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On the hydroperoxyl radical scavenging activity of two Edaravone derivatives: mechanism and kinetics

The free radical scavenging activity of two Edaravone (EDA) derivatives (C1 and D1) has been studied in aqueous and lipid solutions using the Density Functional Theory. Different mechanisms of reaction have been considered, as well as the acid/base equilibrium in aqueous solution. The studied compou...

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Published in:Journal of physical organic chemistry 2013-03, Vol.26 (3), p.261-268
Main Authors: Pérez-González, Adriana, Galano, Annia
Format: Article
Language:English
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Summary:The free radical scavenging activity of two Edaravone (EDA) derivatives (C1 and D1) has been studied in aqueous and lipid solutions using the Density Functional Theory. Different mechanisms of reaction have been considered, as well as the acid/base equilibrium in aqueous solution. The studied compounds were found to be rather poor •OOH scavengers in non‐polar environments, but better than the parent molecule, EDA, which suggests that the peroxyl scavenging activity of this kind of compounds in lipid media could be increased via structural modifications. In aqueous solution, at physiological pH, D1 is predicted to be a better peroxyl scavenger than C1, and slightly better than its parent molecule, EDA. Their excellent activity, under such conditions, is attributed to the electron transfer from their anionic forms. D1 was found to be among the best peroxyl scavengers known so far, with a rate constant for its reaction with •OOH near the diffusion limit regime (2.3 × 108 M−1s−1). Copyright © 2013 John Wiley & Sons, Ltd. On the hydroperoxyl radical scavenging activity of two Edaravone derivatives: Mechanism and Kinetics C1 and D1 are excellent peroxyl scavengers in aqueous solution, at physiological pH. Their excellent activity, under such conditions, is attributed to the electron transfer from their anionic forms. D1 was found to be among the best peroxyl scavengers known so far, better than C1 and slightly better to the parent compound, Edaravone.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.3082