Department of Chemistry, Sookmyung Women's University, Seoul 04310, Korea.
School of Chemical and Biological Engineering, Seoul National University, Seoul 151-742, Korea.
Sensors (Basel). 2018 Sep 1;18(9):2897. doi: 10.3390/s18092897.
We describe a near-infrared (NIR) fluorescent probe for the selective detection of GSH over Hcy and Cys under physiological conditions. Probe was composed of Cy7 as a NIR dye and 2-mercaptopyridine as a GSH-reactive site and fluorescence quencher. In the presence of GSH, the 2-mercaptopyridine functionality of probe was replaced by the thiolate group of GSH through a nucleophilic substitution reaction with a fluorescence increase at 818 nm. The probe was found to be highly selective for GSH over Hcy, Cys, and other tested potential interferants, including ROS and metal ions. In addition, probe successfully displayed fluorescence changes in response to changing the GSH concentrations in MDA-MB-231 cells in the presence of external agents i.e., -acetyl-l-cysteine (NAC; as GSH inducer) or buthionine sulfoximine (BSO; as GSH inhibitor). We envision that probe will serve as a promising sensing tool for monitoring the changes of the GSH level and the understanding of the roles of GSH under physiological and pathological conditions.
我们描述了一种近红外（NIR）荧光探针，用于在生理条件下选择性检测 GSH 相对于 Hcy 和 Cys。探针由 Cy7 作为 NIR 染料和 2-巯基吡啶作为 GSH 反应性位点和荧光猝灭剂组成。在 GSH 的存在下，探针的 2-巯基吡啶官能团通过亲核取代反应被 GSH 的硫醇基团取代，在 818nm 处荧光增强。该探针对 GSH 具有高度选择性，相对于 Hcy、Cys 和其他测试的潜在干扰物，包括 ROS 和金属离子。此外，探针在存在外部试剂（即 -乙酰-l-半胱氨酸（NAC；作为 GSH 诱导剂）或丁硫氨酸亚砜（BSO；作为 GSH 抑制剂）时，成功地响应 MDA-MB-231 细胞中 GSH 浓度的变化显示出荧光变化。我们设想，探针将成为监测 GSH 水平变化和理解生理和病理条件下 GSH 作用的有前途的传感工具。
