New planar trans-copper(II) β-dithioester chelate complexes: synthesis, characterization, anticancer activity and DNA-binding/cleavage studies

New planar trans-copper(II) β-dithioester complexes, [Cu(L) 2 ] (L = methyl-3-hydroxy-(3-pyridyl)-2-propenedithioate (L1 in 1), methyl-3-hydroxy-(2-naphthyl)-2-propenedithioate (L2 in 2), methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate (L3 in 3), methyl-3-hydroxy-3-(p-fluorophenyl)-2-propene...

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Bibliographic Details
Published in:Journal of coordination chemistry 2017-02, Vol.70 (4), p.565-583
Main Authors: Yadav, Manoj Kumar, Maurya, Akhilendra Kumar, Rajput, Gunjan, Manar, Krishna Kumar, Vinayak, Manjula, Drew, Michael G. B., Singh, Nanhai
Format: Article
Language:English
Subjects:
anticancer
Biotechnology
Chelates
Cleavage
Coordination compounds
copper
DNA binding
Efficiency
Spectra
Synthesis
Voltammetry
β-dithioester
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Summary:New planar trans-copper(II) β-dithioester complexes, [Cu(L) 2 ] (L = methyl-3-hydroxy-(3-pyridyl)-2-propenedithioate (L1 in 1), methyl-3-hydroxy-(2-naphthyl)-2-propenedithioate (L2 in 2), methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate (L3 in 3), methyl-3-hydroxy-3-(p-fluorophenyl)-2-propenedithioate (L4 in 4), and methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate (L5 in 5)), have been synthesized and characterized by elemental (C, H, N and S) analysis, ESI-MS, IR, and UV-vis spectra. The structures of HL3 and its corresponding complex 3 have been determined by X-ray crystallography. Electrochemical behavior of all complexes has been studied by cyclic voltammetry. All five planar complexes show efficient DNA-binding and DNA (PBR322)-cleavage in a concentration-dependent manner (1 > 3 > 5 > 2 > 4). Cleavage efficiency is enhanced in the presence of H 2 O 2 as well as ascorbic acid. However, the order of increased efficiency of Cu(II) chelates differs in the presence of H 2 O 2 as 4 > 1 > 2 > 3 > 5. Among these complexes, the pyridyl- and methoxy-functionalized 1 and 3 have shown higher self-activating capability in DNA-cleavage. All complexes show significant variation in IC 50 on MCF-7 cell line. Additionally, treatment with the complexes gradually increases apoptotic cell death in dose-dependent manner in RAW 264.7 cell line. These findings highlight potential cancer protective nature of these complexes.
ISSN:0095-8972
1029-0389
DOI:10.1080/00958972.2016.1275589