Citation: ZHANG Chenglu, SUN Yuedong, DING Yanwei, WANG Jing, LIU Xingbing, WANG Nan, SONG Fulu. A Quinolinone-Based Fluorescent Probe for Rapid and Highly Selective Detection of Glutathione[J]. Chinese Journal of Applied Chemistry, ;2020, 37(7): 847-854. doi: 10.11944/j.issn.1000-0518.2020.07.200025 shu

A Quinolinone-Based Fluorescent Probe for Rapid and Highly Selective Detection of Glutathione

College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China

Corresponding author: ZHANG Chenglu, zhangchenglu@lnnu.edu.cn
Received Date: 17 January 2020
Revised Date: 9 March 2020
Accepted Date: 31 March 2020

Fund Project: the Science and Technology Project of Liaoning Education Department 2009A426Supported by the Science and Technology Project of Liaoning Education Department(No.2009A426)

Figures(6)

In order to recognize small-molecule biothiols selectively, quinolinone was used as a fluorophore. Since thiol molecules can easily break the Se—N bond, a new fluorescent probe (E)-N-(4-methyl-2-oxo-1, 2-dihydroquinolin-7-yl)-3-(5-((4-(3-oxobenzo[d][1, 2]selenazol-2(3H)-yl)phenyl)thio)-1, 3, 4-oxadiazol-2-yl)acrylamide (MNQ) was designed and synthesized by splicing quinolinone (E)-3-(5-mercapto-1, 3, 4-oxadiazol-2-yl)-N-(4-methyl-2-oxo-1, 2-dihydroquinolin-7-yl)acrylamide (MQ5) with ebselen 2-(4-bromophenyl)benzo[d][1, 2]selenazol-3(2H)-one (SQ6). The structure was characterized by infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectrometry (HRMS), and its fluorescence properties were explored by fluorescence spectroscopy. The result shows that MNQ has obvious fluorescence quenching ability for glutathione (GSH). When other amino acids exist, the probe has good anti-interference ability, and can be used as a fluorescence quenching probe for identifying and detecting GSH. The detection limit is 2.99×10^-7 mol/L, and the response time can be as low as 35 s. It has potential application as a fluorescent probe for detecting GSH.
- quinolinone,
- fluorescence recognition,
- glutathione,
- ebselen
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