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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 7: 1934 - 1940

DOI: https://doi.org/10.6023/cjoc202003042

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
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  • 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 date: 2020-03-16

  Revised date: 2020-04-30

  Online 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).

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Abstract

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

Cite this article

Li Wei , Jia Xu , Guo Zhenbo , Jiang Wenting , Zhang Pingzhu , Wei Chao , Li Xiaoliu . Imaging of Hydrogen Peroxide During the Ischemia Reperfusion Process in Living Cells with An Aggregation Induced-Emission Probe[J]. Chinese Journal of Organic Chemistry, 2020 , 40(7) : 1934 -1940 . DOI: 10.6023/cjoc202003042

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