Research output: Contribution to journal › Article › peer-review
4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe. / Danilkina , Natalia A. ; Andrievskaya , Ekaterina V. ; Vasileva , Anna V. ; Lyapunova, Anna G. ; Rumyantsev, Andrey M. ; Kuzmin , Andrey A. ; Bessonova, Elena A. ; Balova , Irina A. .
In: Molecules, Vol. 26, No. 24, 7460, 01.12.2021.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - 4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe
AU - Danilkina , Natalia A.
AU - Andrievskaya , Ekaterina V.
AU - Vasileva , Anna V.
AU - Lyapunova, Anna G.
AU - Rumyantsev, Andrey M.
AU - Kuzmin , Andrey A.
AU - Bessonova, Elena A.
AU - Balova , Irina A.
N1 - Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).
PY - 2021/12/1
Y1 - 2021/12/1
N2 - 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
AB - 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
KW - AIE and ESPT fluorescence mechanisms
KW - Amines
KW - Azides
KW - Cinnolines
KW - Environment-sensitive probe
KW - Fluorescence
KW - Fluorochromic probe
KW - Fluorogenic probe
KW - Richer cyclization
UR - http://www.scopus.com/inward/record.url?scp=85121548664&partnerID=8YFLogxK
U2 - https://doi.org/10.3390/molecules26247460
DO - https://doi.org/10.3390/molecules26247460
M3 - Article
VL - 26
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 24
M1 - 7460
ER -
ID: 89742965