Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors

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Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors (en)
Фармакодинамска и фармакогеномска испитивања новијих лекова у лечењу солидних тумора (sr)
Farmakodinamska i farmakogenomska ispitivanja novijih lekova u lečenju solidnih tumora (sr_RS)
Authors

Publications

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; 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
AU  - Kaczmarek, Anna M.
AU  - Radulović, Siniša
AU  - Van Deun, Rik
AU  - Van Hecke, Kristof
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3352
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
T2  - Journal of Inorganic Biochemistry
T1  - Antitumor activity of organoruthenium complexes with chelate aromatic ligands, derived from 1,10-phenantroline: Synthesis and biological activity
VL  - 202
SP  - 110869
SP  - 110869
DO  - 10.1016/j.jinorgbio.2019.110869
ER  - 
@article{
author = "Savić, Aleksandar and Gligorijević, Nevenka and Aranđelović, Sandra and Dojčinović, Biljana and Kaczmarek, Anna M. and Radulović, Siniša and Van Deun, Rik and Van Hecke, Kristof",
year = "2020",
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",
journal = "Journal of Inorganic Biochemistry",
title = "Antitumor activity of organoruthenium complexes with chelate aromatic ligands, derived from 1,10-phenantroline: Synthesis and biological activity",
volume = "202",
pages = "110869-110869",
doi = "10.1016/j.jinorgbio.2019.110869"
}
Savić, A., Gligorijević, N., Aranđelović, S., Dojčinović, B., 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. in Journal of Inorganic Biochemistry
Elsevier., 202, 110869.
https://doi.org/10.1016/j.jinorgbio.2019.110869
Savić A, Gligorijević N, Aranđelović S, Dojčinović B, 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. in Journal of Inorganic Biochemistry. 2020;202:110869.
doi:10.1016/j.jinorgbio.2019.110869 .
Savić, Aleksandar, Gligorijević, Nevenka, Aranđelović, Sandra, Dojčinović, Biljana, 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" in Journal of Inorganic Biochemistry, 202 (2020):110869,
https://doi.org/10.1016/j.jinorgbio.2019.110869 . .
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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; Aranđelović, Sandra; Grgurić-Šipka, Sanja; Radulović, Siniša

(Springer Link, 2019)

TY  - JOUR
AU  - Pavlović, Marijana
AU  - Nikolić, Stefan
AU  - Gligorijević, Nevenka
AU  - Dojčinović, Biljana
AU  - Aranđelović, Sandra
AU  - Grgurić-Šipka, Sanja
AU  - Radulović, Siniša
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2963
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 and Aranđelović, Sandra and Grgurić-Šipka, Sanja and Radulović, Siniša",
year = "2019",
abstract = "Three new ruthenium(II)-arene complexes with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline (ppf) of general formula: C1 ([(ƞ 6 -benzene)Ru(ppf)Cl]PF 6 , C2 ([(ƞ 6 -toluene)Ru(ppf)Cl]PF 6 ) and C3 ([(ƞ 6 -p-cymene)Ru(ppf)Cl]PF 6 ) have been synthesized. The structures of complexes were determined by elemental analysis, IR, ESI–MS, as well as with 1 H and 13 C NMR spectroscopy. Cytotoxic activity has been evaluated in three different human neoplastic cell lines (A549, A375, LS 174T) and in one human non-tumor cell line (MRC-5), by the MTT assay. Complexes C1–C3 showed IC 50 values in the micromolar range below 100 µM. Complex C3, carrying ƞ 6 -p-cymene as the arene ligand, exhibited cytoselective activity toward human malignant melanoma A375 cells (IC 50 = 15.8 ± 2.7 µM), and has been selected for further analyses of its biological effects. Drug-accumulation study performed in the A375 cells disclosed that C3 possess lower ability of entering the cells compared to cisplatin and distributes approximately equally in the cytosol and membrane/organelle fraction of cells. Investigations in the 3D model of A375 cells, disclosed different effects of the complex C3 and cisplatin on growth of multicellular tumor spheroids (MCTSs). While the size of cisplatin-treated MCTSs decreased with time, MCTSs treated with C3 continued to growth. Differences in structural organization and biological activity of this type of ruthenium(II)-arene complexes versus cisplatin in A375 malignant melanoma cells pointed out their different modes of action, and necessity for further biological studies and optimizations for potential applications.",
publisher = "Springer Link",
journal = "Journal of Biological Inorganic Chemistry",
title = "New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action",
volume = "24",
number = "2",
pages = "297-310",
doi = "10.1007/s00775-019-01647-4"
}
Pavlović, M., Nikolić, S., Gligorijević, N., Dojčinović, B., Aranđelović, S., Grgurić-Šipka, S.,& Radulović, S.. (2019). New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action. in Journal of Biological Inorganic Chemistry
Springer Link., 24(2), 297-310.
https://doi.org/10.1007/s00775-019-01647-4
Pavlović M, Nikolić S, Gligorijević N, Dojčinović B, Aranđelović S, Grgurić-Šipka S, Radulović S. New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action. in Journal of Biological Inorganic Chemistry. 2019;24(2):297-310.
doi:10.1007/s00775-019-01647-4 .
Pavlović, Marijana, Nikolić, Stefan, Gligorijević, Nevenka, Dojčinović, Biljana, Aranđelović, Sandra, Grgurić-Šipka, Sanja, Radulović, Siniša, "New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action" in Journal of Biological Inorganic Chemistry, 24, no. 2 (2019):297-310,
https://doi.org/10.1007/s00775-019-01647-4 . .
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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; Pantelic, Nebojsa; Filipovic, Lana; Arandelovic, Sandra; Radulovic, Sinisa; Sabo, Tibor; Kaluđerović, Goran N.

(Bentham Science Publ Ltd, Sharjah, 2017)

TY  - JOUR
AU  - Zmejkovski, Bojana
AU  - Pantelic, Nebojsa
AU  - Filipovic, Lana
AU  - Arandelovic, Sandra
AU  - Radulovic, Sinisa
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2132
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 and Pantelic, Nebojsa and Filipovic, Lana and Arandelovic, Sandra and Radulovic, Sinisa and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
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., Pantelic, N., Filipovic, L., Arandelovic, S., Radulovic, 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. in Anti-Cancer Agents in Medicinal Chemistry
Bentham Science Publ Ltd, Sharjah., 17(8), 1136-1143.
https://doi.org/10.2174/1871520616666161207155634
Zmejkovski B, Pantelic N, Filipovic L, Arandelovic S, Radulovic 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. in Anti-Cancer Agents in Medicinal Chemistry. 2017;17(8):1136-1143.
doi:10.2174/1871520616666161207155634 .
Zmejkovski, Bojana, Pantelic, Nebojsa, Filipovic, Lana, Arandelovic, Sandra, Radulovic, Sinisa, 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" in Anti-Cancer Agents in Medicinal Chemistry, 17, no. 8 (2017):1136-1143,
https://doi.org/10.2174/1871520616666161207155634 . .
1
1

Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides

Čobeljić, Božidar; Milenković, Milica R.; Pevec, Andrej; Turel, Iztok; Vujčić, Miroslava; Janović, Barbara; Gligorijević, Nevenka; Sladić, Dušan; Radulovic, Sinisa; Jovanovic, Katarina; Anđelković, Katarina

(Springer, New York, 2016)

TY  - JOUR
AU  - Čobeljić, Božidar
AU  - Milenković, Milica R.
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Gligorijević, Nevenka
AU  - Sladić, Dušan
AU  - Radulovic, Sinisa
AU  - Jovanovic, Katarina
AU  - Anđelković, Katarina
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2039
AB  - Square-planar azido Ni(II) complex with condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent was synthesized and its crystal structure was determined. Cytotoxic activity of the azido complex and previously synthesized isothiocyanato, cyanato and chlorido Ni(II) complexes with this ligand was examined on six tumor cell lines (HeLa, A549, K562, MDA-MB-453, MDA-MB-361 and LS-174) and two normal cell line (MRC-5 and BEAS-2B). All the investigated nickel(II) complexes were cytotoxic against all tumor cell lines. The newly synthesized azido complex showed selectivity to HeLa and A549 tumor cell lines compared to the normal cells (for A549 IC50 was similar to that of cisplatin). Azido complex interferes with cell cycle phase distribution of A549 and HeLa cells and possesses nuclease activity towards supercoiled DNA. The observed selectivity of the azido complex for some tumor cell lines can be connected with its strong DNA damaging activity.
PB  - Springer, New York
T2  - Journal of Biological Inorganic Chemistry
T1  - Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides
VL  - 21
IS  - 2
SP  - 145
EP  - 162
DO  - 10.1007/s00775-015-1315-x
ER  - 
@article{
author = "Čobeljić, Božidar and Milenković, Milica R. and Pevec, Andrej and Turel, Iztok and Vujčić, Miroslava and Janović, Barbara and Gligorijević, Nevenka and Sladić, Dušan and Radulovic, Sinisa and Jovanovic, Katarina and Anđelković, Katarina",
year = "2016",
abstract = "Square-planar azido Ni(II) complex with condensation product of 2-(diphenylphosphino)benzaldehyde and Girard's T reagent was synthesized and its crystal structure was determined. Cytotoxic activity of the azido complex and previously synthesized isothiocyanato, cyanato and chlorido Ni(II) complexes with this ligand was examined on six tumor cell lines (HeLa, A549, K562, MDA-MB-453, MDA-MB-361 and LS-174) and two normal cell line (MRC-5 and BEAS-2B). All the investigated nickel(II) complexes were cytotoxic against all tumor cell lines. The newly synthesized azido complex showed selectivity to HeLa and A549 tumor cell lines compared to the normal cells (for A549 IC50 was similar to that of cisplatin). Azido complex interferes with cell cycle phase distribution of A549 and HeLa cells and possesses nuclease activity towards supercoiled DNA. The observed selectivity of the azido complex for some tumor cell lines can be connected with its strong DNA damaging activity.",
publisher = "Springer, New York",
journal = "Journal of Biological Inorganic Chemistry",
title = "Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides",
volume = "21",
number = "2",
pages = "145-162",
doi = "10.1007/s00775-015-1315-x"
}
Čobeljić, B., Milenković, M. R., Pevec, A., Turel, I., Vujčić, M., Janović, B., Gligorijević, N., Sladić, D., Radulovic, S., Jovanovic, K.,& Anđelković, K.. (2016). Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides. in Journal of Biological Inorganic Chemistry
Springer, New York., 21(2), 145-162.
https://doi.org/10.1007/s00775-015-1315-x
Čobeljić B, Milenković MR, Pevec A, Turel I, Vujčić M, Janović B, Gligorijević N, Sladić D, Radulovic S, Jovanovic K, Anđelković K. Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides. in Journal of Biological Inorganic Chemistry. 2016;21(2):145-162.
doi:10.1007/s00775-015-1315-x .
Čobeljić, Božidar, Milenković, Milica R., Pevec, Andrej, Turel, Iztok, Vujčić, Miroslava, Janović, Barbara, Gligorijević, Nevenka, Sladić, Dušan, Radulovic, Sinisa, Jovanovic, Katarina, Anđelković, Katarina, "Investigation of antitumor potential of Ni(II) complexes with tridentate PNO acylhydrazones of 2-(diphenylphosphino)benzaldehyde and monodentate pseudohalides" in Journal of Biological Inorganic Chemistry, 21, no. 2 (2016):145-162,
https://doi.org/10.1007/s00775-015-1315-x . .
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18

Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand

Jovanovic, Katarina K.; Tanic, Miljana; Ivanovic, Ivanka; Gligorijević, Nevenka; Dojčinović, Biljana; Radulovic, Sinisa

(Elsevier, 2016)

TY  - JOUR
AU  - Jovanovic, Katarina K.
AU  - Tanic, Miljana
AU  - Ivanovic, Ivanka
AU  - Gligorijević, Nevenka
AU  - Dojčinović, Biljana
AU  - Radulovic, Sinisa
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4386
AB  - Ruthenium(II)-arene complexes are promising drug candidates for the therapy of solid tumors. In previous work, seven new compounds of the general formula [Ru(eta(6)-p-cymene)(L1-7)Cl] were synthesized and characterized, of which the complex with L = isoquinoline-3-carboxylic acid (RuT7) was two times as active on HeLa cells compared to normal cell line MRC-5, as indicated by ICso values determined after 48 h of incubation (45.4 +/- 3.0 vs. 842 +/- 5.7 mu M, respectively). In the present study, cell cycle analysis of HeLa cells treated with RuT7 showed S phase arrest and an increase in sub-G1 population. The apoptotic potential of the title compound was confirmed with the Annexin V-FITC/PI assay together with a morphological evaluation of cells using fluorescent microscopy. Analysis of the intracellular accumulation of ruthenium showed 8.9 ng Ru/10(6) cells after 6 h of incubation. To gain further insight in the molecular mechanism of action of RuT7 on HeLa cells, a whole-transcriptome microarray gene expression analysis was performed. Analysis of functional categories and signaling and biochemical pathways associated with the response of HeLa cells to treatment with RuT7 showed that it leads the cells through the intrinsic (mitochondrial) apoptotic pathway, via indirect DNA damage due to the action of reactive oxygen species, and through direct DNA binding of RuT7. Statistical analysis for enrichment of gene sets associated with known drug-induced toxicities identified fewer associated toxicity profiles in RuT7-treated cells compared to cisplatin treatment. Altogether these results provide the basis for further development of RuT7 in animal and pre-clinical studies as a potential drug candidate.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand
VL  - 163
SP  - 362
EP  - 373
DO  - 10.1016/j.jinorgbio.2016.04.011
ER  - 
@article{
author = "Jovanovic, Katarina K. and Tanic, Miljana and Ivanovic, Ivanka and Gligorijević, Nevenka and Dojčinović, Biljana and Radulovic, Sinisa",
year = "2016",
abstract = "Ruthenium(II)-arene complexes are promising drug candidates for the therapy of solid tumors. In previous work, seven new compounds of the general formula [Ru(eta(6)-p-cymene)(L1-7)Cl] were synthesized and characterized, of which the complex with L = isoquinoline-3-carboxylic acid (RuT7) was two times as active on HeLa cells compared to normal cell line MRC-5, as indicated by ICso values determined after 48 h of incubation (45.4 +/- 3.0 vs. 842 +/- 5.7 mu M, respectively). In the present study, cell cycle analysis of HeLa cells treated with RuT7 showed S phase arrest and an increase in sub-G1 population. The apoptotic potential of the title compound was confirmed with the Annexin V-FITC/PI assay together with a morphological evaluation of cells using fluorescent microscopy. Analysis of the intracellular accumulation of ruthenium showed 8.9 ng Ru/10(6) cells after 6 h of incubation. To gain further insight in the molecular mechanism of action of RuT7 on HeLa cells, a whole-transcriptome microarray gene expression analysis was performed. Analysis of functional categories and signaling and biochemical pathways associated with the response of HeLa cells to treatment with RuT7 showed that it leads the cells through the intrinsic (mitochondrial) apoptotic pathway, via indirect DNA damage due to the action of reactive oxygen species, and through direct DNA binding of RuT7. Statistical analysis for enrichment of gene sets associated with known drug-induced toxicities identified fewer associated toxicity profiles in RuT7-treated cells compared to cisplatin treatment. Altogether these results provide the basis for further development of RuT7 in animal and pre-clinical studies as a potential drug candidate.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand",
volume = "163",
pages = "362-373",
doi = "10.1016/j.jinorgbio.2016.04.011"
}
Jovanovic, K. K., Tanic, M., Ivanovic, I., Gligorijević, N., Dojčinović, B.,& Radulovic, S.. (2016). Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand. in Journal of Inorganic Biochemistry
Elsevier., 163, 362-373.
https://doi.org/10.1016/j.jinorgbio.2016.04.011
Jovanovic KK, Tanic M, Ivanovic I, Gligorijević N, Dojčinović B, Radulovic S. Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand. in Journal of Inorganic Biochemistry. 2016;163:362-373.
doi:10.1016/j.jinorgbio.2016.04.011 .
Jovanovic, Katarina K., Tanic, Miljana, Ivanovic, Ivanka, Gligorijević, Nevenka, Dojčinović, Biljana, Radulovic, Sinisa, "Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand" in Journal of Inorganic Biochemistry, 163 (2016):362-373,
https://doi.org/10.1016/j.jinorgbio.2016.04.011 . .
2
20
19
20

Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand

Jovanovic, Katarina K.; Tanic, Miljana; Ivanovic, Ivanka; Gligorijević, Nevenka; Dojčinović, Biljana; Radulovic, Sinisa

(Elsevier Science Inc, New York, 2016)

TY  - JOUR
AU  - Jovanovic, Katarina K.
AU  - Tanic, Miljana
AU  - Ivanovic, Ivanka
AU  - Gligorijević, Nevenka
AU  - Dojčinović, Biljana
AU  - Radulovic, Sinisa
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1984
AB  - Ruthenium(II)-arene complexes are promising drug candidates for the therapy of solid tumors. In previous work, seven new compounds of the general formula [Ru(eta(6)-p-cymene)(L1-7)Cl] were synthesized and characterized, of which the complex with L = isoquinoline-3-carboxylic acid (RuT7) was two times as active on HeLa cells compared to normal cell line MRC-5, as indicated by ICso values determined after 48 h of incubation (45.4 +/- 3.0 vs. 842 +/- 5.7 mu M, respectively). In the present study, cell cycle analysis of HeLa cells treated with RuT7 showed S phase arrest and an increase in sub-G1 population. The apoptotic potential of the title compound was confirmed with the Annexin V-FITC/PI assay together with a morphological evaluation of cells using fluorescent microscopy. Analysis of the intracellular accumulation of ruthenium showed 8.9 ng Ru/10(6) cells after 6 h of incubation. To gain further insight in the molecular mechanism of action of RuT7 on HeLa cells, a whole-transcriptome microarray gene expression analysis was performed. Analysis of functional categories and signaling and biochemical pathways associated with the response of HeLa cells to treatment with RuT7 showed that it leads the cells through the intrinsic (mitochondrial) apoptotic pathway, via indirect DNA damage due to the action of reactive oxygen species, and through direct DNA binding of RuT7. Statistical analysis for enrichment of gene sets associated with known drug-induced toxicities identified fewer associated toxicity profiles in RuT7-treated cells compared to cisplatin treatment. Altogether these results provide the basis for further development of RuT7 in animal and pre-clinical studies as a potential drug candidate.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand
VL  - 163
SP  - 362
EP  - 373
DO  - 10.1016/j.jinorgbio.2016.04.011
ER  - 
@article{
author = "Jovanovic, Katarina K. and Tanic, Miljana and Ivanovic, Ivanka and Gligorijević, Nevenka and Dojčinović, Biljana and Radulovic, Sinisa",
year = "2016",
abstract = "Ruthenium(II)-arene complexes are promising drug candidates for the therapy of solid tumors. In previous work, seven new compounds of the general formula [Ru(eta(6)-p-cymene)(L1-7)Cl] were synthesized and characterized, of which the complex with L = isoquinoline-3-carboxylic acid (RuT7) was two times as active on HeLa cells compared to normal cell line MRC-5, as indicated by ICso values determined after 48 h of incubation (45.4 +/- 3.0 vs. 842 +/- 5.7 mu M, respectively). In the present study, cell cycle analysis of HeLa cells treated with RuT7 showed S phase arrest and an increase in sub-G1 population. The apoptotic potential of the title compound was confirmed with the Annexin V-FITC/PI assay together with a morphological evaluation of cells using fluorescent microscopy. Analysis of the intracellular accumulation of ruthenium showed 8.9 ng Ru/10(6) cells after 6 h of incubation. To gain further insight in the molecular mechanism of action of RuT7 on HeLa cells, a whole-transcriptome microarray gene expression analysis was performed. Analysis of functional categories and signaling and biochemical pathways associated with the response of HeLa cells to treatment with RuT7 showed that it leads the cells through the intrinsic (mitochondrial) apoptotic pathway, via indirect DNA damage due to the action of reactive oxygen species, and through direct DNA binding of RuT7. Statistical analysis for enrichment of gene sets associated with known drug-induced toxicities identified fewer associated toxicity profiles in RuT7-treated cells compared to cisplatin treatment. Altogether these results provide the basis for further development of RuT7 in animal and pre-clinical studies as a potential drug candidate.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand",
volume = "163",
pages = "362-373",
doi = "10.1016/j.jinorgbio.2016.04.011"
}
Jovanovic, K. K., Tanic, M., Ivanovic, I., Gligorijević, N., Dojčinović, B.,& Radulovic, S.. (2016). Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 163, 362-373.
https://doi.org/10.1016/j.jinorgbio.2016.04.011
Jovanovic KK, Tanic M, Ivanovic I, Gligorijević N, Dojčinović B, Radulovic S. Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand. in Journal of Inorganic Biochemistry. 2016;163:362-373.
doi:10.1016/j.jinorgbio.2016.04.011 .
Jovanovic, Katarina K., Tanic, Miljana, Ivanovic, Ivanka, Gligorijević, Nevenka, Dojčinović, Biljana, Radulovic, Sinisa, "Cell cycle, apoptosis, cellular uptake and whole-transcriptome microarray gene expression analysis of HeLa cells treated with a ruthenium(II)-arene complex with an isoquinoline-3-carboxylic acid ligand" in Journal of Inorganic Biochemistry, 163 (2016):362-373,
https://doi.org/10.1016/j.jinorgbio.2016.04.011 . .
2
20
19
20

Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes

Nikolić, Stefan; Opsenica, Dejan; Filipović, Vuk; Dojčinović, Biljana; Arandelovic, Sandra; Radulovic, Singa; Grgurić-Šipka, Sanja

(American Chemical Society (ACS), 2015)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Opsenica, Dejan
AU  - Filipović, Vuk
AU  - Dojčinović, Biljana
AU  - Arandelovic, Sandra
AU  - Radulovic, Singa
AU  - Grgurić-Šipka, Sanja
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1618
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  - American Chemical Society (ACS)
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 and Filipović, Vuk and Dojčinović, Biljana and Arandelovic, Sandra and Radulovic, Singa and Grgurić-Šipka, Sanja",
year = "2015",
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 = "American Chemical Society (ACS)",
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., Filipović, V., Dojčinović, B., Arandelovic, S., Radulovic, S.,& Grgurić-Šipka, S.. (2015). Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. in Organometallics
American Chemical Society (ACS)., 34(14), 3464-3473.
https://doi.org/10.1021/acs.organomet.5b00041
Nikolić S, Opsenica D, Filipović V, Dojčinović B, Arandelovic S, Radulovic S, Grgurić-Šipka S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. in Organometallics. 2015;34(14):3464-3473.
doi:10.1021/acs.organomet.5b00041 .
Nikolić, Stefan, Opsenica, Dejan, Filipović, Vuk, Dojčinović, Biljana, Arandelovic, Sandra, Radulovic, Singa, Grgurić-Šipka, Sanja, "Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes" in Organometallics, 34, no. 14 (2015):3464-3473,
https://doi.org/10.1021/acs.organomet.5b00041 . .
1
43
35
42

Heteropentanuclear Oxalato-Bridged nd-4f (n=4, 5) Metal Complexes with NO Ligand: Synthesis, Crystal Structures, Aqueous Stability and Antiproliferative Activity

Kuhn, Paul-Steffen; Cremer, Laura; Gavriluta, Anatolie; Jovanovic, Katarina K; Filipovic, Lana; Hummer, Alfred A; Buechel, Gabriel E; Dojčinović, Biljana; Meier, Samuel M; Rompel, Annette; Radulovic, Sinisa; Tommasino, Jean Bernard; Luneau, Dominique; Arion, Vladimir B

(Wiley-V C H Verlag Gmbh, Weinheim, 2015)

TY  - JOUR
AU  - Kuhn, Paul-Steffen
AU  - Cremer, Laura
AU  - Gavriluta, Anatolie
AU  - Jovanovic, Katarina K
AU  - Filipovic, Lana
AU  - Hummer, Alfred A
AU  - Buechel, Gabriel E
AU  - Dojčinović, Biljana
AU  - Meier, Samuel M
AU  - Rompel, Annette
AU  - Radulovic, Sinisa
AU  - Tommasino, Jean Bernard
AU  - Luneau, Dominique
AU  - Arion, Vladimir B
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1680
AB  - A series of heteropentanuclear oxalate-bridged Ru(NO)-Ln (4d-4f) metal complexes of the general formula (nBu(4)N)(5)[Ln{RuCl3(-ox)(NO)}(4)], where Ln=Y (2), Gd (3), Tb (4), Dy (5) and ox=oxalate anion, were obtained by treatment of (nBu(4)N)(2)[RuCl3(ox)(NO)] (1) with the respective lanthanide salt in 4:1 molar ratio. The compounds were characterized by elemental analysis, IR spectroscopy, electrospray ionization (ESI) mass spectrometry, while 1, 2, and 5 were in addition analyzed by X-ray crystallography, 1 by Ru K-edge XAS and 1 and 2 by (CNMR)-C-13 spectroscopy. X-ray diffraction showed that in 2 and 5 four complex anions [RuCl3(ox)(NO)](2-) are coordinated to Y-III and Dy-III, respectively, with formation of [Ln{RuCl3(-ox)(NO)}(4)](5-) (Ln=Y, Dy). While Y-III is eight-coordinate in 2, Dy-III is nine-coordinate in 5, with an additional coordination of an EtOH molecule. The negative charge is counterbalanced by five nBu(4)N(+) ions present in the crystal structure. The stability of complexes 2 and 5 in aqueous medium was monitored by UV/Vis spectroscopy. The antiproliferative activity of ruthenium-lanthanide complexes 2-5 were assayed in two human cancer cell lines (HeLa and A549) and in a noncancerous cell line (MRC-5) and compared with those obtained for the previously reported Os(NO)-Ln (5d-4f) analogues (nBu(4)N)(5)[Ln{OsCl3(ox)(NO)}(4)] (Ln=Y (6), Gd (7), Tb (8), Dy (9)). Complexes 2-5 were found to be slightly more active than 1 in inhibiting the proliferation of HeLa and A549 cells, and significantly more cytotoxic than 5d-4f metal complexes 6-9 in terms of IC50 values. The highest antiproliferative activity with IC50 values of 20.0 and 22.4M was found for 4 in HeLa and A549 cell lines, respectively. These cytotoxicity results are in accord with the presented ICP-MS data, indicating five- to eightfold greater accumulation of ruthenium versus osmium in human A549 cancer cells.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry-A European Journal
T1  - Heteropentanuclear Oxalato-Bridged nd-4f (n=4, 5) Metal Complexes with NO Ligand: Synthesis, Crystal Structures, Aqueous Stability and Antiproliferative Activity
VL  - 21
IS  - 39
SP  - 13703
EP  - 13713
DO  - 10.1002/chem.201502026
ER  - 
@article{
author = "Kuhn, Paul-Steffen and Cremer, Laura and Gavriluta, Anatolie and Jovanovic, Katarina K and Filipovic, Lana and Hummer, Alfred A and Buechel, Gabriel E and Dojčinović, Biljana and Meier, Samuel M and Rompel, Annette and Radulovic, Sinisa and Tommasino, Jean Bernard and Luneau, Dominique and Arion, Vladimir B",
year = "2015",
abstract = "A series of heteropentanuclear oxalate-bridged Ru(NO)-Ln (4d-4f) metal complexes of the general formula (nBu(4)N)(5)[Ln{RuCl3(-ox)(NO)}(4)], where Ln=Y (2), Gd (3), Tb (4), Dy (5) and ox=oxalate anion, were obtained by treatment of (nBu(4)N)(2)[RuCl3(ox)(NO)] (1) with the respective lanthanide salt in 4:1 molar ratio. The compounds were characterized by elemental analysis, IR spectroscopy, electrospray ionization (ESI) mass spectrometry, while 1, 2, and 5 were in addition analyzed by X-ray crystallography, 1 by Ru K-edge XAS and 1 and 2 by (CNMR)-C-13 spectroscopy. X-ray diffraction showed that in 2 and 5 four complex anions [RuCl3(ox)(NO)](2-) are coordinated to Y-III and Dy-III, respectively, with formation of [Ln{RuCl3(-ox)(NO)}(4)](5-) (Ln=Y, Dy). While Y-III is eight-coordinate in 2, Dy-III is nine-coordinate in 5, with an additional coordination of an EtOH molecule. The negative charge is counterbalanced by five nBu(4)N(+) ions present in the crystal structure. The stability of complexes 2 and 5 in aqueous medium was monitored by UV/Vis spectroscopy. The antiproliferative activity of ruthenium-lanthanide complexes 2-5 were assayed in two human cancer cell lines (HeLa and A549) and in a noncancerous cell line (MRC-5) and compared with those obtained for the previously reported Os(NO)-Ln (5d-4f) analogues (nBu(4)N)(5)[Ln{OsCl3(ox)(NO)}(4)] (Ln=Y (6), Gd (7), Tb (8), Dy (9)). Complexes 2-5 were found to be slightly more active than 1 in inhibiting the proliferation of HeLa and A549 cells, and significantly more cytotoxic than 5d-4f metal complexes 6-9 in terms of IC50 values. The highest antiproliferative activity with IC50 values of 20.0 and 22.4M was found for 4 in HeLa and A549 cell lines, respectively. These cytotoxicity results are in accord with the presented ICP-MS data, indicating five- to eightfold greater accumulation of ruthenium versus osmium in human A549 cancer cells.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry-A European Journal",
title = "Heteropentanuclear Oxalato-Bridged nd-4f (n=4, 5) Metal Complexes with NO Ligand: Synthesis, Crystal Structures, Aqueous Stability and Antiproliferative Activity",
volume = "21",
number = "39",
pages = "13703-13713",
doi = "10.1002/chem.201502026"
}
Kuhn, P., Cremer, L., Gavriluta, A., Jovanovic, K. K., Filipovic, L., Hummer, A. A., Buechel, G. E., Dojčinović, B., Meier, S. M., Rompel, A., Radulovic, S., Tommasino, J. B., Luneau, D.,& Arion, V. B.. (2015). Heteropentanuclear Oxalato-Bridged nd-4f (n=4, 5) Metal Complexes with NO Ligand: Synthesis, Crystal Structures, Aqueous Stability and Antiproliferative Activity. in Chemistry-A European Journal
Wiley-V C H Verlag Gmbh, Weinheim., 21(39), 13703-13713.
https://doi.org/10.1002/chem.201502026
Kuhn P, Cremer L, Gavriluta A, Jovanovic KK, Filipovic L, Hummer AA, Buechel GE, Dojčinović B, Meier SM, Rompel A, Radulovic S, Tommasino JB, Luneau D, Arion VB. Heteropentanuclear Oxalato-Bridged nd-4f (n=4, 5) Metal Complexes with NO Ligand: Synthesis, Crystal Structures, Aqueous Stability and Antiproliferative Activity. in Chemistry-A European Journal. 2015;21(39):13703-13713.
doi:10.1002/chem.201502026 .
Kuhn, Paul-Steffen, Cremer, Laura, Gavriluta, Anatolie, Jovanovic, Katarina K, Filipovic, Lana, Hummer, Alfred A, Buechel, Gabriel E, Dojčinović, Biljana, Meier, Samuel M, Rompel, Annette, Radulovic, Sinisa, Tommasino, Jean Bernard, Luneau, Dominique, Arion, Vladimir B, "Heteropentanuclear Oxalato-Bridged nd-4f (n=4, 5) Metal Complexes with NO Ligand: Synthesis, Crystal Structures, Aqueous Stability and Antiproliferative Activity" in Chemistry-A European Journal, 21, no. 39 (2015):13703-13713,
https://doi.org/10.1002/chem.201502026 . .
14
13
13

Synthesis, characterization, DFT calculation and biological activity of square-planar Ni(II) complexes with tridentate PNO ligands and monodentate pseudohalides. Part II

Milenković, Milica R.; Pevec, Andrej; Turel, Iztok; Vujčić, Miroslava; Milenković, Marina; Jovanovic, Katarina; Gligorijević, Nevenka; Radulovic, Sinisa; Swart, Marcel; Gruden-Pavlović, Maja; Adaila, Kawther; Čobeljić, Božidar; Anđelković, Katarina

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

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Vujčić, Miroslava
AU  - Milenković, Marina
AU  - Jovanovic, Katarina
AU  - Gligorijević, Nevenka
AU  - Radulovic, Sinisa
AU  - Swart, Marcel
AU  - Gruden-Pavlović, Maja
AU  - Adaila, Kawther
AU  - Čobeljić, Božidar
AU  - Anđelković, Katarina
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1464
AB  - Three square-planar complexes of Ni(II) with condensation derivative of 2-(diphenylphosphino)benzaldehyde and 4-phenylsemicarbazide and monodentate pseudohalides have been synthesized and characterized on the basis of the results of X-ray. NMR and IR spectroscopy and elemental analysis. Investigated complexes exhibited moderate antibacterial and cytotoxic activity. The most pronounced cytotoxic activity (in the range of cisplatin) to HeLa cell line was observed for ligand and all the complexes. Azido complex and ligand induced concentration dependent cell cycle arrest in the S phase, as well as decrease of percentage of cells in G1 phase, without significant increase of apoptotic fraction of cells. The interaction of the azido complex and ligand with CT-DNA results in changes in UV-Vis spectra typical for non-covalent bonding. The observed intrinsic binding constant of azido complex CT-DNA and ligand-CT-DNA were 3.22 x 10(5) M-1 and 2.79 x 10(5) M-1. The results of DNA cleavage experiments showed that azido complex nicked supercoiled plasmid DNA.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, characterization, DFT calculation and biological activity of square-planar Ni(II) complexes with tridentate PNO ligands and monodentate pseudohalides. Part II
VL  - 87
SP  - 284
EP  - 297
DO  - 10.1016/j.ejmech.2014.06.079
ER  - 
@article{
author = "Milenković, Milica R. and Pevec, Andrej and Turel, Iztok and Vujčić, Miroslava and Milenković, Marina and Jovanovic, Katarina and Gligorijević, Nevenka and Radulovic, Sinisa and Swart, Marcel and Gruden-Pavlović, Maja and Adaila, Kawther and Čobeljić, Božidar and Anđelković, Katarina",
year = "2014",
abstract = "Three square-planar complexes of Ni(II) with condensation derivative of 2-(diphenylphosphino)benzaldehyde and 4-phenylsemicarbazide and monodentate pseudohalides have been synthesized and characterized on the basis of the results of X-ray. NMR and IR spectroscopy and elemental analysis. Investigated complexes exhibited moderate antibacterial and cytotoxic activity. The most pronounced cytotoxic activity (in the range of cisplatin) to HeLa cell line was observed for ligand and all the complexes. Azido complex and ligand induced concentration dependent cell cycle arrest in the S phase, as well as decrease of percentage of cells in G1 phase, without significant increase of apoptotic fraction of cells. The interaction of the azido complex and ligand with CT-DNA results in changes in UV-Vis spectra typical for non-covalent bonding. The observed intrinsic binding constant of azido complex CT-DNA and ligand-CT-DNA were 3.22 x 10(5) M-1 and 2.79 x 10(5) M-1. The results of DNA cleavage experiments showed that azido complex nicked supercoiled plasmid DNA.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, characterization, DFT calculation and biological activity of square-planar Ni(II) complexes with tridentate PNO ligands and monodentate pseudohalides. Part II",
volume = "87",
pages = "284-297",
doi = "10.1016/j.ejmech.2014.06.079"
}
Milenković, M. R., Pevec, A., Turel, I., Vujčić, M., Milenković, M., Jovanovic, K., Gligorijević, N., Radulovic, S., Swart, M., Gruden-Pavlović, M., Adaila, K., Čobeljić, B.,& Anđelković, K.. (2014). Synthesis, characterization, DFT calculation and biological activity of square-planar Ni(II) complexes with tridentate PNO ligands and monodentate pseudohalides. Part II. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 87, 284-297.
https://doi.org/10.1016/j.ejmech.2014.06.079
Milenković MR, Pevec A, Turel I, Vujčić M, Milenković M, Jovanovic K, Gligorijević N, Radulovic S, Swart M, Gruden-Pavlović M, Adaila K, Čobeljić B, Anđelković K. Synthesis, characterization, DFT calculation and biological activity of square-planar Ni(II) complexes with tridentate PNO ligands and monodentate pseudohalides. Part II. in European Journal of Medicinal Chemistry. 2014;87:284-297.
doi:10.1016/j.ejmech.2014.06.079 .
Milenković, Milica R., Pevec, Andrej, Turel, Iztok, Vujčić, Miroslava, Milenković, Marina, Jovanovic, Katarina, Gligorijević, Nevenka, Radulovic, Sinisa, Swart, Marcel, Gruden-Pavlović, Maja, Adaila, Kawther, Čobeljić, Božidar, Anđelković, Katarina, "Synthesis, characterization, DFT calculation and biological activity of square-planar Ni(II) complexes with tridentate PNO ligands and monodentate pseudohalides. Part II" in European Journal of Medicinal Chemistry, 87 (2014):284-297,
https://doi.org/10.1016/j.ejmech.2014.06.079 . .
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19

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

Zmejkovski, Bojana; Savic, Aleksandar; Poljarevic, Jelena; Pantelić, Nebojša Đ.; Arandelovic, Sandra; Radulovic, Sinisa; Grgurić-Šipka, Sanja; Kaluđerović, Goran N.; Sabo, Tibor

(Oxford : Pergamon-Elsevier Science Ltd, 2014)

TY  - JOUR
AU  - Zmejkovski, Bojana
AU  - Savic, Aleksandar
AU  - Poljarevic, Jelena
AU  - Pantelić, Nebojša Đ.
AU  - Arandelovic, Sandra
AU  - Radulovic, Sinisa
AU  - Grgurić-Šipka, Sanja
AU  - Kaluđerović, Goran N.
AU  - Sabo, Tibor
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1442
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).
PB  - Oxford : Pergamon-Elsevier Science Ltd
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 and Savic, Aleksandar and Poljarevic, Jelena and Pantelić, Nebojša Đ. and Arandelovic, Sandra and Radulovic, Sinisa and Grgurić-Šipka, Sanja and Kaluđerović, Goran N. and Sabo, Tibor",
year = "2014",
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).",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
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., Savic, A., Poljarevic, J., Pantelić, N. Đ., Arandelovic, S., Radulovic, 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. in Polyhedron
Oxford : Pergamon-Elsevier Science Ltd., 80, 106-111.
https://doi.org/10.1016/j.poly.2014.02.026
Zmejkovski B, Savic A, Poljarevic J, Pantelić NĐ, Arandelovic S, Radulovic 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. in Polyhedron. 2014;80:106-111.
doi:10.1016/j.poly.2014.02.026 .
Zmejkovski, Bojana, Savic, Aleksandar, Poljarevic, Jelena, Pantelić, Nebojša Đ., Arandelovic, Sandra, Radulovic, Sinisa, 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" in Polyhedron, 80 (2014):106-111,
https://doi.org/10.1016/j.poly.2014.02.026 . .
18
11
17

Synthesis, characterisation and biological activity of Co(III) complex with the condensation product of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate

Milenković, Milica R.; Bacchi, Alessia; Cantoni, Giulia; Radulovic, Sinisa; Gligorijević, Nevenka; Arandelovic, Sandra; Sladić, Dušan; Vujčić, Miroslava; Mitić, Dragana; Anđelković, Katarina

(Elsevier Science Sa, Lausanne, 2013)

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Bacchi, Alessia
AU  - Cantoni, Giulia
AU  - Radulovic, Sinisa
AU  - Gligorijević, Nevenka
AU  - Arandelovic, Sandra
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Mitić, Dragana
AU  - Anđelković, Katarina
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1356
AB  - A cobalt(III) complex with the condensation derivative of 2-(diphenylphosphino) benzaldehyde and ethyl carbazate was synthesized. X-ray crystal structure was determined for both the ligand and the complex. In the cobalt(III) complex two deprotonated ligand molecules coordinate the metal atom in a distorted octahedral geometry by chelation through the PNO donor system formed by the phosphorus, the imine nitrogen and the carbonyl oxygen. The complex showed a moderate antibacterial activity and a strong cytotoxic activity, stronger than cisplatin. Based on cell cycle progression, apoptotic assays, spectroscopic and electrophoretic studies, it was shown that high cytotoxicity and moderate potential of induction of apoptosis are not consequence of interactions with DNA.
PB  - Elsevier Science Sa, Lausanne
T2  - Inorganica Chimica Acta
T1  - Synthesis, characterisation and biological activity of Co(III) complex with the condensation product of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate
VL  - 395
SP  - 33
EP  - 43
DO  - 10.1016/j.ica.2012.09.043
ER  - 
@article{
author = "Milenković, Milica R. and Bacchi, Alessia and Cantoni, Giulia and Radulovic, Sinisa and Gligorijević, Nevenka and Arandelovic, Sandra and Sladić, Dušan and Vujčić, Miroslava and Mitić, Dragana and Anđelković, Katarina",
year = "2013",
abstract = "A cobalt(III) complex with the condensation derivative of 2-(diphenylphosphino) benzaldehyde and ethyl carbazate was synthesized. X-ray crystal structure was determined for both the ligand and the complex. In the cobalt(III) complex two deprotonated ligand molecules coordinate the metal atom in a distorted octahedral geometry by chelation through the PNO donor system formed by the phosphorus, the imine nitrogen and the carbonyl oxygen. The complex showed a moderate antibacterial activity and a strong cytotoxic activity, stronger than cisplatin. Based on cell cycle progression, apoptotic assays, spectroscopic and electrophoretic studies, it was shown that high cytotoxicity and moderate potential of induction of apoptosis are not consequence of interactions with DNA.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Inorganica Chimica Acta",
title = "Synthesis, characterisation and biological activity of Co(III) complex with the condensation product of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate",
volume = "395",
pages = "33-43",
doi = "10.1016/j.ica.2012.09.043"
}
Milenković, M. R., Bacchi, A., Cantoni, G., Radulovic, S., Gligorijević, N., Arandelovic, S., Sladić, D., Vujčić, M., Mitić, D.,& Anđelković, K.. (2013). Synthesis, characterisation and biological activity of Co(III) complex with the condensation product of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate. in Inorganica Chimica Acta
Elsevier Science Sa, Lausanne., 395, 33-43.
https://doi.org/10.1016/j.ica.2012.09.043
Milenković MR, Bacchi A, Cantoni G, Radulovic S, Gligorijević N, Arandelovic S, Sladić D, Vujčić M, Mitić D, Anđelković K. Synthesis, characterisation and biological activity of Co(III) complex with the condensation product of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate. in Inorganica Chimica Acta. 2013;395:33-43.
doi:10.1016/j.ica.2012.09.043 .
Milenković, Milica R., Bacchi, Alessia, Cantoni, Giulia, Radulovic, Sinisa, Gligorijević, Nevenka, Arandelovic, Sandra, Sladić, Dušan, Vujčić, Miroslava, Mitić, Dragana, Anđelković, Katarina, "Synthesis, characterisation and biological activity of Co(III) complex with the condensation product of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate" in Inorganica Chimica Acta, 395 (2013):33-43,
https://doi.org/10.1016/j.ica.2012.09.043 . .
1
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Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides

Milenković, Milica R.; Bacchi, Alessia; Cantoni, Giulia; Vilipić, Jovana; Sladić, Dušan; Vujčić, Miroslava; Gligorijević, Nevenka; Jovanovic, Katarina; Radulovic, Sinisa; Anđelković, Katarina

(Elsevier France-Editions Scientifiques Medicales Elsevier, Paris, 2013)

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Bacchi, Alessia
AU  - Cantoni, Giulia
AU  - Vilipić, Jovana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Gligorijević, Nevenka
AU  - Jovanovic, Katarina
AU  - Radulovic, Sinisa
AU  - Anđelković, Katarina
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1266
AB  - Three square-planar complexes of nickel(II) with the tridentate condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate, and monodentate pseudohalides, have been synthesized. Their crystal structures have been determined. All the complexes showed a significant antifungal activity, while only the azido complex displayed antibacterial activity. All the complexes were cytotoxic to a panel of six tumor cell lines, the azido complex showing a similar activity as cisplatin to leukemia cell line K562 and lower toxicity to normal MRC-5 cells than that anticancer agent. The complexes interfered with cell cycle of tumor cells and induced plasmid DNA cleavage.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides
VL  - 68
SP  - 111
EP  - 120
DO  - 10.1016/j.ejmech.2013.07.039
ER  - 
@article{
author = "Milenković, Milica R. and Bacchi, Alessia and Cantoni, Giulia and Vilipić, Jovana and Sladić, Dušan and Vujčić, Miroslava and Gligorijević, Nevenka and Jovanovic, Katarina and Radulovic, Sinisa and Anđelković, Katarina",
year = "2013",
abstract = "Three square-planar complexes of nickel(II) with the tridentate condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate, and monodentate pseudohalides, have been synthesized. Their crystal structures have been determined. All the complexes showed a significant antifungal activity, while only the azido complex displayed antibacterial activity. All the complexes were cytotoxic to a panel of six tumor cell lines, the azido complex showing a similar activity as cisplatin to leukemia cell line K562 and lower toxicity to normal MRC-5 cells than that anticancer agent. The complexes interfered with cell cycle of tumor cells and induced plasmid DNA cleavage.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides",
volume = "68",
pages = "111-120",
doi = "10.1016/j.ejmech.2013.07.039"
}
Milenković, M. R., Bacchi, A., Cantoni, G., Vilipić, J., Sladić, D., Vujčić, M., Gligorijević, N., Jovanovic, K., Radulovic, S.,& Anđelković, K.. (2013). Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 68, 111-120.
https://doi.org/10.1016/j.ejmech.2013.07.039
Milenković MR, Bacchi A, Cantoni G, Vilipić J, Sladić D, Vujčić M, Gligorijević N, Jovanovic K, Radulovic S, Anđelković K. Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides. in European Journal of Medicinal Chemistry. 2013;68:111-120.
doi:10.1016/j.ejmech.2013.07.039 .
Milenković, Milica R., Bacchi, Alessia, Cantoni, Giulia, Vilipić, Jovana, Sladić, Dušan, Vujčić, Miroslava, Gligorijević, Nevenka, Jovanovic, Katarina, Radulovic, Sinisa, Anđelković, Katarina, "Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides" in European Journal of Medicinal Chemistry, 68 (2013):111-120,
https://doi.org/10.1016/j.ejmech.2013.07.039 . .
29
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Synthesis, characterization, cytotoxic activity and DNA binding properties of the novel dinuclear cobalt(III) complex with the condensation product of 2-acetylpyridine and malonic acid dihydrazide

Eshkourfu, Rabia; Čobeljić, Božidar; Vujčić, Miroslava; Turel, Iztok; Pevec, Andrej; Sepcic, Kristina; Zec, Manja; Radulovic, Sinisa; Srdic-Radic, Tatjana; Mitić, Dragana; Anđelković, Katarina; Sladić, Dušan

(Elsevier Science Inc, New York, 2011)

TY  - JOUR
AU  - Eshkourfu, Rabia
AU  - Čobeljić, Božidar
AU  - Vujčić, Miroslava
AU  - Turel, Iztok
AU  - Pevec, Andrej
AU  - Sepcic, Kristina
AU  - Zec, Manja
AU  - Radulovic, Sinisa
AU  - Srdic-Radic, Tatjana
AU  - Mitić, Dragana
AU  - Anđelković, Katarina
AU  - Sladić, Dušan
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/769
AB  - A novel dinuclear cobalt(III) complex with the condensation product of 2-acetylpyridine and malonic acid dihydrazide, N',N'(2)-bis[(1E)-1-(2-pyridyl)ethylidene]propanedihydrazide was synthesized and characterized by elemental analysis, spectroscopy (NMR and infrared), and X-ray crystal analysis. The complex showed a moderate activity towards Artemia salina. The highest cytotoxic potential of the complex was observed on the epithelial breast cancer (MDA-361) cell line. The investigated complex induced apoptosis, the early apoptotic cells comprising 28.18%, compared to 5.64% of control cells in the same phase. The interaction of the complex with calf thymus DNA (CT-DNA) was monitored by blue shift and hyperchromism in the UV-vis spectra. The observed intrinsic binding constant (K(b) = 4.2 x 10(5) M(-1)) together with structural analysis of the complex indicate the groove binding.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization, cytotoxic activity and DNA binding properties of the novel dinuclear cobalt(III) complex with the condensation product of 2-acetylpyridine and malonic acid dihydrazide
VL  - 105
IS  - 9
SP  - 1196
EP  - 1203
DO  - 10.1016/j.jinorgbio.2011.05.024
ER  - 
@article{
author = "Eshkourfu, Rabia and Čobeljić, Božidar and Vujčić, Miroslava and Turel, Iztok and Pevec, Andrej and Sepcic, Kristina and Zec, Manja and Radulovic, Sinisa and Srdic-Radic, Tatjana and Mitić, Dragana and Anđelković, Katarina and Sladić, Dušan",
year = "2011",
abstract = "A novel dinuclear cobalt(III) complex with the condensation product of 2-acetylpyridine and malonic acid dihydrazide, N',N'(2)-bis[(1E)-1-(2-pyridyl)ethylidene]propanedihydrazide was synthesized and characterized by elemental analysis, spectroscopy (NMR and infrared), and X-ray crystal analysis. The complex showed a moderate activity towards Artemia salina. The highest cytotoxic potential of the complex was observed on the epithelial breast cancer (MDA-361) cell line. The investigated complex induced apoptosis, the early apoptotic cells comprising 28.18%, compared to 5.64% of control cells in the same phase. The interaction of the complex with calf thymus DNA (CT-DNA) was monitored by blue shift and hyperchromism in the UV-vis spectra. The observed intrinsic binding constant (K(b) = 4.2 x 10(5) M(-1)) together with structural analysis of the complex indicate the groove binding.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization, cytotoxic activity and DNA binding properties of the novel dinuclear cobalt(III) complex with the condensation product of 2-acetylpyridine and malonic acid dihydrazide",
volume = "105",
number = "9",
pages = "1196-1203",
doi = "10.1016/j.jinorgbio.2011.05.024"
}
Eshkourfu, R., Čobeljić, B., Vujčić, M., Turel, I., Pevec, A., Sepcic, K., Zec, M., Radulovic, S., Srdic-Radic, T., Mitić, D., Anđelković, K.,& Sladić, D.. (2011). Synthesis, characterization, cytotoxic activity and DNA binding properties of the novel dinuclear cobalt(III) complex with the condensation product of 2-acetylpyridine and malonic acid dihydrazide. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 105(9), 1196-1203.
https://doi.org/10.1016/j.jinorgbio.2011.05.024
Eshkourfu R, Čobeljić B, Vujčić M, Turel I, Pevec A, Sepcic K, Zec M, Radulovic S, Srdic-Radic T, Mitić D, Anđelković K, Sladić D. Synthesis, characterization, cytotoxic activity and DNA binding properties of the novel dinuclear cobalt(III) complex with the condensation product of 2-acetylpyridine and malonic acid dihydrazide. in Journal of Inorganic Biochemistry. 2011;105(9):1196-1203.
doi:10.1016/j.jinorgbio.2011.05.024 .
Eshkourfu, Rabia, Čobeljić, Božidar, Vujčić, Miroslava, Turel, Iztok, Pevec, Andrej, Sepcic, Kristina, Zec, Manja, Radulovic, Sinisa, Srdic-Radic, Tatjana, Mitić, Dragana, Anđelković, Katarina, Sladić, Dušan, "Synthesis, characterization, cytotoxic activity and DNA binding properties of the novel dinuclear cobalt(III) complex with the condensation product of 2-acetylpyridine and malonic acid dihydrazide" in Journal of Inorganic Biochemistry, 105, no. 9 (2011):1196-1203,
https://doi.org/10.1016/j.jinorgbio.2011.05.024 . .
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