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Structural Chemistry

, Volume 30, Issue 6, pp 2301–2310 | Cite as

Relationship between electronic structures and antiplasmodial activities of xanthone derivatives: a 2D-QSAR approach

  • Gaston A. KpotinEmail author
  • Affoué Lucie Bédé
  • Alice Houngue-Kpota
  • Wilfried Anatovi
  • Urbain A. Kuevi
  • Guy S. Atohoun
  • Jean-Baptiste Mensah
  • Juan S. Gómez-Jeria
  • Michael BadawiEmail author
Original Research
  • 80 Downloads

Abstract

Malaria is an important disease causing many death in several countries of Africa and Asia. In these continents, some plants such as Garcinia cola are used to fight against this disease because they contain xanthone derivatives which present antiplasmodial activity. The present theoretical study aims to establish a relationship between the electronic structure and the antiplasmodial activity of some xanthone derivatives, and more specifically to build a 2D-pharmacophore model in order to predict the biological activity of xanthone derivatives. The calculations are performed within the density functional theory (DFT) using the B3LYP/6-31G(d,p) level of theory. The developed approach quantitative structure-activity relationship (QSAR) follows the Klopman-Peradejordi-Gómez (KPG) methodology. We obtain a statistically significant equation relating the variation of the logarithm of half maximal inhibitory concentration (log(IC50)) with the variation of the numerical values of a set of eight local atomic reactivity descriptors (R = 0.98, R2 = 0.97, adj-R2 = 0.95, F(8.13) = 48.63, p < 0.00000, SD 0.08). The antiplasmodial activity seems to be driven by atomic orbitals and charges. Our 2D-pharmacophore model should be useful to propose new xanthone derivatives with higher antiplasmodial activity.

Keywords

Xanthone Antiplasmodial QSAR DFT Klopman-Peradejordi-Gómez approach Malaria 

Notes

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Laboratory of Theoretical Chemistry and Molecular Spectroscopy, Faculty of Sciences and TechniquesUniversity of Abomey - CalaviCotonouBenin
  2. 2.Laboratoire de Chimie Organique StructuraleUniversité Félix Houphouët-BoignyAbidjanCôte d’Ivoire
  3. 3.Quantum Pharmacology Unit, Department of Chemistry, Faculty of SciencesUniversity of ChileSantiagoChile
  4. 4.Laboratoire de Physique et Chimie ThéoriquesUniversité de Lorraine - CNRSNancyFrance

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