TY  - JOUR
AU  - Filipović, Lana
AU  - Aranđelović, Sandra
AU  - Gligorijević, Nevenka
AU  - Krivokuca, Ana
AU  - Jankovic, Radmila
AU  - Srdić-Rajić, Tatjana
AU  - Rakic, Gordana
AU  - Tešić, Živoslav Lj.
AU  - Radulović, Siniša
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1414
AB  - Background. In our previous study we reported the synthesis and cytotoxicity of two trans-platinum(II) complexes: trans-[PtCl2(3-acetylpyridine)(2)] (1) and trans-[PtCl2(4-acetylpyridine)(2)] (2), revealing significant cytotoxic potential of 2. In order to evaluate the mechanism underlying biological activity of both trans-Pt(II) isomers, comparative studies versus cisplatin were performed in HeLa, MRC-5 and MS1 cells. Materials and methods. The cytotoxic activity of the investigated complexes was determined using SRB assay. The colagenolytic activity was determined using gelatin zymography, while the effect of platinum complexes on matrix metalloproteinases 2 and 9 mRNA expression was evaluated by quantitative real-time PCR. Apoptotic potential and cell cycle alterations were determined by FACS analyses. Western blot analysis was used to evaluate the effect on expression of DNA-repair enzyme ERCC1, and quantitative real-time PCR was used for the ERCC1 mRNA expression analysis. In vitro antiangiogenic potential was determined by tube formation assay. Platinum content in intracellular DNA and proteins was determined by inductively coupled plasma-optical emission spectrometry. Results. Compound 2 displayed an apparent cytoselective profile, and flow cytometry analysis in HeLa cells indicated that 2 exerted antiproliferative effect through apoptosis induction, while 1 induced both apoptosis and necrosis. Action of 1 and 2, as analyzed by quantitative real-time PCR and Western blot, was associated with down-regulation of ERCC1. Both trans-complexes inhibited MMP-9 mRNA expression in HeLa, while 2 significantly abrogated in vitro tubulogenesis in MS1 cells. Conclusions. The ability of 2 to induce multiple and selective in vitro cytotoxic effects encourages further investigations of trans-platinum(II) complexes with substituted pyridines.
PB  - Assoc Radiology & Oncology, Ljubljana
T2  - Radiology and Oncology
T1  - Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin
VL  - 47
IS  - 4
SP  - 346
EP  - 357
DO  - 10.2478/raon-2013-0050
ER  - 

@article{
author = "Filipović, Lana and Aranđelović, Sandra and Gligorijević, Nevenka and Krivokuca, Ana and Jankovic, Radmila and Srdić-Rajić, Tatjana and Rakic, Gordana and Tešić, Živoslav Lj. and Radulović, Siniša",
year = "2013",
abstract = "Background. In our previous study we reported the synthesis and cytotoxicity of two trans-platinum(II) complexes: trans-[PtCl2(3-acetylpyridine)(2)] (1) and trans-[PtCl2(4-acetylpyridine)(2)] (2), revealing significant cytotoxic potential of 2. In order to evaluate the mechanism underlying biological activity of both trans-Pt(II) isomers, comparative studies versus cisplatin were performed in HeLa, MRC-5 and MS1 cells. Materials and methods. The cytotoxic activity of the investigated complexes was determined using SRB assay. The colagenolytic activity was determined using gelatin zymography, while the effect of platinum complexes on matrix metalloproteinases 2 and 9 mRNA expression was evaluated by quantitative real-time PCR. Apoptotic potential and cell cycle alterations were determined by FACS analyses. Western blot analysis was used to evaluate the effect on expression of DNA-repair enzyme ERCC1, and quantitative real-time PCR was used for the ERCC1 mRNA expression analysis. In vitro antiangiogenic potential was determined by tube formation assay. Platinum content in intracellular DNA and proteins was determined by inductively coupled plasma-optical emission spectrometry. Results. Compound 2 displayed an apparent cytoselective profile, and flow cytometry analysis in HeLa cells indicated that 2 exerted antiproliferative effect through apoptosis induction, while 1 induced both apoptosis and necrosis. Action of 1 and 2, as analyzed by quantitative real-time PCR and Western blot, was associated with down-regulation of ERCC1. Both trans-complexes inhibited MMP-9 mRNA expression in HeLa, while 2 significantly abrogated in vitro tubulogenesis in MS1 cells. Conclusions. The ability of 2 to induce multiple and selective in vitro cytotoxic effects encourages further investigations of trans-platinum(II) complexes with substituted pyridines.",
publisher = "Assoc Radiology & Oncology, Ljubljana",
journal = "Radiology and Oncology",
title = "Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin",
volume = "47",
number = "4",
pages = "346-357",
doi = "10.2478/raon-2013-0050"
}

Filipović, L., Aranđelović, S., Gligorijević, N., Krivokuca, A., Jankovic, R., Srdić-Rajić, T., Rakic, G., Tešić, Ž. Lj.,& Radulović, S.. (2013). Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin. in Radiology and Oncology
Assoc Radiology & Oncology, Ljubljana., 47(4), 346-357.
https://doi.org/10.2478/raon-2013-0050

Filipović L, Aranđelović S, Gligorijević N, Krivokuca A, Jankovic R, Srdić-Rajić T, Rakic G, Tešić ŽL, Radulović S. Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin. in Radiology and Oncology. 2013;47(4):346-357.
doi:10.2478/raon-2013-0050 .

Filipović, Lana, Aranđelović, Sandra, Gligorijević, Nevenka, Krivokuca, Ana, Jankovic, Radmila, Srdić-Rajić, Tatjana, Rakic, Gordana, Tešić, Živoslav Lj., Radulović, Siniša, "Biological evaluation of transdichloridoplatinum( II) complexes with 3-and 4-acetylpyridine in comparison to cisplatin" in Radiology and Oncology, 47, no. 4 (2013):346-357,
https://doi.org/10.2478/raon-2013-0050 . .

TY  - JOUR
AU  - Grgurić-Šipka, Sanja
AU  - Ivanović, Ivanka
AU  - Rakic, Gordana
AU  - Todorović, Nina
AU  - Gligorijević, Nevenka
AU  - Radulović, Siniša
AU  - Arion, Vladimir B.
AU  - Keppler, Bernhard K.
AU  - Tešić, Živoslav Lj.
PY  - 2010
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1058
AB  - Ruthenium(II)-arene complexes of general formulae [(eta(6)-p-cymene)Ru(L1-3)Cl-2], where L1-3 is 3-acetylpyridine (1), 4-acetylpyridine (2) and 2-amino-5-chloropyridine (3), Correspondingly, [(eta(6)-p-cymene)Ru(HL4,5)Cl-2], where HL4 and HL5 are respectively isonicotinic acid (4) and nicotinic acid (5) and [(eta(6)-p-cymene)Ru(HL6-9)Cl], where H2L6-9 represent 2,3-pyridinedicarboxylic acid (6), 2,4-pyidinedicarboxylic acid (7), 2,5-pyridinedicarboxylic acid (8) and 2,6-pyridinedicarboxylic acid (9), were prepared by the reaction of (eta(6)-p-cymene)(2)RuCl2](2) (10) with the corresponding ligand in 1:2 molar ratio in isopropanol. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. According to these data the molecules adopt the usual "three-leg piano-stool" geometry which is common for this type of complexes. The structures of I and 7 were determined by X-ray crystallography. The complexes revealed low antiproliferative activity in six investigated tumor cell lines (HeLa, B16, FemX, MDA-MB-361, MDA-MB-453 and LS-174). The reaction of 6 with 9-methyladenine was studied by H-1 NMR, H-1, H-1 COSY and H-1, H-1 NOESY spectroscopy. (C) 2009 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity
VL  - 45
IS  - 3
SP  - 1051
EP  - 1058
DO  - 10.1016/j.ejmech.2009.11.055
ER  - 

@article{
author = "Grgurić-Šipka, Sanja and Ivanović, Ivanka and Rakic, Gordana and Todorović, Nina and Gligorijević, Nevenka and Radulović, Siniša and Arion, Vladimir B. and Keppler, Bernhard K. and Tešić, Živoslav Lj.",
year = "2010",
abstract = "Ruthenium(II)-arene complexes of general formulae [(eta(6)-p-cymene)Ru(L1-3)Cl-2], where L1-3 is 3-acetylpyridine (1), 4-acetylpyridine (2) and 2-amino-5-chloropyridine (3), Correspondingly, [(eta(6)-p-cymene)Ru(HL4,5)Cl-2], where HL4 and HL5 are respectively isonicotinic acid (4) and nicotinic acid (5) and [(eta(6)-p-cymene)Ru(HL6-9)Cl], where H2L6-9 represent 2,3-pyridinedicarboxylic acid (6), 2,4-pyidinedicarboxylic acid (7), 2,5-pyridinedicarboxylic acid (8) and 2,6-pyridinedicarboxylic acid (9), were prepared by the reaction of (eta(6)-p-cymene)(2)RuCl2](2) (10) with the corresponding ligand in 1:2 molar ratio in isopropanol. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. According to these data the molecules adopt the usual "three-leg piano-stool" geometry which is common for this type of complexes. The structures of I and 7 were determined by X-ray crystallography. The complexes revealed low antiproliferative activity in six investigated tumor cell lines (HeLa, B16, FemX, MDA-MB-361, MDA-MB-453 and LS-174). The reaction of 6 with 9-methyladenine was studied by H-1 NMR, H-1, H-1 COSY and H-1, H-1 NOESY spectroscopy. (C) 2009 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity",
volume = "45",
number = "3",
pages = "1051-1058",
doi = "10.1016/j.ejmech.2009.11.055"
}

Grgurić-Šipka, S., Ivanović, I., Rakic, G., Todorović, N., Gligorijević, N., Radulović, S., Arion, V. B., Keppler, B. K.,& Tešić, Ž. Lj.. (2010). Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 45(3), 1051-1058.
https://doi.org/10.1016/j.ejmech.2009.11.055

Grgurić-Šipka S, Ivanović I, Rakic G, Todorović N, Gligorijević N, Radulović S, Arion VB, Keppler BK, Tešić ŽL. Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity. in European Journal of Medicinal Chemistry. 2010;45(3):1051-1058.
doi:10.1016/j.ejmech.2009.11.055 .

Grgurić-Šipka, Sanja, Ivanović, Ivanka, Rakic, Gordana, Todorović, Nina, Gligorijević, Nevenka, Radulović, Siniša, Arion, Vladimir B., Keppler, Bernhard K., Tešić, Živoslav Lj., "Ruthenium(II)-arene complexes with functionalized pyridines: Synthesis, characterization and cytotoxic activity" in European Journal of Medicinal Chemistry, 45, no. 3 (2010):1051-1058,
https://doi.org/10.1016/j.ejmech.2009.11.055 . .

TY  - JOUR
AU  - Rakic, Gordana M.
AU  - Grgurić-Šipka, Sanja
AU  - Kaluđerović, Goran N.
AU  - Gomez-Ruiz, Santiago
AU  - Bjelogrlić, Snežana K.
AU  - Radulović, Siniša
AU  - Tešić, Živoslav Lj.
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/630
AB  - Novel complexes of platinum(II) with 3- (1) or 4-acetylpyridine (2) have been synthesized and characterized by elemental analyses, IR, H-1 and C-13 NMR spectroscopy. Single crystal X-ray diffraction revealed the trans geometry of complex 2. DFT calculations confirm formation of trans isomers for both complexes. The complexes have been tested for their cytotoxicity against HeLa (human cervical cancer), U2OS (human osteosarcoma), U2OScisR (human osteosarcoma cisplatin resistant), B16 (murine melanoma), MDA-453, MDA-361, and MCF-7 (human breast cancer), LS-174 (human colon cancer) and Femx (human melanoma) cell lines. The most promising compound trans-dichloridobis(4-acetylpyridine)platinum(II) (2) overcomes cisplatin resistance of U2OScisR cells after 48 h of drug exposure. (C) 2008 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Novel trans-dichloridoplatinum(II) complexes with 3-and 4-acetylpyridine: Synthesis, characterization, DFT calculations and cytotoxicity
VL  - 44
IS  - 5
SP  - 1921
EP  - 1925
DO  - 10.1016/j.ejmech.2008.11.004
ER  - 

@article{
author = "Rakic, Gordana M. and Grgurić-Šipka, Sanja and Kaluđerović, Goran N. and Gomez-Ruiz, Santiago and Bjelogrlić, Snežana K. and Radulović, Siniša and Tešić, Živoslav Lj.",
year = "2009",
abstract = "Novel complexes of platinum(II) with 3- (1) or 4-acetylpyridine (2) have been synthesized and characterized by elemental analyses, IR, H-1 and C-13 NMR spectroscopy. Single crystal X-ray diffraction revealed the trans geometry of complex 2. DFT calculations confirm formation of trans isomers for both complexes. The complexes have been tested for their cytotoxicity against HeLa (human cervical cancer), U2OS (human osteosarcoma), U2OScisR (human osteosarcoma cisplatin resistant), B16 (murine melanoma), MDA-453, MDA-361, and MCF-7 (human breast cancer), LS-174 (human colon cancer) and Femx (human melanoma) cell lines. The most promising compound trans-dichloridobis(4-acetylpyridine)platinum(II) (2) overcomes cisplatin resistance of U2OScisR cells after 48 h of drug exposure. (C) 2008 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Novel trans-dichloridoplatinum(II) complexes with 3-and 4-acetylpyridine: Synthesis, characterization, DFT calculations and cytotoxicity",
volume = "44",
number = "5",
pages = "1921-1925",
doi = "10.1016/j.ejmech.2008.11.004"
}

Rakic, G. M., Grgurić-Šipka, S., Kaluđerović, G. N., Gomez-Ruiz, S., Bjelogrlić, S. K., Radulović, S.,& Tešić, Ž. Lj.. (2009). Novel trans-dichloridoplatinum(II) complexes with 3-and 4-acetylpyridine: Synthesis, characterization, DFT calculations and cytotoxicity. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 44(5), 1921-1925.
https://doi.org/10.1016/j.ejmech.2008.11.004

Rakic GM, Grgurić-Šipka S, Kaluđerović GN, Gomez-Ruiz S, Bjelogrlić SK, Radulović S, Tešić ŽL. Novel trans-dichloridoplatinum(II) complexes with 3-and 4-acetylpyridine: Synthesis, characterization, DFT calculations and cytotoxicity. in European Journal of Medicinal Chemistry. 2009;44(5):1921-1925.
doi:10.1016/j.ejmech.2008.11.004 .

Rakic, Gordana M., Grgurić-Šipka, Sanja, Kaluđerović, Goran N., Gomez-Ruiz, Santiago, Bjelogrlić, Snežana K., Radulović, Siniša, Tešić, Živoslav Lj., "Novel trans-dichloridoplatinum(II) complexes with 3-and 4-acetylpyridine: Synthesis, characterization, DFT calculations and cytotoxicity" in European Journal of Medicinal Chemistry, 44, no. 5 (2009):1921-1925,
https://doi.org/10.1016/j.ejmech.2008.11.004 . .

TY  - JOUR
AU  - Tosti, Tomislav
AU  - Rakic, Gordana
AU  - Natić, Maja
AU  - Milojković-Opsenica, Dušanka
AU  - Husinec, Suren
AU  - Savić, Vladimir
AU  - Tešić, Živoslav Lj.
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/874
AB  - The chromatographic behavior of three biocidal technical materials, rodenticide active ingredients brodifacoum, bromadiolone, and coumatetralyl, and impurities present in the technical material was investigated by both normal-phase (NP) and reversed-phase (RP) planar chromatography. The research was carried out using thin-layers of silica gel, alumina, cellulose, and C(18) silica. Several solvents on their own or in various combinations and proportions were used for separation. The optimum chromatographic systems for separation of the substances from each other and from their impurities were selected. Under reversed-phase chromatographic (RPC) conditions a linear correlation between R(M) values and mobile phase composition was established. From results obtained, the lipophilicity R(M)(o) and C(0) were determined. Possible separation mechanisms are discussed on the basis of the established retention behavior.
PB  - Research Inst Medicinal Plants, Budakalasz
T2  - Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography
T1  - TLC Retention Behavior of Brodifacoum, Bromadiolone, and Coumatetralyl and their Impurities on Different Adsorbents
VL  - 22
IS  - 5
SP  - 333
EP  - 343
DO  - 10.1556/JPC.22.2009.5.4
ER  - 

@article{
author = "Tosti, Tomislav and Rakic, Gordana and Natić, Maja and Milojković-Opsenica, Dušanka and Husinec, Suren and Savić, Vladimir and Tešić, Živoslav Lj.",
year = "2009",
abstract = "The chromatographic behavior of three biocidal technical materials, rodenticide active ingredients brodifacoum, bromadiolone, and coumatetralyl, and impurities present in the technical material was investigated by both normal-phase (NP) and reversed-phase (RP) planar chromatography. The research was carried out using thin-layers of silica gel, alumina, cellulose, and C(18) silica. Several solvents on their own or in various combinations and proportions were used for separation. The optimum chromatographic systems for separation of the substances from each other and from their impurities were selected. Under reversed-phase chromatographic (RPC) conditions a linear correlation between R(M) values and mobile phase composition was established. From results obtained, the lipophilicity R(M)(o) and C(0) were determined. Possible separation mechanisms are discussed on the basis of the established retention behavior.",
publisher = "Research Inst Medicinal Plants, Budakalasz",
journal = "Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography",
title = "TLC Retention Behavior of Brodifacoum, Bromadiolone, and Coumatetralyl and their Impurities on Different Adsorbents",
volume = "22",
number = "5",
pages = "333-343",
doi = "10.1556/JPC.22.2009.5.4"
}

Tosti, T., Rakic, G., Natić, M., Milojković-Opsenica, D., Husinec, S., Savić, V.,& Tešić, Ž. Lj.. (2009). TLC Retention Behavior of Brodifacoum, Bromadiolone, and Coumatetralyl and their Impurities on Different Adsorbents. in Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography
Research Inst Medicinal Plants, Budakalasz., 22(5), 333-343.
https://doi.org/10.1556/JPC.22.2009.5.4

Tosti T, Rakic G, Natić M, Milojković-Opsenica D, Husinec S, Savić V, Tešić ŽL. TLC Retention Behavior of Brodifacoum, Bromadiolone, and Coumatetralyl and their Impurities on Different Adsorbents. in Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography. 2009;22(5):333-343.
doi:10.1556/JPC.22.2009.5.4 .

Tosti, Tomislav, Rakic, Gordana, Natić, Maja, Milojković-Opsenica, Dušanka, Husinec, Suren, Savić, Vladimir, Tešić, Živoslav Lj., "TLC Retention Behavior of Brodifacoum, Bromadiolone, and Coumatetralyl and their Impurities on Different Adsorbents" in Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography, 22, no. 5 (2009):333-343,
https://doi.org/10.1556/JPC.22.2009.5.4 . .