title: Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N'-diacetate.
abstract: Six novel gold(III) complexes containing O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate ([AuCl2{(S,S)-R2eddch}]PF6, R=Me, Et, n-Pr, n-Bu, i-Bu, i-Am; 1-6, respectively) were synthesized and characterized by elemental analysis, UV/Visible, IR and NMR spectroscopy, mass spectrometry and differential pulse voltammetry. Density functional theory (DFT) calculations confirmed that diastereoisomer with the N,N' atoms configured (S,S) was the most stable. In vitro antiproliferative activity was determined against human cervix adenocarcinoma HeLa and human myelogenous leukemia K562 tumor cell lines, as well as against rested and stimulated normal immunocompetent human peripheral blood mononuclear cells (PBMC) using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Complex 6 expressed the highest activity against K562 cells (IC50 = 3.8 ± 0.5 μM). Apoptosis, seen as condensation of HeLa cell nuclei was the mode of cell death induced by complexes 2-6. Complexes 3-6 induced death of K562 cells inhibiting cell entry in mitosis.
authors.affiliation: Faculty of Agriculture, University of Belgrade, Nemanjina 6, Belgrade-Zemun, Serbia.
authors.forename: Nebojša
authors.initials: N
authors.lastname: Pantelić
authors.forename: Bojana B
authors.initials: BB
authors.lastname: Zmejkovski
authors.forename: Jelena
authors.initials: J
authors.lastname: Trifunović-Macedoljan
authors.forename: Aleksandar
authors.initials: A
authors.lastname: Savić
authors.forename: Dalibor
authors.initials: D
authors.lastname: Stanković
authors.forename: Ana
authors.initials: A
authors.lastname: Damjanović
authors.forename: Zorica
authors.initials: Z
authors.lastname: Juranić
authors.forename: Goran N
authors.initials: GN
authors.lastname: Kaluđerović
authors.forename: Tibor J
authors.initials: TJ
authors.lastname: Sabo
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002453:Cell Cycle / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D004952:Esters / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D020014:K562 Cells; D008956:Models, Chemical; D015394:Molecular Structure; D009944:Organoplatinum Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010084:Oxidation-Reduction
chemical_list: D000970:Antineoplastic Agents; D004952:Esters; D009944:Organoplatinum Compounds; D006046:Gold
keywords: Apoptosis; Cell cycle; Cytotoxicity; DFT; Gold(III) complexes; R(2)edda-type ligands