Aranđelović, Sandra

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Authority KeyName Variants
orcid::0000-0002-3180-1439
  • Aranđelović, Sandra (37)
Projects
Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology
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 COST Action [CM1105]
Structure-properties relationships of natural and synthetic molecules and their metal complexes 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]
Strengthening of the MagBioVin Research and Innovation Team for Development of Novel Approaches for Tumour Therapy based on Nanostructured Materials The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors
Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids
Biological response modifiers in physiological and pathological conditions 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)
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200168 (University of Belgrade, Faculty of Chemistry) Amorphous and nanostructural chalcogenides
Research Fund-Flanders (FWO) Erasmus Mundus Basileus V project
Hercules Foundation (project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) Special Research Fund (BOF) – UGent (project 01N03217)

Author's Bibliography

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  - http://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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4048",
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.
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. Journal of Inorganic Biochemistry. 2020;210:111155
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" Journal of Inorganic Biochemistry, 210 (2020):111155,
https://doi.org/10.1016/j.jinorgbio.2020.111155 .
1
4
1
4

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  - BOOK
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  - http://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
ER  - 
@book{
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4049",
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"
}
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.
Journal of Inorganic Biochemistry
Elsevier..
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. Journal of Inorganic Biochemistry. 2020;
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" Journal of Inorganic Biochemistry (2020)

Antitumor activity of organoruthenium complexes with chelate aromatic ligands, derived from 1,10-phenantroline: Synthesis and biological activity

Savić, Aleksandar; Gligorijević, Nevenka; Aranđelović, Sandra; Dojčinović, Biljana P.; Kaczmarek, Anna M.; Radulović, Siniša; Van Deun, Rik; Van Hecke, Kristof

(Elsevier, 2020)

TY  - JOUR
AU  - Savić, Aleksandar
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Dojčinović, Biljana P.
AU  - Kaczmarek, Anna M.
AU  - Radulović, Siniša
AU  - Van Deun, Rik
AU  - Van Hecke, Kristof
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3781
AB  - The monocationic chloro complexes containing chelating N∩N ligands: [(η6-p-cymene)Ru(L1–4)Cl]+ (1–4), where L1 = 4-methyl-1,10-phenantroline, L2 = dipyrido[3,2-a:2′,3′-c]phenazine, L3 = 11-chloro-dipyrido[3,2-a:2′,3′-c]phenazine, L4 = 11-nitro-dipyrido[3,2-a:2′,3′-c]phenazine; p-cymene = 1-methyl-4-isopropylbenzene) have been prepared and characterized as the hexafluorophosphate salts. The biological activity of 1–4 has been investigated in selected 2D monolayer cell cultures (A549, PANC-1, MDA-MB-231, MRC-5). All investigated ruthenium complexes showed similar or even better cytotoxicity to cisplatin. However, there was no significant reduction in growth of PANC-1 cells in a 3D cell culture of multicellular tumor spheroids (MCTS) after treatment with 2–4, while the cisplatin treatment induced retardation in MCTS growth. Flow cytometry analysis of the cell cycle of PANC-1 cells shows that 3 caused changes of cell cycle phase distribution characterized by slight accumulation of cells in the G2-M phase. Absence of the Sub-G1 phase in the cell cycle of the treated cells indicated that there was no fragmentation of DNA for the analyzed time intervals (48 and 72 h treatment). Fluorescent microscopy, after acridine orange/ethidium bromide staining, revealed that the investigated ruthenium complexes induced some characteristics of apoptotic morphology (shrinking and condensation of chromatin) with notably preserved integrity of the plasma membrane. Investigation of cellular uptake and DNA - fraction accumulation performed by inductively coupled plasma mass spectrometry in PANC-1 cells with equimolar concentrations (5 μM) of 2–4 and cisplatin showed more efficient cellular uptake and DNA - fraction accumulation of complex 3 compared to complexes 2 and 4.
PB  - Elsevier
T1  - Antitumor activity of organoruthenium complexes with chelate aromatic ligands, derived from 1,10-phenantroline: Synthesis and biological activity
VL  - 202
SP  - 110869
DO  - 10.1016/j.jinorgbio.2019.110869
ER  - 
@article{
author = "Savić, Aleksandar and Gligorijević, Nevenka and Aranđelović, Sandra and Dojčinović, Biljana P. and Kaczmarek, Anna M. and Radulović, Siniša and Van Deun, Rik and Van Hecke, Kristof",
year = "2020",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3781",
abstract = "The monocationic chloro complexes containing chelating N∩N ligands: [(η6-p-cymene)Ru(L1–4)Cl]+ (1–4), where L1 = 4-methyl-1,10-phenantroline, L2 = dipyrido[3,2-a:2′,3′-c]phenazine, L3 = 11-chloro-dipyrido[3,2-a:2′,3′-c]phenazine, L4 = 11-nitro-dipyrido[3,2-a:2′,3′-c]phenazine; p-cymene = 1-methyl-4-isopropylbenzene) have been prepared and characterized as the hexafluorophosphate salts. The biological activity of 1–4 has been investigated in selected 2D monolayer cell cultures (A549, PANC-1, MDA-MB-231, MRC-5). All investigated ruthenium complexes showed similar or even better cytotoxicity to cisplatin. However, there was no significant reduction in growth of PANC-1 cells in a 3D cell culture of multicellular tumor spheroids (MCTS) after treatment with 2–4, while the cisplatin treatment induced retardation in MCTS growth. Flow cytometry analysis of the cell cycle of PANC-1 cells shows that 3 caused changes of cell cycle phase distribution characterized by slight accumulation of cells in the G2-M phase. Absence of the Sub-G1 phase in the cell cycle of the treated cells indicated that there was no fragmentation of DNA for the analyzed time intervals (48 and 72 h treatment). Fluorescent microscopy, after acridine orange/ethidium bromide staining, revealed that the investigated ruthenium complexes induced some characteristics of apoptotic morphology (shrinking and condensation of chromatin) with notably preserved integrity of the plasma membrane. Investigation of cellular uptake and DNA - fraction accumulation performed by inductively coupled plasma mass spectrometry in PANC-1 cells with equimolar concentrations (5 μM) of 2–4 and cisplatin showed more efficient cellular uptake and DNA - fraction accumulation of complex 3 compared to complexes 2 and 4.",
publisher = "Elsevier",
title = "Antitumor activity of organoruthenium complexes with chelate aromatic ligands, derived from 1,10-phenantroline: Synthesis and biological activity",
volume = "202",
pages = "110869",
doi = "10.1016/j.jinorgbio.2019.110869"
}
Savić, A., Gligorijević, N., Aranđelović, S., Dojčinović, B. P., Kaczmarek, A. M., Radulović, S., Van Deun, R.,& Van Hecke, K. (2020). Antitumor activity of organoruthenium complexes with chelate aromatic ligands, derived from 1,10-phenantroline: Synthesis and biological activity.

Elsevier., 202, 110869.
https://doi.org/10.1016/j.jinorgbio.2019.110869
Savić A, Gligorijević N, Aranđelović S, Dojčinović BP, Kaczmarek AM, Radulović S, Van Deun R, Van Hecke K. Antitumor activity of organoruthenium complexes with chelate aromatic ligands, derived from 1,10-phenantroline: Synthesis and biological activity. 2020;202:110869
Savić Aleksandar, Gligorijević Nevenka, Aranđelović Sandra, Dojčinović Biljana P., Kaczmarek Anna M., Radulović Siniša, Van Deun Rik, Van Hecke Kristof, "Antitumor activity of organoruthenium complexes with chelate aromatic ligands, derived from 1,10-phenantroline: Synthesis and biological activity", 202 (2020):110869,
https://doi.org/10.1016/j.jinorgbio.2019.110869 .
1
5
1
5

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  - http://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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2854",
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.
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. Journal of Biological Inorganic Chemistry. 2019;24(2):297-310
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" Journal of Biological Inorganic Chemistry, 24, no. 2 (2019):297-310,
https://doi.org/10.1007/s00775-019-01647-4 .
3
2
4

Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid

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

(2019)

TY  - JOUR
AU  - Pantić, Darko N.
AU  - Mihajlović-Lalić, Ljiljana
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3116
AB  - Three new ruthenium(II)-arene halido complexes, [(η 6 -p-cymene) RuX(L)] (1–3), were synthesized in a reaction of [(η 6 -p-cymene)RuX 2 ] 2 with 5-chloro-1H-benzimidazole-2-carboxylic acid (HL) in ethanol (X – = Cl – (1), Br – (2), I – (3)). The complexes were characterized by elemental analysis, mass spectrometry, IR, 1 H and 13 C NMR spectroscopy. The cytotoxic activity of the ligand precursor and its ruthenium complexes was tested by MTT assay in human cancer cell lines: lung adenocarcinoma (A549), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5). The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to HL in the range of concentrations up to 300 µM. In terms of halido ligand substitution, cytotoxic activity toward A549 and K562 cell lines in 1–3 serie significantly increased (e.g., IC 50 values for K562: 1: 205.76 µM; 2: 174.77 µM; 3: 83.97 µM). All studied compounds were found to be ineffective toward MRC-5. Hydrolysis of 1–3 was followed by UV-vis spectroscopy at 25 °C, revealing ligand-substitution reactions at the Ru(II) center. Compounds 2 and 3 underwent rapid hydrolysis ranging from a few minutes for the aquation to ca. 20 min, confirming typical Ru-arene behavior in aqueous solutions.
T2  - Journal of Coordination Chemistry
T1  - Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid
VL  - 72
IS  - 5-7
SP  - 908
EP  - 919
DO  - 10.1080/00958972.2019.1583332
ER  - 
@article{
author = "Pantić, Darko N. and Mihajlović-Lalić, Ljiljana and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3116",
abstract = "Three new ruthenium(II)-arene halido complexes, [(η 6 -p-cymene) RuX(L)] (1–3), were synthesized in a reaction of [(η 6 -p-cymene)RuX 2 ] 2 with 5-chloro-1H-benzimidazole-2-carboxylic acid (HL) in ethanol (X – = Cl – (1), Br – (2), I – (3)). The complexes were characterized by elemental analysis, mass spectrometry, IR, 1 H and 13 C NMR spectroscopy. The cytotoxic activity of the ligand precursor and its ruthenium complexes was tested by MTT assay in human cancer cell lines: lung adenocarcinoma (A549), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5). The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to HL in the range of concentrations up to 300 µM. In terms of halido ligand substitution, cytotoxic activity toward A549 and K562 cell lines in 1–3 serie significantly increased (e.g., IC 50 values for K562: 1: 205.76 µM; 2: 174.77 µM; 3: 83.97 µM). All studied compounds were found to be ineffective toward MRC-5. Hydrolysis of 1–3 was followed by UV-vis spectroscopy at 25 °C, revealing ligand-substitution reactions at the Ru(II) center. Compounds 2 and 3 underwent rapid hydrolysis ranging from a few minutes for the aquation to ca. 20 min, confirming typical Ru-arene behavior in aqueous solutions.",
journal = "Journal of Coordination Chemistry",
title = "Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid",
volume = "72",
number = "5-7",
pages = "908-919",
doi = "10.1080/00958972.2019.1583332"
}
Pantić, D. N., Mihajlović-Lalić, L., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S. (2019). Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid.
Journal of Coordination Chemistry, 72(5-7), 908-919.
https://doi.org/10.1080/00958972.2019.1583332
Pantić DN, Mihajlović-Lalić L, 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
Pantić Darko N., Mihajlović-Lalić Ljiljana, Aranđelović Sandra, Radulović Siniša, Grgurić-Šipka Sanja, "Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid" Journal of Coordination Chemistry, 72, no. 5-7 (2019):908-919,
https://doi.org/10.1080/00958972.2019.1583332 .
2
2
3

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  - BOOK
AU  - Pantić, Darko N.
AU  - Mihajlović-Lalić, Ljiljana
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2019
UR  - http://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
ER  - 
@book{
author = "Pantić, Darko N. and Mihajlović-Lalić, Ljiljana and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3117",
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"
}
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.
Journal of Coordination Chemistry.
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. Journal of Coordination Chemistry. 2019;
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" Journal of Coordination Chemistry (2019)

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  - http://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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3640",
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.
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. Journal of Organometallic Chemistry. 2019;902
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" Journal of Organometallic Chemistry, 902 (2019),
https://doi.org/10.1016/j.jorganchem.2019.120966 .
2
1
2

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  - http://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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3641",
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.
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. Journal of Organometallic Chemistry. 2019;902
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" Journal of Organometallic Chemistry, 902 (2019),
https://doi.org/10.1016/j.jorganchem.2019.120966 .
2
1
2

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  - BOOK
AU  - Nikolić, Stefan
AU  - Mihajlović-Lalić, Ljiljana
AU  - Vidosavljević, Marija
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2019
UR  - http://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
ER  - 
@book{
author = "Nikolić, Stefan and Mihajlović-Lalić, Ljiljana and Vidosavljević, Marija and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3642",
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"
}
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.
Journal of Organometallic Chemistry, 902.
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. Journal of Organometallic Chemistry. 2019;902
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" Journal of Organometallic Chemistry, 902 (2019)

Supplementary data for the article: Tadić, A.; Poljarević, J.; Krstić, M.; Kajzerberger, M.; Aranelović, S.; Radulović, S.; Kakoulidou, C.; Papadopoulos, A. N.; Psomas, G.; Grgurić-Šipka, S. Ruthenium-Arene Complexes with NSAIDs: Synthesis, Characterization and Bioactivity. New Journal of Chemistry 2018, 42 (4), 3001–3019. https://doi.org/10.1039/c7nj04416j

Tadić, Ana; Poljarević, Jelena; Krstić, Milena; Kajzerberger, Marijana; Aranđelović, Sandra; Radulović, Siniša; Kakoulidou, Chrisoula; Papadopoulos, Athanasios N.; Psomas, George; Grgurić-Šipka, Sanja

(Royal Soc Chemistry, Cambridge, 2018)

TY  - BOOK
AU  - Tadić, Ana
AU  - Poljarević, Jelena
AU  - Krstić, Milena
AU  - Kajzerberger, Marijana
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Kakoulidou, Chrisoula
AU  - Papadopoulos, Athanasios N.
AU  - Psomas, George
AU  - Grgurić-Šipka, Sanja
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3038
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Supplementary data for the article: Tadić, A.; Poljarević, J.; Krstić, M.; Kajzerberger, M.; Aranelović, S.; Radulović, S.; Kakoulidou, C.; Papadopoulos, A. N.; Psomas, G.; Grgurić-Šipka, S. Ruthenium-Arene Complexes with NSAIDs: Synthesis, Characterization and Bioactivity. New Journal of Chemistry 2018, 42 (4), 3001–3019. https://doi.org/10.1039/c7nj04416j
ER  - 
@book{
author = "Tadić, Ana and Poljarević, Jelena and Krstić, Milena and Kajzerberger, Marijana and Aranđelović, Sandra and Radulović, Siniša and Kakoulidou, Chrisoula and Papadopoulos, Athanasios N. and Psomas, George and Grgurić-Šipka, Sanja",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3038",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Supplementary data for the article: Tadić, A.; Poljarević, J.; Krstić, M.; Kajzerberger, M.; Aranelović, S.; Radulović, S.; Kakoulidou, C.; Papadopoulos, A. N.; Psomas, G.; Grgurić-Šipka, S. Ruthenium-Arene Complexes with NSAIDs: Synthesis, Characterization and Bioactivity. New Journal of Chemistry 2018, 42 (4), 3001–3019. https://doi.org/10.1039/c7nj04416j"
}
Tadić, A., Poljarević, J., Krstić, M., Kajzerberger, M., Aranđelović, S., Radulović, S., Kakoulidou, C., Papadopoulos, A. N., Psomas, G.,& Grgurić-Šipka, S. (2018). Supplementary data for the article: Tadić, A.; Poljarević, J.; Krstić, M.; Kajzerberger, M.; Aranelović, S.; Radulović, S.; Kakoulidou, C.; Papadopoulos, A. N.; Psomas, G.; Grgurić-Šipka, S. Ruthenium-Arene Complexes with NSAIDs: Synthesis, Characterization and Bioactivity. New Journal of Chemistry 2018, 42 (4), 3001–3019. https://doi.org/10.1039/c7nj04416j.
New Journal of Chemistry
Royal Soc Chemistry, Cambridge..
Tadić A, Poljarević J, Krstić M, Kajzerberger M, Aranđelović S, Radulović S, Kakoulidou C, Papadopoulos AN, Psomas G, Grgurić-Šipka S. Supplementary data for the article: Tadić, A.; Poljarević, J.; Krstić, M.; Kajzerberger, M.; Aranelović, S.; Radulović, S.; Kakoulidou, C.; Papadopoulos, A. N.; Psomas, G.; Grgurić-Šipka, S. Ruthenium-Arene Complexes with NSAIDs: Synthesis, Characterization and Bioactivity. New Journal of Chemistry 2018, 42 (4), 3001–3019. https://doi.org/10.1039/c7nj04416j. New Journal of Chemistry. 2018;
Tadić Ana, Poljarević Jelena, Krstić Milena, Kajzerberger Marijana, Aranđelović Sandra, Radulović Siniša, Kakoulidou Chrisoula, Papadopoulos Athanasios N., Psomas George, Grgurić-Šipka Sanja, "Supplementary data for the article: Tadić, A.; Poljarević, J.; Krstić, M.; Kajzerberger, M.; Aranelović, S.; Radulović, S.; Kakoulidou, C.; Papadopoulos, A. N.; Psomas, G.; Grgurić-Šipka, S. Ruthenium-Arene Complexes with NSAIDs: Synthesis, Characterization and Bioactivity. New Journal of Chemistry 2018, 42 (4), 3001–3019. https://doi.org/10.1039/c7nj04416j" New Journal of Chemistry (2018)

Ruthenium-arene complexes with NSAIDs: synthesis, characterization and bioactivity

Tadić, Ana; Poljarević, Jelena; Krstić, Milena; Kajzerberger, Marijana; Aranđelović, Sandra; Radulović, Siniša; Kakoulidou, Chrisoula; Papadopoulos, Athanasios N.; Psomas, George; Grgurić-Šipka, Sanja

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Tadić, Ana
AU  - Poljarević, Jelena
AU  - Krstić, Milena
AU  - Kajzerberger, Marijana
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Kakoulidou, Chrisoula
AU  - Papadopoulos, Athanasios N.
AU  - Psomas, George
AU  - Grgurić-Šipka, Sanja
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2093
AB  - Two non-steroidal antiinflammatory drugs indomethacin and mefenamic acid were coordinated to Ru(II)-arenes to afford four new complexes. The cytotoxic activities of the ligands and ruthenium complexes were tested in three human cancer cell lines (K562, A549, MDA-MB-231) and non-tumour human fetal lung fibroblast cells (MRC-5) by MTT assay. Cytotoxicity studies revealed that indomethacin Ru(II)-arene complexes 1 and 3 displayed good cytotoxicity and apparent cytoselective profiles. The IC50 values obtained in leukemia K562 cells were comparable to those of cisplatin (10.3 mu M (CDDP), 11.9 mu M (1) and 13.2 mu M (3)). Flow cytometric analysis of 1 and 3 in triple-negative breast cancer MDA-MB-231 cells revealed an interesting mechanism of action. At IC50 concentrations, 1 and 3 arrested cell cycle progression in S phase and caused rapid accumulation of cells in sub-G1 phase (up to 48%), while Annexin V-FITC/PI staining showed simultaneous occurrence of apoptotic and necrotic cell populations at approximately similar levels of 20%. Measurement of reactive oxygen species (ROS) production by DCFH-DA staining confirmed the potential of 1 and 3 to increase ROS even more than cisplatin. The interaction of the complexes with serum albumins showed their potential ability to bind tightly and reversibly to albumins. The affinity of the complexes to calf-thymus DNA was investigated by UV-vis spectroscopy, viscosity measurements and fluorescence emission spectroscopy for competitive studies of the complexes with ethidium bromide, revealing that their interaction probably occurs via intercalation. Taken together, the results strongly suggest the potential of complexes 1 and 3 to alter cell cycle progression and cause DNA-damage by means of direct DNA-binding or indirectly by ROS production.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Ruthenium-arene complexes with NSAIDs: synthesis, characterization and bioactivity
VL  - 42
IS  - 4
SP  - 3001
EP  - 3019
DO  - 10.1039/c7nj04416j
ER  - 
@article{
author = "Tadić, Ana and Poljarević, Jelena and Krstić, Milena and Kajzerberger, Marijana and Aranđelović, Sandra and Radulović, Siniša and Kakoulidou, Chrisoula and Papadopoulos, Athanasios N. and Psomas, George and Grgurić-Šipka, Sanja",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2093",
abstract = "Two non-steroidal antiinflammatory drugs indomethacin and mefenamic acid were coordinated to Ru(II)-arenes to afford four new complexes. The cytotoxic activities of the ligands and ruthenium complexes were tested in three human cancer cell lines (K562, A549, MDA-MB-231) and non-tumour human fetal lung fibroblast cells (MRC-5) by MTT assay. Cytotoxicity studies revealed that indomethacin Ru(II)-arene complexes 1 and 3 displayed good cytotoxicity and apparent cytoselective profiles. The IC50 values obtained in leukemia K562 cells were comparable to those of cisplatin (10.3 mu M (CDDP), 11.9 mu M (1) and 13.2 mu M (3)). Flow cytometric analysis of 1 and 3 in triple-negative breast cancer MDA-MB-231 cells revealed an interesting mechanism of action. At IC50 concentrations, 1 and 3 arrested cell cycle progression in S phase and caused rapid accumulation of cells in sub-G1 phase (up to 48%), while Annexin V-FITC/PI staining showed simultaneous occurrence of apoptotic and necrotic cell populations at approximately similar levels of 20%. Measurement of reactive oxygen species (ROS) production by DCFH-DA staining confirmed the potential of 1 and 3 to increase ROS even more than cisplatin. The interaction of the complexes with serum albumins showed their potential ability to bind tightly and reversibly to albumins. The affinity of the complexes to calf-thymus DNA was investigated by UV-vis spectroscopy, viscosity measurements and fluorescence emission spectroscopy for competitive studies of the complexes with ethidium bromide, revealing that their interaction probably occurs via intercalation. Taken together, the results strongly suggest the potential of complexes 1 and 3 to alter cell cycle progression and cause DNA-damage by means of direct DNA-binding or indirectly by ROS production.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Ruthenium-arene complexes with NSAIDs: synthesis, characterization and bioactivity",
volume = "42",
number = "4",
pages = "3001-3019",
doi = "10.1039/c7nj04416j"
}
Tadić, A., Poljarević, J., Krstić, M., Kajzerberger, M., Aranđelović, S., Radulović, S., Kakoulidou, C., Papadopoulos, A. N., Psomas, G.,& Grgurić-Šipka, S. (2018). Ruthenium-arene complexes with NSAIDs: synthesis, characterization and bioactivity.
New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 42(4), 3001-3019.
https://doi.org/10.1039/c7nj04416j
Tadić A, Poljarević J, Krstić M, Kajzerberger M, Aranđelović S, Radulović S, Kakoulidou C, Papadopoulos AN, Psomas G, Grgurić-Šipka S. Ruthenium-arene complexes with NSAIDs: synthesis, characterization and bioactivity. New Journal of Chemistry. 2018;42(4):3001-3019
Tadić Ana, Poljarević Jelena, Krstić Milena, Kajzerberger Marijana, Aranđelović Sandra, Radulović Siniša, Kakoulidou Chrisoula, Papadopoulos Athanasios N., Psomas George, Grgurić-Šipka Sanja, "Ruthenium-arene complexes with NSAIDs: synthesis, characterization and bioactivity" New Journal of Chemistry, 42, no. 4 (2018):3001-3019,
https://doi.org/10.1039/c7nj04416j .
14
14
16

Supplementary data for article: Baroud, A. A.; Mihajlović-Lalić, L. E.; Gligorijević, N.; Aranđelović, S.; Stanković, D.; Radulović, S.; Van Hecke, K.; Savić, A.; Grgurić-Šipka, S. Ruthenium(II) Bipyridine Complexes: From Synthesis and Crystal Structures to Electrochemical and Cytotoxicity Investigation. Journal of Coordination Chemistry 2017, 70 (5), 831–847. https://doi.org/10.1080/00958972.2017.1282611

Baroud, Afya A.; Mihajlović-Lalić, Ljiljana; Gligorijević, Nevenka; Aranđelović, Sandra; Stanković, Dalibor; Radulović, Siniša; Van Hecke, Kristof; Savić, Aleksandar; Grgurić-Šipka, Sanja

(Taylor & Francis Ltd, Abingdon, 2017)

TY  - BOOK
AU  - Baroud, Afya A.
AU  - Mihajlović-Lalić, Ljiljana
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Stanković, Dalibor
AU  - Radulović, Siniša
AU  - Van Hecke, Kristof
AU  - Savić, Aleksandar
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3138
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Coordination Chemistry
T1  - Supplementary data for article:  Baroud, A. A.; Mihajlović-Lalić, L. E.; Gligorijević, N.; Aranđelović, S.; Stanković, D.; Radulović, S.; Van Hecke, K.; Savić, A.; Grgurić-Šipka, S. Ruthenium(II) Bipyridine Complexes: From Synthesis and Crystal Structures to Electrochemical and Cytotoxicity Investigation. Journal of Coordination Chemistry 2017, 70 (5), 831–847. https://doi.org/10.1080/00958972.2017.1282611
ER  - 
@book{
author = "Baroud, Afya A. and Mihajlović-Lalić, Ljiljana and Gligorijević, Nevenka and Aranđelović, Sandra and Stanković, Dalibor and Radulović, Siniša and Van Hecke, Kristof and Savić, Aleksandar and Grgurić-Šipka, Sanja",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3138",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Coordination Chemistry",
title = "Supplementary data for article:  Baroud, A. A.; Mihajlović-Lalić, L. E.; Gligorijević, N.; Aranđelović, S.; Stanković, D.; Radulović, S.; Van Hecke, K.; Savić, A.; Grgurić-Šipka, S. Ruthenium(II) Bipyridine Complexes: From Synthesis and Crystal Structures to Electrochemical and Cytotoxicity Investigation. Journal of Coordination Chemistry 2017, 70 (5), 831–847. https://doi.org/10.1080/00958972.2017.1282611"
}
Baroud, A. A., Mihajlović-Lalić, L., Gligorijević, N., Aranđelović, S., Stanković, D., Radulović, S., Van Hecke, K., Savić, A.,& Grgurić-Šipka, S. (2017). Supplementary data for article:  Baroud, A. A.; Mihajlović-Lalić, L. E.; Gligorijević, N.; Aranđelović, S.; Stanković, D.; Radulović, S.; Van Hecke, K.; Savić, A.; Grgurić-Šipka, S. Ruthenium(II) Bipyridine Complexes: From Synthesis and Crystal Structures to Electrochemical and Cytotoxicity Investigation. Journal of Coordination Chemistry 2017, 70 (5), 831–847. https://doi.org/10.1080/00958972.2017.1282611.
Journal of Coordination Chemistry
Taylor & Francis Ltd, Abingdon..
Baroud AA, Mihajlović-Lalić L, Gligorijević N, Aranđelović S, Stanković D, Radulović S, Van Hecke K, Savić A, Grgurić-Šipka S. Supplementary data for article:  Baroud, A. A.; Mihajlović-Lalić, L. E.; Gligorijević, N.; Aranđelović, S.; Stanković, D.; Radulović, S.; Van Hecke, K.; Savić, A.; Grgurić-Šipka, S. Ruthenium(II) Bipyridine Complexes: From Synthesis and Crystal Structures to Electrochemical and Cytotoxicity Investigation. Journal of Coordination Chemistry 2017, 70 (5), 831–847. https://doi.org/10.1080/00958972.2017.1282611. Journal of Coordination Chemistry. 2017;
Baroud Afya A., Mihajlović-Lalić Ljiljana, Gligorijević Nevenka, Aranđelović Sandra, Stanković Dalibor, Radulović Siniša, Van Hecke Kristof, Savić Aleksandar, Grgurić-Šipka Sanja, "Supplementary data for article:  Baroud, A. A.; Mihajlović-Lalić, L. E.; Gligorijević, N.; Aranđelović, S.; Stanković, D.; Radulović, S.; Van Hecke, K.; Savić, A.; Grgurić-Šipka, S. Ruthenium(II) Bipyridine Complexes: From Synthesis and Crystal Structures to Electrochemical and Cytotoxicity Investigation. Journal of Coordination Chemistry 2017, 70 (5), 831–847. https://doi.org/10.1080/00958972.2017.1282611" Journal of Coordination Chemistry (2017)

Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation

Baroud, Afya A.; Mihajlović-Lalić, Ljiljana; Gligorijević, Nevenka; Aranđelović, Sandra; Stanković, Dalibor; Radulović, Siniša; Van Hecke, Kristof; Savić, Aleksandar; Grgurić-Šipka, Sanja

(Taylor & Francis Ltd, Abingdon, 2017)

TY  - JOUR
AU  - Baroud, Afya A.
AU  - Mihajlović-Lalić, Ljiljana
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Stanković, Dalibor
AU  - Radulović, Siniša
AU  - Van Hecke, Kristof
AU  - Savić, Aleksandar
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2423
AB  - Complexes 1-4, [Ru(L)(bpy)(2)]PF6, where bpy=2,2-bipyridine; HL=3-methylpyridine-2-carboxylic acid (HL1), 6-methylpyridine-2-carboxylic acid (HL2), 5-bromopyridine-2-carboxylic acid (HL3) and 6-bromopyridine-2-carboxylic acid (HL4), were synthesized and characterized. The electrochemical character of the complexes was investigated by cyclic voltammetry revealing two reversible reduction waves in the negative range of potentials, most likely due to a reduction of the bipyridine moiety. Cytotoxicity studies by MTT assay for 72h of drug action revealed that 2-4 exhibited moderate activity in cervical human tumor cells (HeLa). Complex 2 exhibited low activity in colon cancer LS-174 cells (180 +/- 10), while all complexes were devoid of activity in lung cancer A549 and non-tumor MRC-5 cells, up to 200M. Combinational studies of the most active complex 2, with pharmacological modulators of cell redox status, L-buthionine-sulfoximine (L-BSO) or N-acetyl-L-cysteine (NAC), showed that when L-BSO potentiated, 2 induced a sub-G1 peak of the cell cycle in the HeLa cell line. UV-vis and cyclic voltammetry were performed in order to investigate the binding mode of 2 to DNA and suggested intercalation for the complex-DNA interaction. [GRAPHICS]
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Coordination Chemistry
T1  - Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation
VL  - 70
IS  - 5
SP  - 831
EP  - 847
DO  - 10.1080/00958972.2017.1282611
ER  - 
@article{
author = "Baroud, Afya A. and Mihajlović-Lalić, Ljiljana and Gligorijević, Nevenka and Aranđelović, Sandra and Stanković, Dalibor and Radulović, Siniša and Van Hecke, Kristof and Savić, Aleksandar and Grgurić-Šipka, Sanja",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2423",
abstract = "Complexes 1-4, [Ru(L)(bpy)(2)]PF6, where bpy=2,2-bipyridine; HL=3-methylpyridine-2-carboxylic acid (HL1), 6-methylpyridine-2-carboxylic acid (HL2), 5-bromopyridine-2-carboxylic acid (HL3) and 6-bromopyridine-2-carboxylic acid (HL4), were synthesized and characterized. The electrochemical character of the complexes was investigated by cyclic voltammetry revealing two reversible reduction waves in the negative range of potentials, most likely due to a reduction of the bipyridine moiety. Cytotoxicity studies by MTT assay for 72h of drug action revealed that 2-4 exhibited moderate activity in cervical human tumor cells (HeLa). Complex 2 exhibited low activity in colon cancer LS-174 cells (180 +/- 10), while all complexes were devoid of activity in lung cancer A549 and non-tumor MRC-5 cells, up to 200M. Combinational studies of the most active complex 2, with pharmacological modulators of cell redox status, L-buthionine-sulfoximine (L-BSO) or N-acetyl-L-cysteine (NAC), showed that when L-BSO potentiated, 2 induced a sub-G1 peak of the cell cycle in the HeLa cell line. UV-vis and cyclic voltammetry were performed in order to investigate the binding mode of 2 to DNA and suggested intercalation for the complex-DNA interaction. [GRAPHICS]",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Coordination Chemistry",
title = "Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation",
volume = "70",
number = "5",
pages = "831-847",
doi = "10.1080/00958972.2017.1282611"
}
Baroud, A. A., Mihajlović-Lalić, L., Gligorijević, N., Aranđelović, S., Stanković, D., Radulović, S., Van Hecke, K., Savić, A.,& Grgurić-Šipka, S. (2017). Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation.
Journal of Coordination Chemistry
Taylor & Francis Ltd, Abingdon., 70(5), 831-847.
https://doi.org/10.1080/00958972.2017.1282611
Baroud AA, Mihajlović-Lalić L, Gligorijević N, Aranđelović S, Stanković D, Radulović S, Van Hecke K, Savić A, Grgurić-Šipka S. Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation. Journal of Coordination Chemistry. 2017;70(5):831-847
Baroud Afya A., Mihajlović-Lalić Ljiljana, Gligorijević Nevenka, Aranđelović Sandra, Stanković Dalibor, Radulović Siniša, Van Hecke Kristof, Savić Aleksandar, Grgurić-Šipka Sanja, "Ruthenium(II) bipyridine complexes: from synthesis and crystal structures to electrochemical and cytotoxicity investigation" Journal of Coordination Chemistry, 70, no. 5 (2017):831-847,
https://doi.org/10.1080/00958972.2017.1282611 .
7
7
7

In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid

Zmejkovski, Bojana B.; Pantelić, Nebojša Đ.; Filipović, Lana; Aranđelović, Sandra; Radulović, Siniša; Sabo, Tibor; Kaluđerović, Goran N.

(Bentham Science Publ Ltd, Sharjah, 2017)

TY  - JOUR
AU  - Zmejkovski, Bojana B.
AU  - Pantelić, Nebojša Đ.
AU  - Filipović, Lana
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2501
AB  - Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy and mass spectrometry. Method: Quantum chemical calculations were used to predict formed isomers of 1 and 2. Furthermore, reduction of 2 with ascorbic acid was followed by time-dependant C-13 NMR spectroscopy in order to enable assignation of the formed isomers for complex 1. In vitro cytotoxic activity was determined for 1 and 2 on a panel of five human tumor cell lines derived from cervix adenocarcinoma (HeLa), alveolar basal adenocarcinoma (A549), breast adenocarcinoma (MDA-453), colorectal cancer (LS 174), erythromyeloblastoid leukemia (K562), as well as one non-malignant human lung fibroblast cell line (MRC-5), using MTT assay. Result: Both complexes exhibited high (2 against K562: IC50 = 5.4 mu M), more active than cisplatin, to moderate activity (1). Both complexes caused considerable decrease of cell number in K562 cells in G1, S and G2 phases, concordantly increasing subpopulation in sub-G1 fraction. Morphological analysis of K562 cell death induced by platinum(II/IV) complexes indicate apoptosis.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Anti-Cancer Agents in Medicinal Chemistry
T1  - In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid
VL  - 17
IS  - 8
SP  - 1136
EP  - 1143
DO  - 10.2174/1871520616666161207155634
ER  - 
@article{
author = "Zmejkovski, Bojana B. and Pantelić, Nebojša Đ. and Filipović, Lana and Aranđelović, Sandra and Radulović, Siniša and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2501",
abstract = "Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy and mass spectrometry. Method: Quantum chemical calculations were used to predict formed isomers of 1 and 2. Furthermore, reduction of 2 with ascorbic acid was followed by time-dependant C-13 NMR spectroscopy in order to enable assignation of the formed isomers for complex 1. In vitro cytotoxic activity was determined for 1 and 2 on a panel of five human tumor cell lines derived from cervix adenocarcinoma (HeLa), alveolar basal adenocarcinoma (A549), breast adenocarcinoma (MDA-453), colorectal cancer (LS 174), erythromyeloblastoid leukemia (K562), as well as one non-malignant human lung fibroblast cell line (MRC-5), using MTT assay. Result: Both complexes exhibited high (2 against K562: IC50 = 5.4 mu M), more active than cisplatin, to moderate activity (1). Both complexes caused considerable decrease of cell number in K562 cells in G1, S and G2 phases, concordantly increasing subpopulation in sub-G1 fraction. Morphological analysis of K562 cell death induced by platinum(II/IV) complexes indicate apoptosis.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Anti-Cancer Agents in Medicinal Chemistry",
title = "In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid",
volume = "17",
number = "8",
pages = "1136-1143",
doi = "10.2174/1871520616666161207155634"
}
Zmejkovski, B. B., Pantelić, N. Đ., Filipović, L., Aranđelović, S., Radulović, S., Sabo, T.,& Kaluđerović, G. N. (2017). In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid.
Anti-Cancer Agents in Medicinal Chemistry
Bentham Science Publ Ltd, Sharjah., 17(8), 1136-1143.
https://doi.org/10.2174/1871520616666161207155634
Zmejkovski BB, Pantelić NĐ, Filipović L, Aranđelović S, Radulović S, Sabo T, Kaluđerović GN. In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid. Anti-Cancer Agents in Medicinal Chemistry. 2017;17(8):1136-1143
Zmejkovski Bojana B., Pantelić Nebojša Đ., Filipović Lana, Aranđelović Sandra, Radulović Siniša, Sabo Tibor, Kaluđerović Goran N., "In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid" Anti-Cancer Agents in Medicinal Chemistry, 17, no. 8 (2017):1136-1143,
https://doi.org/10.2174/1871520616666161207155634 .

Supplementary data for the article: Pantić, D. N.; Arancrossed D Signelović, S.; Radulović, S.; Roller, A.; Arion, V. B.; Grgurić-Šipka, S. Synthesis, Characterisation and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes with 1H-Benzimidazole-2-Carboxylic Acid. Journal of Organometallic Chemistry 2016, 819, 61–68. https://doi.org/10.1016/j.jorganchem.2016.06.024

Pantić, Darko N.; Aranđelović, Sandra; Radulović, Siniša; Roller, Alexander; Arion, Vladimir B.; Grgurić-Šipka, Sanja

(Elsevier Science Sa, Lausanne, 2016)

TY  - BOOK
AU  - Pantić, Darko N.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Roller, Alexander
AU  - Arion, Vladimir B.
AU  - Grgurić-Šipka, Sanja
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3633
PB  - Elsevier Science Sa, Lausanne
T2  - Journal of Organometallic Chemistry
T1  - Supplementary data for the article: Pantić, D. N.; Arancrossed D Signelović, S.; Radulović, S.; Roller, A.; Arion, V. B.; Grgurić-Šipka, S. Synthesis, Characterisation and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes with 1H-Benzimidazole-2-Carboxylic Acid. Journal of Organometallic Chemistry 2016, 819, 61–68. https://doi.org/10.1016/j.jorganchem.2016.06.024
ER  - 
@book{
author = "Pantić, Darko N. and Aranđelović, Sandra and Radulović, Siniša and Roller, Alexander and Arion, Vladimir B. and Grgurić-Šipka, Sanja",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3633",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Journal of Organometallic Chemistry",
title = "Supplementary data for the article: Pantić, D. N.; Arancrossed D Signelović, S.; Radulović, S.; Roller, A.; Arion, V. B.; Grgurić-Šipka, S. Synthesis, Characterisation and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes with 1H-Benzimidazole-2-Carboxylic Acid. Journal of Organometallic Chemistry 2016, 819, 61–68. https://doi.org/10.1016/j.jorganchem.2016.06.024"
}
Pantić, D. N., Aranđelović, S., Radulović, S., Roller, A., Arion, V. B.,& Grgurić-Šipka, S. (2016). Supplementary data for the article: Pantić, D. N.; Arancrossed D Signelović, S.; Radulović, S.; Roller, A.; Arion, V. B.; Grgurić-Šipka, S. Synthesis, Characterisation and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes with 1H-Benzimidazole-2-Carboxylic Acid. Journal of Organometallic Chemistry 2016, 819, 61–68. https://doi.org/10.1016/j.jorganchem.2016.06.024.
Journal of Organometallic Chemistry
Elsevier Science Sa, Lausanne..
Pantić DN, Aranđelović S, Radulović S, Roller A, Arion VB, Grgurić-Šipka S. Supplementary data for the article: Pantić, D. N.; Arancrossed D Signelović, S.; Radulović, S.; Roller, A.; Arion, V. B.; Grgurić-Šipka, S. Synthesis, Characterisation and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes with 1H-Benzimidazole-2-Carboxylic Acid. Journal of Organometallic Chemistry 2016, 819, 61–68. https://doi.org/10.1016/j.jorganchem.2016.06.024. Journal of Organometallic Chemistry. 2016;
Pantić Darko N., Aranđelović Sandra, Radulović Siniša, Roller Alexander, Arion Vladimir B., Grgurić-Šipka Sanja, "Supplementary data for the article: Pantić, D. N.; Arancrossed D Signelović, S.; Radulović, S.; Roller, A.; Arion, V. B.; Grgurić-Šipka, S. Synthesis, Characterisation and Cytotoxic Activity of Organoruthenium(II)-Halido Complexes with 1H-Benzimidazole-2-Carboxylic Acid. Journal of Organometallic Chemistry 2016, 819, 61–68. https://doi.org/10.1016/j.jorganchem.2016.06.024" Journal of Organometallic Chemistry (2016)

Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands

Nikolić, Stefan; Rangasamy, Loganathan; Gligorijević, Nevenka; Aranđelović, Sandra; Radulović, Siniša; Gasser, Gilles; Grgurić-Šipka, Sanja

(Elsevier Science Inc, New York, 2016)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Rangasamy, Loganathan
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Gasser, Gilles
AU  - Grgurić-Šipka, Sanja
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3638
AB  - Three new ruthenium(II)-arene complexes, namely [(eta(6)-p-cymene)Ru(Me(2)dppz)Cl]PF6 (1), [(eta(6)-benzene)Ru(Me(2)dppz)Cl]PF6 (2) and [(eta(6)-p-cymene)Ru(aip)Cl]PF6 (3) (Me(2)dppz = 11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine; aip = 2-(9-anthryl)-1H-imidazo[4,5-f] [1,10] phenanthroline) have been synthesized and characterized using different spectroscopic techniques including elemental analysis. The complexes were found to be well soluble and stable in DMSO. The biological activity of the three complexes was tested in three different human cancer cell lines (A549, MDA-MB-231 and HeLa) and in one human non-cancerous cell line (MRC-5). Complexes 1 and 3, carrying eta(6)-p-cymene as the arene ligand, were shown to be toxic in all cell lines in the low micromolar/subnanomolar range, with complex 1 being the most cytotoxic complex of the series. Flow cytometry analysis revealed that complex 1 caused concentration- and time-dependent arrest of the cell cycle in G2-M and S phases in HeLa cells. This event is followed by the accumulation of the sub-G1 DNA content after 48 h, in levels higher than cisplatin and in the absence of phosphatidylserine externalization. Fluorescent microscopy and acridine orange/ethidium bromide staining revealed that complex 1 induced both apoptotic and necrotic cell morphology characteristics. Drug-accumulation and DNA-binding studies performed by inductively coupled plasma mass spectrometry in HeLa cells showed that the total ruthenium uptake increased in a time- and concentration-dependent manner, and that complex 1 accumulated more efficiently than cisplatin at equimolar concentrations. The introduction of a Me(2)dppz ligand into the ruthenium(II)-p-cymene scaffold was found to allow the discovery of a strongly cytotoxic complex with significantly higher cellular uptake and DNA-binding properties than cisplatin. (C) 2016 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands
VL  - 160
SP  - 156
EP  - 165
DO  - 10.1016/j.jinorgbio.2016.01.005
ER  - 
@article{
author = "Nikolić, Stefan and Rangasamy, Loganathan and Gligorijević, Nevenka and Aranđelović, Sandra and Radulović, Siniša and Gasser, Gilles and Grgurić-Šipka, Sanja",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3638",
abstract = "Three new ruthenium(II)-arene complexes, namely [(eta(6)-p-cymene)Ru(Me(2)dppz)Cl]PF6 (1), [(eta(6)-benzene)Ru(Me(2)dppz)Cl]PF6 (2) and [(eta(6)-p-cymene)Ru(aip)Cl]PF6 (3) (Me(2)dppz = 11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine; aip = 2-(9-anthryl)-1H-imidazo[4,5-f] [1,10] phenanthroline) have been synthesized and characterized using different spectroscopic techniques including elemental analysis. The complexes were found to be well soluble and stable in DMSO. The biological activity of the three complexes was tested in three different human cancer cell lines (A549, MDA-MB-231 and HeLa) and in one human non-cancerous cell line (MRC-5). Complexes 1 and 3, carrying eta(6)-p-cymene as the arene ligand, were shown to be toxic in all cell lines in the low micromolar/subnanomolar range, with complex 1 being the most cytotoxic complex of the series. Flow cytometry analysis revealed that complex 1 caused concentration- and time-dependent arrest of the cell cycle in G2-M and S phases in HeLa cells. This event is followed by the accumulation of the sub-G1 DNA content after 48 h, in levels higher than cisplatin and in the absence of phosphatidylserine externalization. Fluorescent microscopy and acridine orange/ethidium bromide staining revealed that complex 1 induced both apoptotic and necrotic cell morphology characteristics. Drug-accumulation and DNA-binding studies performed by inductively coupled plasma mass spectrometry in HeLa cells showed that the total ruthenium uptake increased in a time- and concentration-dependent manner, and that complex 1 accumulated more efficiently than cisplatin at equimolar concentrations. The introduction of a Me(2)dppz ligand into the ruthenium(II)-p-cymene scaffold was found to allow the discovery of a strongly cytotoxic complex with significantly higher cellular uptake and DNA-binding properties than cisplatin. (C) 2016 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands",
volume = "160",
pages = "156-165",
doi = "10.1016/j.jinorgbio.2016.01.005"
}
Nikolić, S., Rangasamy, L., Gligorijević, N., Aranđelović, S., Radulović, S., Gasser, G.,& Grgurić-Šipka, S. (2016). Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands.
Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 160, 156-165.
https://doi.org/10.1016/j.jinorgbio.2016.01.005
Nikolić S, Rangasamy L, Gligorijević N, Aranđelović S, Radulović S, Gasser G, Grgurić-Šipka S. Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. Journal of Inorganic Biochemistry. 2016;160:156-165
Nikolić Stefan, Rangasamy Loganathan, Gligorijević Nevenka, Aranđelović Sandra, Radulović Siniša, Gasser Gilles, Grgurić-Šipka Sanja, "Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands" Journal of Inorganic Biochemistry, 160 (2016):156-165,
https://doi.org/10.1016/j.jinorgbio.2016.01.005 .
30
29
30

Supplementary data for the article: Nikolic, S.; Rangasamy, L.; Gligorijevic, N.; Arandelovic, S.; Radulovic, S.; Gasser, G.; Grguric-Sipka, S. Synthesis, Characterization and Biological Evaluation of Novel Ru(II)-Arene Complexes Containing Intercalating Ligands. J. Inorg. Biochem. 2016, 160, 156–165. https://doi.org/10.1016/j.jinorgbio.2016.01.005

Nikolić, Stefan; Rangasamy, Loganathan; Gligorijević, Nevenka; Aranđelović, Sandra; Radulović, Siniša; Gasser, Gilles; Grgurić-Šipka, Sanja

(Elsevier Science Inc, New York, 2016)

TY  - BOOK
AU  - Nikolić, Stefan
AU  - Rangasamy, Loganathan
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Gasser, Gilles
AU  - Grgurić-Šipka, Sanja
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3639
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Supplementary data for the article: Nikolic, S.; Rangasamy, L.; Gligorijevic, N.; Arandelovic, S.; Radulovic, S.; Gasser, G.; Grguric-Sipka, S. Synthesis, Characterization and Biological Evaluation of Novel Ru(II)-Arene Complexes Containing Intercalating Ligands. J. Inorg. Biochem. 2016, 160, 156–165. https://doi.org/10.1016/j.jinorgbio.2016.01.005
ER  - 
@book{
author = "Nikolić, Stefan and Rangasamy, Loganathan and Gligorijević, Nevenka and Aranđelović, Sandra and Radulović, Siniša and Gasser, Gilles and Grgurić-Šipka, Sanja",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3639",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Supplementary data for the article: Nikolic, S.; Rangasamy, L.; Gligorijevic, N.; Arandelovic, S.; Radulovic, S.; Gasser, G.; Grguric-Sipka, S. Synthesis, Characterization and Biological Evaluation of Novel Ru(II)-Arene Complexes Containing Intercalating Ligands. J. Inorg. Biochem. 2016, 160, 156–165. https://doi.org/10.1016/j.jinorgbio.2016.01.005"
}
Nikolić, S., Rangasamy, L., Gligorijević, N., Aranđelović, S., Radulović, S., Gasser, G.,& Grgurić-Šipka, S. (2016). Supplementary data for the article: Nikolic, S.; Rangasamy, L.; Gligorijevic, N.; Arandelovic, S.; Radulovic, S.; Gasser, G.; Grguric-Sipka, S. Synthesis, Characterization and Biological Evaluation of Novel Ru(II)-Arene Complexes Containing Intercalating Ligands. J. Inorg. Biochem. 2016, 160, 156–165. https://doi.org/10.1016/j.jinorgbio.2016.01.005.
Journal of Inorganic Biochemistry
Elsevier Science Inc, New York..
Nikolić S, Rangasamy L, Gligorijević N, Aranđelović S, Radulović S, Gasser G, Grgurić-Šipka S. Supplementary data for the article: Nikolic, S.; Rangasamy, L.; Gligorijevic, N.; Arandelovic, S.; Radulovic, S.; Gasser, G.; Grguric-Sipka, S. Synthesis, Characterization and Biological Evaluation of Novel Ru(II)-Arene Complexes Containing Intercalating Ligands. J. Inorg. Biochem. 2016, 160, 156–165. https://doi.org/10.1016/j.jinorgbio.2016.01.005. Journal of Inorganic Biochemistry. 2016;
Nikolić Stefan, Rangasamy Loganathan, Gligorijević Nevenka, Aranđelović Sandra, Radulović Siniša, Gasser Gilles, Grgurić-Šipka Sanja, "Supplementary data for the article: Nikolic, S.; Rangasamy, L.; Gligorijevic, N.; Arandelovic, S.; Radulovic, S.; Gasser, G.; Grguric-Sipka, S. Synthesis, Characterization and Biological Evaluation of Novel Ru(II)-Arene Complexes Containing Intercalating Ligands. J. Inorg. Biochem. 2016, 160, 156–165. https://doi.org/10.1016/j.jinorgbio.2016.01.005" Journal of Inorganic Biochemistry (2016)

Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands

Nikolić, Stefan; Rangasamy, Loganathan; Gligorijević, Nevenka; Aranđelović, Sandra; Radulović, Siniša; Gasser, Gilles; Grgurić-Šipka, Sanja

(Elsevier Science Inc, New York, 2016)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Rangasamy, Loganathan
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Gasser, Gilles
AU  - Grgurić-Šipka, Sanja
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2272
AB  - Three new ruthenium(II)-arene complexes, namely [(eta(6)-p-cymene)Ru(Me(2)dppz)Cl]PF6 (1), [(eta(6)-benzene)Ru(Me(2)dppz)Cl]PF6 (2) and [(eta(6)-p-cymene)Ru(aip)Cl]PF6 (3) (Me(2)dppz = 11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine; aip = 2-(9-anthryl)-1H-imidazo[4,5-f] [1,10] phenanthroline) have been synthesized and characterized using different spectroscopic techniques including elemental analysis. The complexes were found to be well soluble and stable in DMSO. The biological activity of the three complexes was tested in three different human cancer cell lines (A549, MDA-MB-231 and HeLa) and in one human non-cancerous cell line (MRC-5). Complexes 1 and 3, carrying eta(6)-p-cymene as the arene ligand, were shown to be toxic in all cell lines in the low micromolar/subnanomolar range, with complex 1 being the most cytotoxic complex of the series. Flow cytometry analysis revealed that complex 1 caused concentration- and time-dependent arrest of the cell cycle in G2-M and S phases in HeLa cells. This event is followed by the accumulation of the sub-G1 DNA content after 48 h, in levels higher than cisplatin and in the absence of phosphatidylserine externalization. Fluorescent microscopy and acridine orange/ethidium bromide staining revealed that complex 1 induced both apoptotic and necrotic cell morphology characteristics. Drug-accumulation and DNA-binding studies performed by inductively coupled plasma mass spectrometry in HeLa cells showed that the total ruthenium uptake increased in a time- and concentration-dependent manner, and that complex 1 accumulated more efficiently than cisplatin at equimolar concentrations. The introduction of a Me(2)dppz ligand into the ruthenium(II)-p-cymene scaffold was found to allow the discovery of a strongly cytotoxic complex with significantly higher cellular uptake and DNA-binding properties than cisplatin. (C) 2016 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands
VL  - 160
SP  - 156
EP  - 165
DO  - 10.1016/j.jinorgbio.2016.01.005
ER  - 
@article{
author = "Nikolić, Stefan and Rangasamy, Loganathan and Gligorijević, Nevenka and Aranđelović, Sandra and Radulović, Siniša and Gasser, Gilles and Grgurić-Šipka, Sanja",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2272",
abstract = "Three new ruthenium(II)-arene complexes, namely [(eta(6)-p-cymene)Ru(Me(2)dppz)Cl]PF6 (1), [(eta(6)-benzene)Ru(Me(2)dppz)Cl]PF6 (2) and [(eta(6)-p-cymene)Ru(aip)Cl]PF6 (3) (Me(2)dppz = 11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine; aip = 2-(9-anthryl)-1H-imidazo[4,5-f] [1,10] phenanthroline) have been synthesized and characterized using different spectroscopic techniques including elemental analysis. The complexes were found to be well soluble and stable in DMSO. The biological activity of the three complexes was tested in three different human cancer cell lines (A549, MDA-MB-231 and HeLa) and in one human non-cancerous cell line (MRC-5). Complexes 1 and 3, carrying eta(6)-p-cymene as the arene ligand, were shown to be toxic in all cell lines in the low micromolar/subnanomolar range, with complex 1 being the most cytotoxic complex of the series. Flow cytometry analysis revealed that complex 1 caused concentration- and time-dependent arrest of the cell cycle in G2-M and S phases in HeLa cells. This event is followed by the accumulation of the sub-G1 DNA content after 48 h, in levels higher than cisplatin and in the absence of phosphatidylserine externalization. Fluorescent microscopy and acridine orange/ethidium bromide staining revealed that complex 1 induced both apoptotic and necrotic cell morphology characteristics. Drug-accumulation and DNA-binding studies performed by inductively coupled plasma mass spectrometry in HeLa cells showed that the total ruthenium uptake increased in a time- and concentration-dependent manner, and that complex 1 accumulated more efficiently than cisplatin at equimolar concentrations. The introduction of a Me(2)dppz ligand into the ruthenium(II)-p-cymene scaffold was found to allow the discovery of a strongly cytotoxic complex with significantly higher cellular uptake and DNA-binding properties than cisplatin. (C) 2016 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands",
volume = "160",
pages = "156-165",
doi = "10.1016/j.jinorgbio.2016.01.005"
}
Nikolić, S., Rangasamy, L., Gligorijević, N., Aranđelović, S., Radulović, S., Gasser, G.,& Grgurić-Šipka, S. (2016). Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands.
Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 160, 156-165.
https://doi.org/10.1016/j.jinorgbio.2016.01.005
Nikolić S, Rangasamy L, Gligorijević N, Aranđelović S, Radulović S, Gasser G, Grgurić-Šipka S. Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. Journal of Inorganic Biochemistry. 2016;160:156-165
Nikolić Stefan, Rangasamy Loganathan, Gligorijević Nevenka, Aranđelović Sandra, Radulović Siniša, Gasser Gilles, Grgurić-Šipka Sanja, "Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands" Journal of Inorganic Biochemistry, 160 (2016):156-165,
https://doi.org/10.1016/j.jinorgbio.2016.01.005 .
30
29
30

Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid

Pantić, Darko N.; Aranđelović, Sandra; Radulović, Siniša; Roller, Alexander; Arion, Vladimir B.; Grgurić-Šipka, Sanja

(Elsevier Science Sa, Lausanne, 2016)

TY  - JOUR
AU  - Pantić, Darko N.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Roller, Alexander
AU  - Arion, Vladimir B.
AU  - Grgurić-Šipka, Sanja
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2297
AB  - Three new ruthenium(II)-earene halido complexes of general formula [(eta(6-)p-cymene)RuX(L)] (C1-C3) were synthesised by reaction of [(eta(6)-p-cymene)RuX2](2) (X- = Cl-, Br-, I-) with 1H-benzimidazole-2-carboxylic acid (HL) in ethanol. The complexes were characterised by elemental analysis, mass spectrometry, IR, H-1 and C-13 NMR spectroscopy. The 1H-benzimidazole-2-carboxylate was found to act as a bidentate N,-Oechelating ligand. Single-crystal X-ray diffraction analysis confirmed the "piano-stool" geometry of C3. The cytotoxic activity of the ligand precursor and ruthenium complexes was tested in human cancer cell lines: cervical carcinoma (HeLa), breast carcinoma (MDA-MB-231), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5), by MTT assay. The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to that of HL. The latter was devoid of activity in the range of concentrations up to 300 mu M. Complex C3, carrying an iodido leaving ligand, exhibited moderate, but selective cytotoxicity toward HeLa, MDA-MB-231 and K562 cell lines, with IC50 values: 73.7, 60.9 and 53.9 mu M, respectively, being less toxic against MRC-5 cells (IC50 - 175.9 mu M). Complexes C1 and C2 showed moderate to low cytotoxicity in HeLa and K562 cells. (C) 2016 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Sa, Lausanne
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid
VL  - 819
SP  - 61
EP  - 68
DO  - 10.1016/j.jorganchem.2016.06.024
ER  - 
@article{
author = "Pantić, Darko N. and Aranđelović, Sandra and Radulović, Siniša and Roller, Alexander and Arion, Vladimir B. and Grgurić-Šipka, Sanja",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2297",
abstract = "Three new ruthenium(II)-earene halido complexes of general formula [(eta(6-)p-cymene)RuX(L)] (C1-C3) were synthesised by reaction of [(eta(6)-p-cymene)RuX2](2) (X- = Cl-, Br-, I-) with 1H-benzimidazole-2-carboxylic acid (HL) in ethanol. The complexes were characterised by elemental analysis, mass spectrometry, IR, H-1 and C-13 NMR spectroscopy. The 1H-benzimidazole-2-carboxylate was found to act as a bidentate N,-Oechelating ligand. Single-crystal X-ray diffraction analysis confirmed the "piano-stool" geometry of C3. The cytotoxic activity of the ligand precursor and ruthenium complexes was tested in human cancer cell lines: cervical carcinoma (HeLa), breast carcinoma (MDA-MB-231), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5), by MTT assay. The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to that of HL. The latter was devoid of activity in the range of concentrations up to 300 mu M. Complex C3, carrying an iodido leaving ligand, exhibited moderate, but selective cytotoxicity toward HeLa, MDA-MB-231 and K562 cell lines, with IC50 values: 73.7, 60.9 and 53.9 mu M, respectively, being less toxic against MRC-5 cells (IC50 - 175.9 mu M). Complexes C1 and C2 showed moderate to low cytotoxicity in HeLa and K562 cells. (C) 2016 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid",
volume = "819",
pages = "61-68",
doi = "10.1016/j.jorganchem.2016.06.024"
}
Pantić, D. N., Aranđelović, S., Radulović, S., Roller, A., Arion, V. B.,& Grgurić-Šipka, S. (2016). Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid.
Journal of Organometallic Chemistry
Elsevier Science Sa, Lausanne., 819, 61-68.
https://doi.org/10.1016/j.jorganchem.2016.06.024
Pantić DN, Aranđelović S, Radulović S, Roller A, Arion VB, Grgurić-Šipka S. Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid. Journal of Organometallic Chemistry. 2016;819:61-68
Pantić Darko N., Aranđelović Sandra, Radulović Siniša, Roller Alexander, Arion Vladimir B., Grgurić-Šipka Sanja, "Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid" Journal of Organometallic Chemistry, 819 (2016):61-68,
https://doi.org/10.1016/j.jorganchem.2016.06.024 .
12
10
12

Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041

Nikolić, Stefan; Opsenica, Dejan M.; Filipović, Vuk; Dojčinović, Biljana P.; Aranđelović, Sandra; Radulović, Siniša; Grgurić-Šipka, Sanja

(Amer Chemical Soc, Washington, 2015)

TY  - BOOK
AU  - Nikolić, Stefan
AU  - Opsenica, Dejan M.
AU  - Filipović, Vuk
AU  - Dojčinović, Biljana P.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3429
PB  - Amer Chemical Soc, Washington
T2  - Organometallics
T1  - Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041
ER  - 
@book{
author = "Nikolić, Stefan and Opsenica, Dejan M. and Filipović, Vuk and Dojčinović, Biljana P. and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3429",
publisher = "Amer Chemical Soc, Washington",
journal = "Organometallics",
title = "Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041"
}
Nikolić, S., Opsenica, D. M., Filipović, V., Dojčinović, B. P., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S. (2015). Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041.
Organometallics
Amer Chemical Soc, Washington..
Nikolić S, Opsenica DM, Filipović V, Dojčinović BP, Aranđelović S, Radulović S, Grgurić-Šipka S. Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041. Organometallics. 2015;
Nikolić Stefan, Opsenica Dejan M., Filipović Vuk, Dojčinović Biljana P., Aranđelović Sandra, Radulović Siniša, Grgurić-Šipka Sanja, "Supplementary data for article: Nikolić, S.; Opsenica, D. M.; Filipović, V.; Dojčinović, B.; Arandelović, S.; Radulović, S.; Grgurić-Šipka, S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics 2015, 34 (14), 3464–3473. https://doi.org/10.1021/acs.organomet.5b00041" Organometallics (2015)

Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes

Nikolić, Stefan; Opsenica, Dejan M.; Filipović, Vuk; Dojčinović, Biljana P.; Aranđelović, Sandra; Radulović, Siniša; Grgurić-Šipka, Sanja

(Amer Chemical Soc, Washington, 2015)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Opsenica, Dejan M.
AU  - Filipović, Vuk
AU  - Dojčinović, Biljana P.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1746
AB  - Two p-cymenerutheniumchlorido complexes with thiourea derivative of 7-chloroquinoline (C1) and pyridine-3-imidazole (C2) were synthesized starting from [(eta(6)-p-cymene)RuCl2](2) and corresponding ligands. The structures of complexes were determined with elemental analysis and IR, ESIMS, H-1 and C-13{H-1} NMR, and 2D H-1-N-15 correlation NMR spectroscopy. Cytotoxic activities examined by the MTT assay were performed in five human neoplastic cell lines (HeLa, K562, A549, MDA-MB-231, EA.hy926) and one nontumor human fetal lung fibroblast cell line (MRC-5). Tested complexes exhibited low micromolar activities with IC50 in the range 11.03-56.45 mu M, while ligands L1 and L2 were significantly less active. Complex C1 showed cytoselective activity toward the K562 cell line (IC50 = 11.03 +/- 1.39 mu M) and was 3 times less active against the nontumor MRC-5 cell line. Flow cytometry analysis indicated that complexes C1 and C2 after 24 h treatment caused a concentration-dependent increase of the apoptotic sub-G1 fraction (up to 18.4%), comparable to cis-diamminedichloridoplatinum(II) (cisplatin, CDDP), although without other substantial alterations of the cell cycle. A drug-accumulation and DNA-binding study performed by ICP-MS in the K562 cell line revealed that complex C1 had a high intracellular uptake (1.38 mu g Ru/10 (6) cells), which significantly exceeded the intracellular uptake levels of CDDP (0.29 mu g Pt/10 (6) cells) and C2 (0.08 mu g Ru/10 (6) cells). However, both ruthenium complexes C1 and C2 bind to cellular DNA less efficiently in comparison to CDDP. The structure-activity relationship clearly suggested that introduction of a 7-chloroquinoline moiety in the ruthenium(II)-p-cymene complex significantly contributed to the intracellular uptake of C1 and higher cytotoxicity and cytoselectivity.
PB  - Amer Chemical Soc, Washington
T2  - Organometallics
T1  - Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes
VL  - 34
IS  - 14
SP  - 3464
EP  - 3473
DO  - 10.1021/acs.organomet.5b00041
ER  - 
@article{
author = "Nikolić, Stefan and Opsenica, Dejan M. and Filipović, Vuk and Dojčinović, Biljana P. and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1746",
abstract = "Two p-cymenerutheniumchlorido complexes with thiourea derivative of 7-chloroquinoline (C1) and pyridine-3-imidazole (C2) were synthesized starting from [(eta(6)-p-cymene)RuCl2](2) and corresponding ligands. The structures of complexes were determined with elemental analysis and IR, ESIMS, H-1 and C-13{H-1} NMR, and 2D H-1-N-15 correlation NMR spectroscopy. Cytotoxic activities examined by the MTT assay were performed in five human neoplastic cell lines (HeLa, K562, A549, MDA-MB-231, EA.hy926) and one nontumor human fetal lung fibroblast cell line (MRC-5). Tested complexes exhibited low micromolar activities with IC50 in the range 11.03-56.45 mu M, while ligands L1 and L2 were significantly less active. Complex C1 showed cytoselective activity toward the K562 cell line (IC50 = 11.03 +/- 1.39 mu M) and was 3 times less active against the nontumor MRC-5 cell line. Flow cytometry analysis indicated that complexes C1 and C2 after 24 h treatment caused a concentration-dependent increase of the apoptotic sub-G1 fraction (up to 18.4%), comparable to cis-diamminedichloridoplatinum(II) (cisplatin, CDDP), although without other substantial alterations of the cell cycle. A drug-accumulation and DNA-binding study performed by ICP-MS in the K562 cell line revealed that complex C1 had a high intracellular uptake (1.38 mu g Ru/10 (6) cells), which significantly exceeded the intracellular uptake levels of CDDP (0.29 mu g Pt/10 (6) cells) and C2 (0.08 mu g Ru/10 (6) cells). However, both ruthenium complexes C1 and C2 bind to cellular DNA less efficiently in comparison to CDDP. The structure-activity relationship clearly suggested that introduction of a 7-chloroquinoline moiety in the ruthenium(II)-p-cymene complex significantly contributed to the intracellular uptake of C1 and higher cytotoxicity and cytoselectivity.",
publisher = "Amer Chemical Soc, Washington",
journal = "Organometallics",
title = "Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes",
volume = "34",
number = "14",
pages = "3464-3473",
doi = "10.1021/acs.organomet.5b00041"
}
Nikolić, S., Opsenica, D. M., Filipović, V., Dojčinović, B. P., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S. (2015). Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes.
Organometallics
Amer Chemical Soc, Washington., 34(14), 3464-3473.
https://doi.org/10.1021/acs.organomet.5b00041
Nikolić S, Opsenica DM, Filipović V, Dojčinović BP, Aranđelović S, Radulović S, Grgurić-Šipka S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. Organometallics. 2015;34(14):3464-3473
Nikolić Stefan, Opsenica Dejan M., Filipović Vuk, Dojčinović Biljana P., Aranđelović Sandra, Radulović Siniša, Grgurić-Šipka Sanja, "Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes" Organometallics, 34, no. 14 (2015):3464-3473,
https://doi.org/10.1021/acs.organomet.5b00041 .
1
32
32
35

Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters

Zmejkovski, Bojana B.; Savić, Aleksandar; Poljarević, Jelena; Pantelić, Nebojša Đ.; Aranđelović, Sandra; Radulović, Siniša; Grgurić-Šipka, Sanja; Kaluđerović, Goran N.; Sabo, Tibor

(Pergamon-Elsevier Science Ltd, Oxford, 2014)

TY  - JOUR
AU  - Zmejkovski, Bojana B.
AU  - Savić, Aleksandar
AU  - Poljarević, Jelena
AU  - Pantelić, Nebojša Đ.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
AU  - Kaluđerović, Goran N.
AU  - Sabo, Tibor
PY  - 2014
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1840
AB  - Six palladium(II) complexes with (S,S)-R(2)edda-type esters ((S,S)-R2edda-type; (S,S)-eddch = (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, 1-3; (S,S)-pddch = (S,S)-propylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Et, n-Pr, 4, 5; and (S,S)-eddip = (S,S)-ethylenediamne-N,N'-di-2-propanoate, R = i-Am, 6) were synthesized, characterized by IR, NMR spectroscopy, ESI-MS and elemental analysis. DFT calculations indicate that in case of 1-4, the most stable isomers are with (S,S)- and (R,S)-configuration of nitrogen atoms, but for complex 6 (R,R)- and (R,S)-N,N'-configured isomers. Furthermore, complex 5 was obtained as (S,S)-N,N' configured isomer. Cytotoxicity study was performed against human cervical adenocarcinoma (HeLa), human alveolar basal adenocarcinoma (A549) and non-cancerous human fetal lung fibroblast (MRC-5) cell lines using colorimetric MTT assay. From the investigated palladium(II) complexes 2, 3 and 5 exhibited highest cytotoxic potential against HeLa (IC50: 28.5 +/- 3.9, 29.5 +/- 1.3 and 34.3 +/- 3.2, respectively). (C) 2014 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Polyhedron
T1  - Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters
VL  - 80
SP  - 106
EP  - 111
DO  - 10.1016/j.poly.2014.02.026
ER  - 
@article{
author = "Zmejkovski, Bojana B. and Savić, Aleksandar and Poljarević, Jelena and Pantelić, Nebojša Đ. and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja and Kaluđerović, Goran N. and Sabo, Tibor",
year = "2014",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1840",
abstract = "Six palladium(II) complexes with (S,S)-R(2)edda-type esters ((S,S)-R2edda-type; (S,S)-eddch = (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, 1-3; (S,S)-pddch = (S,S)-propylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate, R = Et, n-Pr, 4, 5; and (S,S)-eddip = (S,S)-ethylenediamne-N,N'-di-2-propanoate, R = i-Am, 6) were synthesized, characterized by IR, NMR spectroscopy, ESI-MS and elemental analysis. DFT calculations indicate that in case of 1-4, the most stable isomers are with (S,S)- and (R,S)-configuration of nitrogen atoms, but for complex 6 (R,R)- and (R,S)-N,N'-configured isomers. Furthermore, complex 5 was obtained as (S,S)-N,N' configured isomer. Cytotoxicity study was performed against human cervical adenocarcinoma (HeLa), human alveolar basal adenocarcinoma (A549) and non-cancerous human fetal lung fibroblast (MRC-5) cell lines using colorimetric MTT assay. From the investigated palladium(II) complexes 2, 3 and 5 exhibited highest cytotoxic potential against HeLa (IC50: 28.5 +/- 3.9, 29.5 +/- 1.3 and 34.3 +/- 3.2, respectively). (C) 2014 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Polyhedron",
title = "Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters",
volume = "80",
pages = "106-111",
doi = "10.1016/j.poly.2014.02.026"
}
Zmejkovski, B. B., Savić, A., Poljarević, J., Pantelić, N. Đ., Aranđelović, S., Radulović, S., Grgurić-Šipka, S., Kaluđerović, G. N.,& Sabo, T. (2014). Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters.
Polyhedron
Pergamon-Elsevier Science Ltd, Oxford., 80, 106-111.
https://doi.org/10.1016/j.poly.2014.02.026
Zmejkovski BB, Savić A, Poljarević J, Pantelić NĐ, Aranđelović S, Radulović S, Grgurić-Šipka S, Kaluđerović GN, Sabo T. Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters. Polyhedron. 2014;80:106-111
Zmejkovski Bojana B., Savić Aleksandar, Poljarević Jelena, Pantelić Nebojša Đ., Aranđelović Sandra, Radulović Siniša, Grgurić-Šipka Sanja, Kaluđerović Goran N., Sabo Tibor, "Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R(2)edda-type esters" Polyhedron, 80 (2014):106-111,
https://doi.org/10.1016/j.poly.2014.02.026 .
10
10
10

Biological activity of novel platinum(II)-iodido complexes

Filipović, Lana; Savić, Aleksandar; Aranđelović, Sandra; Sabo, Tibor; Grgurić-Šipka, Sanja; Radulović, Siniša

(Elsevier Sci Ltd, Oxford, 2014)

TY  - CONF
AU  - Filipović, Lana
AU  - Savić, Aleksandar
AU  - Aranđelović, Sandra
AU  - Sabo, Tibor
AU  - Grgurić-Šipka, Sanja
AU  - Radulović, Siniša
PY  - 2014
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1678
PB  - Elsevier Sci Ltd, Oxford
C3  - European Journal of Cancer / EJC
T1  - Biological activity of novel platinum(II)-iodido complexes
VL  - 50
DO  - 10.1016/S0959-8049(14)50095-0
ER  - 
@conference{
author = "Filipović, Lana and Savić, Aleksandar and Aranđelović, Sandra and Sabo, Tibor and Grgurić-Šipka, Sanja and Radulović, Siniša",
year = "2014",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1678",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "European Journal of Cancer / EJC",
title = "Biological activity of novel platinum(II)-iodido complexes",
volume = "50",
doi = "10.1016/S0959-8049(14)50095-0"
}
Filipović, L., Savić, A., Aranđelović, S., Sabo, T., Grgurić-Šipka, S.,& Radulović, S. (2014). Biological activity of novel platinum(II)-iodido complexes.
European Journal of Cancer / EJC
Elsevier Sci Ltd, Oxford., 50.
https://doi.org/10.1016/S0959-8049(14)50095-0
Filipović L, Savić A, Aranđelović S, Sabo T, Grgurić-Šipka S, Radulović S. Biological activity of novel platinum(II)-iodido complexes. European Journal of Cancer / EJC. 2014;50
Filipović Lana, Savić Aleksandar, Aranđelović Sandra, Sabo Tibor, Grgurić-Šipka Sanja, Radulović Siniša, "Biological activity of novel platinum(II)-iodido complexes" European Journal of Cancer / EJC, 50 (2014),
https://doi.org/10.1016/S0959-8049(14)50095-0 .

Synthesis, characterization and cytotoxic activity of novel platinum(II) iodido complexes

Savić, Aleksandar; Filipović, Lana; Aranđelović, Sandra; Dojčinović, Biljana P.; Radulović, Siniša; Sabo, Tibor; Grgurić-Šipka, Sanja

(Elsevier France-Editions Scientifiques Medicales Elsevier, Paris, 2014)

TY  - JOUR
AU  - Savić, Aleksandar
AU  - Filipović, Lana
AU  - Aranđelović, Sandra
AU  - Dojčinović, Biljana P.
AU  - Radulović, Siniša
AU  - Sabo, Tibor
AU  - Grgurić-Šipka, Sanja
PY  - 2014
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1813
AB  - Novel Pt(II) complexes of general formula [PtI2(L1-3)], (C1-C3): where L1-3 are isobutyl, n-pentyl and isopentyl esters of (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid has been synthesized and characterized by elemental analysis, UV/Vis, IR, (H-1, C-13 and HSQC, Pt) NMR spectroscopy and ESI mass spectrometry. Spectroscopic data and computational studies have shown the usual square planar coordination geometry of synthesized complexes, with coordination of ligands via nitrogen donor atoms. The cytotoxic activity of novel ligands and corresponding complexes were investigated on a palette of different cells line. Complexes C1-C3 exhibited activity comparable to cisplatin, with IC50 values (04) ranging from 4.6 +/- 0.6 to 17.2 +/- 2, and showed the highest potential in HeLa, LS-174 and EA.hy.926 cells. Ligands L1-L3 exhibited two- to four-times less activity than corresponding complexes. Analysis of the mode of action in HeLa cells, by ICP-MS study, showed markedly higher intracellular accumulation and DNA binding affinity of C1-C3 versus cisplatin, after 4 h and 20 h post-treatment. Annexin-V-FITC assay, flow cytometry and fluorescence microscopy study demonstrated occurrence of cell death through both apoptotic and necrotic changes. Tested complexes, at corresponding IC50 concentrations, caused considerable "sub-G1" peak, without other substantial alterations of cell cycle, while only Cl induced higher level of phosphatidylserine externalization (11.7%), comparing to ligand L1 (4.9%) and cisplatin (8.4%). Structure-activity comparison indicated variations of C1-C3 cytotoxicity, related to the drug/ligand lipophilicity (C log P value), while intracellular platinum content and DNA platination increased on increase of length and branching of ester chain, in sequence: Cl (isobutyl)  lt  C2 (n-pentyl)  lt  C3 (isopentyl). (C) 2014 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, characterization and cytotoxic activity of novel platinum(II) iodido complexes
VL  - 82
SP  - 372
EP  - 384
DO  - 10.1016/j.ejmech.2014.05.060
ER  - 
@article{
author = "Savić, Aleksandar and Filipović, Lana and Aranđelović, Sandra and Dojčinović, Biljana P. and Radulović, Siniša and Sabo, Tibor and Grgurić-Šipka, Sanja",
year = "2014",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1813",
abstract = "Novel Pt(II) complexes of general formula [PtI2(L1-3)], (C1-C3): where L1-3 are isobutyl, n-pentyl and isopentyl esters of (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid has been synthesized and characterized by elemental analysis, UV/Vis, IR, (H-1, C-13 and HSQC, Pt) NMR spectroscopy and ESI mass spectrometry. Spectroscopic data and computational studies have shown the usual square planar coordination geometry of synthesized complexes, with coordination of ligands via nitrogen donor atoms. The cytotoxic activity of novel ligands and corresponding complexes were investigated on a palette of different cells line. Complexes C1-C3 exhibited activity comparable to cisplatin, with IC50 values (04) ranging from 4.6 +/- 0.6 to 17.2 +/- 2, and showed the highest potential in HeLa, LS-174 and EA.hy.926 cells. Ligands L1-L3 exhibited two- to four-times less activity than corresponding complexes. Analysis of the mode of action in HeLa cells, by ICP-MS study, showed markedly higher intracellular accumulation and DNA binding affinity of C1-C3 versus cisplatin, after 4 h and 20 h post-treatment. Annexin-V-FITC assay, flow cytometry and fluorescence microscopy study demonstrated occurrence of cell death through both apoptotic and necrotic changes. Tested complexes, at corresponding IC50 concentrations, caused considerable "sub-G1" peak, without other substantial alterations of cell cycle, while only Cl induced higher level of phosphatidylserine externalization (11.7%), comparing to ligand L1 (4.9%) and cisplatin (8.4%). Structure-activity comparison indicated variations of C1-C3 cytotoxicity, related to the drug/ligand lipophilicity (C log P value), while intracellular platinum content and DNA platination increased on increase of length and branching of ester chain, in sequence: Cl (isobutyl)  lt  C2 (n-pentyl)  lt  C3 (isopentyl). (C) 2014 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, characterization and cytotoxic activity of novel platinum(II) iodido complexes",
volume = "82",
pages = "372-384",
doi = "10.1016/j.ejmech.2014.05.060"
}
Savić, A., Filipović, L., Aranđelović, S., Dojčinović, B. P., Radulović, S., Sabo, T.,& Grgurić-Šipka, S. (2014). Synthesis, characterization and cytotoxic activity of novel platinum(II) iodido complexes.
European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 82, 372-384.
https://doi.org/10.1016/j.ejmech.2014.05.060
Savić A, Filipović L, Aranđelović S, Dojčinović BP, Radulović S, Sabo T, Grgurić-Šipka S. Synthesis, characterization and cytotoxic activity of novel platinum(II) iodido complexes. European Journal of Medicinal Chemistry. 2014;82:372-384
Savić Aleksandar, Filipović Lana, Aranđelović Sandra, Dojčinović Biljana P., Radulović Siniša, Sabo Tibor, Grgurić-Šipka Sanja, "Synthesis, characterization and cytotoxic activity of novel platinum(II) iodido complexes" European Journal of Medicinal Chemistry, 82 (2014):372-384,
https://doi.org/10.1016/j.ejmech.2014.05.060 .
23
24
25

Supplementary data for article: Milenković, M. R.; Bacchi, A.; Cantoni, G.; Radulović, S. S.; Gligorijević, N.; Aranđelović, S.; Sladić, D.; Vujčić, M.; Mitić, D.; Anđelković, K. K. Synthesis, Characterisation and Biological Activity of Co(III) Complex with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Ethyl Carbazate. Inorganica Chimica Acta 2013, 395, 33–43. https://doi.org/10.1016/j.ica.2012.09.043

Milenković, Milica R.; Bacchi, Alessia; Cantoni, Giulia; Radulović, Siniša; Gligorijević, Nevenka; Aranđelović, Sandra; Sladić, Dušan; Vujčić, Miroslava; Mitić, Dragana; Anđelković, Katarina K.

(Elsevier Science Sa, Lausanne, 2013)

TY  - BOOK
AU  - Milenković, Milica R.
AU  - Bacchi, Alessia
AU  - Cantoni, Giulia
AU  - Radulović, Siniša
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Mitić, Dragana
AU  - Anđelković, Katarina K.
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3533
PB  - Elsevier Science Sa, Lausanne
T2  - Inorganica Chimica Acta
T1  - Supplementary data for article: Milenković, M. R.; Bacchi, A.; Cantoni, G.; Radulović, S. S.; Gligorijević, N.; Aranđelović, S.; Sladić, D.; Vujčić, M.; Mitić, D.; Anđelković, K. K. Synthesis, Characterisation and Biological Activity of Co(III) Complex with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Ethyl Carbazate. Inorganica Chimica Acta 2013, 395, 33–43. https://doi.org/10.1016/j.ica.2012.09.043
ER  - 
@book{
author = "Milenković, Milica R. and Bacchi, Alessia and Cantoni, Giulia and Radulović, Siniša and Gligorijević, Nevenka and Aranđelović, Sandra and Sladić, Dušan and Vujčić, Miroslava and Mitić, Dragana and Anđelković, Katarina K.",
year = "2013",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3533",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Inorganica Chimica Acta",
title = "Supplementary data for article: Milenković, M. R.; Bacchi, A.; Cantoni, G.; Radulović, S. S.; Gligorijević, N.; Aranđelović, S.; Sladić, D.; Vujčić, M.; Mitić, D.; Anđelković, K. K. Synthesis, Characterisation and Biological Activity of Co(III) Complex with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Ethyl Carbazate. Inorganica Chimica Acta 2013, 395, 33–43. https://doi.org/10.1016/j.ica.2012.09.043"
}
Milenković, M. R., Bacchi, A., Cantoni, G., Radulović, S., Gligorijević, N., Aranđelović, S., Sladić, D., Vujčić, M., Mitić, D.,& Anđelković, K. K. (2013). Supplementary data for article: Milenković, M. R.; Bacchi, A.; Cantoni, G.; Radulović, S. S.; Gligorijević, N.; Aranđelović, S.; Sladić, D.; Vujčić, M.; Mitić, D.; Anđelković, K. K. Synthesis, Characterisation and Biological Activity of Co(III) Complex with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Ethyl Carbazate. Inorganica Chimica Acta 2013, 395, 33–43. https://doi.org/10.1016/j.ica.2012.09.043.
Inorganica Chimica Acta
Elsevier Science Sa, Lausanne..
Milenković MR, Bacchi A, Cantoni G, Radulović S, Gligorijević N, Aranđelović S, Sladić D, Vujčić M, Mitić D, Anđelković KK. Supplementary data for article: Milenković, M. R.; Bacchi, A.; Cantoni, G.; Radulović, S. S.; Gligorijević, N.; Aranđelović, S.; Sladić, D.; Vujčić, M.; Mitić, D.; Anđelković, K. K. Synthesis, Characterisation and Biological Activity of Co(III) Complex with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Ethyl Carbazate. Inorganica Chimica Acta 2013, 395, 33–43. https://doi.org/10.1016/j.ica.2012.09.043. Inorganica Chimica Acta. 2013;
Milenković Milica R., Bacchi Alessia, Cantoni Giulia, Radulović Siniša, Gligorijević Nevenka, Aranđelović Sandra, Sladić Dušan, Vujčić Miroslava, Mitić Dragana, Anđelković Katarina K., "Supplementary data for article: Milenković, M. R.; Bacchi, A.; Cantoni, G.; Radulović, S. S.; Gligorijević, N.; Aranđelović, S.; Sladić, D.; Vujčić, M.; Mitić, D.; Anđelković, K. K. Synthesis, Characterisation and Biological Activity of Co(III) Complex with the Condensation Product of 2-(Diphenylphosphino)Benzaldehyde and Ethyl Carbazate. Inorganica Chimica Acta 2013, 395, 33–43. https://doi.org/10.1016/j.ica.2012.09.043" Inorganica Chimica Acta (2013)