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用于在活细胞和斑马鱼模型中区分半胱氨酸、同型半胱氨酸和谷胱甘肽的双发射荧光探针。

A dual-emission fluorescent probe for discriminating cysteine from homocysteine and glutathione in living cells and zebrafish models.

机构信息

School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.

School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.

出版信息

Bioorg Chem. 2019 Nov;92:103215. doi: 10.1016/j.bioorg.2019.103215. Epub 2019 Aug 23.

Abstract

Cellular biothiols function crucially and differently in physiological and pathological processes. However, it is still challenging to detect and discriminate thiols within a single one molecule, especially for cysteine (Cys) and homocysteine (Hcy). In this study, a simple two-emission turn-on fluorescent biothiol probe (ICN-NBD) was rationally designed and synthesized through a facile ether bond linking 7-nitro-1,2,3-benzoxadiazole (NBD) and phenanthroimidazole containing a cyano tail. The probe in the presence of Cys elicited two fluorescence responses at 470 nm and 550 nm under excitation at 365 nm and 480 nm, respectively, because of the concomitant generation of both the fluorophore and NBD-N-Cys. In contrast, addition of Hcy and glutathione (GSH) could result in only a blue fluorescence enhancement at 470 nm. which was reasonably attributed to rearrangement from NBD-S-Hcy/GSH to NBD-N-Hcy/GSH as a result of geometrical constraints or solvent effects. Therefore, the fluorescent probe with the NBD scaffold could detect biothiols and simultaneously discriminate Cys from Hcy/GSH in both blue and green channels. The probe has been successfully applied for visualizing biothiols in living cells and zebrafish.

摘要

细胞生物硫醇在生理和病理过程中起着至关重要且不同的作用。然而,在单个分子内检测和区分硫醇仍然具有挑战性,特别是对于半胱氨酸 (Cys) 和同型半胱氨酸 (Hcy)。在本研究中,通过简便的醚键连接 7-硝基-1,2,3-苯并恶二唑 (NBD) 和含有氰基尾巴的菲咯啉咪唑,合理设计并合成了一种简单的双发射荧光生物硫醇探针 (ICN-NBD)。在存在 Cys 的情况下,探针在 365nm 和 480nm 激发下分别在 470nm 和 550nm 处产生两个荧光响应,这是由于同时生成了荧光团和 NBD-N-Cys。相比之下,加入 Hcy 和谷胱甘肽 (GSH) 只会导致 470nm 处的蓝色荧光增强,这合理归因于 NBD-S-Hcy/GSH 重排为 NBD-N-Hcy/GSH,这是由于几何限制或溶剂效应。因此,具有 NBD 支架的荧光探针可以同时在蓝绿色通道中检测生物硫醇并区分 Cys 与 Hcy/GSH。该探针已成功用于活细胞和斑马鱼中生物硫醇的可视化。

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