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Synthesis, X-ray structure and in vitro cytotoxicity studies of Cu(I/II) complexes of thiosemicarbazone: special emphasis on their interactions with DNA

Saswati, . and Chakraborty, Ayon and Dash, Subhashree P and Panda, Alok K and Acharyya, Rama and Biswas, Ashis and Mukhopadhyay, Subhadip and Bhutia, Sujit K and Crochet, Aurelien and Patil, Yogesh P and Nethajie, M and Dinda, Rupam (2015) Synthesis, X-ray structure and in vitro cytotoxicity studies of Cu(I/II) complexes of thiosemicarbazone: special emphasis on their interactions with DNA. In: DALTON TRANSACTIONS, 44 (13). pp. 6140-6157.

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Official URL: http://dx.doi.org/10.1039/c4dt03764b

Abstract

4-(p-X-phenyl)thiosemicarbazone of napthaldehyde {where X = Cl (HL1) and X = Br (HL2)}, thiosemicarbazone of quinoline-2-carbaldehyde (HL3) and 4-(p-fluorophenyl) thiosemicarbazone of salicylaldehyde (H2L4) and their copper(I) {Cu(HL1)(PPh3)(2)Br]center dot CH3CN (1) and Cu(HL2)(PPh3)(2)Cl]center dot DMSO (2)} and copper(II) {((Cu2L2Cl)-Cl-3)(2)(mu-Cl)(2)]center dot 2H(2)O (3) and Cu(L-4)(Py)] (4)} complexes are reported herein. The synthesized ligands and their copper complexes were successfully characterized by elemental analysis, cyclic voltammetry, NMR, ESI-MS, IR and UV-Vis spectroscopy. Molecular structures of all the Cu(I) and Cu(II) complexes have been determined by X-ray crystallography. All the complexes (1-4) were tested for their ability to exhibit DNA-binding and - cleavage activity. The complexes effectively interact with CT-DNA possibly by groove binding mode, with binding constants ranging from 10(4) to 10(5) M-1. Among the complexes, 3 shows the highest chemical (60%) as well as photo-induced (80%) DNA cleavage activity against pUC19 DNA. Finally, the in vitro antiproliferative activity of all the complexes was assayed against the HeLa cell line. Some of the complexes have proved to be as active as the clinical referred drugs, and the greater potency of 3 may be correlated with its aqueous solubility and the presence of the quinonoidal group in the thiosemicarbazone ligand coordinated to the metal.

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
Keywords: TRANSITION-METAL-COMPLEXES; PROSTATE-CANCER CELLS; COPPER(II) COMPLEXES; ANTITUMOR-ACTIVITY; BIOLOGICAL-ACTIVITY; ANTICANCER ACTIVITY; CRYSTAL-STRUCTURE; CU(II) COMPLEXES; PHENANTHRENEQUINONE THIOSEMICARBAZONE; SUBSTITUTED THIOSEMICARBAZONES
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 24 Apr 2015 06:07
Last Modified: 24 Apr 2015 06:07
URI: http://eprints.iisc.ac.in/id/eprint/51396

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