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

doi:10.6023/cjoc202003042

有机化学 ›› 2020, Vol. 40 ›› Issue (7): 1934-1940.DOI: 10.6023/cjoc202003042 上一篇下一篇

研究论文

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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摘要/Abstract

过氧化氢是一种重要的内源性信号分子，参与调控多种生理和病理过程.缺血再灌注会诱导产生大量内源性过氧化氢，对细胞和组织造成严重损伤.聚集诱导发光探针能够规避常规荧光团浓度过大所引起的聚集荧光淬灭的问题.以4-乙烯吡啶修饰的四苯乙烯为荧光基团，苯硼酸为过氧化氢识别基团，设计合成了一种具有聚集诱导发光性质的长波长过氧化氢荧光探针.光谱测试结果表明，探针对过氧化氢具有较好的选择性和较高的灵敏度，最低检测限为6.9×10^-8 mol/L.共聚焦成像结果表明，探针具有较好的细胞通透性，可用于糖氧剥夺再灌注诱导HeLa细胞和脂多糖诱导斑马鱼内源性过氧化氢生成研究.

关键词: 过氧化氢, 氧糖剥离再灌注, 聚集诱导发光, 荧光探针, 生物成像

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

引用此文

李维, 贾旭, 郭振波, 姜文婷, 张平竹, 魏超, 李小六. 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[J]. 有机化学, 2020, 40(7): 1934-1940.

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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