New photochemically stable riboflavin analogue-3-Methyl-riboflavin tetraacetate

Małgorzata Insińska-Rak, Ewa Sikorska, Jose L. Bourdelande, Igor V. Khmelinskii, Wiesław Prukała, Krzysztof Dobek, Jerzy Karolczak, Isabel F. Machado, Luis F.V. Ferreira, Ewa Dulewicz, Anna Komasa, David R. Worrall, Maciej Kubicki, Marek Sikorski

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18 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)14-23
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume186
Issue number1
DOIs
Publication statusPublished - 5 Feb 2007

Keywords

  • 3-Methyl-riboflavin tetraacetate
  • Crystallographic characteristics
  • Flavin analogue
  • Photodegradation
  • Photosensitizer
  • Riboflavin
  • Singlet oxygen
  • TD-DFT method
  • Time-resolved fluorescence spectra
  • Triplet states

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