The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines
Samo za registrovane korisnike
2012
Autori
Rakic, Gordana M.Grgurić-Šipka, Sanja
Kaluđerović, Goran N.
Bette, Martin
Filipović, Lana
Aranđelović, Sandra
Radulović, Siniša
Tešić, Živoslav Lj.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Platinum(IV) complexes with general formulas [Pt(L1-2)(2)Cl-4]. where L1-2 are 3-acetylpyridine (1) and 4-acetylpyridine (2) respectively, and [Pt(HL3-5)(2)Cl-2], where H2L3-5 are 2,3-pyridinedicarboxylic acid (3), 2,4-pyridinedicarboxylic acid (4) and 2,5-pyridinedicarboxylic acid (5) respectively, were prepared by the reaction of K-2[PtCl6] with the corresponding ligand in 1:2 M ratio in water. The complexes were characterized by elemental analysis and IR and NMR spectroscopy. The structures of complexes 2 and 5 were determined by X-ray crystallography, which revealed the trans orientation of chloride anions around platinum(IV) in the case of both complexes. The antiproliferative activity was investigated in six tumor cell lines (human cervical carcinoma cells (HeLa), murine melanoma cells (B16), human breast carcinoma cells (MDA-MB-453), human colon carcinoma cells (LS-174), transformed human umbilical vein endothelial cells (EA.hy 926) and murine endothelial cells (MS1)) and in one... non-tumor cell line-human fetal lung fibroblast cells (MRC-5). Cytotoxicity studies indicated that Pt(IV) complexes with acetyl-substituted pyridine ligands exhibit significantly higher in vitro antiproliferative activity than the complexes with carboxylato-substituted pyridines. Complexes 1 and 2 showed antiproliferative activity in all tested tumor cell lines, with the highest potential in human endothelial cells EA.hy 926, since they had IC50 values of 13.8 +/- 5.8 mu M and 23.4 +/- 3.3 mu M, respectively and were more active than cisplatin. Complexes 1 and 2 exhibited lower toxicity against the non-tumor human lung fibroblast cell line (MRC-5) than against most of the tested tumor cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.
Ključne reči:
Pt(IV) complexes / Pyridine derivatives / DFT / X-ray / Cytotoxicity / EA.hy 926Izvor:
European Journal of Medicinal Chemistry, 2012, 55, 214-219Izdavač:
- Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
Finansiranje / projekti:
- Farmakodinamska i farmakogenomska ispitivanja novijih lekova u lečenju solidnih tumora (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41026)
- Korelacija strukture i osobina prirodnih i sintetičkih molekula i njihovih kompleksa sa metalima (RS-MESTD-Basic Research (BR or ON)-172017)
DOI: 10.1016/j.ejmech.2012.07.019
ISSN: 0223-5234
PubMed: 22858225
WoS: 000309494100023
Scopus: 2-s2.0-84865759718
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Rakic, Gordana M. AU - Grgurić-Šipka, Sanja AU - Kaluđerović, Goran N. AU - Bette, Martin AU - Filipović, Lana AU - Aranđelović, Sandra AU - Radulović, Siniša AU - Tešić, Živoslav Lj. PY - 2012 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1537 AB - Platinum(IV) complexes with general formulas [Pt(L1-2)(2)Cl-4]. where L1-2 are 3-acetylpyridine (1) and 4-acetylpyridine (2) respectively, and [Pt(HL3-5)(2)Cl-2], where H2L3-5 are 2,3-pyridinedicarboxylic acid (3), 2,4-pyridinedicarboxylic acid (4) and 2,5-pyridinedicarboxylic acid (5) respectively, were prepared by the reaction of K-2[PtCl6] with the corresponding ligand in 1:2 M ratio in water. The complexes were characterized by elemental analysis and IR and NMR spectroscopy. The structures of complexes 2 and 5 were determined by X-ray crystallography, which revealed the trans orientation of chloride anions around platinum(IV) in the case of both complexes. The antiproliferative activity was investigated in six tumor cell lines (human cervical carcinoma cells (HeLa), murine melanoma cells (B16), human breast carcinoma cells (MDA-MB-453), human colon carcinoma cells (LS-174), transformed human umbilical vein endothelial cells (EA.hy 926) and murine endothelial cells (MS1)) and in one non-tumor cell line-human fetal lung fibroblast cells (MRC-5). Cytotoxicity studies indicated that Pt(IV) complexes with acetyl-substituted pyridine ligands exhibit significantly higher in vitro antiproliferative activity than the complexes with carboxylato-substituted pyridines. Complexes 1 and 2 showed antiproliferative activity in all tested tumor cell lines, with the highest potential in human endothelial cells EA.hy 926, since they had IC50 values of 13.8 +/- 5.8 mu M and 23.4 +/- 3.3 mu M, respectively and were more active than cisplatin. Complexes 1 and 2 exhibited lower toxicity against the non-tumor human lung fibroblast cell line (MRC-5) than against most of the tested tumor cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved. PB - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux T2 - European Journal of Medicinal Chemistry T1 - The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines VL - 55 SP - 214 EP - 219 DO - 10.1016/j.ejmech.2012.07.019 ER -
@article{ author = "Rakic, Gordana M. and Grgurić-Šipka, Sanja and Kaluđerović, Goran N. and Bette, Martin and Filipović, Lana and Aranđelović, Sandra and Radulović, Siniša and Tešić, Živoslav Lj.", year = "2012", abstract = "Platinum(IV) complexes with general formulas [Pt(L1-2)(2)Cl-4]. where L1-2 are 3-acetylpyridine (1) and 4-acetylpyridine (2) respectively, and [Pt(HL3-5)(2)Cl-2], where H2L3-5 are 2,3-pyridinedicarboxylic acid (3), 2,4-pyridinedicarboxylic acid (4) and 2,5-pyridinedicarboxylic acid (5) respectively, were prepared by the reaction of K-2[PtCl6] with the corresponding ligand in 1:2 M ratio in water. The complexes were characterized by elemental analysis and IR and NMR spectroscopy. The structures of complexes 2 and 5 were determined by X-ray crystallography, which revealed the trans orientation of chloride anions around platinum(IV) in the case of both complexes. The antiproliferative activity was investigated in six tumor cell lines (human cervical carcinoma cells (HeLa), murine melanoma cells (B16), human breast carcinoma cells (MDA-MB-453), human colon carcinoma cells (LS-174), transformed human umbilical vein endothelial cells (EA.hy 926) and murine endothelial cells (MS1)) and in one non-tumor cell line-human fetal lung fibroblast cells (MRC-5). Cytotoxicity studies indicated that Pt(IV) complexes with acetyl-substituted pyridine ligands exhibit significantly higher in vitro antiproliferative activity than the complexes with carboxylato-substituted pyridines. Complexes 1 and 2 showed antiproliferative activity in all tested tumor cell lines, with the highest potential in human endothelial cells EA.hy 926, since they had IC50 values of 13.8 +/- 5.8 mu M and 23.4 +/- 3.3 mu M, respectively and were more active than cisplatin. Complexes 1 and 2 exhibited lower toxicity against the non-tumor human lung fibroblast cell line (MRC-5) than against most of the tested tumor cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.", publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux", journal = "European Journal of Medicinal Chemistry", title = "The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines", volume = "55", pages = "214-219", doi = "10.1016/j.ejmech.2012.07.019" }
Rakic, G. M., Grgurić-Šipka, S., Kaluđerović, G. N., Bette, M., Filipović, L., Aranđelović, S., Radulović, S.,& Tešić, Ž. Lj.. (2012). The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines. in European Journal of Medicinal Chemistry Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 55, 214-219. https://doi.org/10.1016/j.ejmech.2012.07.019
Rakic GM, Grgurić-Šipka S, Kaluđerović GN, Bette M, Filipović L, Aranđelović S, Radulović S, Tešić ŽL. The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines. in European Journal of Medicinal Chemistry. 2012;55:214-219. doi:10.1016/j.ejmech.2012.07.019 .
Rakic, Gordana M., Grgurić-Šipka, Sanja, Kaluđerović, Goran N., Bette, Martin, Filipović, Lana, Aranđelović, Sandra, Radulović, Siniša, Tešić, Živoslav Lj., "The synthesis, spectroscopic, X-ray characterization and in vitro cytotoxic testing results of activity of five new trans-platinum(IV) complexes with functionalized pyridines" in European Journal of Medicinal Chemistry, 55 (2012):214-219, https://doi.org/10.1016/j.ejmech.2012.07.019 . .