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Antiradical Activity of Dopamine, L-DOPA, Adrenaline, and Noradrenaline in Water/Methanol and in Liposomal Systems

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dc.abstract.enCatecholamines play a crucial role in signal transduction and are also expected to act as endogeneous antioxidants, but the mechanism of their antioxidant action is not fully understood. Here, we describe the impact of pH on the kinetics of reaction of four catecholamines (L-DOPA, dopamine, adrenaline, and noradrenaline) with model 2,2-diphenyl-1-picrylhydrazyl radical (dpph•) in methanol/water. The increase in pH from 5.5 to 7.4 is followed by a 2 order of magnitude increase in the rate constant, e.g., for dopamine (DA) kpH5.5 = 1,200 M-1 s-1 versus kpH7.4 = 170,000 M-1 s-1, and such rate acceleration is attributed to a fast electron transfer from the DA anion to dpph•. We also proved that at pH 7.0 DA breaks the peroxidation chain of methyl linoleate in liposomes assembled from neutral and negatively charged phospholipids. In contrast to no inhibitory effect during peroxidation in non-ionic emulsions, in bilayers one molecule of DA traps approximately four peroxyl radicals, with a rate constant kinh >103 M-1 s-1. Our results from a homogeneous system and bilayers prove that catecholamines act as effective, radical trapping antioxidants with activity depending on the ionization status of the catechol moiety, as well as microenvironment: organization of the lipid system (emulsions vs bilayers) and interactions of catecholamines with the biomembrane.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorLitwinienko, Grzegorz
dc.contributor.authorSikora, Bożena
dc.contributor.authorKluzek, Monika
dc.contributor.authorPrzybylski, Paweł
dc.contributor.authorJodko-Piórecka, Katarzyna
dc.date.accessioned2024-01-24T16:40:59Z
dc.date.available2024-01-24T16:40:59Z
dc.date.copyright2021-12-06
dc.date.issued2022
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number3
dc.description.versionFINAL_PUBLISHED
dc.description.volume87
dc.identifier.doi10.1021/ACS.JOC.1C02308
dc.identifier.issn0022-3263
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/100809
dc.identifier.weblinkhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c02308
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.pages1791-1804
dc.rightsCC-BY
dc.sciencecloudnosend
dc.titleAntiradical Activity of Dopamine, L-DOPA, Adrenaline, and Noradrenaline in Water/Methanol and in Liposomal Systems
dc.typeJournalArticle
dspace.entity.typePublication