Triphenyltin(IV) acylhydrazone compounds: Synthesis, structure and bioactivity

Abstract

Four new triphenyltin(IV) acylhydrazone compounds of the type Ph₃SnCH₂CH₂CONHN=R (where Ph = phenyl; R = isopropyl, isobutyl, cyclopentyl and cyclooctyl) were synthesized and characterized by elemental analysis, infrared spectrum (IR), nuclear magnetic resonance spectrum (NMR) and mass spectrum (MS). The crystal structures were determined and showed that tin atoms were four-coordinated and adopted a pseudo-tetrahedron configuration. Tin(IV) compounds show excellent bovine serum albumin (BSA) binding properties, and can oxidize nicotinamide-adenine dinucleotid (NADH) to generate reactive oxygen species (ROS), which inducing apoptosis effectively. Bioassay results indicated that tin(IV) compounds have stronger cytotoxic activity against A549 human lung cancer cells compared with cis-platin used clinically, and showing some selectivity.

Keywords: Acylhydrazone; Antitumor; Triphenyltin(IV).