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Article

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

by
Natalia A. Danilkina
1,
Ekaterina V. Andrievskaya
2,
Anna V. Vasileva
1,
Anna G. Lyapunova
1,
Andrey M. Rumyantsev
3,
Andrey A. Kuzmin
4,
Elena A. Bessonova
1 and
Irina A. Balova
1,*
1
Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia
2
Faculty of Chemistry, Belarusian State University, Leningradskaya Str. 14, 220006 Minsk, Belarus
3
Department of Genetics and Biotechnology, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia
4
Institute of Cytology, Russian Academy of Sciences, St. Petersburg, Tikhoretsky Avenue 4, 194064 Saint Petersburg, Russia
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(24), 7460; https://doi.org/10.3390/molecules26247460
Submission received: 13 November 2021 / Revised: 1 December 2021 / Accepted: 6 December 2021 / Published: 9 December 2021
(This article belongs to the Special Issue Modern Trends in Heterocyclic Chemistry)
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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.
Keywords: azides; amines; cinnolines; richer cyclization; fluorescence; fluorogenic probe; fluorochromic probe; environment-sensitive probe; AIE and ESPT fluorescence mechanisms azides; amines; cinnolines; richer cyclization; fluorescence; fluorogenic probe; fluorochromic probe; environment-sensitive probe; AIE and ESPT fluorescence mechanisms
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MDPI and ACS Style

Danilkina, N.A.; Andrievskaya, E.V.; Vasileva, A.V.; Lyapunova, A.G.; Rumyantsev, A.M.; Kuzmin, A.A.; Bessonova, E.A.; Balova, I.A. 4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe. Molecules 2021, 26, 7460. https://doi.org/10.3390/molecules26247460

AMA Style

Danilkina NA, Andrievskaya EV, Vasileva AV, Lyapunova AG, Rumyantsev AM, Kuzmin AA, Bessonova EA, Balova IA. 4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe. Molecules. 2021; 26(24):7460. https://doi.org/10.3390/molecules26247460

Chicago/Turabian Style

Danilkina, Natalia A., Ekaterina V. Andrievskaya, Anna V. Vasileva, Anna G. Lyapunova, Andrey M. Rumyantsev, Andrey A. Kuzmin, Elena A. Bessonova, and Irina A. Balova. 2021. "4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe" Molecules 26, no. 24: 7460. https://doi.org/10.3390/molecules26247460

APA Style

Danilkina, N. A., Andrievskaya, E. V., Vasileva, A. V., Lyapunova, A. G., Rumyantsev, A. M., Kuzmin, A. A., Bessonova, E. A., & Balova, I. A. (2021). 4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe. Molecules, 26(24), 7460. https://doi.org/10.3390/molecules26247460

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