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基于 ESIPT 的比率型荧光探针用于活细胞中半胱氨酸的高选择性检测。

Ratiometric fluorescent probe based on ESIPT for the highly selective detection of cysteine in living cells.

机构信息

Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.

State Key Laboratory of Veterinary Etiological Biology and Key Laboratory of Animal Virology of Ministry of Agriculture, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Xujiaping 1, Lanzhou, Gansu Province 730046, PR China.

出版信息

Talanta. 2019 Mar 1;194:717-722. doi: 10.1016/j.talanta.2018.10.095. Epub 2018 Oct 29.

DOI:10.1016/j.talanta.2018.10.095
PMID:30609596
Abstract

A new simple and facile fluorescent ratiometric probe (probe 1) has been designed for the detection of cysteine (Cys). Probe 1 as the fluorophore contains a typical excited-state intramolecular proton transfer (ESIPT) dye. In probe 1 to restore the ESIPT process, the group of acrylate which acts as the recognition unit can block the ESIPT process and can be selectively achieved by Cys, which makes the probe as the ratiometric fluorescent detection for Cys in aqueous solution. This probe shows highly selectivity towards Cys over other biothiols including glutathione (GSH) and homocysteine (Hcy) because of specific cyclization between Cys and acrylate group, and having a detection limit of 42.3 nM. In addition, the experiment of cell imaging shows that probe 1 possesses low cytotoxicity and excellent cell permeability towards the living cells, and has been successfully applied to the ratiometric imaging not only for the endogenous but also for the exogenous cysteine in the living cells effectively.

摘要

一种新的简单荧光比率探针(探针 1)已被设计用于检测半胱氨酸(Cys)。探针 1 作为荧光团含有典型的激发态分子内质子转移(ESIPT)染料。在探针 1 中,恢复 ESIPT 过程,作为识别单元的丙烯酰胺基团可以阻断 ESIPT 过程,并可以被 Cys 选择性地实现,这使得探针可以在水溶液中对半胱氨酸进行比率荧光检测。由于 Cys 与丙烯酰胺基团之间的特异性环化,该探针对半胱氨酸具有高度选择性,超过了其他生物硫醇,包括谷胱甘肽(GSH)和高半胱氨酸(Hcy),并且检测限为 42.3 nM。此外,细胞成像实验表明,探针 1 对活细胞具有低细胞毒性和优异的细胞通透性,并已成功应用于比率成像,不仅可以有效地对活细胞内的内源性和外源性半胱氨酸进行成像。

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