Tetramethylalloxazines as efficient singlet oxygen photosensitizers and potential redox-sensitive agents
Creators
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Golczak, Anna
(Data collector)1
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Prukala, Dorota
(Data collector)1
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Sikorska, Ewa
(Data collector)2
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Gierszewski, Mateusz
(Data collector)1
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Cherkas, Volodymyr
(Data collector)3, 4
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Kwiatek, Dorota
(Data collector)4
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Varma, Naisargi
(Data collector)1
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Pędziński, Tomasz
(Data collector)1, 5
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Murphree, Shaun
(Data collector)1
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Cibulka, Radek
(Contact person)6
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Mrówczyńska, Lucyna
(Data collector)1
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Kolanowski, Jacek
(Data collector)4, 7, 8
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Sikorski, Marek
(Contact person)1
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Adam Mickiewicz University in Poznań
(Hosting institution)
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University of Chemistry and Technology
(Hosting institution)
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1.
Adam Mickiewicz University in Poznań
- 2. Poznan University of Economics and Business
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3.
Bogomoletz Institute of Physiology
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4.
Institute of Bioorganic Chemistry, Polish Academy of Sciences
- 5. Uniwersytet im Adama Mickiewicza w Poznaniu Wydział Chemii
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6.
University of Chemistry and Technology
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7.
Victor Chang Cardiac Research Institute
- 8. Institute of Bioorganic Chemistry Polish Academy of Sciences
Contributors
Hosting institutions:
Description
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 (S0 → Si, S0 → Ti, T1 → Ti) 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.
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Additional details
Funding
- Czech Science Foundation
- Tailoring flavins for organic photocatalysis 21-14200K
- National Science Centre
- Tailoring flavins for organic photocatalysis CEUSUNISONO 2020/02/Y/ST4/00042