6533b859fe1ef96bd12b76ed

RESEARCH PRODUCT

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

Luisa TesoriereGiampaolo BaroneAlessandro AttanzioRiccardo BonsignoreSimona RubinoPiera SabatinoMassimo L. CapobiancoMaria Assunta GirasoloGirolamo Casella

subject

Apoptosis010402 general chemistry01 natural sciencesInorganic ChemistryBoc-Orn-OHTriphenyltin(IV) Boc-Orn-OH NMR Antitumor agents Apoptosischemistry.chemical_compoundProphaseSettore BIO/10 - BiochimicaMaterials ChemistrymedicinePhysical and Theoretical ChemistryFragmentation (cell biology)Antitumor agents010405 organic chemistryChemistryAntitumor agentCancerApoptosiTriphenyltin(IV)Phosphatidylserinemedicine.diseasedigestive system diseasesNMR0104 chemical sciencesBiochemistryTriphenyltin(IV) Boc-Orn-OH NMR Antitumor agents ApoptosisCell cultureApoptosisSettore CHIM/03 - Chimica Generale E InorganicaCancer cellHepatic stellate cell

description

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, solution1H,13C and119Sn 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. 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.

10.1016/j.ica.2016.11.012http://hdl.handle.net/10447/215245