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Unpredicted formation of copper(II) complexes containing 2-thiophen-2-yl-1-thiophen-2-ylmethyl-1H-benzoimidazole and their most promising in vitro cytotoxicity in MCF-7 and HeLa cell lines over cisplatin

Naveen, P and Jain, Ruchi and Kalaivani, P and Shankar, R and Dallemer, F and Prabhakaran, R (2017) Unpredicted formation of copper(II) complexes containing 2-thiophen-2-yl-1-thiophen-2-ylmethyl-1H-benzoimidazole and their most promising in vitro cytotoxicity in MCF-7 and HeLa cell lines over cisplatin. In: NEW JOURNAL OF CHEMISTRY, 41 (17). pp. 8885-8898.

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Official URL: http://doi.org/10.1039/c7nj01273j

Abstract

An in situ reaction of CuCl2 center dot 2H(2)O, o-phenylenediamine, thiophene-2-carbaldehyde and sodium azide in methanol afforded complex 1a. Originally, it was expected to form a binuclear copper(II) complex containing N, N'-bis-thiophene-2-ylmethylene-benzene-1,2-diamine. However, the reaction afforded a binuclear complex 1a bis-(m-azido)-2-thiophene-2-yl-1-thiophen-2-ylmethyl-1(H)-benzoimidazole copper(II) in decent yield. The same reaction carried out in the absence of sodium azide afforded complex 1b. The new complexes were characterized by various spectroscopic (IR, UV-Vis and EPR) techniques and the structure of the complexes is confirmed by X-ray crystallography. Computational details of theoretical calculations (DFT) have been discussed for complex 1a. The interaction of the ligand and complexes with calf thymus (CT-DNA) has been examined by photophysical studies, which revealed that the complexes bound to DNA through an electrostatic mode. Albumin (Bovine Serum Albumin) binding studies of the complexes (1a and 1b) confirmed their effect on altering the albumin structure by quenching the tryptophan and tyrosine residues. Antioxidant studies showed that the Cu(II) complexes exhibited significant antioxidant activity. Cell proliferation MTT assays were performed for all the compounds in breast cancer (MCF-7) and cervical cancer (HeLa) cell lines. The ligand and new complexes overcame cisplatin resistance in the MCF-7 and HeLa cell lines. Further, their nontoxic nature was confirmed when they were tested against human normal Embryonic kidney cells (HEK). Among the two complexes, complex 1a was the most effective against MCF-7 (IC50 value of 3.417 mu M) and HeLa (0.6 mu M) compared with complex 1b (10.2 mu M; 11.7 mu M).

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the ROYAL SOC CHEMISTRY, THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Department/Centre: Division of Biological Sciences > Molecular Reproduction, Development & Genetics
Depositing User: Id for Latest eprints
Date Deposited: 21 Oct 2017 06:17
Last Modified: 21 Oct 2017 06:17
URI: http://eprints.iisc.ac.in/id/eprint/58062

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