A novel compound of triphenyltin(IV) with N-tert-butoxycarbonyl-l-ornithine causes cancer cell death by inducing a p53-dependent activation of the mitochondrial pathway of apoptosis

The triphenyltin(IV) compound with N-tert-butoxycarbonyl-l-ornithine (Boc-Orn-OH), [Ph3Sn(Boc-Orn-O)], was synthesized and characterized in the solid state and in solution. The organotin(IV) compound inhibited, at very low micromolar concentrations, the growth of human tumor cell lines and did not affect the viability of non-malignant cells. The cytotoxicity of Ph3Sn(Boc-Orn-O) is related to the induction of p53-dependent activation of the mitochondrial pathway of apoptosis. [Display omitted] •Triphenyltin(IV) compound with N-tert-butoxycarbonyl-l-ornithine has been synthesized.•Antiproliferative activity was evaluated in vitro on different tumor cell lines.•IC50 values are from 20 to 60 times lower than cisplatin.•Ph3Sn(Boc-Orn-O) induced apoptosis of HepG2 cells via mitochondria-dependent pathway. The triphenyltin(IV) compound with N-tert-butoxycarbonyl-l-ornithine (Boc-Orn-OH), [Ph3Sn(Boc-Orn-O)], was synthesized and characterized by elemental analysis, FT-IR, solution 1H, 13C and 119Sn NMR and ESI mass spectrometry. The organotin(IV) compound inhibited at very low micromolar concentrations the growth of human tumor cell lines HepG2 (hepatocarcinoma cells), MCF-7 (mammary cancer) and HCT116 (colorectal carcinoma) while it did not affect the viability of non-malignant human-derived hepatic cells Chang. The mechanism of the antiproliferative effect of Ph3Sn(Boc-Orn-O), investigated on human hepatoma HepG2 cells, was pro-apoptotic, being associated with externalization of plasma membrane phosphatidylserine, chromatin condensation or fragmentation and mitochondrial dysfunction as well as with increase of p53 levels.