Nikolić, Stefan

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orcid::0000-0002-0164-134X
  • Nikolić, Stefan (18)
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Author's Bibliography

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

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

(Springer, 2020)

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

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

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

(Springer, 2020)

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

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

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

(Springer, 2020)

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

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

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

(Springer Link, 2019)

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

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

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

(Taylor & Francis, 2019)

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

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

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

(2019)

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

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

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

(2019)

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

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

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

(2019)

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

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

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

(Taylor & Francis, 2019)

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

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

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

(Taylor & Francis, 2019)

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

Conversion of hydrazides into: N, N ′-diacylhydrazines in the presence of a ruthenium(II)-arene complex

Nikolić, Stefan; Ćirić, Ivanka; Roller, Alexander; Lukeš, Vladimir; Arion, Vladimir B.; Grgurić-Šipka, Sanja

(Royal Soc Chemistry, Cambridge, 2017)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Ćirić, Ivanka
AU  - Roller, Alexander
AU  - Lukeš, Vladimir
AU  - Arion, Vladimir B.
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3124
AB  - Mono and dinuclear p-cymene-ruthenium(II) complexes [RuCl(L-1)(eta(6)-p-cymene)]Cl, where L-1 is propionic acid hydrazide (1) and [Ru2Cl2(L-2)(eta(6)-p-cymene)2], where H2L2 is N-1,N-2-dipropionylhydrazine (2), were prepared by a reaction of [RuCl2(eta(6)-p-cymene)](2) with the corresponding ligand precursor. Upon the reaction of [RuCl2(eta(6)-p-cymene)](2) with butyric acid hydrazide and pentanoic acid hydrazide in a 1:1 molar ratio in situ formation of tetradentate bridging ligands, N-1,N-2-dibutanoylhydrazine and N1,N2-dipentanoylhydrazine, respectively, occurred and the dinuclear complexes [Ru2Cl2(L-3)(eta(6)-p-cymene)2] (3) and [Ru2Cl2(L-4)(eta(6)-p-cymene)(2)] (4) were isolated. The compounds were characterised by elemental analysis, ESI-mass spectrometry, IR and 1D and 2D NMR spectroscopies. The structures of all complexes were established using single crystal X-ray crystallography. According to these data in both the mono- and dinuclear complexes the ruthenium atoms adopt the usual three-leg piano-stool geometry which is common for this type of complexes. Combining DFT calculations with the characterisation of the final products using X-ray diffraction, a possible reaction mechanism was discussed.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Conversion of hydrazides into: N, N ′-diacylhydrazines in the presence of a ruthenium(II)-arene complex
VL  - 41
IS  - 14
SP  - 6857
EP  - 6865
DO  - 10.1039/c7nj00965h
ER  - 
@article{
author = "Nikolić, Stefan and Ćirić, Ivanka and Roller, Alexander and Lukeš, Vladimir and Arion, Vladimir B. and Grgurić-Šipka, Sanja",
year = "2017",
abstract = "Mono and dinuclear p-cymene-ruthenium(II) complexes [RuCl(L-1)(eta(6)-p-cymene)]Cl, where L-1 is propionic acid hydrazide (1) and [Ru2Cl2(L-2)(eta(6)-p-cymene)2], where H2L2 is N-1,N-2-dipropionylhydrazine (2), were prepared by a reaction of [RuCl2(eta(6)-p-cymene)](2) with the corresponding ligand precursor. Upon the reaction of [RuCl2(eta(6)-p-cymene)](2) with butyric acid hydrazide and pentanoic acid hydrazide in a 1:1 molar ratio in situ formation of tetradentate bridging ligands, N-1,N-2-dibutanoylhydrazine and N1,N2-dipentanoylhydrazine, respectively, occurred and the dinuclear complexes [Ru2Cl2(L-3)(eta(6)-p-cymene)2] (3) and [Ru2Cl2(L-4)(eta(6)-p-cymene)(2)] (4) were isolated. The compounds were characterised by elemental analysis, ESI-mass spectrometry, IR and 1D and 2D NMR spectroscopies. The structures of all complexes were established using single crystal X-ray crystallography. According to these data in both the mono- and dinuclear complexes the ruthenium atoms adopt the usual three-leg piano-stool geometry which is common for this type of complexes. Combining DFT calculations with the characterisation of the final products using X-ray diffraction, a possible reaction mechanism was discussed.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Conversion of hydrazides into: N, N ′-diacylhydrazines in the presence of a ruthenium(II)-arene complex",
volume = "41",
number = "14",
pages = "6857-6865",
doi = "10.1039/c7nj00965h"
}
Nikolić, S., Ćirić, I., Roller, A., Lukeš, V., Arion, V. B.,& Grgurić-Šipka, S.. (2017). Conversion of hydrazides into: N, N ′-diacylhydrazines in the presence of a ruthenium(II)-arene complex. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(14), 6857-6865.
https://doi.org/10.1039/c7nj00965h
Nikolić S, Ćirić I, Roller A, Lukeš V, Arion VB, Grgurić-Šipka S. Conversion of hydrazides into: N, N ′-diacylhydrazines in the presence of a ruthenium(II)-arene complex. in New Journal of Chemistry. 2017;41(14):6857-6865.
doi:10.1039/c7nj00965h .
Nikolić, Stefan, Ćirić, Ivanka, Roller, Alexander, Lukeš, Vladimir, Arion, Vladimir B., Grgurić-Šipka, Sanja, "Conversion of hydrazides into: N, N ′-diacylhydrazines in the presence of a ruthenium(II)-arene complex" in New Journal of Chemistry, 41, no. 14 (2017):6857-6865,
https://doi.org/10.1039/c7nj00965h . .
3
3
3

Supplementary data for article: Nikolić, S.; Ćirić, I.; Roller, A.; Lukeš, V.; Arion, V. B.; Grgurić-Šipka, S. Conversion of Hydrazides into: N, N ′-Diacylhydrazines in the Presence of a Ruthenium(II)-Arene Complex. New Journal of Chemistry 2017, 41 (14), 6857–6865. https://doi.org/10.1039/c7nj00965h

Nikolić, Stefan; Ćirić, Ivanka; Roller, Alexander; Lukeš, Vladimir; Arion, Vladimir B.; Grgurić-Šipka, Sanja

(Royal Soc Chemistry, Cambridge, 2017)

TY  - DATA
AU  - Nikolić, Stefan
AU  - Ćirić, Ivanka
AU  - Roller, Alexander
AU  - Lukeš, Vladimir
AU  - Arion, Vladimir B.
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3125
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Supplementary data for article:           Nikolić, S.; Ćirić, I.; Roller, A.; Lukeš, V.; Arion, V. B.; Grgurić-Šipka, S. Conversion of Hydrazides into: N, N ′-Diacylhydrazines in the Presence of a Ruthenium(II)-Arene Complex. New Journal of Chemistry 2017, 41 (14), 6857–6865. https://doi.org/10.1039/c7nj00965h
ER  - 
@misc{
author = "Nikolić, Stefan and Ćirić, Ivanka and Roller, Alexander and Lukeš, Vladimir and Arion, Vladimir B. and Grgurić-Šipka, Sanja",
year = "2017",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Supplementary data for article:           Nikolić, S.; Ćirić, I.; Roller, A.; Lukeš, V.; Arion, V. B.; Grgurić-Šipka, S. Conversion of Hydrazides into: N, N ′-Diacylhydrazines in the Presence of a Ruthenium(II)-Arene Complex. New Journal of Chemistry 2017, 41 (14), 6857–6865. https://doi.org/10.1039/c7nj00965h"
}
Nikolić, S., Ćirić, I., Roller, A., Lukeš, V., Arion, V. B.,& Grgurić-Šipka, S.. (2017). Supplementary data for article:           Nikolić, S.; Ćirić, I.; Roller, A.; Lukeš, V.; Arion, V. B.; Grgurić-Šipka, S. Conversion of Hydrazides into: N, N ′-Diacylhydrazines in the Presence of a Ruthenium(II)-Arene Complex. New Journal of Chemistry 2017, 41 (14), 6857–6865. https://doi.org/10.1039/c7nj00965h. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge..
Nikolić S, Ćirić I, Roller A, Lukeš V, Arion VB, Grgurić-Šipka S. Supplementary data for article:           Nikolić, S.; Ćirić, I.; Roller, A.; Lukeš, V.; Arion, V. B.; Grgurić-Šipka, S. Conversion of Hydrazides into: N, N ′-Diacylhydrazines in the Presence of a Ruthenium(II)-Arene Complex. New Journal of Chemistry 2017, 41 (14), 6857–6865. https://doi.org/10.1039/c7nj00965h. in New Journal of Chemistry. 2017;..
Nikolić, Stefan, Ćirić, Ivanka, Roller, Alexander, Lukeš, Vladimir, Arion, Vladimir B., Grgurić-Šipka, Sanja, "Supplementary data for article:           Nikolić, S.; Ćirić, I.; Roller, A.; Lukeš, V.; Arion, V. B.; Grgurić-Šipka, S. Conversion of Hydrazides into: N, N ′-Diacylhydrazines in the Presence of a Ruthenium(II)-Arene Complex. New Journal of Chemistry 2017, 41 (14), 6857–6865. https://doi.org/10.1039/c7nj00965h" in New Journal of Chemistry (2017).

Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex

Nikolić, Stefan; Ćirić, Ivanka; Roller, Alexander; Lukeš, Vladimir; Arion, Vladimir B.; Grgurić-Šipka, Sanja

(Royal Soc Chemistry, Cambridge, 2017)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Ćirić, Ivanka
AU  - Roller, Alexander
AU  - Lukeš, Vladimir
AU  - Arion, Vladimir B.
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2485
AB  - Mono and dinuclear p-cymene-ruthenium(II) complexes [RuCl(L-1)(eta(6)-p-cymene)]Cl, where L-1 is propionic acid hydrazide (1) and [Ru2Cl2(L-2)(eta(6)-p-cymene)2], where H2L2 is N-1,N-2-dipropionylhydrazine (2), were prepared by a reaction of [RuCl2(eta(6)-p-cymene)](2) with the corresponding ligand precursor. Upon the reaction of [RuCl2(eta(6)-p-cymene)](2) with butyric acid hydrazide and pentanoic acid hydrazide in a 1:1 molar ratio in situ formation of tetradentate bridging ligands, N-1,N-2-dibutanoylhydrazine and N1,N2-dipentanoylhydrazine, respectively, occurred and the dinuclear complexes [Ru2Cl2(L-3)(eta(6)-p-cymene)2] (3) and [Ru2Cl2(L-4)(eta(6)-p-cymene)(2)] (4) were isolated. The compounds were characterised by elemental analysis, ESI-mass spectrometry, IR and 1D and 2D NMR spectroscopies. The structures of all complexes were established using single crystal X-ray crystallography. According to these data in both the mono- and dinuclear complexes the ruthenium atoms adopt the usual three-leg piano-stool geometry which is common for this type of complexes. Combining DFT calculations with the characterisation of the final products using X-ray diffraction, a possible reaction mechanism was discussed.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex
VL  - 41
IS  - 14
SP  - 6857
EP  - 6865
DO  - 10.1039/c7nj00965h
UR  - Kon_3301
ER  - 
@article{
author = "Nikolić, Stefan and Ćirić, Ivanka and Roller, Alexander and Lukeš, Vladimir and Arion, Vladimir B. and Grgurić-Šipka, Sanja",
year = "2017",
abstract = "Mono and dinuclear p-cymene-ruthenium(II) complexes [RuCl(L-1)(eta(6)-p-cymene)]Cl, where L-1 is propionic acid hydrazide (1) and [Ru2Cl2(L-2)(eta(6)-p-cymene)2], where H2L2 is N-1,N-2-dipropionylhydrazine (2), were prepared by a reaction of [RuCl2(eta(6)-p-cymene)](2) with the corresponding ligand precursor. Upon the reaction of [RuCl2(eta(6)-p-cymene)](2) with butyric acid hydrazide and pentanoic acid hydrazide in a 1:1 molar ratio in situ formation of tetradentate bridging ligands, N-1,N-2-dibutanoylhydrazine and N1,N2-dipentanoylhydrazine, respectively, occurred and the dinuclear complexes [Ru2Cl2(L-3)(eta(6)-p-cymene)2] (3) and [Ru2Cl2(L-4)(eta(6)-p-cymene)(2)] (4) were isolated. The compounds were characterised by elemental analysis, ESI-mass spectrometry, IR and 1D and 2D NMR spectroscopies. The structures of all complexes were established using single crystal X-ray crystallography. According to these data in both the mono- and dinuclear complexes the ruthenium atoms adopt the usual three-leg piano-stool geometry which is common for this type of complexes. Combining DFT calculations with the characterisation of the final products using X-ray diffraction, a possible reaction mechanism was discussed.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex",
volume = "41",
number = "14",
pages = "6857-6865",
doi = "10.1039/c7nj00965h",
url = "Kon_3301"
}
Nikolić, S., Ćirić, I., Roller, A., Lukeš, V., Arion, V. B.,& Grgurić-Šipka, S.. (2017). Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(14), 6857-6865.
https://doi.org/10.1039/c7nj00965h
Kon_3301
Nikolić S, Ćirić I, Roller A, Lukeš V, Arion VB, Grgurić-Šipka S. Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex. in New Journal of Chemistry. 2017;41(14):6857-6865.
doi:10.1039/c7nj00965h
Kon_3301 .
Nikolić, Stefan, Ćirić, Ivanka, Roller, Alexander, Lukeš, Vladimir, Arion, Vladimir B., Grgurić-Šipka, Sanja, "Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex" in New Journal of Chemistry, 41, no. 14 (2017):6857-6865,
https://doi.org/10.1039/c7nj00965h .,
Kon_3301 .
3
3

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

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

(Elsevier Science Inc, New York, 2016)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Rangasamy, Loganathan
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Gasser, Gilles
AU  - Grgurić-Šipka, Sanja
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3638
AB  - Three new ruthenium(II)-arene complexes, namely [(eta(6)-p-cymene)Ru(Me(2)dppz)Cl]PF6 (1), [(eta(6)-benzene)Ru(Me(2)dppz)Cl]PF6 (2) and [(eta(6)-p-cymene)Ru(aip)Cl]PF6 (3) (Me(2)dppz = 11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine; aip = 2-(9-anthryl)-1H-imidazo[4,5-f] [1,10] phenanthroline) have been synthesized and characterized using different spectroscopic techniques including elemental analysis. The complexes were found to be well soluble and stable in DMSO. The biological activity of the three complexes was tested in three different human cancer cell lines (A549, MDA-MB-231 and HeLa) and in one human non-cancerous cell line (MRC-5). Complexes 1 and 3, carrying eta(6)-p-cymene as the arene ligand, were shown to be toxic in all cell lines in the low micromolar/subnanomolar range, with complex 1 being the most cytotoxic complex of the series. Flow cytometry analysis revealed that complex 1 caused concentration- and time-dependent arrest of the cell cycle in G2-M and S phases in HeLa cells. This event is followed by the accumulation of the sub-G1 DNA content after 48 h, in levels higher than cisplatin and in the absence of phosphatidylserine externalization. Fluorescent microscopy and acridine orange/ethidium bromide staining revealed that complex 1 induced both apoptotic and necrotic cell morphology characteristics. Drug-accumulation and DNA-binding studies performed by inductively coupled plasma mass spectrometry in HeLa cells showed that the total ruthenium uptake increased in a time- and concentration-dependent manner, and that complex 1 accumulated more efficiently than cisplatin at equimolar concentrations. The introduction of a Me(2)dppz ligand into the ruthenium(II)-p-cymene scaffold was found to allow the discovery of a strongly cytotoxic complex with significantly higher cellular uptake and DNA-binding properties than cisplatin. (C) 2016 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands
VL  - 160
SP  - 156
EP  - 165
DO  - 10.1016/j.jinorgbio.2016.01.005
UR  - Kon_3088
ER  - 
@article{
author = "Nikolić, Stefan and Rangasamy, Loganathan and Gligorijević, Nevenka and Aranđelović, Sandra and Radulović, Siniša and Gasser, Gilles and Grgurić-Šipka, Sanja",
year = "2016",
abstract = "Three new ruthenium(II)-arene complexes, namely [(eta(6)-p-cymene)Ru(Me(2)dppz)Cl]PF6 (1), [(eta(6)-benzene)Ru(Me(2)dppz)Cl]PF6 (2) and [(eta(6)-p-cymene)Ru(aip)Cl]PF6 (3) (Me(2)dppz = 11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine; aip = 2-(9-anthryl)-1H-imidazo[4,5-f] [1,10] phenanthroline) have been synthesized and characterized using different spectroscopic techniques including elemental analysis. The complexes were found to be well soluble and stable in DMSO. The biological activity of the three complexes was tested in three different human cancer cell lines (A549, MDA-MB-231 and HeLa) and in one human non-cancerous cell line (MRC-5). Complexes 1 and 3, carrying eta(6)-p-cymene as the arene ligand, were shown to be toxic in all cell lines in the low micromolar/subnanomolar range, with complex 1 being the most cytotoxic complex of the series. Flow cytometry analysis revealed that complex 1 caused concentration- and time-dependent arrest of the cell cycle in G2-M and S phases in HeLa cells. This event is followed by the accumulation of the sub-G1 DNA content after 48 h, in levels higher than cisplatin and in the absence of phosphatidylserine externalization. Fluorescent microscopy and acridine orange/ethidium bromide staining revealed that complex 1 induced both apoptotic and necrotic cell morphology characteristics. Drug-accumulation and DNA-binding studies performed by inductively coupled plasma mass spectrometry in HeLa cells showed that the total ruthenium uptake increased in a time- and concentration-dependent manner, and that complex 1 accumulated more efficiently than cisplatin at equimolar concentrations. The introduction of a Me(2)dppz ligand into the ruthenium(II)-p-cymene scaffold was found to allow the discovery of a strongly cytotoxic complex with significantly higher cellular uptake and DNA-binding properties than cisplatin. (C) 2016 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands",
volume = "160",
pages = "156-165",
doi = "10.1016/j.jinorgbio.2016.01.005",
url = "Kon_3088"
}
Nikolić, S., Rangasamy, L., Gligorijević, N., Aranđelović, S., Radulović, S., Gasser, G.,& Grgurić-Šipka, S.. (2016). Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 160, 156-165.
https://doi.org/10.1016/j.jinorgbio.2016.01.005
Kon_3088
Nikolić S, Rangasamy L, Gligorijević N, Aranđelović S, Radulović S, Gasser G, Grgurić-Šipka S. Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. in Journal of Inorganic Biochemistry. 2016;160:156-165.
doi:10.1016/j.jinorgbio.2016.01.005
Kon_3088 .
Nikolić, Stefan, Rangasamy, Loganathan, Gligorijević, Nevenka, Aranđelović, Sandra, Radulović, Siniša, Gasser, Gilles, Grgurić-Šipka, Sanja, "Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands" in Journal of Inorganic Biochemistry, 160 (2016):156-165,
https://doi.org/10.1016/j.jinorgbio.2016.01.005 .,
Kon_3088 .
32
31

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

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

(Elsevier Science Inc, New York, 2016)

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

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

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

(Elsevier Science Inc, New York, 2016)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Rangasamy, Loganathan
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Gasser, Gilles
AU  - Grgurić-Šipka, Sanja
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2272
AB  - Three new ruthenium(II)-arene complexes, namely [(eta(6)-p-cymene)Ru(Me(2)dppz)Cl]PF6 (1), [(eta(6)-benzene)Ru(Me(2)dppz)Cl]PF6 (2) and [(eta(6)-p-cymene)Ru(aip)Cl]PF6 (3) (Me(2)dppz = 11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine; aip = 2-(9-anthryl)-1H-imidazo[4,5-f] [1,10] phenanthroline) have been synthesized and characterized using different spectroscopic techniques including elemental analysis. The complexes were found to be well soluble and stable in DMSO. The biological activity of the three complexes was tested in three different human cancer cell lines (A549, MDA-MB-231 and HeLa) and in one human non-cancerous cell line (MRC-5). Complexes 1 and 3, carrying eta(6)-p-cymene as the arene ligand, were shown to be toxic in all cell lines in the low micromolar/subnanomolar range, with complex 1 being the most cytotoxic complex of the series. Flow cytometry analysis revealed that complex 1 caused concentration- and time-dependent arrest of the cell cycle in G2-M and S phases in HeLa cells. This event is followed by the accumulation of the sub-G1 DNA content after 48 h, in levels higher than cisplatin and in the absence of phosphatidylserine externalization. Fluorescent microscopy and acridine orange/ethidium bromide staining revealed that complex 1 induced both apoptotic and necrotic cell morphology characteristics. Drug-accumulation and DNA-binding studies performed by inductively coupled plasma mass spectrometry in HeLa cells showed that the total ruthenium uptake increased in a time- and concentration-dependent manner, and that complex 1 accumulated more efficiently than cisplatin at equimolar concentrations. The introduction of a Me(2)dppz ligand into the ruthenium(II)-p-cymene scaffold was found to allow the discovery of a strongly cytotoxic complex with significantly higher cellular uptake and DNA-binding properties than cisplatin. (C) 2016 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands
VL  - 160
SP  - 156
EP  - 165
DO  - 10.1016/j.jinorgbio.2016.01.005
UR  - Kon_3088
ER  - 
@article{
author = "Nikolić, Stefan and Rangasamy, Loganathan and Gligorijević, Nevenka and Aranđelović, Sandra and Radulović, Siniša and Gasser, Gilles and Grgurić-Šipka, Sanja",
year = "2016",
abstract = "Three new ruthenium(II)-arene complexes, namely [(eta(6)-p-cymene)Ru(Me(2)dppz)Cl]PF6 (1), [(eta(6)-benzene)Ru(Me(2)dppz)Cl]PF6 (2) and [(eta(6)-p-cymene)Ru(aip)Cl]PF6 (3) (Me(2)dppz = 11,12-dimethyldipyrido[3,2-a:2',3'-c]phenazine; aip = 2-(9-anthryl)-1H-imidazo[4,5-f] [1,10] phenanthroline) have been synthesized and characterized using different spectroscopic techniques including elemental analysis. The complexes were found to be well soluble and stable in DMSO. The biological activity of the three complexes was tested in three different human cancer cell lines (A549, MDA-MB-231 and HeLa) and in one human non-cancerous cell line (MRC-5). Complexes 1 and 3, carrying eta(6)-p-cymene as the arene ligand, were shown to be toxic in all cell lines in the low micromolar/subnanomolar range, with complex 1 being the most cytotoxic complex of the series. Flow cytometry analysis revealed that complex 1 caused concentration- and time-dependent arrest of the cell cycle in G2-M and S phases in HeLa cells. This event is followed by the accumulation of the sub-G1 DNA content after 48 h, in levels higher than cisplatin and in the absence of phosphatidylserine externalization. Fluorescent microscopy and acridine orange/ethidium bromide staining revealed that complex 1 induced both apoptotic and necrotic cell morphology characteristics. Drug-accumulation and DNA-binding studies performed by inductively coupled plasma mass spectrometry in HeLa cells showed that the total ruthenium uptake increased in a time- and concentration-dependent manner, and that complex 1 accumulated more efficiently than cisplatin at equimolar concentrations. The introduction of a Me(2)dppz ligand into the ruthenium(II)-p-cymene scaffold was found to allow the discovery of a strongly cytotoxic complex with significantly higher cellular uptake and DNA-binding properties than cisplatin. (C) 2016 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands",
volume = "160",
pages = "156-165",
doi = "10.1016/j.jinorgbio.2016.01.005",
url = "Kon_3088"
}
Nikolić, S., Rangasamy, L., Gligorijević, N., Aranđelović, S., Radulović, S., Gasser, G.,& Grgurić-Šipka, S.. (2016). Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 160, 156-165.
https://doi.org/10.1016/j.jinorgbio.2016.01.005
Kon_3088
Nikolić S, Rangasamy L, Gligorijević N, Aranđelović S, Radulović S, Gasser G, Grgurić-Šipka S. Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. in Journal of Inorganic Biochemistry. 2016;160:156-165.
doi:10.1016/j.jinorgbio.2016.01.005
Kon_3088 .
Nikolić, Stefan, Rangasamy, Loganathan, Gligorijević, Nevenka, Aranđelović, Sandra, Radulović, Siniša, Gasser, Gilles, Grgurić-Šipka, Sanja, "Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands" in Journal of Inorganic Biochemistry, 160 (2016):156-165,
https://doi.org/10.1016/j.jinorgbio.2016.01.005 .,
Kon_3088 .
32
31
31

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

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

(Amer Chemical Soc, Washington, 2015)

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

Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes

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

(Amer Chemical Soc, Washington, 2015)

TY  - JOUR
AU  - Nikolić, Stefan
AU  - Opsenica, Dejan M.
AU  - Filipović, Vuk
AU  - Dojčinović, Biljana P.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2015
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1746
AB  - Two p-cymenerutheniumchlorido complexes with thiourea derivative of 7-chloroquinoline (C1) and pyridine-3-imidazole (C2) were synthesized starting from [(eta(6)-p-cymene)RuCl2](2) and corresponding ligands. The structures of complexes were determined with elemental analysis and IR, ESIMS, H-1 and C-13{H-1} NMR, and 2D H-1-N-15 correlation NMR spectroscopy. Cytotoxic activities examined by the MTT assay were performed in five human neoplastic cell lines (HeLa, K562, A549, MDA-MB-231, EA.hy926) and one nontumor human fetal lung fibroblast cell line (MRC-5). Tested complexes exhibited low micromolar activities with IC50 in the range 11.03-56.45 mu M, while ligands L1 and L2 were significantly less active. Complex C1 showed cytoselective activity toward the K562 cell line (IC50 = 11.03 +/- 1.39 mu M) and was 3 times less active against the nontumor MRC-5 cell line. Flow cytometry analysis indicated that complexes C1 and C2 after 24 h treatment caused a concentration-dependent increase of the apoptotic sub-G1 fraction (up to 18.4%), comparable to cis-diamminedichloridoplatinum(II) (cisplatin, CDDP), although without other substantial alterations of the cell cycle. A drug-accumulation and DNA-binding study performed by ICP-MS in the K562 cell line revealed that complex C1 had a high intracellular uptake (1.38 mu g Ru/10 (6) cells), which significantly exceeded the intracellular uptake levels of CDDP (0.29 mu g Pt/10 (6) cells) and C2 (0.08 mu g Ru/10 (6) cells). However, both ruthenium complexes C1 and C2 bind to cellular DNA less efficiently in comparison to CDDP. The structure-activity relationship clearly suggested that introduction of a 7-chloroquinoline moiety in the ruthenium(II)-p-cymene complex significantly contributed to the intracellular uptake of C1 and higher cytotoxicity and cytoselectivity.
PB  - Amer Chemical Soc, Washington
T2  - Organometallics
T1  - Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes
VL  - 34
IS  - 14
SP  - 3464
EP  - 3473
DO  - 10.1021/acs.organomet.5b00041
UR  - Kon_2892
ER  - 
@article{
author = "Nikolić, Stefan and Opsenica, Dejan M. and Filipović, Vuk and Dojčinović, Biljana P. and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2015",
abstract = "Two p-cymenerutheniumchlorido complexes with thiourea derivative of 7-chloroquinoline (C1) and pyridine-3-imidazole (C2) were synthesized starting from [(eta(6)-p-cymene)RuCl2](2) and corresponding ligands. The structures of complexes were determined with elemental analysis and IR, ESIMS, H-1 and C-13{H-1} NMR, and 2D H-1-N-15 correlation NMR spectroscopy. Cytotoxic activities examined by the MTT assay were performed in five human neoplastic cell lines (HeLa, K562, A549, MDA-MB-231, EA.hy926) and one nontumor human fetal lung fibroblast cell line (MRC-5). Tested complexes exhibited low micromolar activities with IC50 in the range 11.03-56.45 mu M, while ligands L1 and L2 were significantly less active. Complex C1 showed cytoselective activity toward the K562 cell line (IC50 = 11.03 +/- 1.39 mu M) and was 3 times less active against the nontumor MRC-5 cell line. Flow cytometry analysis indicated that complexes C1 and C2 after 24 h treatment caused a concentration-dependent increase of the apoptotic sub-G1 fraction (up to 18.4%), comparable to cis-diamminedichloridoplatinum(II) (cisplatin, CDDP), although without other substantial alterations of the cell cycle. A drug-accumulation and DNA-binding study performed by ICP-MS in the K562 cell line revealed that complex C1 had a high intracellular uptake (1.38 mu g Ru/10 (6) cells), which significantly exceeded the intracellular uptake levels of CDDP (0.29 mu g Pt/10 (6) cells) and C2 (0.08 mu g Ru/10 (6) cells). However, both ruthenium complexes C1 and C2 bind to cellular DNA less efficiently in comparison to CDDP. The structure-activity relationship clearly suggested that introduction of a 7-chloroquinoline moiety in the ruthenium(II)-p-cymene complex significantly contributed to the intracellular uptake of C1 and higher cytotoxicity and cytoselectivity.",
publisher = "Amer Chemical Soc, Washington",
journal = "Organometallics",
title = "Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes",
volume = "34",
number = "14",
pages = "3464-3473",
doi = "10.1021/acs.organomet.5b00041",
url = "Kon_2892"
}
Nikolić, S., Opsenica, D. M., Filipović, V., Dojčinović, B. P., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2015). Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. in Organometallics
Amer Chemical Soc, Washington., 34(14), 3464-3473.
https://doi.org/10.1021/acs.organomet.5b00041
Kon_2892
Nikolić S, Opsenica DM, Filipović V, Dojčinović BP, Aranđelović S, Radulović S, Grgurić-Šipka S. Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes. in Organometallics. 2015;34(14):3464-3473.
doi:10.1021/acs.organomet.5b00041
Kon_2892 .
Nikolić, Stefan, Opsenica, Dejan M., Filipović, Vuk, Dojčinović, Biljana P., Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes" in Organometallics, 34, no. 14 (2015):3464-3473,
https://doi.org/10.1021/acs.organomet.5b00041 .,
Kon_2892 .
1
33
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