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QSAR of the free radical scavenging potency of selected hydroxyanthraquinones

  • Zoran Marković
  • Miloš Filipović
  • Nedeljko Manojlović
  • Ana Amić
  • Svetlana Jeremić
  • Dejan Milenković
Original Paper
  • 2 Downloads

Abstract

It is well known that anthraquinones are molecules with moderate, but not negligible antioxidative activity. Their chemical behaviour is influenced by different parameters such as thermodynamics, orbital and structural properties, and polarity of environment. To find dependence of antioxidant activity of fourteen selected anthraquinones on the physicochemical parameters, we developed one-, two- and three-descriptor mathematical models. In all quantitative structure–activity relationship models (QSAR), experimentally obtained ABTS values were used as dependent variables. One-descriptor model indicated that in methanol the best correlation give enthalpies that describe stable radical formation following single proton loss, and then transfer of electron. Unexpectedly, the best two-descriptor model shows the best dependence of the experimental results on the combination of the orbital and structural parameters. The best two-parameter model was improved by introducing one thermodynamical parameter, such as bond dissociation enthalpy. On that way the best three-descriptor model was obtained. It indicates that the best insight into the antioxidant capacity of a molecule can be obtained by pooling all types of parameters and influences in a mathematical model.

Keywords

QSAR Anthraquinones ABTS Thermodynamical parameters Vicinal hydroxyl groups 

Notes

Acknowledgements

This work was supported by the Ministry of Science of the Republic of Serbia (Project nos. 172015 and 174028) and by The Foundation of the Croatian Academy of Sciences and Arts, under the Project no. 10-102/244-1-2016. “Investigations of the antioxidant mechanisms of polyphenols and their metabolites” awarded to Ana Amić.

Supplementary material

11696_2018_534_MOESM1_ESM.doc (218 kb)
Supplementary material 1 (DOC 217 kb)

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of Chemical-Technological SciencesState University of Novi PazarNovi PazarSerbia
  2. 2.Faculty of Medical SciencesUniversity of KragujevacKragujevacSerbia
  3. 3.Department of ChemistryJosip Juraj Strossmayer UniversityOsijekCroatia
  4. 4.Bioengineering Research and Development CenterKragujevacSerbia

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