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

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

Nikolić, S., Rangasamy, L., Gligorijević, N., Aranđelović, S., Radulović, S., Gasser, G.,& Grgurić-Šipka, S.. (2016). Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 160, 156-165.
https://doi.org/10.1016/j.jinorgbio.2016.01.005

Nikolić S, Rangasamy L, Gligorijević N, Aranđelović S, Radulović S, Gasser G, Grgurić-Šipka S. Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. in Journal of Inorganic Biochemistry. 2016;160:156-165.
doi:10.1016/j.jinorgbio.2016.01.005 .

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 . .

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  - https://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
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3639
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",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3639"
}

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..
https://hdl.handle.net/21.15107/rcub_cherry_3639

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;.
https://hdl.handle.net/21.15107/rcub_cherry_3639 .

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),
https://hdl.handle.net/21.15107/rcub_cherry_3639 .

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

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

Nikolić, S., Rangasamy, L., Gligorijević, N., Aranđelović, S., Radulović, S., Gasser, G.,& Grgurić-Šipka, S.. (2016). Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 160, 156-165.
https://doi.org/10.1016/j.jinorgbio.2016.01.005

Nikolić S, Rangasamy L, Gligorijević N, Aranđelović S, Radulović S, Gasser G, Grgurić-Šipka S. Synthesis, characterization and biological evaluation of novel Ru(II)-arene complexes containing intercalating ligands. in Journal of Inorganic Biochemistry. 2016;160:156-165.
doi:10.1016/j.jinorgbio.2016.01.005 .

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 . .

TY  - JOUR
AU  - Ivanović, Ivanka
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Roller, Alexander
AU  - Keppler, Bernhard K.
AU  - Tešić, Živoslav Lj.
AU  - Grgurić-Šipka, Sanja
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1386
AB  - Metal semicarbazone and thiosemicarbazone complexes have attracted much attention due to their diverse biological activities. Because of the ability of ruthenium(II)-arene species to coordinate to different classes of ligands, they are suitable for fine-tuning chemical and pharmaceutical properties. Ruthenium(II) arene-complexes containing different types of ligands: namely caprylic hydrazide (a hydrazide with a long hydrocarbon chain), isonicotinic acid hydrazide (a hydrazide with an aromatic pyridine ring), thiosemicarbazones and semicarbazones (derived from the reaction of 3- and 4-acetylpyridine with either thiosemicarbazide or caprylic hydrazide), were obtained in the reaction of [(eta(6)-p-cymene)RuCl2](2) with the corresponding ligands in a 1:2 or 1:2.2 molar ratio in methanol, ethanol or isopropanol with mild heating. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structure of complex 1 was determined by X-ray crystallography. Antiproliferative activity of the investigated complexes, determined for three human cancer cell lines (HeLa, A549 and LS-174) revealed moderate activity without significant influence on the matrix metalloproteinases (MMP-2 and MMP-9) activity.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Polyhedron
T1  - New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity
VL  - 61
SP  - 112
EP  - 118
DO  - 10.1016/j.poly.2013.05.050
ER  - 

@article{
author = "Ivanović, Ivanka and Gligorijević, Nevenka and Aranđelović, Sandra and Radulović, Siniša and Roller, Alexander and Keppler, Bernhard K. and Tešić, Živoslav Lj. and Grgurić-Šipka, Sanja",
year = "2013",
abstract = "Metal semicarbazone and thiosemicarbazone complexes have attracted much attention due to their diverse biological activities. Because of the ability of ruthenium(II)-arene species to coordinate to different classes of ligands, they are suitable for fine-tuning chemical and pharmaceutical properties. Ruthenium(II) arene-complexes containing different types of ligands: namely caprylic hydrazide (a hydrazide with a long hydrocarbon chain), isonicotinic acid hydrazide (a hydrazide with an aromatic pyridine ring), thiosemicarbazones and semicarbazones (derived from the reaction of 3- and 4-acetylpyridine with either thiosemicarbazide or caprylic hydrazide), were obtained in the reaction of [(eta(6)-p-cymene)RuCl2](2) with the corresponding ligands in a 1:2 or 1:2.2 molar ratio in methanol, ethanol or isopropanol with mild heating. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structure of complex 1 was determined by X-ray crystallography. Antiproliferative activity of the investigated complexes, determined for three human cancer cell lines (HeLa, A549 and LS-174) revealed moderate activity without significant influence on the matrix metalloproteinases (MMP-2 and MMP-9) activity.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Polyhedron",
title = "New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity",
volume = "61",
pages = "112-118",
doi = "10.1016/j.poly.2013.05.050"
}

Ivanović, I., Gligorijević, N., Aranđelović, S., Radulović, S., Roller, A., Keppler, B. K., Tešić, Ž. Lj.,& Grgurić-Šipka, S.. (2013). New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity. in Polyhedron
Pergamon-Elsevier Science Ltd, Oxford., 61, 112-118.
https://doi.org/10.1016/j.poly.2013.05.050

Ivanović I, Gligorijević N, Aranđelović S, Radulović S, Roller A, Keppler BK, Tešić ŽL, Grgurić-Šipka S. New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity. in Polyhedron. 2013;61:112-118.
doi:10.1016/j.poly.2013.05.050 .

Ivanović, Ivanka, Gligorijević, Nevenka, Aranđelović, Sandra, Radulović, Siniša, Roller, Alexander, Keppler, Bernhard K., Tešić, Živoslav Lj., Grgurić-Šipka, Sanja, "New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity" in Polyhedron, 61 (2013):112-118,
https://doi.org/10.1016/j.poly.2013.05.050 . .