Synthesis, characterization, molecular docking and DNA binding studies of Cu(II), Ni(II), Zn(II) and Mn(II) complexes

Abstract

The azo dye ligand of Cyano-6-(p-tolyl)azo-7-hydroxy coumarine (HL) was synthesized by coupling of 3-Cyano-7-hydroxy coumarine with p-toluidine. The ligand (HL) was formed novel complexes (1–4) with the formulae [Cu(L)Cl(OH2)]2H2O, [Ni(L)Cl(OH2)3], [Zn(L)Cl(OH2)]H2O and [Mn(L)Cl(OH2)3]2H2O, respectively. HL and its complexes were characterized by elemental analyses, IR, 1H NMR, MS and UV–Visible spectra as well as magnetic and thermal measurements. The molar conductance measurements proved that all the complexes are non-electrolytes. Also, the important fragments in the ligand and Ni(II) complex were done using mass spectra and the main peaks were corresponding to the molecular weights of them. IR spectra shows that the ligand (HL) act as monobasic bidentate coordinated via nitrogen atom of the azo group (NN) and oxygen atom of the deprotonated phenolic OH group. The Thermal decomposition of the complexes revealed the outer and inner water molecules as well as the end product which in most cases is metal oxide. The thermodynamic parameter of the ligand (HL) and its metal complexes are calculated using Coats-Redfern and Horowitz Metzger methods. The molecular and electronic structures of the investigated compounds were also studied using quantum chemical calculations. The bonding parameter of the complexes have been calculated. Molecular docking was used to predict the binding between azo compounds with the receptor of breast cancer 3hb5-oxidoreductase and prostate cancer mutant 2q7k–Hormone. The calf thymus DNA binding activity of the ligand (HL) and its metal complexes were studied by absorption spectra. The cytotoxic activity of ligand (HL) and its metal complexes was tested against human cancer MCF-7 (breast cancer).