Exploration of organotin(IV) derivatives for medicinal applications: Synthesis, spectroscopic characterization, structural elucidation and molecular docking study

摘要

Organotin (IV) derivatives of carboxylate ligand, 4-(4-methoxyanilino)-4-oxobutanoic acid, have been synthesized and characterized by FTIR, NMR, CHN analysis, mass spectrometry and X-ray crystallography. Single crystal data of four compounds (1-4) displayed a distorted trigonal bipyramidal environment around Sn with the three equatorial positions occupied by alkyl group. In compounds 1-3, carboxylate oxygens of ligand play the role of a bridge between the adjacent tin atoms symmetrically giving a polymeric chain structure. In compound 4, oxygen of the amide carbonyl moiety perform the same function and bridges the adjacent tin atoms [Sn-O = 2.155 (3) and 2.428 (3) angstrom, respectively], with the three phenyl ipso-C atoms defining the trigonal plane and the axial positions occupied by O atoms [O1-Sn-O3 = 177.62 (11) angstrom]. The tau values calculated for complexes 1-4 are 0.78, 0.77, 0.82 and 0.92, respectively, also confirm the trigonal bipyramidal geometry. The antimicrobial results of the synthesized compounds illustrate their use as a potential antimicrobial agent. The DNA interaction study performed by UV-visible spectroscopy as well as by molecular docking suggests the tested compounds interact with DNA through intercalation mode. The compounds were screened for anticancer activity performed against lung carcinoma and Vero cell lines resulting in activity that is almost equivalent to that of the standard, vincristine. The biological significance of these compounds is that there affect on the normal cell line is very small i.e., 27.1%. The compounds also exhibit good inhibition of urease enzyme. A good correlation was observed between the docking scores and biological activities of these compounds. (C) 2018 Elsevier B.V. All rights reserved.