Molecular and statistical modeling of reduction peak potential and lipophilicity of platinum(IV) complexes |
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Authors: | James A Platts Giuseppe Ermondi Giulia Caron Mauro Ravera Elisabetta Gabano Luca Gaviglio Giorgio Pelosi Domenico Osella |
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Institution: | 1.School of Chemistry, Cardiff University,Cardiff,UK;2.CASSMedChem, Dipartimento di Scienza e Tecnologia del Farmaco c/o Centro della Innovazione,Università di Torino,Turin,Italy;3.Dipartimento di Scienze dell’Ambiente e della Vita,Università del Piemonte Orientale “Amedeo Avogadro”,Alessandria,Italy;4.Dipartimento di Chimica Generale ed Inorganica,Chimica Analitica, Chimica Fisica, Università di Parma,Parma,Italy |
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Abstract: | We report the results of the quantitative structure–property relationship analysis of 31 Pt(IV) complexes, for three of which
the synthesis is reported for the first time. The X-ray structural analysis of one complex of the series was performed to
demonstrate that the PM6 semiempirical method satisfactorily reproduces key features of the geometry of the complexes investigated.
Molecular properties extracted from such calculations were then used to construct models of experimental data such as electrochemical
peak potentials (evaluated by cyclic voltammetry) and the octanol–water partition coefficient (evaluated by a reversed-phase
high performance liquid chromatography method), which are key aspects in the design of such Pt(IV) complexes as potential
anticancer prodrugs. Statistically accurate models for both properties were found using combinations of surface areas, orbital
energies, dipole moments, and atomic partial charges. These models could form the basis of virtual screening of potential
drug molecules, allowing the prediction of properties, closely related to the antiproliferative activity of Pt(IV) complexes,
directly from calculated data. |
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