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Hydrogen Atom Transfer from HOO. to ortho-Quinones Explains the Antioxidant Activity of Polydopamine

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dc.abstract.enMelanins are stable and non-toxic biomaterials with a great potential as chemopreventive agents for diseases connected with oxidative stress, but the mechanism of their antioxidant action is unclear. Herein, we show that polydopamine (PDA), a well-known synthetic melanin, becomes an excellent trap for alkylperoxyl radicals (ROO., typically formed during autoxidation of lipid substrates) in the presence of hydroperoxyl radicals (HOO.). The key reaction explaining this peculiar antioxidant activity is the reduction of the ortho-quinone moieties present in PDA by the reaction with HOO.. This reaction occurs via a H-atom transfer mechanism, as demonstrated by the large kinetic solvent effect of the reaction of a model quinone (3,5-di-tert-butyl-1,2-benzoquinone) with HOO. (k=1.5×107 and 1.1×105 M−1 s−1 in PhCl and MeCN). The chemistry disclosed herein is an important step to rationalize the redox-mediated bioactivity of melanins and of quinones.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorValgimigli, Luca
dc.contributor.authorMollica, Fabio
dc.contributor.authorBaschieri, Andrea
dc.contributor.authorGuo, Yafang
dc.contributor.authorAmorati, Riccardo
dc.contributor.authorLitwinienko, Grzegorz
dc.contributor.authorCędrowski, Jakub
dc.date.accessioned2024-01-25T03:31:37Z
dc.date.available2024-01-25T03:31:37Z
dc.date.copyright2021-06-04
dc.date.issued2021
dc.description.accesstimeAT_PUBLICATION
dc.description.financeŚrodki finansowe przyznane na realizację projektu w zakresie badań naukowych lub prac rozwojowych
dc.description.number28
dc.description.versionFINAL_PUBLISHED
dc.description.volume60
dc.identifier.doi10.1002/ANIE.202101033
dc.identifier.issn1433-7851
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/108787
dc.identifier.weblinkhttps://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202101033
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofAngewandte Chemie - International Edition
dc.relation.pages15220-15224
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enantioxidants
dc.subject.enperoxyl radicals
dc.subject.enpolydopamine
dc.subject.enquinone
dc.subject.enradical reactions
dc.titleHydrogen Atom Transfer from HOO. to ortho-Quinones Explains the Antioxidant Activity of Polydopamine
dc.typeJournalArticle
dspace.entity.typePublication