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

doi:10.6023/cjoc202003042

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

聚集诱导发光探针用于细胞缺血再灌注诱导过氧化氢成像研究

李维, 贾旭, 郭振波, 姜文婷, 张平竹, 魏超, 李小六

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 E-mail:weichao@hbu.edu.cn;lixl@hbu.cn
基金资助:
河北省自然科学基金（No.B2018201234）和河北省高等学校科学技术研究（No.QN2017015）资助项目.

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

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).

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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

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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.

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聚集诱导发光探针用于细胞缺血再灌注诱导过氧化氢成像研究

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

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