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CoMFA and CoMSIA studies on a new series of xanthone derivatives against the oral human epidermoid carcinoma (KB) cancer cell line

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Abstract

A new series of xanthone derivatives against the oral human epidermoid carcinoma (KB) cancer cell line is examined to determine the relationship between the structural properties and the biological activity of these compounds—the 3-D quantitative structure–activity relationship (3D-QSAR)—using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA). The best CoMFA and CoMSIA models were obtained using the atom-based alignment of 33 compounds, 22 training compounds and 11 tested compounds, and these give desirable statistics; those for the CoMFA standard model were: r 2cv  = 0.691, r 2 = 0.998, S press = 0.178, s = 0.014 and F = 1080.765, while CoMSIA combined steric, electrostatic, hydrophobic and hydrogen-bond acceptor fields: r 2cv  = 0.600, r 2 = 0.988, S press = 0.206, s = 0.034 and F = 284.433. The 3D-QSAR models calculated satisfactory test set activities. The 3D-QSAR contour plots correlated strongly with the experimental data for the binding topology. For this reason, these results would be beneficial for predicting affinities with the compounds of interest, and they are advantageous for guiding the design and synthesis of new and more effective anticancer agents.

Graphical abstract

A new and more effective anticancer agent of xanthone derivatives against the oral human epidermoid carcinoma (KB) cell line, as investigated by CoMFA and CoMSIA analysis

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Acknowledgments

This work is supported by the Thailand Research Fund, the Postgraduate Education and Research Program in Chemistry (PERCH) and in Petroleum and Petrochemical Technology (PPT), and a research team strengthening grant from The National Centre for Genetic Engineering and Biotechnology (BIOTEC). Phornphimon Maitarad is grateful to TGIST for a scholarship and the Graduate school of KU for scholarships and to Ben Parslew for English editing. We would like also to thank the High Performance Computing Center of the National Electronics and Computer Technology Center (NECTEC), the Laboratory for Computational and Applied Chemistry (LCAC), and the computing center of KU for research facilities.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Mahidol University, Rajthevee, Bangkok, 10400, Thailand

    Ketthip Suphavanich & Yuthana Tantirungrotechai

  2. Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok, 10900, Thailand

    Phornphimon Maitarad, Supa Hannongbua & Jumras Limtrakul

  3. Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok, 10110, Thailand

    Pichit Sudta & Sunit Suksamrarn

  4. Center of Nanotechnology, Kasetsart University Research and Development Institute, Kasetsart University, Bangkok, 10900, Thailand

    Jumras Limtrakul

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  1. Ketthip Suphavanich
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  2. Phornphimon Maitarad
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Correspondence to Yuthana Tantirungrotechai.

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Suphavanich, K., Maitarad, P., Hannongbua, S. et al. CoMFA and CoMSIA studies on a new series of xanthone derivatives against the oral human epidermoid carcinoma (KB) cancer cell line. Monatsh Chem 140, 273–280 (2009). https://doi.org/10.1007/s00706-008-0014-5

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  • DOI: https://doi.org/10.1007/s00706-008-0014-5

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