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

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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.

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Acknowledgments

We gratefully acknowledge the Laboratorio de Visualización y Cómputo Paralelo at Universidad Autónoma Metropolitana-Iztapalapa for computing time. This work was partially supported by project SEP-CONACyT 167491. R. A.-D. acknowledges the economic support provided by the same project during his postdoctoral scholarship.

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Authors and Affiliations

  1. Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa, 09340, Mexico, D.F, Mexico

    Ruslán Álvarez-Diduk & Annia Galano

  2. Department of Cellular and Structural Biology, UT Health Science Center, San Antonio, TX, USA

    Dun Xian Tan & Russel J. Reiter

Authors
  1. Ruslán Álvarez-Diduk
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  2. Annia Galano
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  3. Dun Xian Tan
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  4. Russel J. Reiter
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Correspondence to Annia Galano.

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Published as part of the special collection of articles “CHITEL 2015 - Torino - Italy”.

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Álvarez-Diduk, R., Galano, A., Tan, D.X. et al. The key role of the sequential proton loss electron transfer mechanism on the free radical scavenging activity of some melatonin-related compounds. Theor Chem Acc 135, 38 (2016). https://doi.org/10.1007/s00214-015-1785-5

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  • DOI: https://doi.org/10.1007/s00214-015-1785-5

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