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

Abstract The triphenyltin(IV) compound with N - tert -butoxycarbonyl- l -ornithine (Boc-Orn-OH), [Ph 3 Sn(Boc-Orn-O)], was synthesized and characterized by elemental analysis, FT-IR, solution 1 H, 13 C and 119 Sn 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 Ph 3 Sn(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.