological Inorganic Chemistry
T1  - The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c
VL  - 25
IS  - 2
SP  - 253
EP  - 265
DO  - 10.1007/s00775-020-01758-3
ER  - 
@article{
author = "Stanić-Vučinić, Dragana and Nikolić, Stefan and Vlajić, Katarina and Radomirović, Mirjana Ž. and Mihailović, Jelena and Ćirković-Veličković, Tanja and Grgurić-Šipka, Sanja",
year = "2020",
abstract = "The reactions of four cymene-capped ruthenium(II) compounds with pro-apaptotic protein, cytochrome c (Cyt), and anti-proliferating protein lysozyme (Ly) in carbonate buffer were investigated by ESI-MS, UV–Vis absorption and CD spectroscopy. The complexes with two chloride ligands (C2 and C3) were more reactive toward proteins than those with only one (C1 and C4), and the complex with S,N-chelating ligand (C4) was less reactive than one with O,N-chelating ligand (C1). Dehalogenated complexes are most likely species initially coordinating proteins for all tested complexes. During the time, protein adducts vividly exchanged non-arene organic ligand L with CO32- and OH-, while cymene moiety was retained. In water, only dehalogenated adducts were identified suggesting that in vivo, in the presence of various anions, dynamic ligand exchange could generate different intermediate protein species. Although all complexes reduced Cyt, the reduction was not dependent on their reactivity to protein, implying that initially noncovalent binding to Cyt occures, causing its reduction, followed by coordination to protein. Cyt reduction was accompanied with rupture of ferro-Met 80 and occupation of this hem coordination site by a histidine His-33/26. Therefore, in Cyt with C2 and C3 less intensive reduction of hem iron leave more unoccupied target residues for Ru coordination, leading to more efficient formation of covalent adducts, in comparison to C1 and C4. This study contribute to development of new protein-targeted Ru(II) cymene complexes, and to design of new cancer therapies based on targeted delivery of Ru(II) arene complexes bound on pro-apoptotic/anti-proliferating proteins as vehicles.",
publisher = "Springer",
journal = "Journal of Biological Inorganic Chemistry",
title = "The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c",
volume = "25",
number = "2",
pages = "253-265",
doi = "10.1007/s00775-020-01758-3"
}
Stanić-Vučinić, D., Nikolić, S., Vlajić, K., Radomirović, M. Ž., Mihailović, J., Ćirković-Veličković, T.,& Grgurić-Šipka, S.. (2020). The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c. in Journal of Biological Inorganic Chemistry
Springer., 25(2), 253-265.
https://doi.org/10.1007/s00775-020-01758-3
Stanić-Vučinić D, Nikolić S, Vlajić K, Radomirović MŽ, Mihailović J, Ćirković-Veličković T, Grgurić-Šipka S. The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c. in Journal of Biological Inorganic Chemistry. 2020;25(2):253-265.
doi:10.1007/s00775-020-01758-3 .
Stanić-Vučinić, Dragana, Nikolić, Stefan, Vlajić, Katarina, Radomirović, Mirjana Ž., Mihailović, Jelena, Ćirković-Veličković, Tanja, Grgurić-Šipka, Sanja, "The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c" in Journal of Biological Inorganic Chemistry, 25, no. 2 (2020):253-265,
https://doi.org/10.1007/s00775-020-01758-3 . .
6
3
6

Supplementary data for the article: Stanic-Vucinic, D.; Nikolic, S.; Vlajic, K.; Radomirovic, M.; Mihailovic, J.; Cirkovic Velickovic, T.; Grguric-Sipka, S. The Interactions of the Ruthenium(II)-Cymene Complexes with Lysozyme and Cytochrome c. Journal of Biological Inorganic Chemistry 2020. https://doi.org/10.1007/s00775-020-01758-3

Stanić-Vučinić, Dragana; Nikolić, Stefan; Vlajić, Katarina; Radomirović, Mirjana Ž.; Mihailović, Jelena; Ćirković-Veličković, Tanja; Grgurić-Šipka, Sanja

(Springer, 2020)

TY  - DATA
AU  - Stanić-Vučinić, Dragana
AU  - Nikolić, Stefan
AU  - Vlajić, Katarina
AU  - Radomirović, Mirjana Ž.
AU  - Mihailović, Jelena
AU  - Ćirković-Veličković, Tanja
AU  - Grgurić-Šipka, Sanja
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3863
PB  - Springer
T2  - Journal of Biological Inorganic Chemistry
T1  - Supplementary data for the article: Stanic-Vucinic, D.; Nikolic, S.; Vlajic, K.; Radomirovic, M.; Mihailovic, J.; Cirkovic Velickovic, T.; Grguric-Sipka, S. The Interactions of the Ruthenium(II)-Cymene Complexes with Lysozyme and Cytochrome c. Journal of Biological Inorganic Chemistry 2020. https://doi.org/10.1007/s00775-020-01758-3
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3863
ER  - 
@misc{
author = "Stanić-Vučinić, Dragana and Nikolić, Stefan and Vlajić, Katarina and Radomirović, Mirjana Ž. and Mihailović, Jelena and Ćirković-Veličković, Tanja and Grgurić-Šipka, Sanja",
year = "2020",
publisher = "Springer",
journal = "Journal of Biological Inorganic Chemistry",
title = "Supplementary data for the article: Stanic-Vucinic, D.; Nikolic, S.; Vlajic, K.; Radomirovic, M.; Mihailovic, J.; Cirkovic Velickovic, T.; Grguric-Sipka, S. The Interactions of the Ruthenium(II)-Cymene Complexes with Lysozyme and Cytochrome c. Journal of Biological Inorganic Chemistry 2020. https://doi.org/10.1007/s00775-020-01758-3",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3863"
}
Stanić-Vučinić, D., Nikolić, S., Vlajić, K., Radomirović, M. Ž., Mihailović, J., Ćirković-Veličković, T.,& Grgurić-Šipka, S.. (2020). Supplementary data for the article: Stanic-Vucinic, D.; Nikolic, S.; Vlajic, K.; Radomirovic, M.; Mihailovic, J.; Cirkovic Velickovic, T.; Grguric-Sipka, S. The Interactions of the Ruthenium(II)-Cymene Complexes with Lysozyme and Cytochrome c. Journal of Biological Inorganic Chemistry 2020. https://doi.org/10.1007/s00775-020-01758-3. in Journal of Biological Inorganic Chemistry
Springer..
https://hdl.handle.net/21.15107/rcub_cherry_3863
Stanić-Vučinić D, Nikolić S, Vlajić K, Radomirović MŽ, Mihailović J, Ćirković-Veličković T, Grgurić-Šipka S. Supplementary data for the article: Stanic-Vucinic, D.; Nikolic, S.; Vlajic, K.; Radomirovic, M.; Mihailovic, J.; Cirkovic Velickovic, T.; Grguric-Sipka, S. The Interactions of the Ruthenium(II)-Cymene Complexes with Lysozyme and Cytochrome c. Journal of Biological Inorganic Chemistry 2020. https://doi.org/10.1007/s00775-020-01758-3. in Journal of Biological Inorganic Chemistry. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_3863 .
Stanić-Vučinić, Dragana, Nikolić, Stefan, Vlajić, Katarina, Radomirović, Mirjana Ž., Mihailović, Jelena, Ćirković-Veličković, Tanja, Grgurić-Šipka, Sanja, "Supplementary data for the article: Stanic-Vucinic, D.; Nikolic, S.; Vlajic, K.; Radomirovic, M.; Mihailovic, J.; Cirkovic Velickovic, T.; Grguric-Sipka, S. The Interactions of the Ruthenium(II)-Cymene Complexes with Lysozyme and Cytochrome c. Journal of Biological Inorganic Chemistry 2020. https://doi.org/10.1007/s00775-020-01758-3" in Journal of Biological Inorganic Chemistry (2020),
https://hdl.handle.net/21.15107/rcub_cherry_3863 .

The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c

Stanić-Vučinić, Dragana; Nikolić, Stefan; Vlajić, Katarina; Radomirović, Mirjana Ž.; Mihailović, Jelena; Ćirković-Veličković, Tanja; Grgurić-Šipka, Sanja

(Springer, 2020)

TY  - JOUR
AU  - Stanić-Vučinić, Dragana
AU  - Nikolić, Stefan
AU  - Vlajić, Katarina
AU  - Radomirović, Mirjana Ž.
AU  - Mihailović, Jelena
AU  - Ćirković-Veličković, Tanja
AU  - Grgurić-Šipka, Sanja
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3942
AB  - The reactions of four cymene-capped ruthenium(II) compounds with pro-apaptotic protein, cytochrome c (Cyt), and anti-proliferating protein lysozyme (Ly) in carbonate buffer were investigated by ESI-MS, UV–Vis absorption and CD spectroscopy. The complexes with two chloride ligands (C2 and C3) were more reactive toward proteins than those with only one (C1 and C4), and the complex with S,N-chelating ligand (C4) was less reactive than one with O,N-chelating ligand (C1). Dehalogenated complexes are most likely species initially coordinating proteins for all tested complexes. During the time, protein adducts vividly exchanged non-arene organic ligand L with CO32- and OH-, while cymene moiety was retained. In water, only dehalogenated adducts were identified suggesting that in vivo, in the presence of various anions, dynamic ligand exchange could generate different intermediate protein species. Although all complexes reduced Cyt, the reduction was not dependent on their reactivity to protein, implying that initially noncovalent binding to Cyt occures, causing its reduction, followed by coordination to protein. Cyt reduction was accompanied with rupture of ferro-Met 80 and occupation of this hem coordination site by a histidine His-33/26. Therefore, in Cyt with C2 and C3 less intensive reduction of hem iron leave more unoccupied target residues for Ru coordination, leading to more efficient formation of covalent adducts, in comparison to C1 and C4. This study contribute to development of new protein-targeted Ru(II) cymene complexes, and to design of new cancer therapies based on targeted delivery of Ru(II) arene complexes bound on pro-apoptotic/anti-proliferating proteins as vehicles.
PB  - Springer
T2  - Journal of Biological Inorganic Chemistry
T1  - The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c
VL  - 25
IS  - 2
SP  - 253
EP  - 265
DO  - 10.1007/s00775-020-01758-3
ER  - 
@article{
author = "Stanić-Vučinić, Dragana and Nikolić, Stefan and Vlajić, Katarina and Radomirović, Mirjana Ž. and Mihailović, Jelena and Ćirković-Veličković, Tanja and Grgurić-Šipka, Sanja",
year = "2020",
abstract = "The reactions of four cymene-capped ruthenium(II) compounds with pro-apaptotic protein, cytochrome c (Cyt), and anti-proliferating protein lysozyme (Ly) in carbonate buffer were investigated by ESI-MS, UV–Vis absorption and CD spectroscopy. The complexes with two chloride ligands (C2 and C3) were more reactive toward proteins than those with only one (C1 and C4), and the complex with S,N-chelating ligand (C4) was less reactive than one with O,N-chelating ligand (C1). Dehalogenated complexes are most likely species initially coordinating proteins for all tested complexes. During the time, protein adducts vividly exchanged non-arene organic ligand L with CO32- and OH-, while cymene moiety was retained. In water, only dehalogenated adducts were identified suggesting that in vivo, in the presence of various anions, dynamic ligand exchange could generate different intermediate protein species. Although all complexes reduced Cyt, the reduction was not dependent on their reactivity to protein, implying that initially noncovalent binding to Cyt occures, causing its reduction, followed by coordination to protein. Cyt reduction was accompanied with rupture of ferro-Met 80 and occupation of this hem coordination site by a histidine His-33/26. Therefore, in Cyt with C2 and C3 less intensive reduction of hem iron leave more unoccupied target residues for Ru coordination, leading to more efficient formation of covalent adducts, in comparison to C1 and C4. This study contribute to development of new protein-targeted Ru(II) cymene complexes, and to design of new cancer therapies based on targeted delivery of Ru(II) arene complexes bound on pro-apoptotic/anti-proliferating proteins as vehicles.",
publisher = "Springer",
journal = "Journal of Biological Inorganic Chemistry",
title = "The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c",
volume = "25",
number = "2",
pages = "253-265",
doi = "10.1007/s00775-020-01758-3"
}
Stanić-Vučinić, D., Nikolić, S., Vlajić, K., Radomirović, M. Ž., Mihailović, J., Ćirković-Veličković, T.,& Grgurić-Šipka, S.. (2020). The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c. in Journal of Biological Inorganic Chemistry
Springer., 25(2), 253-265.
https://doi.org/10.1007/s00775-020-01758-3
Stanić-Vučinić D, Nikolić S, Vlajić K, Radomirović MŽ, Mihailović J, Ćirković-Veličković T, Grgurić-Šipka S. The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c. in Journal of Biological Inorganic Chemistry. 2020;25(2):253-265.
doi:10.1007/s00775-020-01758-3 .
Stanić-Vučinić, Dragana, Nikolić, Stefan, Vlajić, Katarina, Radomirović, Mirjana Ž., Mihailović, Jelena, Ćirković-Veličković, Tanja, Grgurić-Šipka, Sanja, "The interactions of the ruthenium(II)-cymene complexes with lysozyme and cytochrome c" in Journal of Biological Inorganic Chemistry, 25, no. 2 (2020):253-265,
https://doi.org/10.1007/s00775-020-01758-3 . .
6
3
6

Synthesis, chemical characterization, PARP inhibition, DNA binding and cellular uptake of novel ruthenium(II)-arene complexes bearing benzamide derivatives in human breast cancer cells

Pavlović, Marijana; Tadić, Ana; Gligorijević, Nevenka; Poljarević, Jelena; Petrović, Tamara; Dojčinović, Biljana P.; Savić, Aleksandar; Radulović, Siniša; Grgurić-Šipka, Sanja; Aranđelović, Sandra

(Elsevier, 2020)

TY  - JOUR
AU  - Pavlović, Marijana
AU  - Tadić, Ana
AU  - Gligorijević, Nevenka
AU  - Poljarević, Jelena
AU  - Petrović, Tamara
AU  - Dojčinović, Biljana P.
AU  - Savić, Aleksandar
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
AU  - Aranđelović, Sandra
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4048
AB  - Inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1) showed remarkable clinical efficacy in BRCA-mutated tumors. Based on the rational drug design, derivatives of PARP inhibitor 3-aminobenzamide (3-AB), 2-amino-4-methylbenzamide (L1) and 3-amino-N-methylbenzamide (L2), were coordinated to the ruthenium(II) ion, to form potential drugs affecting DNA and inhibiting PARP enzyme. The four conjugated complexes of formula: C1 [(ƞ6-toluene)Ru(L1)Cl]PF6, C2 [(ƞ6-p-cymene)Ru(L1)Cl]PF6, C3 [(ƞ6-toluene)Ru(L2)Cl2] and C4 [(ƞ6-p-cymene)Ru(L2)Cl2], have been synthesized and characterized. Colorimetric 3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide (MTT) assay showed the highest antiproliferative activity of C1 in HCC1937, MDA-MB-231, and MCF-7 breast cancer cells. Efficiency of inhibition of PARP-1 enzymatic activity in vitro decreased in order: C2 > C4 > 3-AB>C1 > C3. ICP-MS study of intracellular accumulation and distribution in BRCA1-mutated HCC1937 revealed that C1-C4 entered cells within 24 h. The complex C1 showed the highest intracellular accumulation, nuclear-targeting properties, and exhibited the highest DNA binding (39.2 ± 0.6 pg of Ru per μg of DNA) that resulted in the cell cycle arrest in the S phase.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, chemical characterization, PARP inhibition, DNA binding and cellular uptake of novel ruthenium(II)-arene complexes bearing benzamide derivatives in human breast cancer cells
VL  - 210
SP  - 111155
DO  - 10.1016/j.jinorgbio.2020.111155
ER  - 
@article{
author = "Pavlović, Marijana and Tadić, Ana and Gligorijević, Nevenka and Poljarević, Jelena and Petrović, Tamara and Dojčinović, Biljana P. and Savić, Aleksandar and Radulović, Siniša and Grgurić-Šipka, Sanja and Aranđelović, Sandra",
year = "2020",
abstract = "Inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1) showed remarkable clinical efficacy in BRCA-mutated tumors. Based on the rational drug design, derivatives of PARP inhibitor 3-aminobenzamide (3-AB), 2-amino-4-methylbenzamide (L1) and 3-amino-N-methylbenzamide (L2), were coordinated to the ruthenium(II) ion, to form potential drugs affecting DNA and inhibiting PARP enzyme. The four conjugated complexes of formula: C1 [(ƞ6-toluene)Ru(L1)Cl]PF6, C2 [(ƞ6-p-cymene)Ru(L1)Cl]PF6, C3 [(ƞ6-toluene)Ru(L2)Cl2] and C4 [(ƞ6-p-cymene)Ru(L2)Cl2], have been synthesized and characterized. Colorimetric 3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide (MTT) assay showed the highest antiproliferative activity of C1 in HCC1937, MDA-MB-231, and MCF-7 breast cancer cells. Efficiency of inhibition of PARP-1 enzymatic activity in vitro decreased in order: C2 > C4 > 3-AB>C1 > C3. ICP-MS study of intracellular accumulation and distribution in BRCA1-mutated HCC1937 revealed that C1-C4 entered cells within 24 h. The complex C1 showed the highest intracellular accumulation, nuclear-targeting properties, and exhibited the highest DNA binding (39.2 ± 0.6 pg of Ru per μg of DNA) that resulted in the cell cycle arrest in the S phase.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, chemical characterization, PARP inhibition, DNA binding and cellular uptake of novel ruthenium(II)-arene complexes bearing benzamide derivatives in human breast cancer cells",
volume = "210",
pages = "111155",
doi = "10.1016/j.jinorgbio.2020.111155"
}
Pavlović, M., Tadić, A., Gligorijević, N., Poljarević, J., Petrović, T., Dojčinović, B. P., Savić, A., Radulović, S., Grgurić-Šipka, S.,& Aranđelović, S.. (2020). Synthesis, chemical characterization, PARP inhibition, DNA binding and cellular uptake of novel ruthenium(II)-arene complexes bearing benzamide derivatives in human breast cancer cells. in Journal of Inorganic Biochemistry
Elsevier., 210, 111155.
https://doi.org/10.1016/j.jinorgbio.2020.111155
Pavlović M, Tadić A, Gligorijević N, Poljarević J, Petrović T, Dojčinović BP, Savić A, Radulović S, Grgurić-Šipka S, Aranđelović S. Synthesis, chemical characterization, PARP inhibition, DNA binding and cellular uptake of novel ruthenium(II)-arene complexes bearing benzamide derivatives in human breast cancer cells. in Journal of Inorganic Biochemistry. 2020;210:111155.
doi:10.1016/j.jinorgbio.2020.111155 .
Pavlović, Marijana, Tadić, Ana, Gligorijević, Nevenka, Poljarević, Jelena, Petrović, Tamara, Dojčinović, Biljana P., Savić, Aleksandar, Radulović, Siniša, Grgurić-Šipka, Sanja, Aranđelović, Sandra, "Synthesis, chemical characterization, PARP inhibition, DNA binding and cellular uptake of novel ruthenium(II)-arene complexes bearing benzamide derivatives in human breast cancer cells" in Journal of Inorganic Biochemistry, 210 (2020):111155,
https://doi.org/10.1016/j.jinorgbio.2020.111155 . .
1
10
6
10

Supplementary data for the article: Pavlović, M.; Tadić, A.; Gligorijević, N.; Poljarević, J.; Petrović, T.; Dojčinović, B.; Savić, A.; Radulović, S.; Grgurić-Šipka, S.; Aranđelović, S. Synthesis, Chemical Characterization, PARP Inhibition, DNA Binding and Cellular Uptake of Novel Ruthenium(II)-Arene Complexes Bearing Benzamide Derivatives in Human Breast Cancer Cells. Journal of Inorganic Biochemistry 2020, 210, 111155. https://doi.org/10.1016/j.jinorgbio.2020.111155

Pavlović, Marijana; Tadić, Ana; Gligorijević, Nevenka; Poljarević, Jelena; Petrović, Tamara; Dojčinović, Biljana P.; Savić, Aleksandar; Radulović, Siniša; Grgurić-Šipka, Sanja; Aranđelović, Sandra

(Elsevier, 2020)

TY  - DATA
AU  - Pavlović, Marijana
AU  - Tadić, Ana
AU  - Gligorijević, Nevenka
AU  - Poljarević, Jelena
AU  - Petrović, Tamara
AU  - Dojčinović, Biljana P.
AU  - Savić, Aleksandar
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
AU  - Aranđelović, Sandra
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4049
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Supplementary data for the article: Pavlović, M.; Tadić, A.; Gligorijević, N.; Poljarević, J.; Petrović, T.; Dojčinović, B.; Savić, A.; Radulović, S.; Grgurić-Šipka, S.; Aranđelović, S. Synthesis, Chemical Characterization, PARP Inhibition, DNA Binding and Cellular Uptake of Novel Ruthenium(II)-Arene Complexes Bearing Benzamide Derivatives in Human Breast Cancer Cells. Journal of Inorganic Biochemistry 2020, 210, 111155. https://doi.org/10.1016/j.jinorgbio.2020.111155
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4049
ER  - 
@misc{
author = "Pavlović, Marijana and Tadić, Ana and Gligorijević, Nevenka and Poljarević, Jelena and Petrović, Tamara and Dojčinović, Biljana P. and Savić, Aleksandar and Radulović, Siniša and Grgurić-Šipka, Sanja and Aranđelović, Sandra",
year = "2020",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Supplementary data for the article: Pavlović, M.; Tadić, A.; Gligorijević, N.; Poljarević, J.; Petrović, T.; Dojčinović, B.; Savić, A.; Radulović, S.; Grgurić-Šipka, S.; Aranđelović, S. Synthesis, Chemical Characterization, PARP Inhibition, DNA Binding and Cellular Uptake of Novel Ruthenium(II)-Arene Complexes Bearing Benzamide Derivatives in Human Breast Cancer Cells. Journal of Inorganic Biochemistry 2020, 210, 111155. https://doi.org/10.1016/j.jinorgbio.2020.111155",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4049"
}
Pavlović, M., Tadić, A., Gligorijević, N., Poljarević, J., Petrović, T., Dojčinović, B. P., Savić, A., Radulović, S., Grgurić-Šipka, S.,& Aranđelović, S.. (2020). Supplementary data for the article: Pavlović, M.; Tadić, A.; Gligorijević, N.; Poljarević, J.; Petrović, T.; Dojčinović, B.; Savić, A.; Radulović, S.; Grgurić-Šipka, S.; Aranđelović, S. Synthesis, Chemical Characterization, PARP Inhibition, DNA Binding and Cellular Uptake of Novel Ruthenium(II)-Arene Complexes Bearing Benzamide Derivatives in Human Breast Cancer Cells. Journal of Inorganic Biochemistry 2020, 210, 111155. https://doi.org/10.1016/j.jinorgbio.2020.111155. in Journal of Inorganic Biochemistry
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_4049
Pavlović M, Tadić A, Gligorijević N, Poljarević J, Petrović T, Dojčinović BP, Savić A, Radulović S, Grgurić-Šipka S, Aranđelović S. Supplementary data for the article: Pavlović, M.; Tadić, A.; Gligorijević, N.; Poljarević, J.; Petrović, T.; Dojčinović, B.; Savić, A.; Radulović, S.; Grgurić-Šipka, S.; Aranđelović, S. Synthesis, Chemical Characterization, PARP Inhibition, DNA Binding and Cellular Uptake of Novel Ruthenium(II)-Arene Complexes Bearing Benzamide Derivatives in Human Breast Cancer Cells. Journal of Inorganic Biochemistry 2020, 210, 111155. https://doi.org/10.1016/j.jinorgbio.2020.111155. in Journal of Inorganic Biochemistry. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_4049 .
Pavlović, Marijana, Tadić, Ana, Gligorijević, Nevenka, Poljarević, Jelena, Petrović, Tamara, Dojčinović, Biljana P., Savić, Aleksandar, Radulović, Siniša, Grgurić-Šipka, Sanja, Aranđelović, Sandra, "Supplementary data for the article: Pavlović, M.; Tadić, A.; Gligorijević, N.; Poljarević, J.; Petrović, T.; Dojčinović, B.; Savić, A.; Radulović, S.; Grgurić-Šipka, S.; Aranđelović, S. Synthesis, Chemical Characterization, PARP Inhibition, DNA Binding and Cellular Uptake of Novel Ruthenium(II)-Arene Complexes Bearing Benzamide Derivatives in Human Breast Cancer Cells. Journal of Inorganic Biochemistry 2020, 210, 111155. https://doi.org/10.1016/j.jinorgbio.2020.111155" in Journal of Inorganic Biochemistry (2020),
https://hdl.handle.net/21.15107/rcub_cherry_4049 .

Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives

Obradović, Dragiša; Nikolić, Stefan; Milenković, Ivana; Milenković, Marina; Jovanović, Predrag M.; Savić, Vladimir; Roller, Alexander; Đorđi Crnogorac, Marija; Stanojković, Tatjana; Grgurić-Šipka, Sanja

(Elsevier, 2020)

TY  - JOUR
AU  - Obradović, Dragiša
AU  - Nikolić, Stefan
AU  - Milenković, Ivana
AU  - Milenković, Marina
AU  - Jovanović, Predrag M.
AU  - Savić, Vladimir
AU  - Roller, Alexander
AU  - Đorđi Crnogorac, Marija
AU  - Stanojković, Tatjana
AU  - Grgurić-Šipka, Sanja
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5137
AB  - Three new ruthenium(II)-arene complexes, [Ru(η6
-p-cymene)(L1
)Cl2] (C1) where L1 is N-((4 methoxyphenyl)
carbamothioyl)benzamide; [Ru(η6
-p-cymene)(L2
)Cl2] (C2) where L2 is 4-(3-benzoylthioureido)benzoic acid and
[Ru(η6
-p-cymene)(L3
)Cl2] (C3) where L3 is methyl 4-(3- benzoylthioureido)benzoate have been synthetized,
characterized and evaluated for their antimicrobial and anticancer activity. Characterization was performed
using 1
H and 13C NMR, IR spectroscopy, mass spectrometry, electrical conductivity measurements and X-Ray
diffraction analysis. X-Ray diffraction analysis of C1 showed typical expected “piano-stool” geometry with ruthenium coordinated to ligand via nitrogen and sulfur atoms of benzoylthiourea derivatives. Interesting, in
herein described complex, upon coordination the four-membered ring was formed, instead of six-membered
chelate common for this type of ligands. Cytotoxic activity was determined in human cervix adenocarcinoma
(HeLa) cell line and IC50 values ranged from 29.68 to 52.36 μM and the complexes were more active than related
ligands (except in case of C2 where it is found that IC50 value is close to IC50 value of related ligand). Complex
[Ru(η6
-p-cymene)(L1
)Cl2] (C1) expressed the highest cytotoxic activity with IC50 value of 29.7 μM. Complexes
and ligands were tested against nine Gram-positive and Gram-negative bacteria and one yeast- Candida albicans.
Clinical Candida spp. strains from microbiological laboratories were included in testing processes as well.
Minimum inhibitory concentrations values ranged from 62.5 μg/ml for complexes against Candida albicans to
over 1000 μg/ml for several bacterial species.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives
VL  - 210
SP  - 111164
DO  - 10.1016/j.jinorgbio.2020.111164
ER  - 
@article{
author = "Obradović, Dragiša and Nikolić, Stefan and Milenković, Ivana and Milenković, Marina and Jovanović, Predrag M. and Savić, Vladimir and Roller, Alexander and Đorđi Crnogorac, Marija and Stanojković, Tatjana and Grgurić-Šipka, Sanja",
year = "2020",
abstract = "Three new ruthenium(II)-arene complexes, [Ru(η6
-p-cymene)(L1
)Cl2] (C1) where L1 is N-((4 methoxyphenyl)
carbamothioyl)benzamide; [Ru(η6
-p-cymene)(L2
)Cl2] (C2) where L2 is 4-(3-benzoylthioureido)benzoic acid and
[Ru(η6
-p-cymene)(L3
)Cl2] (C3) where L3 is methyl 4-(3- benzoylthioureido)benzoate have been synthetized,
characterized and evaluated for their antimicrobial and anticancer activity. Characterization was performed
using 1
H and 13C NMR, IR spectroscopy, mass spectrometry, electrical conductivity measurements and X-Ray
diffraction analysis. X-Ray diffraction analysis of C1 showed typical expected “piano-stool” geometry with ruthenium coordinated to ligand via nitrogen and sulfur atoms of benzoylthiourea derivatives. Interesting, in
herein described complex, upon coordination the four-membered ring was formed, instead of six-membered
chelate common for this type of ligands. Cytotoxic activity was determined in human cervix adenocarcinoma
(HeLa) cell line and IC50 values ranged from 29.68 to 52.36 μM and the complexes were more active than related
ligands (except in case of C2 where it is found that IC50 value is close to IC50 value of related ligand). Complex
[Ru(η6
-p-cymene)(L1
)Cl2] (C1) expressed the highest cytotoxic activity with IC50 value of 29.7 μM. Complexes
and ligands were tested against nine Gram-positive and Gram-negative bacteria and one yeast- Candida albicans.
Clinical Candida spp. strains from microbiological laboratories were included in testing processes as well.
Minimum inhibitory concentrations values ranged from 62.5 μg/ml for complexes against Candida albicans to
over 1000 μg/ml for several bacterial species.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives",
volume = "210",
pages = "111164",
doi = "10.1016/j.jinorgbio.2020.111164"
}
Obradović, D., Nikolić, S., Milenković, I., Milenković, M., Jovanović, P. M., Savić, V., Roller, A., Đorđi Crnogorac, M., Stanojković, T.,& Grgurić-Šipka, S.. (2020). Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives. in Journal of Inorganic Biochemistry
Elsevier., 210, 111164.
https://doi.org/10.1016/j.jinorgbio.2020.111164
Obradović D, Nikolić S, Milenković I, Milenković M, Jovanović PM, Savić V, Roller A, Đorđi Crnogorac M, Stanojković T, Grgurić-Šipka S. Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives. in Journal of Inorganic Biochemistry. 2020;210:111164.
doi:10.1016/j.jinorgbio.2020.111164 .
Obradović, Dragiša, Nikolić, Stefan, Milenković, Ivana, Milenković, Marina, Jovanović, Predrag M., Savić, Vladimir, Roller, Alexander, Đorđi Crnogorac, Marija, Stanojković, Tatjana, Grgurić-Šipka, Sanja, "Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives" in Journal of Inorganic Biochemistry, 210 (2020):111164,
https://doi.org/10.1016/j.jinorgbio.2020.111164 . .
14
12

Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives

Obradović, Dragiša; Nikolić, Stefan; Milenković, Ivana; Milenković, Marina; Jovanović, Predrag M.; Savić, Vladimir; Roller, Alexander; Đorđi Crnogorac, Marija; Stanojković, Tatjana; Grgurić-Šipka, Sanja

(Elsevier, 2020)

TY  - JOUR
AU  - Obradović, Dragiša
AU  - Nikolić, Stefan
AU  - Milenković, Ivana
AU  - Milenković, Marina
AU  - Jovanović, Predrag M.
AU  - Savić, Vladimir
AU  - Roller, Alexander
AU  - Đorđi Crnogorac, Marija
AU  - Stanojković, Tatjana
AU  - Grgurić-Šipka, Sanja
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5138
AB  - Three new ruthenium(II)-arene complexes, [Ru(η6-p-cymene)(L1)Cl2] (C1) where L1 is N-((4 methoxyphenyl)carbamothioyl)benzamide; [Ru(η6-p-cymene)(L2)Cl2] (C2) where L2 is 4-(3-benzoylthioureido)benzoic acid and[Ru(η6-p-cymene)(L3)Cl2] (C3) where L3 is methyl 4-(3- benzoylthioureido)benzoate have been synthetized,characterized and evaluated for their antimicrobial and anticancer activity. Characterization was performedusing 1H and 13C NMR, IR spectroscopy, mass spectrometry, electrical conductivity measurements and X-Raydiffraction analysis. X-Ray diffraction analysis of C1 showed typical expected “piano-stool” geometry with ruthenium coordinated to ligand via nitrogen and sulfur atoms of benzoylthiourea derivatives. Interesting, inherein described complex, upon coordination the four-membered ring was formed, instead of six-memberedchelate common for this type of ligands. Cytotoxic activity was determined in human cervix adenocarcinoma(HeLa) cell line and IC50 values ranged from 29.68 to 52.36 μM and the complexes were more active than relatedligands (except in case of C2 where it is found that IC50 value is close to IC50 value of related ligand). Complex[Ru(η6-p-cymene)(L1)Cl2] (C1) expressed the highest cytotoxic activity with IC50 value of 29.7 μM. Complexesand ligands were tested against nine Gram-positive and Gram-negative bacteria and one yeast- Candida albicans.Clinical Candida spp. strains from microbiological laboratories were included in testing processes as well.Minimum inhibitory concentrations values ranged from 62.5 μg/ml for complexes against Candida albicans toover 1000 μg/ml for several bacterial species.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives
VL  - 210
SP  - 111164
DO  - 10.1016/j.jinorgbio.2020.111164
ER  - 
@article{
author = "Obradović, Dragiša and Nikolić, Stefan and Milenković, Ivana and Milenković, Marina and Jovanović, Predrag M. and Savić, Vladimir and Roller, Alexander and Đorđi Crnogorac, Marija and Stanojković, Tatjana and Grgurić-Šipka, Sanja",
year = "2020",
abstract = "Three new ruthenium(II)-arene complexes, [Ru(η6-p-cymene)(L1)Cl2] (C1) where L1 is N-((4 methoxyphenyl)carbamothioyl)benzamide; [Ru(η6-p-cymene)(L2)Cl2] (C2) where L2 is 4-(3-benzoylthioureido)benzoic acid and[Ru(η6-p-cymene)(L3)Cl2] (C3) where L3 is methyl 4-(3- benzoylthioureido)benzoate have been synthetized,characterized and evaluated for their antimicrobial and anticancer activity. Characterization was performedusing 1H and 13C NMR, IR spectroscopy, mass spectrometry, electrical conductivity measurements and X-Raydiffraction analysis. X-Ray diffraction analysis of C1 showed typical expected “piano-stool” geometry with ruthenium coordinated to ligand via nitrogen and sulfur atoms of benzoylthiourea derivatives. Interesting, inherein described complex, upon coordination the four-membered ring was formed, instead of six-memberedchelate common for this type of ligands. Cytotoxic activity was determined in human cervix adenocarcinoma(HeLa) cell line and IC50 values ranged from 29.68 to 52.36 μM and the complexes were more active than relatedligands (except in case of C2 where it is found that IC50 value is close to IC50 value of related ligand). Complex[Ru(η6-p-cymene)(L1)Cl2] (C1) expressed the highest cytotoxic activity with IC50 value of 29.7 μM. Complexesand ligands were tested against nine Gram-positive and Gram-negative bacteria and one yeast- Candida albicans.Clinical Candida spp. strains from microbiological laboratories were included in testing processes as well.Minimum inhibitory concentrations values ranged from 62.5 μg/ml for complexes against Candida albicans toover 1000 μg/ml for several bacterial species.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives",
volume = "210",
pages = "111164",
doi = "10.1016/j.jinorgbio.2020.111164"
}
Obradović, D., Nikolić, S., Milenković, I., Milenković, M., Jovanović, P. M., Savić, V., Roller, A., Đorđi Crnogorac, M., Stanojković, T.,& Grgurić-Šipka, S.. (2020). Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives. in Journal of Inorganic Biochemistry
Elsevier., 210, 111164.
https://doi.org/10.1016/j.jinorgbio.2020.111164
Obradović D, Nikolić S, Milenković I, Milenković M, Jovanović PM, Savić V, Roller A, Đorđi Crnogorac M, Stanojković T, Grgurić-Šipka S. Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives. in Journal of Inorganic Biochemistry. 2020;210:111164.
doi:10.1016/j.jinorgbio.2020.111164 .
Obradović, Dragiša, Nikolić, Stefan, Milenković, Ivana, Milenković, Marina, Jovanović, Predrag M., Savić, Vladimir, Roller, Alexander, Đorđi Crnogorac, Marija, Stanojković, Tatjana, Grgurić-Šipka, Sanja, "Synthesis, characterization, antimicrobial and cytotoxic activity of novel half-sandwich Ru(II) arene complexes with benzoylthiourea derivatives" in Journal of Inorganic Biochemistry, 210 (2020):111164,
https://doi.org/10.1016/j.jinorgbio.2020.111164 . .
14
12

Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity

Nikolić, Stefan; Mihajlović-Lalić, Ljiljana; Vidosavljević, Marija; Aranđelović, Sandra; Radulović, Siniša; Grgurić-Šipka, Sanja

(2019)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Mihajlović-Lalić, Ljiljana
AU  - Vidosavljević, Marija
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3640
AB  - Four mono- (1–4) and four binuclear Ru(II) arene (5–8) complexes have been isolated from the reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with 2-pyridinecarboxylic acid and 6-fluoro-2-pyridinecarboxylic acid. Their structural characterization included IR and NMR spectroscopy and MS spectrometry. The cytotoxic potential of the compounds has been tested by MTT assay in seven human cancer cell lines: alveolar basal adenocarcinoma (A549), large cell lung carcinoma (HTB177), colorectal carcinoma (HCT116), malignant melanoma (A375), prostate adenocarcinoma (PC3), breast carcinoma (MDA-MB-453), cervix adenocarcinoma (HeLa), and one human non-malignant lung fibroblast cell line (MRC-5). Mononuclear complexes 1 and 3 carrying 2-pyridinecarboxylic acid have displayed moderate antiproliferative effect toward HCT116 and HeLa, slightly better in comparison to their binuclear analogues, 5 and 7. The highest activity and cytoselectivity has been observed 1 as it has reduced viability of HCT116 cells 1.5 times more efficiently (IC50 = 27.5 μM), than of the MRC-5 cells (IC50 = 41.3 μM). In contrast to 1 and 3, compounds 2, 4–8 have been found to exhibit lack of cytotoxicity or mild cytotoxicity with IC50 values ranging from 100 to 300 μM.
T2  - Journal of Organometallic Chemistry
T1  - Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity
VL  - 902
DO  - 10.1016/j.jorganchem.2019.120966
ER  - 
@article{
author = "Nikolić, Stefan and Mihajlović-Lalić, Ljiljana and Vidosavljević, Marija and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2019",
abstract = "Four mono- (1–4) and four binuclear Ru(II) arene (5–8) complexes have been isolated from the reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with 2-pyridinecarboxylic acid and 6-fluoro-2-pyridinecarboxylic acid. Their structural characterization included IR and NMR spectroscopy and MS spectrometry. The cytotoxic potential of the compounds has been tested by MTT assay in seven human cancer cell lines: alveolar basal adenocarcinoma (A549), large cell lung carcinoma (HTB177), colorectal carcinoma (HCT116), malignant melanoma (A375), prostate adenocarcinoma (PC3), breast carcinoma (MDA-MB-453), cervix adenocarcinoma (HeLa), and one human non-malignant lung fibroblast cell line (MRC-5). Mononuclear complexes 1 and 3 carrying 2-pyridinecarboxylic acid have displayed moderate antiproliferative effect toward HCT116 and HeLa, slightly better in comparison to their binuclear analogues, 5 and 7. The highest activity and cytoselectivity has been observed 1 as it has reduced viability of HCT116 cells 1.5 times more efficiently (IC50 = 27.5 μM), than of the MRC-5 cells (IC50 = 41.3 μM). In contrast to 1 and 3, compounds 2, 4–8 have been found to exhibit lack of cytotoxicity or mild cytotoxicity with IC50 values ranging from 100 to 300 μM.",
journal = "Journal of Organometallic Chemistry",
title = "Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity",
volume = "902",
doi = "10.1016/j.jorganchem.2019.120966"
}
Nikolić, S., Mihajlović-Lalić, L., Vidosavljević, M., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2019). Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity. in Journal of Organometallic Chemistry, 902.
https://doi.org/10.1016/j.jorganchem.2019.120966
Nikolić S, Mihajlović-Lalić L, Vidosavljević M, Aranđelović S, Radulović S, Grgurić-Šipka S. Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity. in Journal of Organometallic Chemistry. 2019;902.
doi:10.1016/j.jorganchem.2019.120966 .
Nikolić, Stefan, Mihajlović-Lalić, Ljiljana, Vidosavljević, Marija, Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity" in Journal of Organometallic Chemistry, 902 (2019),
https://doi.org/10.1016/j.jorganchem.2019.120966 . .
6
4
5

Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity

Nikolić, Stefan; Mihajlović-Lalić, Ljiljana; Vidosavljević, Marija; Aranđelović, Sandra; Radulović, Siniša; Grgurić-Šipka, Sanja

(2019)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Mihajlović-Lalić, Ljiljana
AU  - Vidosavljević, Marija
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3641
AB  - Four mono- (1–4) and four binuclear Ru(II) arene (5–8) complexes have been isolated from the reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with 2-pyridinecarboxylic acid and 6-fluoro-2-pyridinecarboxylic acid. Their structural characterization included IR and NMR spectroscopy and MS spectrometry. The cytotoxic potential of the compounds has been tested by MTT assay in seven human cancer cell lines: alveolar basal adenocarcinoma (A549), large cell lung carcinoma (HTB177), colorectal carcinoma (HCT116), malignant melanoma (A375), prostate adenocarcinoma (PC3), breast carcinoma (MDA-MB-453), cervix adenocarcinoma (HeLa), and one human non-malignant lung fibroblast cell line (MRC-5). Mononuclear complexes 1 and 3 carrying 2-pyridinecarboxylic acid have displayed moderate antiproliferative effect toward HCT116 and HeLa, slightly better in comparison to their binuclear analogues, 5 and 7. The highest activity and cytoselectivity has been observed 1 as it has reduced viability of HCT116 cells 1.5 times more efficiently (IC50 = 27.5 μM), than of the MRC-5 cells (IC50 = 41.3 μM). In contrast to 1 and 3, compounds 2, 4–8 have been found to exhibit lack of cytotoxicity or mild cytotoxicity with IC50 values ranging from 100 to 300 μM.
T2  - Journal of Organometallic Chemistry
T1  - Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity
VL  - 902
DO  - 10.1016/j.jorganchem.2019.120966
ER  - 
@article{
author = "Nikolić, Stefan and Mihajlović-Lalić, Ljiljana and Vidosavljević, Marija and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2019",
abstract = "Four mono- (1–4) and four binuclear Ru(II) arene (5–8) complexes have been isolated from the reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with 2-pyridinecarboxylic acid and 6-fluoro-2-pyridinecarboxylic acid. Their structural characterization included IR and NMR spectroscopy and MS spectrometry. The cytotoxic potential of the compounds has been tested by MTT assay in seven human cancer cell lines: alveolar basal adenocarcinoma (A549), large cell lung carcinoma (HTB177), colorectal carcinoma (HCT116), malignant melanoma (A375), prostate adenocarcinoma (PC3), breast carcinoma (MDA-MB-453), cervix adenocarcinoma (HeLa), and one human non-malignant lung fibroblast cell line (MRC-5). Mononuclear complexes 1 and 3 carrying 2-pyridinecarboxylic acid have displayed moderate antiproliferative effect toward HCT116 and HeLa, slightly better in comparison to their binuclear analogues, 5 and 7. The highest activity and cytoselectivity has been observed 1 as it has reduced viability of HCT116 cells 1.5 times more efficiently (IC50 = 27.5 μM), than of the MRC-5 cells (IC50 = 41.3 μM). In contrast to 1 and 3, compounds 2, 4–8 have been found to exhibit lack of cytotoxicity or mild cytotoxicity with IC50 values ranging from 100 to 300 μM.",
journal = "Journal of Organometallic Chemistry",
title = "Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity",
volume = "902",
doi = "10.1016/j.jorganchem.2019.120966"
}
Nikolić, S., Mihajlović-Lalić, L., Vidosavljević, M., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2019). Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity. in Journal of Organometallic Chemistry, 902.
https://doi.org/10.1016/j.jorganchem.2019.120966
Nikolić S, Mihajlović-Lalić L, Vidosavljević M, Aranđelović S, Radulović S, Grgurić-Šipka S. Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity. in Journal of Organometallic Chemistry. 2019;902.
doi:10.1016/j.jorganchem.2019.120966 .
Nikolić, Stefan, Mihajlović-Lalić, Ljiljana, Vidosavljević, Marija, Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity" in Journal of Organometallic Chemistry, 902 (2019),
https://doi.org/10.1016/j.jorganchem.2019.120966 . .
6
4
5

Supplementary data for the article: Nikolić, S.; Mihajlović-Lalić, L. E.; Vidosavljević, M.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S. Mono- and Binuclear Ru(II) Arene Complexes with (Fluoro Substituted) Picolinic Acid: Synthesis, Characterization and Cytotoxicity. Journal of Organometallic Chemistry 2019, 902. https://doi.org/10.1016/j.jorganchem.2019.120966

Nikolić, Stefan; Mihajlović-Lalić, Ljiljana; Vidosavljević, Marija; Aranđelović, Sandra; Radulović, Siniša; Grgurić-Šipka, Sanja

(2019)

TY  - DATA
AU  - Nikolić, Stefan
AU  - Mihajlović-Lalić, Ljiljana
AU  - Vidosavljević, Marija
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3642
T2  - Journal of Organometallic Chemistry
T1  - Supplementary data for the article: Nikolić, S.; Mihajlović-Lalić, L. E.; Vidosavljević, M.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S. Mono- and Binuclear Ru(II) Arene Complexes with (Fluoro Substituted) Picolinic Acid: Synthesis, Characterization and Cytotoxicity. Journal of Organometallic Chemistry 2019, 902. https://doi.org/10.1016/j.jorganchem.2019.120966
VL  - 902
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3642
ER  - 
@misc{
author = "Nikolić, Stefan and Mihajlović-Lalić, Ljiljana and Vidosavljević, Marija and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2019",
journal = "Journal of Organometallic Chemistry",
title = "Supplementary data for the article: Nikolić, S.; Mihajlović-Lalić, L. E.; Vidosavljević, M.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S. Mono- and Binuclear Ru(II) Arene Complexes with (Fluoro Substituted) Picolinic Acid: Synthesis, Characterization and Cytotoxicity. Journal of Organometallic Chemistry 2019, 902. https://doi.org/10.1016/j.jorganchem.2019.120966",
volume = "902",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3642"
}
Nikolić, S., Mihajlović-Lalić, L., Vidosavljević, M., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2019). Supplementary data for the article: Nikolić, S.; Mihajlović-Lalić, L. E.; Vidosavljević, M.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S. Mono- and Binuclear Ru(II) Arene Complexes with (Fluoro Substituted) Picolinic Acid: Synthesis, Characterization and Cytotoxicity. Journal of Organometallic Chemistry 2019, 902. https://doi.org/10.1016/j.jorganchem.2019.120966. in Journal of Organometallic Chemistry, 902.
https://hdl.handle.net/21.15107/rcub_cherry_3642
Nikolić S, Mihajlović-Lalić L, Vidosavljević M, Aranđelović S, Radulović S, Grgurić-Šipka S. Supplementary data for the article: Nikolić, S.; Mihajlović-Lalić, L. E.; Vidosavljević, M.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S. Mono- and Binuclear Ru(II) Arene Complexes with (Fluoro Substituted) Picolinic Acid: Synthesis, Characterization and Cytotoxicity. Journal of Organometallic Chemistry 2019, 902. https://doi.org/10.1016/j.jorganchem.2019.120966. in Journal of Organometallic Chemistry. 2019;902.
https://hdl.handle.net/21.15107/rcub_cherry_3642 .
Nikolić, Stefan, Mihajlović-Lalić, Ljiljana, Vidosavljević, Marija, Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Supplementary data for the article: Nikolić, S.; Mihajlović-Lalić, L. E.; Vidosavljević, M.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S. Mono- and Binuclear Ru(II) Arene Complexes with (Fluoro Substituted) Picolinic Acid: Synthesis, Characterization and Cytotoxicity. Journal of Organometallic Chemistry 2019, 902. https://doi.org/10.1016/j.jorganchem.2019.120966" in Journal of Organometallic Chemistry, 902 (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3642 .

Supplementary material for the article: Nikolić, S.; Grgurić-Šipka, S.; Djordjević, I. S.; Dahmani, R.; Dekanski, D.; Vidičević, S.; Tošić, J.; Mitić, D.; Grubišić, S. Half-Sandwich Ruthenium(II)-Arene Complexes: Synthesis, Spectroscopic Studies, Biological Properties, and Molecular Modeling. Journal of Coordination Chemistry 2019, 72 (1), 148–163. https://doi.org/10.1080/00958972.2018.1553298

Nikolić, Stefan; Grgurić-Šipka, Sanja; Đorđević, Ivana S.; Dahmani, Rahma; Dekanski, Dragana; Vidičević, Sašenka; Tošić, Jelena; Mitić, Dragana; Grubišić, Sonja

(Taylor & Francis, 2019)

TY  - DATA
AU  - Nikolić, Stefan
AU  - Grgurić-Šipka, Sanja
AU  - Đorđević, Ivana S.
AU  - Dahmani, Rahma
AU  - Dekanski, Dragana
AU  - Vidičević, Sašenka
AU  - Tošić, Jelena
AU  - Mitić, Dragana
AU  - Grubišić, Sonja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3753
PB  - Taylor & Francis
T2  - Journal of Coordination Chemistry
T1  - Supplementary material for the article: Nikolić, S.; Grgurić-Šipka, S.; Djordjević, I. S.; Dahmani, R.; Dekanski, D.; Vidičević, S.;  Tošić, J.; Mitić, D.; Grubišić, S. Half-Sandwich Ruthenium(II)-Arene Complexes: Synthesis,  Spectroscopic Studies, Biological Properties, and Molecular Modeling. Journal of  Coordination Chemistry 2019, 72 (1), 148–163.  https://doi.org/10.1080/00958972.2018.1553298
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3753
ER  - 
@misc{
author = "Nikolić, Stefan and Grgurić-Šipka, Sanja and Đorđević, Ivana S. and Dahmani, Rahma and Dekanski, Dragana and Vidičević, Sašenka and Tošić, Jelena and Mitić, Dragana and Grubišić, Sonja",
year = "2019",
publisher = "Taylor & Francis",
journal = "Journal of Coordination Chemistry",
title = "Supplementary material for the article: Nikolić, S.; Grgurić-Šipka, S.; Djordjević, I. S.; Dahmani, R.; Dekanski, D.; Vidičević, S.;  Tošić, J.; Mitić, D.; Grubišić, S. Half-Sandwich Ruthenium(II)-Arene Complexes: Synthesis,  Spectroscopic Studies, Biological Properties, and Molecular Modeling. Journal of  Coordination Chemistry 2019, 72 (1), 148–163.  https://doi.org/10.1080/00958972.2018.1553298",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3753"
}
Nikolić, S., Grgurić-Šipka, S., Đorđević, I. S., Dahmani, R., Dekanski, D., Vidičević, S., Tošić, J., Mitić, D.,& Grubišić, S.. (2019). Supplementary material for the article: Nikolić, S.; Grgurić-Šipka, S.; Djordjević, I. S.; Dahmani, R.; Dekanski, D.; Vidičević, S.;  Tošić, J.; Mitić, D.; Grubišić, S. Half-Sandwich Ruthenium(II)-Arene Complexes: Synthesis,  Spectroscopic Studies, Biological Properties, and Molecular Modeling. Journal of  Coordination Chemistry 2019, 72 (1), 148–163.  https://doi.org/10.1080/00958972.2018.1553298. in Journal of Coordination Chemistry
Taylor & Francis..
https://hdl.handle.net/21.15107/rcub_cherry_3753
Nikolić S, Grgurić-Šipka S, Đorđević IS, Dahmani R, Dekanski D, Vidičević S, Tošić J, Mitić D, Grubišić S. Supplementary material for the article: Nikolić, S.; Grgurić-Šipka, S.; Djordjević, I. S.; Dahmani, R.; Dekanski, D.; Vidičević, S.;  Tošić, J.; Mitić, D.; Grubišić, S. Half-Sandwich Ruthenium(II)-Arene Complexes: Synthesis,  Spectroscopic Studies, Biological Properties, and Molecular Modeling. Journal of  Coordination Chemistry 2019, 72 (1), 148–163.  https://doi.org/10.1080/00958972.2018.1553298. in Journal of Coordination Chemistry. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3753 .
Nikolić, Stefan, Grgurić-Šipka, Sanja, Đorđević, Ivana S., Dahmani, Rahma, Dekanski, Dragana, Vidičević, Sašenka, Tošić, Jelena, Mitić, Dragana, Grubišić, Sonja, "Supplementary material for the article: Nikolić, S.; Grgurić-Šipka, S.; Djordjević, I. S.; Dahmani, R.; Dekanski, D.; Vidičević, S.;  Tošić, J.; Mitić, D.; Grubišić, S. Half-Sandwich Ruthenium(II)-Arene Complexes: Synthesis,  Spectroscopic Studies, Biological Properties, and Molecular Modeling. Journal of  Coordination Chemistry 2019, 72 (1), 148–163.  https://doi.org/10.1080/00958972.2018.1553298" in Journal of Coordination Chemistry (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3753 .

Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling

Nikolić, Stefan; Grgurić-Šipka, Sanja; Đorđević, Ivana S.; Dahmani, Rahma; Dekanski, Dragana; Vidičević, Sašenka; Tošić, Jelena; Mitić, Dragana; Grubišić, Sonja

(Taylor & Francis, 2019)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Grgurić-Šipka, Sanja
AU  - Đorđević, Ivana S.
AU  - Dahmani, Rahma
AU  - Dekanski, Dragana
AU  - Vidičević, Sašenka
AU  - Tošić, Jelena
AU  - Mitić, Dragana
AU  - Grubišić, Sonja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3758
AB  - In search for antitumor metal-based drugs that would mitigate the severe side-effects of cisplatin, Ru(II) complexes are gaining increasing recent interest. In this work, we report on the synthesis, characterization (1H- and 13C-NMR, FT-IR), and cytotoxicity studies of two new half-sandwich organometallic Ru(II) complexes of the general formula [Ru(η6-arene)(XY)Cl](PF6) where arene = benzene or toluene and XY = bidentates: dipyrido[3,2-a:2′,3′-c]phenazine (dppz) or 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip), which are bound to Ru(II) via two phenanthroline-N atoms in a characteristic “piano-stool” configuration of Ru(II)-arene complexes—as confirmed by vibrational and NMR spectra. In addition, cytotoxic studies were performed for similar half-sandwich organometallic [Ru(η6-p-cymene)(Me2dppz)Cl]PF6 complex (Me2dppz = 11,12-dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine). This study is complemented with elaborate modeling with density functional theory (DFT) calculations, which provided insight into reactive sites of Ru(II) structures, further detailed by molecular docking on the B-DNA dodecamer, which identified binding sites and affinities: most pronounced for the [Ru(η6-benzene)(aip)Cl](PF6) in both A-T and G-C regions of the DNA minor groove. Cytotoxic activity was probed versus tumor cell lines B16, C6, and U251 (B16 mouse melanoma, C6 rat glioma, U251 human glioblastoma) and non-tumor cell line HACAT (HACAT normal human keratinocytes).
PB  - Taylor & Francis
T2  - Journal of Coordination Chemistry
T1  - Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling
VL  - 72
IS  - 1
SP  - 148
EP  - 163
DO  - 10.1080/00958972.2018.1553298
ER  - 
@article{
author = "Nikolić, Stefan and Grgurić-Šipka, Sanja and Đorđević, Ivana S. and Dahmani, Rahma and Dekanski, Dragana and Vidičević, Sašenka and Tošić, Jelena and Mitić, Dragana and Grubišić, Sonja",
year = "2019",
abstract = "In search for antitumor metal-based drugs that would mitigate the severe side-effects of cisplatin, Ru(II) complexes are gaining increasing recent interest. In this work, we report on the synthesis, characterization (1H- and 13C-NMR, FT-IR), and cytotoxicity studies of two new half-sandwich organometallic Ru(II) complexes of the general formula [Ru(η6-arene)(XY)Cl](PF6) where arene = benzene or toluene and XY = bidentates: dipyrido[3,2-a:2′,3′-c]phenazine (dppz) or 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip), which are bound to Ru(II) via two phenanthroline-N atoms in a characteristic “piano-stool” configuration of Ru(II)-arene complexes—as confirmed by vibrational and NMR spectra. In addition, cytotoxic studies were performed for similar half-sandwich organometallic [Ru(η6-p-cymene)(Me2dppz)Cl]PF6 complex (Me2dppz = 11,12-dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine). This study is complemented with elaborate modeling with density functional theory (DFT) calculations, which provided insight into reactive sites of Ru(II) structures, further detailed by molecular docking on the B-DNA dodecamer, which identified binding sites and affinities: most pronounced for the [Ru(η6-benzene)(aip)Cl](PF6) in both A-T and G-C regions of the DNA minor groove. Cytotoxic activity was probed versus tumor cell lines B16, C6, and U251 (B16 mouse melanoma, C6 rat glioma, U251 human glioblastoma) and non-tumor cell line HACAT (HACAT normal human keratinocytes).",
publisher = "Taylor & Francis",
journal = "Journal of Coordination Chemistry",
title = "Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling",
volume = "72",
number = "1",
pages = "148-163",
doi = "10.1080/00958972.2018.1553298"
}
Nikolić, S., Grgurić-Šipka, S., Đorđević, I. S., Dahmani, R., Dekanski, D., Vidičević, S., Tošić, J., Mitić, D.,& Grubišić, S.. (2019). Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling. in Journal of Coordination Chemistry
Taylor & Francis., 72(1), 148-163.
https://doi.org/10.1080/00958972.2018.1553298
Nikolić S, Grgurić-Šipka S, Đorđević IS, Dahmani R, Dekanski D, Vidičević S, Tošić J, Mitić D, Grubišić S. Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling. in Journal of Coordination Chemistry. 2019;72(1):148-163.
doi:10.1080/00958972.2018.1553298 .
Nikolić, Stefan, Grgurić-Šipka, Sanja, Đorđević, Ivana S., Dahmani, Rahma, Dekanski, Dragana, Vidičević, Sašenka, Tošić, Jelena, Mitić, Dragana, Grubišić, Sonja, "Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling" in Journal of Coordination Chemistry, 72, no. 1 (2019):148-163,
https://doi.org/10.1080/00958972.2018.1553298 . .
2
2

New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action

Pavlović, Marijana; Nikolić, Stefan; Gligorijević, Nevenka; Dojčinović, Biljana P.; Aranđelović, Sandra; Grgurić-Šipka, Sanja; Radulović, Siniša

(Springer Link, 2019)

TY  - JOUR
AU  - Pavlović, Marijana
AU  - Nikolić, Stefan
AU  - Gligorijević, Nevenka
AU  - Dojčinović, Biljana P.
AU  - Aranđelović, Sandra
AU  - Grgurić-Šipka, Sanja
AU  - Radulović, Siniša
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2854
AB  - Three new ruthenium(II)-arene complexes with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline (ppf) of general formula: C1 ([(ƞ 6 -benzene)Ru(ppf)Cl]PF 6 , C2 ([(ƞ 6 -toluene)Ru(ppf)Cl]PF 6 ) and C3 ([(ƞ 6 -p-cymene)Ru(ppf)Cl]PF 6 ) have been synthesized. The structures of complexes were determined by elemental analysis, IR, ESI–MS, as well as with 1 H and 13 C NMR spectroscopy. Cytotoxic activity has been evaluated in three different human neoplastic cell lines (A549, A375, LS 174T) and in one human non-tumor cell line (MRC-5), by the MTT assay. Complexes C1–C3 showed IC 50 values in the micromolar range below 100 µM. Complex C3, carrying ƞ 6 -p-cymene as the arene ligand, exhibited cytoselective activity toward human malignant melanoma A375 cells (IC 50 = 15.8 ± 2.7 µM), and has been selected for further analyses of its biological effects. Drug-accumulation study performed in the A375 cells disclosed that C3 possess lower ability of entering the cells compared to cisplatin and distributes approximately equally in the cytosol and membrane/organelle fraction of cells. Investigations in the 3D model of A375 cells, disclosed different effects of the complex C3 and cisplatin on growth of multicellular tumor spheroids (MCTSs). While the size of cisplatin-treated MCTSs decreased with time, MCTSs treated with C3 continued to growth. Differences in structural organization and biological activity of this type of ruthenium(II)-arene complexes versus cisplatin in A375 malignant melanoma cells pointed out their different modes of action, and necessity for further biological studies and optimizations for potential applications.
PB  - Springer Link
T2  - Journal of Biological Inorganic Chemistry
T1  - New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action
VL  - 24
IS  - 2
SP  - 297
EP  - 310
DO  - 10.1007/s00775-019-01647-4
ER  - 
@article{
author = "Pavlović, Marijana and Nikolić, Stefan and Gligorijević, Nevenka and Dojčinović, Biljana P. and Aranđelović, Sandra and Grgurić-Šipka, Sanja and Radulović, Siniša",
year = "2019",
abstract = "Three new ruthenium(II)-arene complexes with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline (ppf) of general formula: C1 ([(ƞ 6 -benzene)Ru(ppf)Cl]PF 6 , C2 ([(ƞ 6 -toluene)Ru(ppf)Cl]PF 6 ) and C3 ([(ƞ 6 -p-cymene)Ru(ppf)Cl]PF 6 ) have been synthesized. The structures of complexes were determined by elemental analysis, IR, ESI–MS, as well as with 1 H and 13 C NMR spectroscopy. Cytotoxic activity has been evaluated in three different human neoplastic cell lines (A549, A375, LS 174T) and in one human non-tumor cell line (MRC-5), by the MTT assay. Complexes C1–C3 showed IC 50 values in the micromolar range below 100 µM. Complex C3, carrying ƞ 6 -p-cymene as the arene ligand, exhibited cytoselective activity toward human malignant melanoma A375 cells (IC 50 = 15.8 ± 2.7 µM), and has been selected for further analyses of its biological effects. Drug-accumulation study performed in the A375 cells disclosed that C3 possess lower ability of entering the cells compared to cisplatin and distributes approximately equally in the cytosol and membrane/organelle fraction of cells. Investigations in the 3D model of A375 cells, disclosed different effects of the complex C3 and cisplatin on growth of multicellular tumor spheroids (MCTSs). While the size of cisplatin-treated MCTSs decreased with time, MCTSs treated with C3 continued to growth. Differences in structural organization and biological activity of this type of ruthenium(II)-arene complexes versus cisplatin in A375 malignant melanoma cells pointed out their different modes of action, and necessity for further biological studies and optimizations for potential applications.",
publisher = "Springer Link",
journal = "Journal of Biological Inorganic Chemistry",
title = "New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action",
volume = "24",
number = "2",
pages = "297-310",
doi = "10.1007/s00775-019-01647-4"
}
Pavlović, M., Nikolić, S., Gligorijević, N., Dojčinović, B. P., Aranđelović, S., Grgurić-Šipka, S.,& Radulović, S.. (2019). New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action. in Journal of Biological Inorganic Chemistry
Springer Link., 24(2), 297-310.
https://doi.org/10.1007/s00775-019-01647-4
Pavlović M, Nikolić S, Gligorijević N, Dojčinović BP, Aranđelović S, Grgurić-Šipka S, Radulović S. New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action. in Journal of Biological Inorganic Chemistry. 2019;24(2):297-310.
doi:10.1007/s00775-019-01647-4 .
Pavlović, Marijana, Nikolić, Stefan, Gligorijević, Nevenka, Dojčinović, Biljana P., Aranđelović, Sandra, Grgurić-Šipka, Sanja, Radulović, Siniša, "New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action" in Journal of Biological Inorganic Chemistry, 24, no. 2 (2019):297-310,
https://doi.org/10.1007/s00775-019-01647-4 . .
9
2
10

Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling

Nikolić, Stefan; Grgurić-Šipka, Sanja; Đorđević, Ivana S.; Dahmani, Rahma; Dekanski, Dragana; Vidičević, Sašenka; Tošić, Jelena; Mitić, Dragana; Grubišić, Sonja

(Taylor & Francis, 2019)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Grgurić-Šipka, Sanja
AU  - Đorđević, Ivana S.
AU  - Dahmani, Rahma
AU  - Dekanski, Dragana
AU  - Vidičević, Sašenka
AU  - Tošić, Jelena
AU  - Mitić, Dragana
AU  - Grubišić, Sonja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2934
AB  - In search for antitumor metal-based drugs that would mitigate the severe side-effects of cisplatin, Ru(II) complexes are gaining increasing recent interest. In this work, we report on the synthesis, characterization (1H- and 13C-NMR, FT-IR), and cytotoxicity studies of two new half-sandwich organometallic Ru(II) complexes of the general formula [Ru(η6-arene)(XY)Cl](PF6) where arene = benzene or toluene and XY = bidentates: dipyrido[3,2-a:2′,3′-c]phenazine (dppz) or 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip), which are bound to Ru(II) via two phenanthroline-N atoms in a characteristic “piano-stool” configuration of Ru(II)-arene complexes—as confirmed by vibrational and NMR spectra. In addition, cytotoxic studies were performed for similar half-sandwich organometallic [Ru(η6-p-cymene)(Me2dppz)Cl]PF6 complex (Me2dppz = 11,12-dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine). This study is complemented with elaborate modeling with density functional theory (DFT) calculations, which provided insight into reactive sites of Ru(II) structures, further detailed by molecular docking on the B-DNA dodecamer, which identified binding sites and affinities: most pronounced for the [Ru(η6-benzene)(aip)Cl](PF6) in both A-T and G-C regions of the DNA minor groove. Cytotoxic activity was probed versus tumor cell lines B16, C6, and U251 (B16 mouse melanoma, C6 rat glioma, U251 human glioblastoma) and non-tumor cell line HACAT (HACAT normal human keratinocytes).
PB  - Taylor & Francis
T2  - Journal of Coordination Chemistry
T1  - Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling
VL  - 72
IS  - 1
SP  - 148
EP  - 163
DO  - 10.1080/00958972.2018.1553298
ER  - 
@article{
author = "Nikolić, Stefan and Grgurić-Šipka, Sanja and Đorđević, Ivana S. and Dahmani, Rahma and Dekanski, Dragana and Vidičević, Sašenka and Tošić, Jelena and Mitić, Dragana and Grubišić, Sonja",
year = "2019",
abstract = "In search for antitumor metal-based drugs that would mitigate the severe side-effects of cisplatin, Ru(II) complexes are gaining increasing recent interest. In this work, we report on the synthesis, characterization (1H- and 13C-NMR, FT-IR), and cytotoxicity studies of two new half-sandwich organometallic Ru(II) complexes of the general formula [Ru(η6-arene)(XY)Cl](PF6) where arene = benzene or toluene and XY = bidentates: dipyrido[3,2-a:2′,3′-c]phenazine (dppz) or 2-(9-anthryl)-1H-imidazo[4,5-f][1,10]phenanthroline (aip), which are bound to Ru(II) via two phenanthroline-N atoms in a characteristic “piano-stool” configuration of Ru(II)-arene complexes—as confirmed by vibrational and NMR spectra. In addition, cytotoxic studies were performed for similar half-sandwich organometallic [Ru(η6-p-cymene)(Me2dppz)Cl]PF6 complex (Me2dppz = 11,12-dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine). This study is complemented with elaborate modeling with density functional theory (DFT) calculations, which provided insight into reactive sites of Ru(II) structures, further detailed by molecular docking on the B-DNA dodecamer, which identified binding sites and affinities: most pronounced for the [Ru(η6-benzene)(aip)Cl](PF6) in both A-T and G-C regions of the DNA minor groove. Cytotoxic activity was probed versus tumor cell lines B16, C6, and U251 (B16 mouse melanoma, C6 rat glioma, U251 human glioblastoma) and non-tumor cell line HACAT (HACAT normal human keratinocytes).",
publisher = "Taylor & Francis",
journal = "Journal of Coordination Chemistry",
title = "Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling",
volume = "72",
number = "1",
pages = "148-163",
doi = "10.1080/00958972.2018.1553298"
}
Nikolić, S., Grgurić-Šipka, S., Đorđević, I. S., Dahmani, R., Dekanski, D., Vidičević, S., Tošić, J., Mitić, D.,& Grubišić, S.. (2019). Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling. in Journal of Coordination Chemistry
Taylor & Francis., 72(1), 148-163.
https://doi.org/10.1080/00958972.2018.1553298
Nikolić S, Grgurić-Šipka S, Đorđević IS, Dahmani R, Dekanski D, Vidičević S, Tošić J, Mitić D, Grubišić S. Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling. in Journal of Coordination Chemistry. 2019;72(1):148-163.
doi:10.1080/00958972.2018.1553298 .
Nikolić, Stefan, Grgurić-Šipka, Sanja, Đorđević, Ivana S., Dahmani, Rahma, Dekanski, Dragana, Vidičević, Sašenka, Tošić, Jelena, Mitić, Dragana, Grubišić, Sonja, "Half-sandwich ruthenium(II)-arene complexes: synthesis, spectroscopic studies, biological properties, and molecular modeling" in Journal of Coordination Chemistry, 72, no. 1 (2019):148-163,
https://doi.org/10.1080/00958972.2018.1553298 . .
2
2

Supplementary material for the article: Pantić, D. N.; Mihajlović-Lalić, L. E.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S. Synthesis, Characterization and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes with 5-Chloro-1H-Benzimidazole-2-Carboxylic Acid. Journal of Coordination Chemistry 2019, 72 (5–7), 908–919. https://doi.org/10.1080/00958972.2019.1583332

Pantić, Darko N.; Mihajlović-Lalić, Ljiljana; Aranđelović, Sandra; Radulović, Siniša; Grgurić-Šipka, Sanja

(2019)

TY  - DATA
AU  - Pantić, Darko N.
AU  - Mihajlović-Lalić, Ljiljana
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3117
T2  - Journal of Coordination Chemistry
T1  - Supplementary material for the article:
Pantić, D. N.; Mihajlović-Lalić, L. E.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S.
Synthesis, Characterization and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes
with 5-Chloro-1H-Benzimidazole-2-Carboxylic Acid. Journal of Coordination Chemistry 2019,
72 (5–7), 908–919. https://doi.org/10.1080/00958972.2019.1583332
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3117
ER  - 
@misc{
author = "Pantić, Darko N. and Mihajlović-Lalić, Ljiljana and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2019",
journal = "Journal of Coordination Chemistry",
title = "Supplementary material for the article:
Pantić, D. N.; Mihajlović-Lalić, L. E.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S.
Synthesis, Characterization and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes
with 5-Chloro-1H-Benzimidazole-2-Carboxylic Acid. Journal of Coordination Chemistry 2019,
72 (5–7), 908–919. https://doi.org/10.1080/00958972.2019.1583332",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3117"
}
Pantić, D. N., Mihajlović-Lalić, L., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2019). Supplementary material for the article:
Pantić, D. N.; Mihajlović-Lalić, L. E.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S.
Synthesis, Characterization and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes
with 5-Chloro-1H-Benzimidazole-2-Carboxylic Acid. Journal of Coordination Chemistry 2019,
72 (5–7), 908–919. https://doi.org/10.1080/00958972.2019.1583332. in Journal of Coordination Chemistry.
https://hdl.handle.net/21.15107/rcub_cherry_3117
Pantić DN, Mihajlović-Lalić L, Aranđelović S, Radulović S, Grgurić-Šipka S. Supplementary material for the article:
Pantić, D. N.; Mihajlović-Lalić, L. E.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S.
Synthesis, Characterization and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes
with 5-Chloro-1H-Benzimidazole-2-Carboxylic Acid. Journal of Coordination Chemistry 2019,
72 (5–7), 908–919. https://doi.org/10.1080/00958972.2019.1583332. in Journal of Coordination Chemistry. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3117 .
Pantić, Darko N., Mihajlović-Lalić, Ljiljana, Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Supplementary material for the article:
Pantić, D. N.; Mihajlović-Lalić, L. E.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S.
Synthesis, Characterization and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes
with 5-Chloro-1H-Benzimidazole-2-Carboxylic Acid. Journal of Coordination Chemistry 2019,
72 (5–7), 908–919. https://doi.org/10.1080/00958972.2019.1583332" in Journal of Coordination Chemistry (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3117 .