Investigation of the binding ability of a new thiosemicarbazone-based ligand and its Zn(II) complex toward proteins and DNA: spectral, structural, theoretical, and docking studies

Abstract

A new thiosemicarbazone derivative ligand N-(4-chlorophenyl)-2-(pyridin-2-ylmethylene)hydra­zine-1-carbothioamide (HL) and its zinc(II) complex [ZnL2]·CH2Cl2 (1) are prepared and cha­racterized by elemental analysis, FTIR and 1H NMR spectroscopy, and single crystal X-ray diffraction (for 1). The X-ray analysis reveals that the zinc atom is octahedrally coordinated by two NpyNimineSthiolate-donor ligands with the mer form. The HL ligand is deprotonated during the complexation process through the thiol group. In the crystal network of 1, the N—H⋯S hydrogen bonds form R22(8) hydrogen bond motifs. In addition, the crystal network is more stabilized by π—π stacking and C—H⋯π interactions. The ability of complex 1 to interact with ten selected biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II, and B-DNA) is investigated by docking studies. The results show that in many cases, complex 1 can interact with proteins better than doxorubicin.