Abstract
The interactions of the one-electron oxidants, N3• and Br2•- radicals, with serotonin, tryptamine and their analogues 5-methoxytryptamine, N-methyltryptamine and N(1)-methyltryptophan were studied using the technique of pulse radiolysis with spectrophotometric detection. One-electron oxidation of serotonin results in the formation of an indoloxyl radical with a pKa value ≪3. With tryptamine, N-methyltryptamine and 5-methoxytryptamine, their one-electron oxidation gives indolyl radicals with pKa values of 4.2, 4.3 and 4.8, respectively. The reactions of OH radicals (•OH) with serotonin and tryptamine lead to the formation of the respective •OH-adducts, which decay by acid catalyzed water elimination to give almost quantitatively the corresponding indoloxyl and indolyl radicals, respectively. The first-order rate constants determined for water elimination are pH dependent, suggesting that the dehydration reaction is acid and base catalyzed. The •OH- adduct of serotonin reacts with oxygen in competition with...
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