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Structural Chemistry

, Volume 29, Issue 4, pp 957–965 | Cite as

A molecular modeling study of combretastatin-like chalcones as anticancer agents using PLS, ANN and consensus models

  • Célio Fernando Lipinski
  • Aline Alves Oliveira
  • Kathia Maria Honorio
  • Patrícia Rufino Oliveira
  • Albérico Borges Ferreira da SilvaEmail author
Original Research

Abstract

Combretastatin-like chalcones are promising anticancer compounds that inhibit the mitotic process through interactions with β-tubulin. A detailed study of these compounds can contribute for the rational drug design of new structures aiming at compounds with high biological activity. For this purpose, we have studied 87 combretastatin-like chalcones and proposed multivariate models based on partial least squares (PLS), artificial neural network consensus model (ANN-CM), and general consensus model (GCM). The proposed models have showed good predictive ability with r2test = 0.812 and MSE (test set) = 0.327 for the PLS model, r2test = 0.829 and MSE (test set) = 0.286 for the ANN-CM, and r2test = 0.822 and and MSE (test set) = 0.302 for the GCM. The selected molecular and electronic descriptors (RDF045e, RTv, RDF155u, RDF035m, SP02, PI, UNIP and EHOMO-3) represent molecular features of the compounds that can be associated to the biological activity and can be employed to help the design of new bioactive ligands with improved biological activity.

Keywords

Cancer Microtubules Chalcones QSAR ANN Consensus modeling 

Notes

Acknowledgements

The authors would like to thank CNPq, CAPES and FAPESP (Brazilian agencies) for the financial support.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11224_2017_1072_MOESM1_ESM.pdf (360 kb)
ESM 1 (PDF 359 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Célio Fernando Lipinski
    • 1
  • Aline Alves Oliveira
    • 2
  • Kathia Maria Honorio
    • 2
  • Patrícia Rufino Oliveira
    • 2
  • Albérico Borges Ferreira da Silva
    • 1
    Email author
  1. 1.Instituto de Química de São CarlosUniversidade de São PauloSão CarlosBrazil
  2. 2.Escola de Artes, Ciências e HumanidadesUniversidade de São PauloSão PauloBrazil

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