Molecular design and synthesis of dithiocarbazate-based potential biomaterials: Crystal structure, apoptotic activity and protein binding studies

A series of organic based heterocyclic dithiocarbazate ligands N'-(1-methyl-1H-imidazol-2-ylmethylene)-hydrazinecarbodithioic acid methyl ester ( L1 ), N'-(1-methyl-1H-imidazol-2-ylmethylene)-hydrazinecarbodithioic acid benzyl ester ( L2 ), N'-[1-(1H-benzoimidazol-2-yl)-ethylidene]-hydrazinecarbodithioic acid methyl ester ( L3 ) and N'-[1-(1H-benzoimidazol-2-yl)-ethylidene]-hydrazinecarbodithioic acid benzyl ester ( L4 ) has been prepared along with characterization by various spectroscopic techniques (IR, 1 H and 13 C NMR, mass and UV-Visible) and thermal analysis. Single crystal X-ray diffraction analysis is used to determine the crystal structure of the synthesized ligands L1 and L3 crystallizes as orthorhombic and monoclinic crystals, respectively. Fluorescence spectrophotometry is used to study the interaction of the ligands with bovine serum albumin (BSA) and the quenching of BSA followed a static type. MTT assay against H520 (Squamous cell lung carcinoma) cell reveals that L1 and L3 ligands shows higher cytotoxic value than the remaining L2 and L4 ligands and could be a better choice as chemotherapeutic agent. Apoptotic activity was assayed using AO/EB staining and Hoechst 33258 staining, the early apoptotic features such as cell shrinkage and condensation were majorly observed in cells treated with all four ligands.(c) 2023 Elsevier B.V. All rights reserved.