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

doi:10.1016/j.jphotochem.2006.07.005

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

Department of Chemistry

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21 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 language	English
Pages (from-to)	14-23
Journal	Journal of Photochemistry and Photobiology A: Chemistry
Volume	186
Issue number	1
DOIs	https://doi.org/10.1016/j.jphotochem.2006.07.005
Publication status	Published - 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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10.1016/j.jphotochem.2006.07.005

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Insińska-Rak, M., Sikorska, E., Bourdelande, J. L., Khmelinskii, I. V., Prukała, W., Dobek, K., Karolczak, J., Machado, I. F., Ferreira, L. F. V., Dulewicz, E., Komasa, A., Worrall, D. R., Kubicki, M., & Sikorski, M. (2007). New photochemically stable riboflavin analogue-3-Methyl-riboflavin tetraacetate. Journal of Photochemistry and Photobiology A: Chemistry, 186(1), 14-23. https://doi.org/10.1016/j.jphotochem.2006.07.005

Insińska-Rak, Małgorzata ; Sikorska, Ewa ; Bourdelande, Jose L. ; Khmelinskii, Igor V. ; Prukała, Wiesław ; Dobek, Krzysztof ; Karolczak, Jerzy ; Machado, Isabel F. ; Ferreira, Luis F.V. ; Dulewicz, Ewa ; Komasa, Anna ; Worrall, David R. ; Kubicki, Maciej ; Sikorski, Marek. / New photochemically stable riboflavin analogue-3-Methyl-riboflavin tetraacetate. In: Journal of Photochemistry and Photobiology A: Chemistry. 2007 ; Vol. 186, No. 1. pp. 14-23.

@article{53d4169fcd624d2ba9a350cdea8f4655,

title = "New photochemically stable riboflavin analogue-3-Methyl-riboflavin tetraacetate",

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. {\textcopyright} 2006 Elsevier B.V. All rights reserved.",

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

author = "Ma{\l}gorzata Insi{\'n}ska-Rak and Ewa Sikorska and Bourdelande, {Jose L.} and Khmelinskii, {Igor V.} and Wies{\l}aw Pruka{\l}a and Krzysztof Dobek and Jerzy Karolczak and Machado, {Isabel F.} and Ferreira, {Luis F.V.} and Ewa Dulewicz and Anna Komasa and Worrall, {David R.} and Maciej Kubicki and Marek Sikorski",

year = "2007",

month = feb,

day = "5",

doi = "10.1016/j.jphotochem.2006.07.005",

language = "English",

volume = "186",

pages = "14--23",

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Insińska-Rak, M, Sikorska, E, Bourdelande, JL, Khmelinskii, IV, Prukała, W, Dobek, K, Karolczak, J, Machado, IF, Ferreira, LFV, Dulewicz, E, Komasa, A, Worrall, DR, Kubicki, M & Sikorski, M 2007, 'New photochemically stable riboflavin analogue-3-Methyl-riboflavin tetraacetate', Journal of Photochemistry and Photobiology A: Chemistry, vol. 186, no. 1, pp. 14-23. https://doi.org/10.1016/j.jphotochem.2006.07.005

New photochemically stable riboflavin analogue-3-Methyl-riboflavin tetraacetate. / Insińska-Rak, Małgorzata; Sikorska, Ewa; Bourdelande, Jose L.; Khmelinskii, Igor V.; Prukała, Wiesław; Dobek, Krzysztof; Karolczak, Jerzy; Machado, Isabel F.; Ferreira, Luis F.V.; Dulewicz, Ewa; Komasa, Anna; Worrall, David R.; Kubicki, Maciej; Sikorski, Marek.

In: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 186, No. 1, 05.02.2007, p. 14-23.

Research output: Contribution to journal › Article › Research › peer-review

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

IS - 1

ER -

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

Abstract

Keywords

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