Synthesis and Characterization of Copper(II) Complexes with Aroylhydrazone Ligands Containing Quaternary Ammonium Salts: in Vitro DNA Binding and Nuclease Activity

Abstract

Two new N, N, N-trimethylpropane-1-ammonium and N, N,N-trimethylpentane-1-ammonium conjugated acetophenone-(4-hydroxybenzohydrazone) ligands, (E)-3-(4-(1-(2-(4-hydroxybenzoyl)hydrazono)ethyl)phenoxy)-N,N, N-trimethylpropan-1-mmonium perchlorate (H2L1) and (E)-3-(4-(1-(2-(4-hydroxybenzoyl) hydrazono)ethyl)phenoxy). N, N,N-trimethylpentane-1-ammonium perchlorate (H2L2), and two new copper complexes with the formulation [Cu (HL1)(2)] and [Cu(HL2)(2)] were synthesized and their DNA binding and cleavage activities of the compounds were inves. tigated. The mechanism of DNA cleavage and the effect of the compound concentration on the DNA cleavage reac. tion were also studied. UV. Vis spectroscopy results suggest that all compounds preferably bind to DNA via major groove binding mode. This is also supported that DNA cleavage activity was inhibited in the presence of methyl green, a major groove binder. According to the results of electrophoresis studies, the compounds exhibit significant cleavage activity on the plasmid DNA both in the presence and absence of an oxidative agent (H2O2), which strongly depends on the concentration of the compound. The compounds cleavage pBR322 DNA via hydrolytic pathway, which is also supported by the DNA cleavage experiments in the presence of different radical scavengers.