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• Three organotin(IV) Schiff base carboxylates suppressing the growth of four cis- platin-resistent human lung and colon cancer cells were synthesized. • Di- n ‑butyl and triphenyltin(IV) Schiff base carboxylates present higher in vitro cytotoxicities against four cisplatin-resistent cancer cell lines than the dimethyl derivative. • Di- n -butyltin(IV) Schiff base carboxylate presents a promising drug lead for anticancer treatment through producing ROS to induce the death of cancer cells. Three new organotin(IV) complexes, namely trimethyltin(IV) [3‑methoxy-2-hydroxyphenyl-N-(3-carboxyphenyl) imine] monohydrate carboxylate, [Me 3 Sn(L)(H 2 O), 1], triphenyltin(IV) [3‑methoxy-2-hydroxyphenyl-N-(3-carboxyphenyl) imine] carboxylate, [Ph 3 Sn(L), 2], and di-n-butyltin(IV) [3‑methoxy-2-hydroxyphenyl-N-(3-carboxyphenyl) imine] carboxylate, ({[(n-Bu) 2 Sn(L)] 2 O} 2 , 3), [HL = 3‑methoxy-2-hydroxyphenyl-N-(3-carboxyphenyl) imine Schiff base ligand], have been synthesized by the reaction of organotin(IV) chlorides with Schiff base carboxylic acid ligand HL derived from o -vanillin and 3-aminobenzoic acid. All complexes have been characterized using spectroscopic (IR, 1H, 13C, 119Sn NMR, and ESI-MS) and single-crystal X-ray diffraction techniques. Structural analyses reveal that the ligand presents as monodentate in five-coordinate trimethyltin(IV) complex 1 and four-coordinate triphenyltin(IV) complex 2. But in di- n -butyltin(IV) complex 3, the ligands coordinate to tin(IV) atoms through bi- and monodentate two different forms. Also through intermolecular Sn···O weak interaction, complex 3 presents a weakly bridged dimmeric structure which will decompose to monomer in solution. The in vitro cytotoxicities of the title complexes determined against four cis- platin-resistent cancer cell lines (A549, Caco-2, HCT-116 and HT-29) reveal that the di- n -butyltin(IV) and triphenyltin(IV) complexes show higher cytotoxicities than trimethlytin(IV) derivative. The main anticancer mechanism should be due to the generation of intracellular reactive oxygen species (ROS). [Display omitted] Synthesized three organotin(IV) complexes that present strong in vitro cytotoxicity againt cis-platin-resistent cancer cells, of which complex 3 could stimulate ROS production in colon cancer cells and this makes it exhibit a potential anticancer drug. [ABSTRACT FROM AUTHOR]