pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

Photo-controlled or photo-regulated molecules, especially biologically active and operating in physiological conditions, are in steady demand. Herein, furocoumaric and furocoumarinic acids being ( )-isomers relative to each other were obtained in two stages starting from psoralen: the alkaline solvo...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Vol. 26; no. 9; p. 2800
Main Authors: Skarga, Vladislav V, Matrosov, Anton A, Nichugovskiy, Artemiy I, Negrebetsky, Vadim V, Maslov, Mikhail A, Boldyrev, Ivan A, Malakhov, Mikhail V
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 10-05-2021
MDPI
Subjects:
(E → Z)-photoisomerization
(Z → E)-photoisomerization
Acidification
Acids
Apoptosis
Biological activity
Cell cycle
Emission spectra
Ficusin - chemistry
Fluorescence
furocoumaric acid
furocoumarinic acid
Furocoumarins - chemistry
Furocoumarins - radiation effects
High-performance liquid chromatography
Hydrogen-Ion Concentration
Isomerism
Isomers
Light
Liquid chromatography
Molecular Conformation
pH dependence
Psoralen
Pyrones - chemistry
Solvolysis
Spectrophotometry
Spectrophotometry, Ultraviolet
UV irradiation
photoproducts
pH dependence
psoralens
fluorescence
furocoumarinic acid
UV irradiation
furocoumaric acid
(Z → E)-photoisomerization
quantum chemistry calculations
(E → Z)-photoisomerization
furocoumarins
photoswitch
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Summary:Photo-controlled or photo-regulated molecules, especially biologically active and operating in physiological conditions, are in steady demand. Herein, furocoumaric and furocoumarinic acids being ( )-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 → photoisomerized (365 nm) to furocoumarinic acid. The kinetics of → photoisomerization was monitored by HPLC and UV-vis spectrophotometry. Photophysical characteristics in the aqueous phase for both acids, as well as the reversibility of ( / ) 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 → 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.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26092800