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Ternary copper(II)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property


Citation

Ng, Chew Hee and Wang, Wai San and Chong, Kok Vei and Win, Yip Foo and Neo, Kian Eang and Lee, Hong Boon and San, Swee Lan and Raja Abdul Rahman, Raja Noor Zaliha and Leong, Weng Kee (2013) Ternary copper(II)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property. Dalton Transactions, 42 (28). pp. 10233-10243. ISSN 1477-9226; ESSN: 1477-9234

Abstract

Chiral enantiomers [Cu(phen)(l-threo)(H2O)]NO31 and [Cu(phen)(d-threo)(H2O)]NO32 (threo = threoninate) 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)(5MeOCA)(H2O)]NO3·xH 2O (3 and 4; phen = 1,10-phenanthroline; 5MeOCA = 5-methyloxazolidine-4-carboxylate; x = 0-3) 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. Analysis of restriction enzyme inhibition by these four complexes revealed modulation of DNA binding selectivity by the type of ligand, ligand modification and chirality. Their interaction with bovine serum albumin was investigated by FL and electronic spectroscopy. With the aid of the crystal structure of BSA, spectroscopic evidence suggested their binding at the cavity containing Trp134 with numerous Tyr residues in subdomain IA. The products were more antiproliferative than cisplatin against cancer cell lines HK-1, MCF-7, HCT116, HSC-2 and C666-1 except HL-60, and were selective towards nasopharyngeal cancer HK-1 cells over normal NP69 cells of the same organ type.


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Additional Metadata

Item Type: Article
Divisions: Faculty of Biotechnology and Biomolecular Sciences
DOI Number: https://doi.org/10.1039/c3dt50884f
Publisher: Royal Society of Chemistry
Keywords: Chiral enantiomers; Aldol-type condensation; DNA binding
Depositing User: Umikalthom Abdullah
Date Deposited: 28 May 2014 10:38
Last Modified: 28 Sep 2016 03:52
Altmetrics: http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.1039/c3dt50884f
URI: http://psasir.upm.edu.my/id/eprint/28122
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