Edaravone toxicity can be related to redox properties of their oxidized derivatives

Quantum chemical calculations at DFT/B3LYP/6-31+G(d,p) level of theory were employed for the proposed mechanism for edaravone toxicity by redox properties of possible hydroxylated metabolites using energy (E), ionization potential (IP) as electron redox or bond dissociation energy (BDE) as hydrogen...

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Bibliographic Details
Published in:Chemical Data Collections 2017-03, Vol.7-8, p.51-57
Main Authors: Carvalho, Ederson S., Santa-Brígida, Sheise A., Queiroz, Auriekson N., Silva, Joseane R., Silva, Osmarina P.P., Barros, Carlos A.L., Borges, Rosivaldo S.
Format: Article
Language:English
Subjects:
DFT
Edaravone oxidation
Electron transfer
Hydrogen transfer
Redox capacity
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Summary:Quantum chemical calculations at DFT/B3LYP/6-31+G(d,p) level of theory were employed for the proposed mechanism for edaravone toxicity by redox properties of possible hydroxylated metabolites using energy (E), ionization potential (IP) as electron redox or bond dissociation energy (BDE) as hydrogen redox, and spin density calculations were also performed for the proposed regioselective hydroxylation on pyrazolone or benzene rings. Electron transfer can be related to phenyl and hydrogen transfer related to pyrazolone both on 4-positions for hydroxylation. The phenolic derivatives have more redox capacity than hydroxyl pyrazolone. The toxicity mechanism may be related to redox properties of hydroxylated derivatives. [Display omitted]
ISSN:2405-8300
2405-8300
DOI:10.1016/j.cdc.2017.02.001