Abstract
Four new mononuclear copper(II) complexes with methyl acetoacetate and benzoylacetone in the presence of 1,10-phenanthroline and 2,2′-bipyridine were synthesized and characterized by elemental analyses, FT-IR, and UV–Vis spectroscopy. The molecular structures of complexes [Cu(MAA)(bpy)(ClO4)] (1a), [Cu(bzac)(bpy)]ClO4 (2a), [Cu(MAA)(phen)(ClO4)] (1b) and [Cu(bzac)(phen)(ClO4)] (2b) were determined by single crystal X-ray diffraction technique. 1a, 1b, and 2b are five coordinate with a distorted square pyramidal geometry and the structure of 2a consists of isolated [Cu(bzac)(bpy)]+ cations and perchlorate counter anions. The electrochemical studies of copper complexes in acetonitrile solution showed that CuII/CuI reduction processes are electrochemically irreversible. Cytotoxic activity of complexes was screened, including an MTT assay against gastric cancer cell line (MKN-45). The four Cu(II) complexes exhibited lethal effects against MKN-45 cell lines and the half maximal inhibitory concentration (IC50) values obtained were much lower in comparison with 5-fluorouracil. In addition, MTT and migration studies revealed that benzoylacetone complexes are more active than complexes of methyl acetoacetate against the MKN-45 cancer cell lines. Docking simulations of Cu(II) complexes on DNA revealed that the most stable adducts with DNA bind in the minor groove. All complexes display a binding specificity to the A/T rich regions.
Acknowledgements
We thank Semnan University for supporting this study.