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一种用于从半胱氨酸、谷胱甘肽和高半胱氨酸中区分半胱氨酸的双响应荧光探针。

A dual-response fluorescent probe for the discrimination of cysteine from glutathione and homocysteine.

机构信息

Key Laboratory for Special Functional Materials of the Ministry of Education, Henan University, Kaifeng 475004, PR China.

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng 475004, PR China.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Jan 5;206:1-7. doi: 10.1016/j.saa.2018.07.102. Epub 2018 Aug 1.

DOI:10.1016/j.saa.2018.07.102
PMID:30077035
Abstract

A highly selective and sensitive turn-on fluorescent BODIPY-based probe for the simultaneous and selective detection of Cys and Hcy/GSH from dual emission channels was developed. The spatial steric hindrance of the methyl groups at 1- and 7-positions in BODIPY skeleton prevented intramolecular displacement of sulfur with amino group of Hcy but not of Cys. GSH molecular skeleton is larger and amino is far away from sulfydryl group, and the product of the reaction of probe with GSH canstay in thiol phase. Therefore, the probe was successfully applied to the detection of Cys from GSH/Hcy. The confocal microscopy experiments implied that this probe is a promising candidate for imaging of Cys and Hcy/GSH in Hela cells.

摘要

开发了一种基于 BODIPY 的高选择性和高灵敏度的荧光探针,可通过双通道发射同时选择性检测 Cys 和 Hcy/GSH。BODIPY 骨架上 1-位和 7-位甲基的空间位阻阻止了 Hcy 中氨基与硫原子的分子内取代,但不能阻止 Cys 的取代。GSH 的分子骨架较大,氨基远离巯基,且与 GSH 反应的产物仍处于疏巯基相。因此,该探针可成功用于从 GSH/Hcy 中检测 Cys。共聚焦显微镜实验表明,该探针是用于在 Hela 细胞中成像 Cys 和 Hcy/GSH 的有前途的候选物。

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Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species: Recent progress, applications, and design strategies.
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