Enantiomeric pairs of ternary copper(ii) complexes and their aldol-type condensation products: Synthesis, characterization, and anticancer and epigenetic properties

Khei Yan Lee, Yi Ling Ng, Wai San Wang, Pei Ying Ng, Cheang Wei Chan, Jing Wei Lai, Fabian Davamani, Ebenezer Chitra, Wei Meng Lim, Rakesh Ganguly, Mohd Jamil Maah, Foo Win Yip, Chew Hee Ng

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10 Citations (Scopus)

Abstract

Chiral enantiomers [Cu(phen)(l-ser)(H 2 O)]NO 3 1 and [Cu(phen)(d-ser)(H 2 O)]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)(H 2 O)]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.

Original languageEnglish
Pages (from-to)4987-4999
Number of pages13
JournalDalton Transactions
Volume48
Issue number15
DOIs
Publication statusPublished - 21 Apr 2019

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