Phenyl carbohydrazone conjugated 2-oxoindoline as a new scaffold that augments the DNA and BSA binding affinity and anti-proliferative activity of a 1,10-phenanthroline based copper(II) complex

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Anbu, Sellamuthu ORCID: https://orcid.org/0000-0002-7176-330X, Paul, Anup, Ravishankaran, Rajendran, Guedes da Silva, M. Fátima C., Karande, Anjali A. and Pombeiro, Armando J. L. (2014) Phenyl carbohydrazone conjugated 2-oxoindoline as a new scaffold that augments the DNA and BSA binding affinity and anti-proliferative activity of a 1,10-phenanthroline based copper(II) complex. Inorganica Chimica Acta, 423 (Part B). pp. 183-193. ISSN 0020-1693

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Abstract

A new type of copper(II) complex, [CuL(phen)2](NO3) (CuIP), where L ((E)-N′-(2-oxoindolin-3-ylidene)benzohydrazide) is a N donor ligand and phen is the N, N-donor heterocyclic 1,10-phenanthroline, has been synthesized. The phenyl carbohydrazone conjugated isatin-based ligand L and CuIP were characterized by elemental analysis, infrared, UV–Vis, 1H and 13C NMR and ESI-mass spectral data, as well as single-crystal X-ray diffraction. The interaction of calf thymus DNA (CT DNA) with L and CuIP has been investigated by absorption, fluorescence and viscosity titration methods. The complex CuIP displays better binding affinity than the ligand L. The observed DNA binding constant (Kb = 4.15(±0.18) × 105 M−1) and binding site size (s = 0.19), viscosity data together with molecular docking studies of CuIP suggest groove binding and/or a partial intercalative mode of binding to CT DNA. In addition, CuIP shows good binding propensity to the bovine serum albumin (BSA) protein, giving a KBSA value of 1.25(±0.24) × 106 M−1. In addition, the docking studies on DNA and human serum albumin (HSA) CuIP interactions are consistent with the consequence of binding experiments. The in vitro anti-proliferative study establishes the anticancer potency of the CuIP against the human cervical (HeLa) and breast (MCF7) cancer cells; noncancer breast epithelial (MCF10a) cells have also been investigated. CuIP shows better cytotoxicity and sensitivity towards cancer cells over noncancer ones than L under identical conditions, with the appearance of apoptotic bodies.

Item Type:	Article
Uncontrolled Keywords:	sdg 3 - good health and well-being ,/dk/atira/pure/sustainabledevelopmentgoals/good_health_and_well_being
Faculty \ School:	Faculty of Science > School of Chemistry
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	20 Feb 2023 15:30
Last Modified:	30 Jan 2024 03:32
URI:	https://ueaeprints.uea.ac.uk/id/eprint/91209
DOI:	10.1016/j.ica.2014.07.016

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