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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 (<jats:bold>1a<\/jats:bold>) in water, acetonitrile, and some other solvents. In particular, triplet excited states of <jats:bold>1a<\/jats:bold> in water and in acetonitrile were investigated using ultraviolet\u2013visible (UV\u2013Vis) transient absorption spectroscopy. The measured triplet lifetimes for <jats:bold>1a<\/jats:bold> were all on the microsecond time scale (\u2248 60\u00a0\u03bcs) in deoxygenated solutions. The quantum yield of S<jats:sub>1<\/jats:sub>\u2009\u2192\u2009T<jats:sub>1<\/jats:sub> intersystem crossing for <jats:bold>1a<\/jats:bold> in water was 0.43 based on T<jats:sub>1<\/jats:sub> energy transfer from <jats:bold>1a<\/jats:bold> to indicaxanthin (<jats:bold>5<\/jats:bold>) acting as acceptor and on comparative actinometric measurements using benzophenone (<jats:bold>6<\/jats:bold>). <jats:bold>1a<\/jats:bold> 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\u2009~\u20090.74, dichloromethane\u2009~\u20090.64 and 1,2-dichloroethane\u2009~\u20090.54. Significantly lower singlet oxygen quantum yields were obtained in water and deuterated water (\u0424<jats:sub>\u0394<\/jats:sub>\u2009~\u20090.42 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 <jats:bold>1a<\/jats:bold>. 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 <jats:bold>1a<\/jats:bold> 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\u2013property relationship contribute to the body of information required for a rational design of flavin-based tools for\u00a0future\u00a0biological and biochemical applications.<\/jats:p>\n                <jats:p><jats:bold>Graphical abstract<\/jats:bold><\/jats:p>","DOI":"10.1007\/s43630-023-00401-9","type":"journal-article","created":{"date-parts":[[2023,3,19]],"date-time":"2023-03-19T13:02:28Z","timestamp":1679230948000},"page":"1655-1671","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["5-Deazaalloxazine as photosensitizer of singlet oxygen and potential redox-sensitive agent"],"prefix":"10.1007","volume":"22","author":[{"given":"Ma\u0142gorzata","family":"Insi\u0144ska-Rak","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anna","family":"Golczak","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mateusz","family":"Gierszewski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zubair","family":"Anwar","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Volodymyr","family":"Cherkas","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dorota","family":"Kwiatek","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ewa","family":"Sikorska","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Igor","family":"Khmelinskii","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gotard","family":"Burdzi\u0144ski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Radek","family":"Cibulka","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lucyna","family":"Mr\u00f3wczy\u0144ska","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jacek Lukasz","family":"Kolanowski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9527-7322","authenticated-orcid":false,"given":"Marek","family":"Sikorski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2023,3,19]]},"reference":[{"key":"401_CR1","doi-asserted-by":"publisher","first-page":"8181","DOI":"10.1039\/c4cc03464c","volume":"50","author":"J Yeow","year":"2014","unstructured":"Yeow, J., Kaur, A., Anscomb, M. 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