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Effect of chirality on the anticancer activity of Pt(II) and Pt(IV) complexes containing 1,2 and 1,2 enantiomers of the -1,2-diamino-4-cyclohexene ligand (DACHEX), an analogue of diaminocyclohexane used in oxaliplatin. | LitMetric

AI Article Synopsis

Article Abstract

Six enantiomerically pure, oxaliplatin-like, platinum compounds (two platinum(II) and four platinum(IV)), all containing unsaturated cyclic diamine -1,2-diamino-4-cyclohexene (DACHEX) as a substitute for the -1,2-diaminocyclohexane used in oxaliplatin, were investigated. The complexes were characterized by elemental analyses, ESI-MS, and H-NMR spectroscopy. For the four Pt(IV) complexes the electrochemical redox behaviour, investigated by cyclic voltammetry, showed that all complexes possess reduction potentials suitable for activation . The antiproliferative activity was assessed on human cancer cell lines, also selected for resistance to platinum-based drugs or belonging to the MultiDrug-Resistant (MDR) phenotype. All complexes exhibited antiproliferative activity superior to that of cisplatin and almost equivalent to or better than that of oxaliplatin; moreover, most complexes were also capable of overcoming both the cisplatin- and the oxaliplatin-resistance. By comparing the effectiveness of the enantiomerically pure compounds with the racemic one, the , enantiomer emerged as the most effective in the case of Pt(II) complexes whereas the , enantiomer was the most effective in the case of the Pt(IV) derivatives. From the results obtained also against 3D spheroid tumor models, ,,-[Pt(OXA)(OBz)(1,2-DACHEX)] (OBz = benzoate) emerged as the most promising candidate for further preclinical investigation.

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Source
http://dx.doi.org/10.1039/d1dt02255eDOI Listing

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