Open Access
Molecules, volume 26, issue 9, pages 2800
pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids
Skarga Vladislav V
1, 2
,
Matrosov Anton A
1
,
Nichugovskiy A I
2
,
Negrebetsky Vadim V
1
,
Maslov Michael
2
,
Boldyrev Ivan A
1, 3
,
Malakhov Mikhail V
1
Publication type: Journal Article
Publication date: 2021-05-10
PubMed ID:
34068591
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
Photo-controlled or photo-regulated molecules, especially biologically active and operating in physiological conditions, are in steady demand. Herein, furocoumaric and furocoumarinic acids being (Z/E)-isomers relative to each other were obtained in two stages starting from psoralen: the alkaline solvolysis of psoralen led to furocoumaric acid, which was further Z → E photoisomerized (365 nm) to furocoumarinic acid. The kinetics of Z → E photoisomerization was monitored by HPLC and UV-vis spectrophotometry. Photophysical characteristics in the aqueous phase for both acids, as well as the reversibility of (Z/E) photoisomerization process, were also assessed. Furocoumarinic acid was found to be visibly fluorescent at pH 2.0–12.0, with the maxima of fluorescence emission spectra being pH-dependent. The reverse E → Z photoisomerization predicted by quantum chemistry calculations as energetically favorable for the monoanionic form of furocoumarinic acid was proved in the experiment while being complicated by pyrone ring closure back to psoralen in acidic and neutral conditions. The preparative synthesis of furocoumarinic acid outlined in this work is particularly valuable in view of a wide range of pharmacological effects previously predicted for this compound.
Citations by journals
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Molecules
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Molecules
2 publications, 66.67%
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Citations by publishers
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 66.67%
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- Statistics recalculated weekly.
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Skarga V. V. et al. pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids // Molecules. 2021. Vol. 26. No. 9. p. 2800.
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Skarga V. V., Matrosov A. A., Nichugovskiy A. I., Negrebetsky V. V., Maslov M., Boldyrev I. A., Malakhov M. V. pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids // Molecules. 2021. Vol. 26. No. 9. p. 2800.
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TY - JOUR
DO - 10.3390/molecules26092800
UR - https://doi.org/10.3390%2Fmolecules26092800
TI - pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids
T2 - Molecules
AU - Skarga, Vladislav V
AU - Matrosov, Anton A
AU - Boldyrev, Ivan A
AU - Malakhov, Mikhail V
AU - Negrebetsky, Vadim V
AU - Nichugovskiy, A I
AU - Maslov, Michael
PY - 2021
DA - 2021/05/10 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 2800
IS - 9
VL - 26
PMID - 34068591
SN - 1420-3049
ER -
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@article{2021_Skarga,
author = {Vladislav V Skarga and Anton A Matrosov and Ivan A Boldyrev and Mikhail V Malakhov and Vadim V Negrebetsky and A I Nichugovskiy and Michael Maslov},
title = {pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {may},
url = {https://doi.org/10.3390%2Fmolecules26092800},
number = {9},
pages = {2800},
doi = {10.3390/molecules26092800}
}
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Skarga, Vladislav V., et al. “pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids.” Molecules, vol. 26, no. 9, May. 2021, p. 2800. https://doi.org/10.3390%2Fmolecules26092800.
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