Issue 10, 2013

Molecular interaction fields vs. quantum-mechanical-based descriptors in the modelling of lipophilicity of platinum(iv) complexes

Abstract

We report QSAR calculations using VolSurf descriptors to model the lipophilicity of 53 Pt(IV) complexes with a diverse range of axial and equatorial ligands. Lipophilicity is measured using an efficient HPLC method. Previous models based on a subset of these data are shown to be inadequate, due to incompatibility of whole molecule descriptors between carboxylato and hydroxido ligands. Instead, the interaction surfaces of complexes with various probes are used as independent descriptors. Partial least squares modelling using three latent variables results in an accurate (R2 = 0.92) and robust model (Q2 = 0.87) of lipophilicity, that moreover highlights the importance of size and hydrophobicity terms and the modest relevance of hydrogen bonding.

Graphical abstract: Molecular interaction fields vs. quantum-mechanical-based descriptors in the modelling of lipophilicity of platinum(iv) complexes

Supplementary files

Article information

Article type
Paper
Submitted
05 Oct 2012
Accepted
05 Dec 2012
First published
05 Dec 2012

Dalton Trans., 2013,42, 3482-3489

Molecular interaction fields vs. quantum-mechanical-based descriptors in the modelling of lipophilicity of platinum(IV) complexes

G. Ermondi, G. Caron, M. Ravera, E. Gabano, S. Bianco, J. A. Platts and D. Osella, Dalton Trans., 2013, 42, 3482 DOI: 10.1039/C2DT32360E

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