Abstract
We describe a near-infrared (NIR) fluorescent probe 1 for the selective detection of GSH over Hcy and Cys under physiological conditions. Probe 1 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 1 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 1 successfully displayed fluorescence changes in response to changing the GSH concentrations in MDA-MB-231 cells in the presence of external agents i.e., N-acetyl-l-cysteine (NAC; as GSH inducer) or buthionine sulfoximine (BSO; as GSH inhibitor). We envision that probe 1 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.
Highlights
Bio-thiols, e.g., glutathione (GSH), cysteine (Cys), and homocysteine (Hcy), play important roles in maintaining the redox status of biological systems [1,2]
We presented a highly selective NIR fluorescent probe (1) that can detect GSH selectively over
We propose that in the presence of GSH and Hcy/Cys, 2-mercaptopyridine of 1 is replaced by the thiolate of GSH to form the sulfur-substituted Cy7, 1-GSH, the 2-mercaptopyridine of 1 is replaced by the thiolate of GSH to form the sulfur-substituted Cy7, displaying a strong fluorescence at 818 nm
Summary
Bio-thiols, e.g., glutathione (GSH), cysteine (Cys), and homocysteine (Hcy), play important roles in maintaining the redox status of biological systems [1,2]. Most probes were constructed by fluorophores, e.g., coumarin, naphthalimide, rhodamine, that absorb and emit the lights in the UV-Vis region, which can damage rhodamine, that absorb and emit theautofluorescence lights in the UV-Vis region, which Recently, can damage living living cells and be affected by the of biomolecules. Yang andcells his and cobe affected by the autofluorescence of biomolecules. The fluorescent probes for the selective detection of selective detection of GSH over Hcy and Cys are still rarely reported [18,19,20].
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