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基于 1,4-加成反应机制的红色发射荧光探针用于体外和体内生物硫醇的检测。

A red-emission fluorescence probe based on 1,4-addition reaction mechanism for the detection of biothiols in vitro and in vivo.

机构信息

School of Chemical Engineering, University of Science and Technology Liaoning, Anshan, 114051, Liaoning, People's Republic of China.

School of Forensic Medicine, Xinxiang Medical University, Jinsui Road No. 601, Xinxiang, 453003, Henan, People's Republic of China.

出版信息

Anal Sci. 2022 Mar;38(3):505-514. doi: 10.2116/analsci.21P177. Epub 2022 Apr 1.

DOI:10.2116/analsci.21P177
PMID:35359268
Abstract

In this work, a new fluorescence probe (DC) with a donor-π-acceptor (D-π-A) structure was designed and synthesized for the detection of three kinds of biothiols (Cys, Hcy and GSH) in live cells and organisms. DC displayed an intense red-emission centered at 625 nm. In the presence of biothiols, the nucleophilic addition reaction between the C=C double bond of DC and the sulfhydryl group (-SH) of biothiols occurred, resulting in obvious fluorescence quenching responses. DC exhibited high selectivity towards biothiols over other common bioactive species with low detection limits (0.26, 0.43, and 0.44 µM for Cys, Hcy and GSH, respectively). In addition, DC displayed a rapid response to biothiols within 4 min. The applications of DC in biothiols detection and imaging were then successfully demonstrated for the real-time monitoring of endogenous and exogenous biothiols in live cells and live animals.

摘要

在这项工作中,设计并合成了一种具有给体-π-受体(D-π-A)结构的新型荧光探针(DC),用于检测活细胞和生物体内的三种生物硫醇(Cys、Hcy 和 GSH)。DC 呈现出中心位于 625nm 的强烈红光发射。在生物硫醇存在下,DC 的 C=C 双键与生物硫醇的巯基(-SH)之间发生亲核加成反应,导致明显的荧光猝灭响应。DC 对生物硫醇表现出高选择性,对其他常见生物活性物质的检测限较低(Cys、Hcy 和 GSH 的检测限分别为 0.26、0.43 和 0.44µM)。此外,DC 对生物硫醇的响应非常迅速,在 4 分钟内即可完成响应。然后,成功地将 DC 应用于生物硫醇的检测和成像,用于实时监测活细胞和活体动物内源性和外源性生物硫醇。

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