TY - JOUR
T1 - New photochemically stable riboflavin analogue-3-Methyl-riboflavin tetraacetate
AU - Insińska-Rak, Małgorzata
AU - Sikorska, Ewa
AU - Bourdelande, Jose L.
AU - Khmelinskii, Igor V.
AU - Prukała, Wiesław
AU - Dobek, Krzysztof
AU - Karolczak, Jerzy
AU - Machado, Isabel F.
AU - Ferreira, Luis F.V.
AU - Dulewicz, Ewa
AU - Komasa, Anna
AU - Worrall, David R.
AU - Kubicki, Maciej
AU - Sikorski, Marek
PY - 2007/2/5
Y1 - 2007/2/5
N2 - Spectroscopic and photophysical properties of a flavin analogue - 3-methyl-riboflavin tetraacetate - were studied in methanol, ethanol, water and acetonitrile. We compared experimental spectroscopic data with the results of theoretical predictions, obtained using the TD-DFT method. Based on these calculations, we assigned (π,π*) symmetry to both the lowest excited singlet and triplet states. We found the title compound to be a very efficient photosensitizer of singlet oxygen production (φ{symbol}Δ = 0.61). The triplet state quantum yield of 3-methyl-riboflavin tetraacetate was determined as 0.54 in methanolic solutions. Photodegradation quantum yield measurements demonstrate that the title compound may be used as a much more stable substitute of riboflavin, being two orders of magnitude more photostable (φR = 2 × 10-5). We also present exhaustive crystallographic characteristics of 3-methyl-riboflavin tetraacetate, along with time-resolved fluorescence spectra of its polycrystals. © 2006 Elsevier B.V. All rights reserved.
AB - Spectroscopic and photophysical properties of a flavin analogue - 3-methyl-riboflavin tetraacetate - were studied in methanol, ethanol, water and acetonitrile. We compared experimental spectroscopic data with the results of theoretical predictions, obtained using the TD-DFT method. Based on these calculations, we assigned (π,π*) symmetry to both the lowest excited singlet and triplet states. We found the title compound to be a very efficient photosensitizer of singlet oxygen production (φ{symbol}Δ = 0.61). The triplet state quantum yield of 3-methyl-riboflavin tetraacetate was determined as 0.54 in methanolic solutions. Photodegradation quantum yield measurements demonstrate that the title compound may be used as a much more stable substitute of riboflavin, being two orders of magnitude more photostable (φR = 2 × 10-5). We also present exhaustive crystallographic characteristics of 3-methyl-riboflavin tetraacetate, along with time-resolved fluorescence spectra of its polycrystals. © 2006 Elsevier B.V. All rights reserved.
KW - 3-Methyl-riboflavin tetraacetate
KW - Crystallographic characteristics
KW - Flavin analogue
KW - Photodegradation
KW - Photosensitizer
KW - Riboflavin
KW - Singlet oxygen
KW - TD-DFT method
KW - Time-resolved fluorescence spectra
KW - Triplet states
U2 - 10.1016/j.jphotochem.2006.07.005
DO - 10.1016/j.jphotochem.2006.07.005
M3 - Article
VL - 186
SP - 14
EP - 23
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
SN - 1010-6030
IS - 1
ER -