Journal
DALTON TRANSACTIONS
Volume 48, Issue 15, Pages 4987-4999Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9dt00506d
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Funding
- Malaysian Ministry of Higher Education [FRGS/1/2012/SG01/UTAR/02/1]
- University of Malaya Frontier Research Grant [FG036-17AFR]
- International Medical University project [BP1-01/14(59)2017]
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Chiral enantiomers [Cu(phen)(l-ser)(H2O)]NO(3)1 and [Cu(phen)(d-ser)(H2O)]NO(3)2 (ser = serinato) underwent aldol-type condensation with formaldehyde, with retention of chirality, to yield their respective enantiomeric ternary copper(ii) complexes, viz. l- and d-[Cu(phen)(OCA)(H2O)]NO(3)xH(2)O (3 and 4; phen = 1,10-phenanthroline; OCA = oxazolidine-4-carboxylate; x = 1/2, 0-2) respectively. These chiral complexes were characterized by FTIR, elemental analysis, circular dichroism, UV-visible spectroscopy, fluorescence spectroscopy (FL), molar conductivity measurement, ESI-MS and X-ray crystallography. The crystal structures of 1 and 3 showed both the cationic complexes to have a square pyramidal geometry. These complexes were about nine fold more potent than cisplatin against metastatic MDA-MB-231 breast cancer cells, inducing apoptotic cell death via ROS generation and a massive drop in mitochondrial membrane potential. The results of monitoring EZH1, EZH2 and H3K27me3 revealed that the mode of action of 1-4 also involved the downregulation of EZH2 and it seemed to be independent of the H3K27me3 status.
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