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Issue 13, 2015
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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

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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)2Br]·CH3CN (1) and [Cu(HL2)(PPh3)2Cl]·DMSO (2)} and copper(II) {[(Cu2L32Cl)2(μ-Cl)2]·2H2O (3) and [Cu(L4)(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 104 to 105 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.

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

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Publication details

The article was received on 09 Dec 2014, accepted on 14 Feb 2015 and first published on 18 Feb 2015


Article type: Paper
DOI: 10.1039/C4DT03764B
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Dalton Trans., 2015,44, 6140-6157
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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, A. Chakraborty, S. P. Dash, A. K. Panda, R. Acharyya, A. Biswas, S. Mukhopadhyay, S. K. Bhutia, A. Crochet, Y. P. Patil, M. Nethaji and R. Dinda, Dalton Trans., 2015, 44, 6140
    DOI: 10.1039/C4DT03764B

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