4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe

Natalia A. Danilkina , Ekaterina V. Andrievskaya , Anna V. Vasileva , Anna G. Lyapunova, Andrey M. Rumyantsev, Andrey A. Kuzmin , Elena A. Bessonova, Irina A. Balova

Результат исследований: Научные публикации в периодических изданияхстатьярецензирование

1 Цитирования (Scopus)

Аннотация

A new type of fluorogenic and fluorochromic probe based on the reduction of weakly fluorescent 4-azido-6-(4-cyanophenyl)cinnoline to the corresponding fluorescent cinnoline-4-amine was developed. We found that the fluorescence of 6-(4-cyanophenyl)cinnoline-4-amine is strongly affected by the nature of the solvent. The fluorogenic effect for the amine was detected in polar solvents with the strongest fluorescence increase in water. The environment-sensitive fluorogenic properties of cinnoline-4-amine in water were explained as a combination of two types of fluorescence mechanisms: aggregation-induced emission (AIE) and excited state intermolecular proton transfer (ESPT). The suitability of an azide–amine pair as a fluorogenic probe was tested using a HepG2 hepatic cancer cell line with detection by fluorescent microscopy, flow cytometry, and HPLC analysis of cells lysates. The results obtained confirm the possibility of the transformation of the azide to amine in cells and the potential applicability of the discovered fluorogenic and fluorochromic probe for different analytical and biological applications in aqueous medium
Язык оригиналаанглийский
Номер статьи7460
ЖурналMolecules
Том26
Номер выпуска24
DOI
СостояниеОпубликовано - 9 дек 2021

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