Citation: Guo Zhenbo, Zheng Xueyang, Li Xueyan, Jia Qingfei, Zhang Pingzhu, Wei Chao, Li Xiaoliu. A Nitroolefin Based Thiol Fluorescent Probe: Synthesis and Application in Bioimaging[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1239-1245. doi: 10.6023/cjoc201911015 shu

A Nitroolefin Based Thiol Fluorescent Probe: Synthesis and Application in Bioimaging

Key Laboratory of Chemical Biology of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002

Corresponding author: Wei Chao, weichao@hbu.edu.cn Li Xiaoliu, lixl@hbu.edu.cn
Received Date: 8 November 2019
Revised Date: 4 December 2019
Available Online: 3 January 2020
Fund Project: the Colleges and Universities Science Technology Research Project of Hebei Province QN2017015Project supported by the National Natural Science Foundation of China (No. 21572044), the Natural Science Foundation of Hebei Province (No. B2018201234) and the Colleges and Universities Science Technology Research Project of Hebei Province (No. QN2017015)the Natural Science Foundation of Hebei Province B2018201234the National Natural Science Foundation of China 21572044

Figures(9)

Intracellular small-molecule thiols, such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play pivotal roles in several physiological and pathological processes. A bodipy-nitroolefin-conjugated fluorescent probe based on photoinduced electron transfer (PET) mechanism was designed and successfully constructed. The probe selectively responds to biothiols by Michael addition reaction of the sulfhydryl group to the double bond activated by Nitroolefin moiety and gives an off-on fluorescent response. The fluorescence detection limit for GSH was calculated to be 11×10^-9 mol/L. The results of fluorescence confocal imaging indicated that the probe has appreciable cell permeability and can serve as a fluorescent probe for detecting biothiols in living cells and zebrafish.
- thiol,
- nitroolefin,
- fluorescent probe,
- bioimaging
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