Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 1934-1940.DOI: 10.6023/cjoc202003042 Previous Articles     Next Articles


李维, 贾旭, 郭振波, 姜文婷, 张平竹, 魏超, 李小六   

  1. 河北大学化学与环境科学学院 河北省化学生物学重点实验室 药物化学与分子诊断教育部重点实验室 河北保定 071002
  • 收稿日期:2020-03-16 修回日期:2020-04-30 发布日期:2020-05-15
  • 通讯作者: 魏超, 李小六;
  • 基金资助:

Imaging of Hydrogen Peroxide During the Ischemia Reperfusion Process in Living Cells with An Aggregation Induced-Emission Probe

Li Wei, Jia Xu, Guo Zhenbo, Jiang Wenting, 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:2020-03-16 Revised:2020-04-30 Published:2020-05-15
  • Supported by:
    Project supported by the Natural Science Foundation of Hebei Province (No. B2018201234) and the Colleges and Universities Science Technology Research Project of Hebei Province (No. QN2017015).

As an important endogenous signaling molecule, hydrogen peroxide (H2O2) is involved in regulating many physiological and pathological processes. Ischemia-reperfusion can induce the production of large amount of endogenous hydrogen peroxide, which can cause seriously damage to cells and tissues. The fluorescent probe with aggregation induced emission can avoid the shortage of the aggregation caused quenching of conventional fluorophores. A H2O2 fluorescent probe with aggregation induced emission properties was designed and synthesized by using 4-vinylpyridinyl modified tetraphenylethylene as the fluorophore and phenylboronic acid as the H2O2 sensing group. The structure of the probe was characterized by NMR and HRMS. The recognition behaviors of the probe to H2O2 were investigated by the UV-Vis absorption and fluorescence spectra, and the results exhibit its good selectivity and high sensitivity to H2O2. The fluorescence off-on enhancement was ca. 100-fold and the detection limit was 6.9×10-8 mol/L. The reaction of the probe and H2O2 resulted in the H2O2-mediated oxidation of phenylboronic acid, followed by hydrolysis and 1,6-elimination of p-quinone-methide to generate (E)-4-(4-(2,2-bis(4-methoxyphenyl)-1-phenylvinyl)styryl)pyridine (TPE-Py), which was confirmed by 1H NMR. The results of confocal imaging indicated that the probe was cell-permeable and capable of visualization of endogenous H2O2 in oxygen glucose deprivation/reoxygenation (OGD/R) model HeLa cells and lipopolysaccharide-treated zebrafish.

Key words: hydrogen peroxide, oxygen glucose deprivation/reoxygenation (OGD/R), aggregation induced-emission, fluorescent probe, bioimaging