基于水解识别机制的过氧化亚硝酸盐荧光探针的合成及性质研究

何潞潞, 张珍, 李佳佳, 曾竟

现代化工 ›› 2023, Vol. 43 ›› Issue (12) : 230 -236.

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现代化工 ›› 2023, Vol. 43 ›› Issue (12) : 230-236. DOI: 10.16606/j.cnki.issn0253-4320.2023.12.042
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基于水解识别机制的过氧化亚硝酸盐荧光探针的合成及性质研究

    何潞潞, 张珍, 李佳佳, 曾竟
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Synthesis and properties of peroxynitrite fluorescent probe based on hydrolysis recognition mechanism

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摘要

以典型聚集诱导发光(AIE)性质的四苯乙烯基为荧光母体,通过酯基连接上水溶性佳的聚乙二醇基合成了具有AIE特性的化合物TPE-PEG2000-TPE;利用光谱法研究探针TPE-PEG2000-TPE的光学性能,结果表明,探针在DMF/H2O混合溶液中具有典型的AIE性能,其溶液(探针溶液浓度为10 μmol/L,DMF/H2O体积比为1/4,在PBS缓冲溶液中pH值为7.4)对ONOO-表现出"turn-off"特异性识别,猝灭比可达97.86%,检出限为1.26×10-6 mol/L,具有较好的选择性、较高的灵敏度和较大的Stokes位移(164 nm)。通过薄层色谱法和高分辨质谱法对探针识别ONOO-的机制进行研究,结果表明,该探针通过酯基水解生成TPE-COOH,进而使荧光发生变化,实现对ONOO-的特异性识别。

Abstract

TPE-PEG2000-TPE, a compound with aggregation-induced luminescence (AIE) characteristics, is synthesized by using tetraphenylethylene group with typical AIE property as the fluorescent parent through the ester group connecting water-soluble polyethylene glycol group.The optical properties of TPE-PEG2000-TPE probe are studied by means of spectroscopy, and it is shown that TPE-PEG2000-TPE probe has a typical AIE performance in a DMF/H2O mixed solution.The solution of TPE-PEG2000-TPE probe (10 μmol/L, v/v, 1/4, PBS, pH=7.4) shows a "turn-off" specific recognition to ONOO-, with a quenching ratio of 97.86% and a detection limit of 1.26×10-6 mol·L-1, and also presenting a better selectivity, a relatively high sensitivity and a large Stokes displacement (164 nm).It is indicated through exploring the recognition mechanism of the probe for ONOO- by TLC and ESI-MS that this probe generates TPE-COOH through ester group hydrolysis, which enables specific recognition of ONOO-.

关键词

四苯乙烯 / 荧光探针 / 过氧化亚硝酸盐 / 聚集诱导发光

Key words

tetraphenylethylene / fluorescence probe / peroxynitrite / aggregation induced luminescence

Author summay

何潞潞(1998-),女,硕士生。

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基于水解识别机制的过氧化亚硝酸盐荧光探针的合成及性质研究[J]. 现代化工, 2023, 43(12): 230-236 DOI:10.16606/j.cnki.issn0253-4320.2023.12.042

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