Synthesis, crystal structures and spectroscopy of meclofenamic acid and its metal complexes with manganese(II), copper(II), zinc(II) and cadmium(II). Antiproliferative and superoxide dismutase activity |
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| Authors: | Kovala-Demertzi Dimitra Staninska Malgorzata Garcia-Santos Isabel Castineiras Alfonso Demertzis Mavroudis A |
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| Affiliation: | a Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45100 Ioannina, Greeceb Departamento de Qu?mica Inorganica, Universidad de Santiago de Compostela, E-15706 Santiago de Compostela, Spain |
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| Abstract: | Some new complexes of meclofenamic acid (N-(2,6-dichloro-m-tolyl)anthranilic acid), Hmeclo (1), with potentially interesting biological activities are described. Complexes [Mn(meclo)2] (2), [Cu(meclo)2(H2O)2] (3), [Zn(meclo)2(H2O)2] (4) and [Cd(meclo)2(H2O)2] (5) were prepared and structurally characterized by means of vibrational, electronic and 1H and 13C NMR spectroscopies. The crystal structure of complexes [Cu4(meclo)6(OH)2(DMSO)2] 2DMSO (3a) and [Cd(meclo)2(DMSO)3] (5a) have been determined by X-ray crystallography. Complex (3a) is a centrosymmetric tetramer built up around the planar cyclic Cu2(OH)2 unit. Complex 5a is mononuclear seven-coordinated complex with the meclofenamato ligand behaving as a bidentate deprotonated chelating ligand. Intra and intermolecular hydrogen bonds stabilize these two structures, while the crystal packing is determined by π-π and C−H−-π interactions. Meclofenamic acid and its metal complexes have been evaluated for antiproliferative activity in vitro against the cells of three human cancer cell lines, MCF-7 (breast cancer cell line), T24 (bladder cancer cell line), and A-549 (non-small cell lung carcinoma), and a mouse fibroblast L-929 cell line. Complex 5 exhibits the highest selectivity against MCF-7 and 4 shows the highest selectivity against T-24. Complexes 2-5 were found to be more potent cytotoxic agents against T-24 and complex 5 against MCF-7 cancer cell lines than the prevalent benchmark metallodrug, cis-platin. The superoxide dismutase activity was measured by the Fridovich test which showed that complex [Cu(meclo)2(H2O)2] is a good superoxide scavenger. |
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| Keywords: | Metal complexes Meclofenamic acid Crystal structures Spectroscopic studies Antineoplastic activity Sod activity |
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