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5-Deazaalloxazine as photosensitizer of singlet oxygen and potential redox-sensitive agent

2023-03Journal article Open access
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dc.contributor.authorInsińska-Rak, Małgorzata
dc.contributor.authorGolczak, Anna
dc.contributor.authorGierszewski, Mateusz
dc.contributor.authorAnwar, Zubair
dc.contributor.authorCherkas, Volodymyr
dc.contributor.authorKwiatek, Dorota
dc.contributor.authorSikorska, Ewa
dc.contributor.authorKhmelinskii, Igor
dc.contributor.authorBurdziński, Gotard
dc.contributor.authorCibulka, Radek
dc.contributor.authorMrówczyńska, Lucyna
dc.contributor.authorKolanowski, Jacek Lukasz
dc.contributor.authorSikorski, Marek
dc.date.accessioned2023-04-20T12:49:52Z
dc.date.available2023-04-20T12:49:52Z
dc.date.issued2023-03
dc.description.abstractFlavins are a unique class of compounds that combine the features of singlet oxygen generators and redox-dependent fluorophores. From a broad family of flavin derivatives, deazaalloxazines are significantly underdeveloped from the point of view of photophysical properties. Herein, we report photophysics of 5-deazaalloxazine (1a) in water, acetonitrile, and some other solvents. In particular, triplet excited states of 1ain water and in acetonitrile were investigated using ultraviolet-visible (UV-Vis) transient absorption spectroscopy. The measured triplet lifetimes for 1a were all on the microsecond time scale (approximate to 60 mu s) in deoxygenated solutions. The quantum yield of S-1 -> T-1 intersystem crossing for 1ain water was 0.43 based on T1 energy transfer from 1a to indicaxanthin (5) acting as acceptor and on comparative actinometric measurements using benzophenone (6). 1a was an efficient photosensitizer for singlet oxygen in aerated solutions, with quantum yields of singlet oxygen in methanol of about 0.76, compared to acetonitrile similar to 0.74, dichloromethane similar to 0.64 and 1,2-dichloroethane similar to 0.54. Significantly lower singlet oxygen quantum yields were obtained in water and deuterated water (Phi(Delta)similar to 0.42 and 0.44, respectively). Human red blood cells (RBC) were used as a cell model to study the antioxidant capacity in vitro and cytotoxic activity of 1a. Fluorescence-lifetime imaging microscopy (FLIM) data were analyzed by fluorescence lifetime parameters and distribution for different parts of the emission spectrum. Comparison of multidimensional fluorescent properties of RBC under physiological-like and oxidative-stress conditions in the presence and absence of 1a suggests its dual activity as probe and singlet-oxygen generator and opens up a pathway for using FLIM to analyze complex intracellular behavior of flavin-like compounds. These new data on structure-property relationship contribute to the body of information required for a rational design of flavin-based tools for future biological and biochemical applications.pt_PT
dc.description.sponsorshipNational Science Centre, Poland 2017/27/B/ST4/02494 (OPUS), NCN CEUS-UNISONO 2020/02/Y/ST4/00042, 2018/29/B/ST4/01498 (Opus), POIR.04.04.00-00-441F/17-00, Grant Agency of the Czech Republic 2013/08/T/ST4/00640 (Etiuda), Foundation for Polish Science 21-14200K, Smart Growth Operational Programme 2014-2020 POIR.04.02.00-00-C004/19-00, Ministry of Science and Higher Education, Poland DIR/WK/2018/06pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1007/s43630-023-00401-9pt_PT
dc.identifier.eissn1474-9092
dc.identifier.urihttp://hdl.handle.net/10400.1/19481
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherSpringernaturept_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subject5-deazaflavinpt_PT
dc.subject5-deazaalloxazinept_PT
dc.subjectAlloxazinept_PT
dc.subjectSinglet oxygenpt_PT
dc.subjectTriplet excited statept_PT
dc.subjectRed blood cellspt_PT
dc.subjectOxidative stresspt_PT
dc.subjectFluorescence-lifetime imaging microscopy (FLIM)pt_PT
dc.title5-Deazaalloxazine as photosensitizer of singlet oxygen and potential redox-sensitive agentpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.titlePhotochemical & Photobiological Sciencespt_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.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublicationfcb9f09f-2e99-41fb-8c08-7e1acbc65076
relation.isAuthorOfPublication.latestForDiscoveryfcb9f09f-2e99-41fb-8c08-7e1acbc65076

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