Tetramethylalloxazines as efficient singlet oxygen photosensitizers and potential redox-sensitive agents.

Autor: Golczak A; Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznan, Poland., Prukała D; Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznan, Poland., Sikorska E; Poznań University of Economics and Business, Al. Niepodległości 10, 61-875, Poznan, Poland., Gierszewski M; Faculty of Physics, Adam Mickiewicz University, Uniwersytetu Poznańskiego 2, 61-614, Poznan, Poland., Cherkas V; Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704, Poznan, Poland., Kwiatek D; Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704, Poznan, Poland., Kubiak A; Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznan, Poland., Varma N; Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznan, Poland., Pędziński T; Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznan, Poland., Murphree S; Department of Chemistry, Allegheny College, 520 N. Main Street, Meadville, PA, USA., Cibulka R; Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technicka 5, 16628, Prague 6, Czech Republic. radek.cibulka@vscht.cz., Mrówczyńska L; Faculty of Biology, Adam Mickiewicz University, Uniwersytetu Poznańskiego 6, 61-614, Poznan, Poland. lumro@amu.edu.pl., Kolanowski JL; Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704, Poznan, Poland. jacek.kolanowski@ibch.poznan.pl., Sikorski M; Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznan, Poland. sikorski@amu.edu.pl.
Jazyk: angličtina
Zdroj: Scientific reports [Sci Rep] 2023 Aug 17; Vol. 13 (1), pp. 13426. Date of Electronic Publication: 2023 Aug 17.
DOI: 10.1038/s41598-023-40536-4
Abstrakt: Tetramethylalloxazines (TMeAll) have been found to have a high quantum yield of singlet oxygen generation when used as photosensitizers. Their electronic structure and transition energies (S 0  → S i , S 0  → T i , T 1  → T i ) were calculated using DFT and TD-DFT methods and compared to experimental absorption spectra. Generally, TMeAll display an energy diagram similar to other derivatives belonging to the alloxazine class of compounds, namely π,π* transitions are accompanied by closely located n,π* transitions. Photophysical data such as quantum yields of fluorescence, fluorescence lifetimes, and nonradiative rate constants were also studied in methanol (MeOH), acetonitrile (ACN), and 1,2-dichloroethane (DCE). The transient absorption spectra were also analyzed. To assess cytotoxicity of new compounds, a hemolytic assay was performed using human red blood cells (RBC) in vitro. Subsequently, fluorescence lifetime imaging experiments (FLIM) were performed on RBC under physiological and oxidative stress conditions alone or in the presence of TMeAll allowing for pinpointing changes caused by those compounds on the intracellular environment of these cells.
(© 2023. Springer Nature Limited.)
Databáze: MEDLINE
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