Theoretical Chemistry Accounts

, 135:38

The key role of the sequential proton loss electron transfer mechanism on the free radical scavenging activity of some melatonin-related compounds

  • Ruslán Álvarez-Diduk
  • Annia Galano
  • Dun Xian Tan
  • Russel J. Reiter
Regular Article

DOI: 10.1007/s00214-015-1785-5

Cite this article as:
Álvarez-Diduk, R., Galano, A., Tan, D.X. et al. Theor Chem Acc (2016) 135: 38. doi:10.1007/s00214-015-1785-5
Part of the following topical collections:
  1. CHITEL 2015 - Torino - Italy

Abstract

The role of the acid–base equilibria and the sequential proton loss electron transfer mechanism (SPLET) on the free radical scavenging activity of six melatonin-related compounds was investigated using the density functional theory. It was found that this chemical route is particularly important for about half of the studied compounds. Some of their pKa values are reported here for the first time. In addition, our results also indicate that anionic species, presenting the phenolate moiety, may be crucial to scavenge peroxyl radicals albeit their populations are relatively low at physiological pH. The key number to consider in this context should be the product of the molar fraction of the reacting compound, at the pH of interest, by the corresponding rate constant.

Keywords

pKa Reaction mechanisms Kinetics Antioxidant activity SPLET DFT 

Supplementary material

214_2015_1785_MOESM1_ESM.pdf (83 kb)
Supplementary material 1 (PDF 83 kb)

Copyright information

© Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  • Ruslán Álvarez-Diduk
    • 1
  • Annia Galano
    • 1
  • Dun Xian Tan
    • 2
  • Russel J. Reiter
    • 2
  1. 1.Departamento de QuímicaUniversidad Autónoma Metropolitana-IztapalapaMexicoMexico
  2. 2.Department of Cellular and Structural BiologyUT Health Science CenterSan AntonioUSA

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