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Issue 12, 2016
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Synthesis, characterization, thermal properties and antiproliferative potential of copper(II) 4′-phenyl-terpyridine compounds

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Abstract

Reactions between 4′-phenyl-terpyridine (L) and several Cu(II) salts (p-toluenesulfonate, benzoate and o-, m- or p-hydroxybenzoate) led to the formation of [Cu(p-SO3C6H4CH3)L(H2O)2](p-SO3C6H4CH3) (1), [Cu(OCOPh)2L] (2), [Cu(o-OCOC6H4OH)2L] (3), [Cu(m-OCOC6H4OH)2L]·MeOH (4·MeOH) and [Cu(p-OCOC6H4OH)2L]·2H2O (5·2H2O), which were characterized by elemental and TG-DTA analyses, ESI-MS, IR spectroscopy and single crystal X-ray diffraction, as well as by conductivimetry. In all structures the Cu atoms present N3O3 octahedral coordination geometries, which, in 2–5, are highly distorted as a result of the chelating-bidentate mode of one of the carboxylate ligands. Intermolecular π⋯π stacking interactions could also be found in 2–5 (in the 3.569–3.651 Å range and involving solely the pyridyl rings). Medium–strong hydrogen bond interactions lead to infinite 1D chains (in 1 and 4) and to an infinite 2D network (in 5). Compounds 1 and 4 show high in vitro cytotoxicity towards HCT116 colorectal carcinoma and HepG2 hepatocellular carcinoma cell lines. The antiproliferative potential of compound 1 is due to an increase of the apoptotic process that was confirmed by Hoechst staining, flow cytometry and RT-qPCR. All compounds able to non-covalently intercalate the DNA helix and induce in vitro pDNA double-strand breaks in the absence of H2O2. Concerning compound 1, the hydroxyl radical and singlet oxygen do not appear to be involved in the pDNA cleavage process and the fact that this cleavage also occurs in the absence of molecular oxygen points to a hydrolytic mechanism of cleavage.

Graphical abstract: Synthesis, characterization, thermal properties and antiproliferative potential of copper(ii) 4′-phenyl-terpyridine compounds

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Publication details

The article was received on 19 Jul 2015, accepted on 02 Feb 2016 and first published on 09 Feb 2016


Article type: Paper
DOI: 10.1039/C5DT02744F
Author version available: Download Author version (PDF)
Citation: Dalton Trans., 2016,45, 5339-5355
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    Synthesis, characterization, thermal properties and antiproliferative potential of copper(II) 4′-phenyl-terpyridine compounds

    Z. Ma, B. Zhang, M. F. C. Guedes da Silva, J. Silva, A. S. Mendo, P. V. Baptista, A. R. Fernandes and A. J. L. Pombeiro, Dalton Trans., 2016, 45, 5339
    DOI: 10.1039/C5DT02744F

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