Copper(II) complexes of acylhydrazones: synthesis, characterization and DNA interaction

Abstract

Two new acylhydrazone copper(II) complexes of 4-hydroxy-N-[(1E)-1-(4-methylphenyl)ethylidene]benzohydrazide (HL1) and 4 ethyl [4-({(2E)-2-[1-(4-methylphenyl)ethylidene]hydrazinyl}carbonyl)phenoxy]acetate (HL2) have been synthesized and characterized. The structures of both acylhydrazone and copper(II) complexes were identified by elemental analysis, infrared spectra, UVvisible electronic absorption spectra, magnetic susceptibility measurements, TGA and powder X-ray diffraction. DNA binding and DNA cleavage activities of the synthesized copper complexes were examined by using UV-visible titration and agarose gel electrophoresis, respectively. The effect of complex concentration on the DNA cleavage reactions in the absence and presence of H2O2 was also investigated. The results indicate that all the complexes bind slightly to calf thymus DNA and cleavage pBR322 DNA. The mechanistic studies demonstrate that a hydrogen peroxide-derived species and singlet oxygen (1O2) are the active oxidative species for DNA cleavage. Copyright (c) 2013 John Wiley & Sons, Ltd.