QSAR modeling of anxiolytic activity taking into account the presence of keto- and enol-tautomers by balance of correlations with ideal slopes

• Authors: Alla. Toropova , Andrey Toropov , Emilio Benfenati , Giuseppina Gini , Danuta Leszczynska , Jerzy Leszczynski
• Languages of publication: EN

Abstracts

EN

Optimal descriptors calculated with simplified molecular input line entry system (SMILES) have been examined as a tool for prediction of anxiolytic activity. Descriptors calculated with SMILES (a) of keto-isomers; (b) of enol-isomers; and (c) of both keto-isomers together with enol-isomers have been studied. Three approaches have been compared: 1. classic’ training-test’ system 2. balance of correlations and 3. balance of correlations with ideal slopes. The best statistical characteristics for the external validation set took place for optimal descriptors calculated with SMILES of both keto-form and enol-form (i.e., molecular structure was represented in the format: ’sMILES of keto-form. SMILES of enol-form’) by means of balance of correlations with ideal slopes. The predictive potential of this model was checked with three random splits. [...]

Keywords

EN

QSAR; SMILES; Tautomerism; Anxiolytic activity; Balance of correlation

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2011
• Volume: 9
• Issue: 5
• Pages: 846-854

Dates

published

1 - 10 - 2011

online

24 - 7 - 2011

Contributors

author

Alla. Toropova

• Institute of Pharmacological Researches “Mario Negri”, 20156, Milan, Italy

author

Andrey Toropov

• Institute of Pharmacological Researches “Mario Negri”, 20156, Milan, Italy

author

Emilio Benfenati

• Institute of Pharmacological Researches “Mario Negri”, 20156, Milan, Italy

author

Giuseppina Gini

• Department of Electronics and Information, Polytechnical Institute of Milan, 20133, Milan, Italy

author

Danuta Leszczynska

• Interdisciplinary Nanotoxicity Center, Department of Civil and Environmental Engineering, Jackson State University, Jackson, MS, 39217-0510, USA

author

Jerzy Leszczynski

• Interdisciplinary Nanotoxicity Center, Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS, 39217, USA

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Identifiers

DOI

10.2478/s11532-011-0064-0