Synthesis, crystal structures, DNA-binding properties, cytotoxic and antioxidation activities of several new ternary copper(II) complexes of N,N′-(p-xylylene)di-alanine acid and 1,10-phenanthroline

Abstract

Three novel ternary copper(II) complexes, [Cu2(phen)2(l-PDIAla)(H2O)2](ClO4)2·2.5H2O (1), [Cu4(phen)6(d,l-PDIAla)(H2O)2](ClO4)6·3H2O (2) and [Cu2(phen)2(d,l-PDIAla)(H2O)](ClO4)2·0.5H2O (3) (phen = 1,10-phenanthroline, H2PDIAla = N,N'-(p-xylylene)di-alanine acid) have been synthesized and structurally characterized by single-crystal X-ray crystallography and other structural analysis. Spectrometric titrations, ethidium bromide displacement experiments, CD (circular dichroism) spectral analysis and viscosity measurements indicate that the three compounds, especially the complex 3, strongly bind to calf-thymus DNA (CT-DNA). The intrinsic binding constants of the ternary copper(II) complexes with CT-DNA are 0.89 × 105, 1.14 × 105 and 1.72 × 105 M-1, for 1, 2 and 3, respectively. Comparative cytotoxic activities of the copper(II) complexes are also determined by acid phosphatase assay. The results show that the ternary copper(II) complexes have significant cytotoxic activity against the HeLa (Cervical cancer), HepG2 (hepatocarcinoma), HL-60 cells (myeloid leukemia), A-549 cells (pulmonary carcinoma) and L02 (liver cells). Investigations of antioxidation properties show that all the copper(II) complexes have strong scavenging effects for hydroxyl radicals and superoxide radicals. © 2009 Elsevier B.V. All rights reserved.