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Photophysical properties of alloxazine derivatives with extended aromaticity – Potential redox-sensitive fluorescent probe

2022Journal article Restricted access
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dc.contributor.authorGolczak, Anna
dc.contributor.authorInsińska-Rak, Małgorzata
dc.contributor.authorDavoudpour, Amirali
dc.contributor.authorHama Saeed, Daban
dc.contributor.authorMénová, Petra
dc.contributor.authorMojr, Viktor
dc.contributor.authorCibulka, Radek
dc.contributor.authorKhmelinskii, Igor
dc.contributor.authorMrówczyńska, Lucyna
dc.contributor.authorSikorski, Marek
dc.date.accessioned2022-10-12T13:14:24Z
dc.date.available2022-10-12T13:14:24Z
dc.date.issued2022
dc.description.abstractThe spectral and photophysical properties of two four-ring alloxazine derivatives, naphtho[2,3-g] pteridine-2,4(1H,3H)-dione (1a) and 1,3-dimethylnaphtho[2,3-g]pteridine-2,4(1H,3H)-dione, (1b) were studied. The propensity of 1a for excited-state proton transfer reactions in the presence of acetic acid as a catalyst was also studied, showing no signature of the reaction occurring. In addition, quenching of 1a fluorescence by acetic acid was investigated. Singlet and triplet states and spectral data for 1a and 1b were calculated using density functional theory TD-DFT at B3LYP/6-31G(d) and UB3LYP levels. Finally, fluorescence lifetime imaging microscopy (FLIM) using 1a and 1b as fluorescence probes was applied to in vitro human red blood cells (RBCs) with and without tert-butyl hydroperoxide (TB) as an oxidising agent. To evaluate and compare the effects of 1a and 1b on the redox properties of RBCs, the fluorescence lifetime, amplitude and fractional intensities were calculated, and phasor plot analysis was performed. The results obtained show the appearance of a new proximal cluster in the phasor fingerprint of RBCs in the presence of 1b and a shorter fluorescence lifetime of RBCs in the presence of 1a.pt_PT
dc.description.sponsorshipPOWR.03.02.00-00-I020/17
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1016/j.saa.2022.120985pt_PT
dc.identifier.issn1386-1425
dc.identifier.urihttp://hdl.handle.net/10400.1/18380
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.subjectFlavinspt_PT
dc.subjectFluorescencept_PT
dc.subjectAlloxazinespt_PT
dc.subjectQuenchingpt_PT
dc.subjectProton transferpt_PT
dc.subjectPhasor analysispt_PT
dc.subjectOxidative stresspt_PT
dc.titlePhotophysical properties of alloxazine derivatives with extended aromaticity – Potential redox-sensitive fluorescent probept_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.startPage120985pt_PT
oaire.citation.titleSpectrochimica Acta Part A: Molecular and Biomolecular Spectroscopypt_PT
oaire.citation.volume272pt_PT
person.familyNameKhmelinskii
person.givenNameIgor
person.identifier0000000420541031
person.identifier.ciencia-id0D1A-CB6C-6316
person.identifier.orcid0000-0002-6116-184X
person.identifier.ridC-9587-2011
person.identifier.scopus-author-id6701444934
rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublicationfcb9f09f-2e99-41fb-8c08-7e1acbc65076
relation.isAuthorOfPublication.latestForDiscoveryfcb9f09f-2e99-41fb-8c08-7e1acbc65076

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