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

Autor: Golczak A; Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland., Insińska-Rak M; Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland., Davoudpour A; Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland., Hama Saeed D; Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland., Ménová P; Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic., Mojr V; Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic., Cibulka R; Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic., Khmelinskii I; Department of Chemistry and Pharmacy, Faculty of Sciences and Technology and Centre for Electronics, Optoelectronics and Telecommunications, University of the Algarve, 8005-139 Faro, Portugal., Mrówczyńska L; Faculty of Biology, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 6, 61-614 Poznań, Poland. Electronic address: lumro@amu.edu.pl., Sikorski M; Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland. Electronic address: sikorski@amu.edu.pl.
Jazyk: angličtina
Zdroj: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy [Spectrochim Acta A Mol Biomol Spectrosc] 2022 May 05; Vol. 272, pp. 120985. Date of Electronic Publication: 2022 Feb 04.
DOI: 10.1016/j.saa.2022.120985
Abstrakt: The 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.
Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2022 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
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