Reaction of anthryltricyanoethylene with biothiols

It is established that anthryltricyanoethylene reacts with cysteine and glutathione. The addition of biothiols to an anthryltricyanoethylene solution leads to a strong change in the color of the latter compound, which potentially opens up the possibility of using this dye for quantitative determinat...

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Bibliographic Details
Published in:Russian chemical bulletin 2024-04, Vol.73 (4), p.980-988
Main Authors: Lyubova, T. S., Lermontova, S. A., Cherkasov, A. V., Fukin, G. K., Klapshina, L. G., Ladilina, E. Yu
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Glutathione
Inorganic Chemistry
Organic Chemistry
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Summary:It is established that anthryltricyanoethylene reacts with cysteine and glutathione. The addition of biothiols to an anthryltricyanoethylene solution leads to a strong change in the color of the latter compound, which potentially opens up the possibility of using this dye for quantitative determination of the concentration of biothiols in living cells. The study of the model reaction of anthryltricyanoethylene with benzyl mercaptan and the isolation of a new compound, 5-amino-4-(anthracen-9-yl)-2-(benzylthio)-1 H -pyrrole-3-carbonitrile, made it possible to propose the mechanism for the reaction of anthryltricyanoethylene with biothiols.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-024-4211-0