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Antioxidant Activity of Bilirubin in Micellar and Liposomal Systems Is pH-Dependent

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dc.abstract.enBilirubin (BR), a product of heme catabolism, plays a critical role in biological systems. Although increased levels of BR result in hyperbilirubinemia or jaundice, there is increasing evidence that lower concentrations substantially decrease the risk of oxidative stress-mediated diseases due to antioxidant functions of BR. We studied the radical-trapping ability of BR in two model systems, micellar and liposomal, at a broad pH range. At pH < 6.0, BR behaves as a retardant; however, at pH ≥ 6.0, BR becomes strong radical trapping antioxidant, with rate constants for reaction with lipidperoxyl radicals (kinh) within the range from 1.2 × 104 M−1 s−1 to 3.5 × 104 M−1 s−1, and in liposomal system, the activity of BR is comparable to α-tocopherol. This transition is likely facilitated by the ionization of carboxyl groups, leading to a conformational shift in BR and improved solubility/localization at the water/lipid interface. This is the first experimental evidence of the role of pH on the antioxidant activity of bilirubin, and the observed pH-dependent radical-trapping ability of BR holds practical significance, particularly in jaundice treatment where light therapy targets the skin’s weakly acidic surface. Minor adjustments toward neutral or alkaline pH can enhance radical-trapping action of BR, thereby mitigating oxidative stress induced with blue or violet light exposure.
dc.affiliationUniwersytet Warszawski
dc.affiliation.departmentWydział Chemii
dc.affiliation.otherZakład Chemii Organicznej i Technologii Chemicznej
dc.contributor.authorPrzybylski, Paweł
dc.contributor.authorŻebrowski, Michał
dc.contributor.authorWitkowski, Wojciech
dc.contributor.authorCybularczyk-Cecotka, Martyna
dc.contributor.authorLitwinienko, Grzegorz
dc.date.access2025
dc.date.accessioned2025-03-18T07:38:43Z
dc.date.available2025-03-18T07:38:43Z
dc.date.copyright2024-03-30
dc.date.issued2024-03-30
dc.description.accesstimeat_publication
dc.description.additionalDane badawcze dostępne pod linkiem: https://danebadawcze.uw.edu.pl/dataset.xhtml?persistentId=doi:10.58132/SCHDDJ&version=DRAFT
dc.description.fininstitutionNarodowe Centrym Nauki (National Science Center) - OPUS 22
dc.description.fininstitutionInicjatywa Doskonałosći Uczelnia Badawcza (Excellence Initiative Research University) - II.2.1.
dc.description.grantnumberNCN - OPUS 22 No. 2021/43/B/ST4/00840
dc.description.grantnumberIDUB - PSP 501-D112-20-0002210
dc.description.granttitleOdrażający, Brudni i Źli? – poszukiwanie mechanizmów antyoksydacyjnego działania wybranych organicznych związków azotu i siarki
dc.description.granttitleProgram dla naukowców wizytujących: „Tandemy dla doskonałości”
dc.description.number4
dc.description.versionfinal_published
dc.description.volume13
dc.formatpdf
dc.identifier.doi10.3390/antiox13040426
dc.identifier.eissn2076-3921
dc.identifier.issn2076-3921
dc.identifier.orcid0000-0002-5245-7622
dc.identifier.orcid0009-0003-6781-165X
dc.identifier.orcid0000-0003-2186-7028
dc.identifier.orcid0000-0002-5523-0888
dc.identifier.orcid0000-0003-4231-2929
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/166210
dc.identifier.weblinkhttps://www.mdpi.com/2076-3921/13/4/426
dc.identifier.weblinkhttps://danebadawcze.uw.edu.pl/dataset.xhtml?persistentId=doi:10.58132/SCHDDJ&version=DRAFT
dc.languageen
dc.pbn.affiliationchemical sciences
dc.relation.documentshttps://projekty.ncn.gov.pl/en/index.php?projekt_id=539894
dc.relation.documentshttps://inicjatywadoskonalosci.uw.edu.pl/dzialania/ii-2-1/edycja1/
dc.relation.ispartofAntioxidants
dc.relation.pages426
dc.rightsCC-BY
dc.rights.weblinkhttps://creativecommons.org/licenses/by/4.0/deed.en
dc.sciencecloudnosend
dc.share.typeOPEN_JOURNAL
dc.subject.enbilirubin
dc.subject.enperoxidation
dc.subject.enperoxyl radicals
dc.subject.enmicelles
dc.subject.enliposomes
dc.subject.enantioxidant
dc.subject.enradicals
dc.titleAntioxidant Activity of Bilirubin in Micellar and Liposomal Systems Is pH-Dependent
dc.typeJournalArticle
dspace.entity.typePublication