Back to Search Start Over

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

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

Authors :
Natalia A. Danilkina
Ekaterina V. Andrievskaya
Anna V. Vasileva
Anna G. Lyapunova
Andrey M. Rumyantsev
Andrey A. Kuzmin
Elena A. Bessonova
Irina A. Balova
Source :
Molecules, Vol 26, Iss 24, p 7460 (2021)
Publication Year :
2021
Publisher :
MDPI AG, 2021.

Abstract

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.

Details

Language :
English
ISSN :
14203049
Volume :
26
Issue :
24
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.8226b0cf7744ebcac2c7d449c50ba2f
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules26247460