Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1239-1245.DOI: 10.6023/cjoc201911015 Previous Articles     Next Articles


郭振波, 郑雪阳, 李雪艳, 贾清菲, 张平竹, 魏超, 李小六   

  1. 河北大学化学与环境科学学院 药物化学与分子诊断教育部重点实验室 河北省化学生物学重点实验室 河北保定 071002
  • 收稿日期:2019-11-08 修回日期:2019-12-04 发布日期:2020-01-03
  • 通讯作者: 魏超, 李小六;
  • 基金资助:

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

Guo Zhenbo, Zheng Xueyang, Li Xueyan, Jia Qingfei, Zhang Pingzhu, Wei Chao, Li Xiaoliu   

  1. 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
  • Received:2019-11-08 Revised:2019-12-04 Published:2020-01-03
  • Supported by:
    Project 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).

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.

Key words: thiol, nitroolefin, fluorescent probe, bioimaging