This study elucidates a molecular understanding of how 5-amino-2-hydroxybenzoic acid eliminates the superoxide radical anion (O2•) (mesalazine, 5-ASA). Using cyclic voltammetry and electron spin resonance (ESR) investigations supplemented by density functional theory (DFT) calculations, the removal of O2• by 5-ASA, 4-amino-2-hydroxybenzoic acid (4-ASA), and related drugs used for ulcerative colitis treatment was examined. The chemicals altered the quasi-reversible O2/O2• redox, implying that an acid–base reaction occurs in which a hydroperoxyl radical (HO2•) is generated from O2•. The deprotonated 5-ASA anion, on the other hand, can remove O2• via proton-coupled electron transfer (PCET), resulting in a radical product. ESR research verified this electron transfer (ET). The PCET, which involves two proton transfers and one ET based on -conjugation, is aided by the 4-aminophenol moiety in 5-ASA. After deprotonation of the 1-carboxyl group, O2• removal by 5-ASA occurs efficiently through the PCET mechanism, according to electrochemical and DFT studies. Through PCET-based O2• removal, 5-ASA may operate as an anti-inflammatory drug in the alkali gut.
Author(S) Details
Tatsushi Nakayama
Department of Pharmacy, Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan.
Ryo Honda
United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
View Book:- https://stm.bookpi.org/CAPRD-V5/article/view/4929
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