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Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

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cris.lastimport.scopus2024-02-12T20:12:27Z
dc.abstract.enHerein, we describe the synthesis of a fluorescent probe NB-2 and its use for the detection of peroxyl radicals. This probe is composed of two receptor segments (4-hydroxycinnamyl moieties) sensitive towards peroxyl radicals that are conjugated with a fluorescent reporter, dipyrrometheneboron difluoride (BODIPY), whose emission changes depend on the oxidation state of the receptors. The measurement of the rate of peroxidation of methyl linoleate in a micellar system in the presence of 1.0 M NB-2 confirmed its ability to trap lipid peroxyl radicals with the rate constant kinh = 1000 M1s1, which is ten-fold smaller than for pentamethylchromanol (an analog of -tocopherol). The reaction of NB-2 with peroxyl radicals was further studied via fluorescence measurements in methanol, with ,0-azobisisobutyronitrile (AIBN) used as a source of radicals generated by photolysis or thermolysis, and in the micellar system at pH 7.4, with 2,20-azobis(2-amidinopropane) (ABAP) used as a thermal source of the radicals. The reaction of NB-2 receptors with peroxyl radicals manifests itself by the strong increase of a fluorescence with a maximum at 612–616 nm, with a 14-fold enhancement of emission in methanol and a 4-fold enhancement in the micelles, as compared to the unoxidized probe. Our preliminary results indicate that NB-2 behaves as a “switch on” fluorescent probe that is suitable for sensing peroxyl radicals in an organic lipid environment and in bi-phasic dispersed lipid systems.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorKusio, Jaroslaw
dc.contributor.authorSitkowska, Kaja
dc.contributor.authorKonopko, Adrian
dc.contributor.authorLitwinienko, Grzegorz
dc.date.accessioned2024-01-25T03:31:52Z
dc.date.available2024-01-25T03:31:52Z
dc.date.copyright2020-01-20
dc.date.issued2020
dc.description.accesstimeAT_PUBLICATION
dc.description.financeŚrodki finansowe, o których mowa w art. 365 pkt. 2 ustawy
dc.description.number1
dc.description.versionFINAL_PUBLISHED
dc.description.volume9
dc.identifier.doi10.3390/ANTIOX9010088
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/108806
dc.identifier.weblinkhttps://www.mdpi.com/2076-3921/9/1/88/pdf
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofAntioxidants
dc.relation.pages88
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enantioxidant activity
dc.subject.enperoxyl radicals
dc.subject.enfluorescent probes
dc.subject.enrate constant
dc.subject.enmicelles
dc.titleHydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals
dc.typeJournalArticle
dspace.entity.typePublication