Filipović, Lana

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  • Filipović, Lana (7)
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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 .

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 .
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Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin

Filipović, Lana; Aranđelović, Sandra; Gligorijević, Nevenka; Krivokuca, Ana; Jankovic, Radmila; Srdić-Rajić, Tatjana; Rakic, Gordana; Tešić, Živoslav Lj.; Radulović, Siniša

(Assoc Radiology & Oncology, Ljubljana, 2013)

TY  - JOUR
AU  - Filipović, Lana
AU  - Aranđelović, Sandra
AU  - Gligorijević, Nevenka
AU  - Krivokuca, Ana
AU  - Jankovic, Radmila
AU  - Srdić-Rajić, Tatjana
AU  - Rakic, Gordana
AU  - Tešić, Živoslav Lj.
AU  - Radulović, Siniša
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1414
AB  - Background. In our previous study we reported the synthesis and cytotoxicity of two trans-platinum(II) complexes: trans-[PtCl2(3-acetylpyridine)(2)] (1) and trans-[PtCl2(4-acetylpyridine)(2)] (2), revealing significant cytotoxic potential of 2. In order to evaluate the mechanism underlying biological activity of both trans-Pt(II) isomers, comparative studies versus cisplatin were performed in HeLa, MRC-5 and MS1 cells. Materials and methods. The cytotoxic activity of the investigated complexes was determined using SRB assay. The colagenolytic activity was determined using gelatin zymography, while the effect of platinum complexes on matrix metalloproteinases 2 and 9 mRNA expression was evaluated by quantitative real-time PCR. Apoptotic potential and cell cycle alterations were determined by FACS analyses. Western blot analysis was used to evaluate the effect on expression of DNA-repair enzyme ERCC1, and quantitative real-time PCR was used for the ERCC1 mRNA expression analysis. In vitro antiangiogenic potential was determined by tube formation assay. Platinum content in intracellular DNA and proteins was determined by inductively coupled plasma-optical emission spectrometry. Results. Compound 2 displayed an apparent cytoselective profile, and flow cytometry analysis in HeLa cells indicated that 2 exerted antiproliferative effect through apoptosis induction, while 1 induced both apoptosis and necrosis. Action of 1 and 2, as analyzed by quantitative real-time PCR and Western blot, was associated with down-regulation of ERCC1. Both trans-complexes inhibited MMP-9 mRNA expression in HeLa, while 2 significantly abrogated in vitro tubulogenesis in MS1 cells. Conclusions. The ability of 2 to induce multiple and selective in vitro cytotoxic effects encourages further investigations of trans-platinum(II) complexes with substituted pyridines.
PB  - Assoc Radiology & Oncology, Ljubljana
T2  - Radiology and Oncology
T1  - Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin
VL  - 47
IS  - 4
SP  - 346
EP  - 357
DO  - 10.2478/raon-2013-0050
ER  - 
@article{
author = "Filipović, Lana and Aranđelović, Sandra and Gligorijević, Nevenka and Krivokuca, Ana and Jankovic, Radmila and Srdić-Rajić, Tatjana and Rakic, Gordana and Tešić, Živoslav Lj. and Radulović, Siniša",
year = "2013",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1414",
abstract = "Background. In our previous study we reported the synthesis and cytotoxicity of two trans-platinum(II) complexes: trans-[PtCl2(3-acetylpyridine)(2)] (1) and trans-[PtCl2(4-acetylpyridine)(2)] (2), revealing significant cytotoxic potential of 2. In order to evaluate the mechanism underlying biological activity of both trans-Pt(II) isomers, comparative studies versus cisplatin were performed in HeLa, MRC-5 and MS1 cells. Materials and methods. The cytotoxic activity of the investigated complexes was determined using SRB assay. The colagenolytic activity was determined using gelatin zymography, while the effect of platinum complexes on matrix metalloproteinases 2 and 9 mRNA expression was evaluated by quantitative real-time PCR. Apoptotic potential and cell cycle alterations were determined by FACS analyses. Western blot analysis was used to evaluate the effect on expression of DNA-repair enzyme ERCC1, and quantitative real-time PCR was used for the ERCC1 mRNA expression analysis. In vitro antiangiogenic potential was determined by tube formation assay. Platinum content in intracellular DNA and proteins was determined by inductively coupled plasma-optical emission spectrometry. Results. Compound 2 displayed an apparent cytoselective profile, and flow cytometry analysis in HeLa cells indicated that 2 exerted antiproliferative effect through apoptosis induction, while 1 induced both apoptosis and necrosis. Action of 1 and 2, as analyzed by quantitative real-time PCR and Western blot, was associated with down-regulation of ERCC1. Both trans-complexes inhibited MMP-9 mRNA expression in HeLa, while 2 significantly abrogated in vitro tubulogenesis in MS1 cells. Conclusions. The ability of 2 to induce multiple and selective in vitro cytotoxic effects encourages further investigations of trans-platinum(II) complexes with substituted pyridines.",
publisher = "Assoc Radiology & Oncology, Ljubljana",
journal = "Radiology and Oncology",
title = "Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin",
volume = "47",
number = "4",
pages = "346-357",
doi = "10.2478/raon-2013-0050"
}
Filipović, L., Aranđelović, S., Gligorijević, N., Krivokuca, A., Jankovic, R., Srdić-Rajić, T., Rakic, G., Tešić, Ž. Lj.,& Radulović, S. (2013). Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin.
Radiology and Oncology
Assoc Radiology & Oncology, Ljubljana., 47(4), 346-357.
https://doi.org/10.2478/raon-2013-0050
Filipović L, Aranđelović S, Gligorijević N, Krivokuca A, Jankovic R, Srdić-Rajić T, Rakic G, Tešić ŽL, Radulović S. Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin. Radiology and Oncology. 2013;47(4):346-357
Filipović Lana, Aranđelović Sandra, Gligorijević Nevenka, Krivokuca Ana, Jankovic Radmila, Srdić-Rajić Tatjana, Rakic Gordana, Tešić Živoslav Lj., Radulović Siniša, "Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin" Radiology and Oncology, 47, no. 4 (2013):346-357,
https://doi.org/10.2478/raon-2013-0050 .
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The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines

Rakic, Gordana M.; Grgurić-Šipka, Sanja; Kaluđerović, Goran N.; Bette, Martin; Filipović, Lana; Aranđelović, Sandra; Radulović, Siniša; Tešić, Živoslav Lj.

(Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux, 2012)

TY  - JOUR
AU  - Rakic, Gordana M.
AU  - Grgurić-Šipka, Sanja
AU  - Kaluđerović, Goran N.
AU  - Bette, Martin
AU  - Filipović, Lana
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Tešić, Živoslav Lj.
PY  - 2012
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1537
AB  - Platinum(IV) complexes with general formulas [Pt(L1-2)(2)Cl-4]. where L1-2 are 3-acetylpyridine (1) and 4-acetylpyridine (2) respectively, and [Pt(HL3-5)(2)Cl-2], where H2L3-5 are 2,3-pyridinedicarboxylic acid (3), 2,4-pyridinedicarboxylic acid (4) and 2,5-pyridinedicarboxylic acid (5) respectively, were prepared by the reaction of K-2[PtCl6] with the corresponding ligand in 1:2 M ratio in water. The complexes were characterized by elemental analysis and IR and NMR spectroscopy. The structures of complexes 2 and 5 were determined by X-ray crystallography, which revealed the trans orientation of chloride anions around platinum(IV) in the case of both complexes. The antiproliferative activity was investigated in six tumor cell lines (human cervical carcinoma cells (HeLa), murine melanoma cells (B16), human breast carcinoma cells (MDA-MB-453), human colon carcinoma cells (LS-174), transformed human umbilical vein endothelial cells (EA.hy 926) and murine endothelial cells (MS1)) and in one non-tumor cell line-human fetal lung fibroblast cells (MRC-5). Cytotoxicity studies indicated that Pt(IV) complexes with acetyl-substituted pyridine ligands exhibit significantly higher in vitro antiproliferative activity than the complexes with carboxylato-substituted pyridines. Complexes 1 and 2 showed antiproliferative activity in all tested tumor cell lines, with the highest potential in human endothelial cells EA.hy 926, since they had IC50 values of 13.8 +/- 5.8 mu M and 23.4 +/- 3.3 mu M, respectively and were more active than cisplatin. Complexes 1 and 2 exhibited lower toxicity against the non-tumor human lung fibroblast cell line (MRC-5) than against most of the tested tumor cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines
VL  - 55
SP  - 214
EP  - 219
DO  - 10.1016/j.ejmech.2012.07.019
ER  - 
@article{
author = "Rakic, Gordana M. and Grgurić-Šipka, Sanja and Kaluđerović, Goran N. and Bette, Martin and Filipović, Lana and Aranđelović, Sandra and Radulović, Siniša and Tešić, Živoslav Lj.",
year = "2012",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1537",
abstract = "Platinum(IV) complexes with general formulas [Pt(L1-2)(2)Cl-4]. where L1-2 are 3-acetylpyridine (1) and 4-acetylpyridine (2) respectively, and [Pt(HL3-5)(2)Cl-2], where H2L3-5 are 2,3-pyridinedicarboxylic acid (3), 2,4-pyridinedicarboxylic acid (4) and 2,5-pyridinedicarboxylic acid (5) respectively, were prepared by the reaction of K-2[PtCl6] with the corresponding ligand in 1:2 M ratio in water. The complexes were characterized by elemental analysis and IR and NMR spectroscopy. The structures of complexes 2 and 5 were determined by X-ray crystallography, which revealed the trans orientation of chloride anions around platinum(IV) in the case of both complexes. The antiproliferative activity was investigated in six tumor cell lines (human cervical carcinoma cells (HeLa), murine melanoma cells (B16), human breast carcinoma cells (MDA-MB-453), human colon carcinoma cells (LS-174), transformed human umbilical vein endothelial cells (EA.hy 926) and murine endothelial cells (MS1)) and in one non-tumor cell line-human fetal lung fibroblast cells (MRC-5). Cytotoxicity studies indicated that Pt(IV) complexes with acetyl-substituted pyridine ligands exhibit significantly higher in vitro antiproliferative activity than the complexes with carboxylato-substituted pyridines. Complexes 1 and 2 showed antiproliferative activity in all tested tumor cell lines, with the highest potential in human endothelial cells EA.hy 926, since they had IC50 values of 13.8 +/- 5.8 mu M and 23.4 +/- 3.3 mu M, respectively and were more active than cisplatin. Complexes 1 and 2 exhibited lower toxicity against the non-tumor human lung fibroblast cell line (MRC-5) than against most of the tested tumor cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines",
volume = "55",
pages = "214-219",
doi = "10.1016/j.ejmech.2012.07.019"
}
Rakic, G. M., Grgurić-Šipka, S., Kaluđerović, G. N., Bette, M., Filipović, L., Aranđelović, S., Radulović, S.,& Tešić, Ž. Lj. (2012). The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines.
European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 55, 214-219.
https://doi.org/10.1016/j.ejmech.2012.07.019
Rakic GM, Grgurić-Šipka S, Kaluđerović GN, Bette M, Filipović L, Aranđelović S, Radulović S, Tešić ŽL. The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines. European Journal of Medicinal Chemistry. 2012;55:214-219
Rakic Gordana M., Grgurić-Šipka Sanja, Kaluđerović Goran N., Bette Martin, Filipović Lana, Aranđelović Sandra, Radulović Siniša, Tešić Živoslav Lj., "The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines" European Journal of Medicinal Chemistry, 55 (2012):214-219,
https://doi.org/10.1016/j.ejmech.2012.07.019 .
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Picolinate ruthenium(II)-arene complex with in vitro antiproliferative and antimetastatic properties: Comparison to a series of ruthenium(II)-arene complexes with similar structure

Gligorijević, Nevenka; Aranđelović, Sandra; Filipović, Lana; Jakovljević, Ksenija; Jankovic, Radmila; Grgurić-Šipka, Sanja; Ivanovic, Ivanka; Radulović, Siniša; Tešić, Živoslav Lj.

(Elsevier Science Inc, New York, 2012)

TY  - JOUR
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Filipović, Lana
AU  - Jakovljević, Ksenija
AU  - Jankovic, Radmila
AU  - Grgurić-Šipka, Sanja
AU  - Ivanovic, Ivanka
AU  - Radulović, Siniša
AU  - Tešić, Živoslav Lj.
PY  - 2012
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1270
AB  - In our previous study, ruthenium(II)-p-cymene complexes of general formula [(eta(6)-p-cymene)Ru(L)Cl2], L: 3-acetylpyridine (1), 2-amino-5-chloropyridine (2); and [(eta(6)-p-cymene)Ru(HL)Cl], HL: 2,3-pyridinedicarboxylic acid (3), 2,4-pyridinedicarboxylic acid (4), revealed low antiproliferative activity, except complex [(eta(6)-p-cymene)RuCl(picolinic acid)]center dot H2O (5) which exhibited IC50 around 80 mu M. In this study we further investigated in vitro potential of antimetastatic action of ruthenium complexes on HeLa and two endothelial cell lines. Comparison of structure and activity of five complexes indicated heterogenic mode of activity, with regard to the potential of antimetastatic and antiproliferative effect. Replacement of substituted pyridine ligand with picolinic acid (complex 5) around Ru(II) center contributed to complex cytotoxicity and ruthenium DNA binding affinity. Analysis of ruthenium(II) accumulation in DNA and protein fractions of HeLa cells, using ICP-OES revealed significantly higher content of complex 5 in DNA fraction in comparison to the other tested compounds. It also altered cell cycle progression, affected expression of DNA repair enzymes ERCC1 and MSH2, and showed enhanced activity in combination with 3-aminobenzamide. Regardless of their effect on cell growth, Ru(II) complexes exerted antimetastatic effect on several tumor cell lines in vitro, achieved mostly by the effect on cell adhesion, migration and angiogenesis, while picolinate ruthenium(II)-arene additionally exerted inhibitory effect on extracellular matrix degradation. (c) 2011 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Picolinate ruthenium(II)-arene complex with in vitro antiproliferative and antimetastatic properties: Comparison to a series of ruthenium(II)-arene complexes with similar structure
VL  - 108
SP  - 53
EP  - 61
DO  - 10.1016/j.jinorgbio.2011.12.002
ER  - 
@article{
author = "Gligorijević, Nevenka and Aranđelović, Sandra and Filipović, Lana and Jakovljević, Ksenija and Jankovic, Radmila and Grgurić-Šipka, Sanja and Ivanovic, Ivanka and Radulović, Siniša and Tešić, Živoslav Lj.",
year = "2012",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1270",
abstract = "In our previous study, ruthenium(II)-p-cymene complexes of general formula [(eta(6)-p-cymene)Ru(L)Cl2], L: 3-acetylpyridine (1), 2-amino-5-chloropyridine (2); and [(eta(6)-p-cymene)Ru(HL)Cl], HL: 2,3-pyridinedicarboxylic acid (3), 2,4-pyridinedicarboxylic acid (4), revealed low antiproliferative activity, except complex [(eta(6)-p-cymene)RuCl(picolinic acid)]center dot H2O (5) which exhibited IC50 around 80 mu M. In this study we further investigated in vitro potential of antimetastatic action of ruthenium complexes on HeLa and two endothelial cell lines. Comparison of structure and activity of five complexes indicated heterogenic mode of activity, with regard to the potential of antimetastatic and antiproliferative effect. Replacement of substituted pyridine ligand with picolinic acid (complex 5) around Ru(II) center contributed to complex cytotoxicity and ruthenium DNA binding affinity. Analysis of ruthenium(II) accumulation in DNA and protein fractions of HeLa cells, using ICP-OES revealed significantly higher content of complex 5 in DNA fraction in comparison to the other tested compounds. It also altered cell cycle progression, affected expression of DNA repair enzymes ERCC1 and MSH2, and showed enhanced activity in combination with 3-aminobenzamide. Regardless of their effect on cell growth, Ru(II) complexes exerted antimetastatic effect on several tumor cell lines in vitro, achieved mostly by the effect on cell adhesion, migration and angiogenesis, while picolinate ruthenium(II)-arene additionally exerted inhibitory effect on extracellular matrix degradation. (c) 2011 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Picolinate ruthenium(II)-arene complex with in vitro antiproliferative and antimetastatic properties: Comparison to a series of ruthenium(II)-arene complexes with similar structure",
volume = "108",
pages = "53-61",
doi = "10.1016/j.jinorgbio.2011.12.002"
}
Gligorijević, N., Aranđelović, S., Filipović, L., Jakovljević, K., Jankovic, R., Grgurić-Šipka, S., Ivanovic, I., Radulović, S.,& Tešić, Ž. Lj. (2012). Picolinate ruthenium(II)-arene complex with in vitro antiproliferative and antimetastatic properties: Comparison to a series of ruthenium(II)-arene complexes with similar structure.
Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 108, 53-61.
https://doi.org/10.1016/j.jinorgbio.2011.12.002
Gligorijević N, Aranđelović S, Filipović L, Jakovljević K, Jankovic R, Grgurić-Šipka S, Ivanovic I, Radulović S, Tešić ŽL. Picolinate ruthenium(II)-arene complex with in vitro antiproliferative and antimetastatic properties: Comparison to a series of ruthenium(II)-arene complexes with similar structure. Journal of Inorganic Biochemistry. 2012;108:53-61
Gligorijević Nevenka, Aranđelović Sandra, Filipović Lana, Jakovljević Ksenija, Jankovic Radmila, Grgurić-Šipka Sanja, Ivanovic Ivanka, Radulović Siniša, Tešić Živoslav Lj., "Picolinate ruthenium(II)-arene complex with in vitro antiproliferative and antimetastatic properties: Comparison to a series of ruthenium(II)-arene complexes with similar structure" Journal of Inorganic Biochemistry, 108 (2012):53-61,
https://doi.org/10.1016/j.jinorgbio.2011.12.002 .
39
39
42

Sensitivity of Human Melanoma Cells on the Activity of Picolinate Ruthenium(Ii)-P-Cymene Complex Alone Or in Combination with Parp Inhibitor

Gligorijević, Nikola; Aranđelović, Sandra; Filipović, Lana; Krivokuca, A.; Jankovic, R.; Radulović, Siniša; Ivanović, I.; Grgurić-Šipka, Sanja; Tešić, Živoslav Lj.

(Oxford Univ Press, Oxford, 2012)

TY  - CONF
AU  - Gligorijević, Nikola
AU  - Aranđelović, Sandra
AU  - Filipović, Lana
AU  - Krivokuca, A.
AU  - Jankovic, R.
AU  - Radulović, Siniša
AU  - Ivanović, I.
AU  - Grgurić-Šipka, Sanja
AU  - Tešić, Živoslav Lj.
PY  - 2012
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1296
PB  - Oxford Univ Press, Oxford
C3  - Annals of Oncology
T1  - Sensitivity of Human Melanoma Cells on the Activity of Picolinate Ruthenium(Ii)-P-Cymene Complex Alone Or in Combination with Parp Inhibitor
VL  - 23
SP  - 30
EP  - 31
ER  - 
@conference{
author = "Gligorijević, Nikola and Aranđelović, Sandra and Filipović, Lana and Krivokuca, A. and Jankovic, R. and Radulović, Siniša and Ivanović, I. and Grgurić-Šipka, Sanja and Tešić, Živoslav Lj.",
year = "2012",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1296",
publisher = "Oxford Univ Press, Oxford",
journal = "Annals of Oncology",
title = "Sensitivity of Human Melanoma Cells on the Activity of Picolinate Ruthenium(Ii)-P-Cymene Complex Alone Or in Combination with Parp Inhibitor",
volume = "23",
pages = "30-31"
}
Gligorijević, N., Aranđelović, S., Filipović, L., Krivokuca, A., Jankovic, R., Radulović, S., Ivanović, I., Grgurić-Šipka, S.,& Tešić, Ž. Lj. (2012). Sensitivity of Human Melanoma Cells on the Activity of Picolinate Ruthenium(Ii)-P-Cymene Complex Alone Or in Combination with Parp Inhibitor.
Annals of Oncology
Oxford Univ Press, Oxford., 23, 30-31.
Gligorijević N, Aranđelović S, Filipović L, Krivokuca A, Jankovic R, Radulović S, Ivanović I, Grgurić-Šipka S, Tešić ŽL. Sensitivity of Human Melanoma Cells on the Activity of Picolinate Ruthenium(Ii)-P-Cymene Complex Alone Or in Combination with Parp Inhibitor. Annals of Oncology. 2012;23:30-31
Gligorijević Nikola, Aranđelović Sandra, Filipović Lana, Krivokuca A., Jankovic R., Radulović Siniša, Ivanović I., Grgurić-Šipka Sanja, Tešić Živoslav Lj., "Sensitivity of Human Melanoma Cells on the Activity of Picolinate Ruthenium(Ii)-P-Cymene Complex Alone Or in Combination with Parp Inhibitor" Annals of Oncology, 23 (2012):30-31