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QSAR models for ACE-inhibitor activity of tri-peptides based on representation of the molecular structure by graph of atomic orbitals and SMILES

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Abstract

The CORAL software (http:/www.insilico.eu/CORAL) has been examined as a tool of modeling of the angiotensin-converting enzyme-inhibitor activity of 54 tri-peptides. Three versions of the models were examined: (i) models based on the graph of atomic orbitals (GAO); (ii) models based on the simplified molecular input-line entry systems (SMILES); and (iii) hybrid models based on both GAO and SMILES. The hybrid models have provided the best prediction. The robustness of the approach has been checked with four random splits into training set and test set.

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Acknowledgments

We thank ANTARES (the project number LIFE08-ENV/IT/00435), and the National Science Foundation (NSF/CREST HRD-0833178, and EPSCoR Award no. 362492-190200-01\NSFEPS-090378) for financial support. Also we express our gratitude to Dr. L. Cappellini, Dr. G. Bianchi, and Dr. R. Bagnati for valuable consultations on the computer science, and to J. Baggott for English editing.

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Authors and Affiliations

  1. Istituto di Ricerche Farmacologiche Mario Negri, Via La Masa 19, 20156, Milan, Italy

    A. P. Toropova, A. A. Toropov & E. Benfenati

  2. Department of Chemistry and Biochemistry, Interdisciplinary Nanotoxicity Center, Jackson State University, 1400 J. R. Lynch Street, P.O. Box 17910, Jackson, MS, 39217, USA

    B. F. Rasulev & J. Leszczynski

  3. Department of Electronics and Information, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milan, Italy

    G. Gini

  4. Department of Civil and Environmental Engineering, Interdisciplinary Nanotoxicity Center, Jackson State University, 1325 Lynch Street, Jackson, MS, 39217-0510, USA

    D. Leszczynska

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  1. A. P. Toropova
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  2. A. A. Toropov
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  3. B. F. Rasulev
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  4. E. Benfenati
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  5. G. Gini
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  7. J. Leszczynski
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Correspondence to A. A. Toropov.

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Toropova, A.P., Toropov, A.A., Rasulev, B.F. et al. QSAR models for ACE-inhibitor activity of tri-peptides based on representation of the molecular structure by graph of atomic orbitals and SMILES. Struct Chem 23, 1873–1878 (2012). https://doi.org/10.1007/s11224-012-9996-z

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  • DOI: https://doi.org/10.1007/s11224-012-9996-z

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