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Sensors 2018, 18(9), 2897; https://doi.org/10.3390/s18092897

A Fluorescent Cy7-Mercaptopyridine for the Selective Detection of Glutathione over Homocysteine and Cysteine

1
Department of Chemistry, Sookmyung Women’s University, Seoul 04310, Korea
2
School of Chemical and Biological Engineering, Seoul National University, Seoul 151-742, Korea
3
Department of Chemistry, Korea University, Seoul 02841, Korea
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 31 July 2018 / Revised: 26 August 2018 / Accepted: 30 August 2018 / Published: 1 September 2018
(This article belongs to the Special Issue Colorimetric and Fluorescent Sensors 2018)
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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. View Full-Text
Keywords: NIR fluorescent probe; Cy7 dye; glutathione (GSH); 2-mercaptopyridine NIR fluorescent probe; Cy7 dye; glutathione (GSH); 2-mercaptopyridine
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Yoon, S.A.; Kim, W.; Sharma, A.; Verwilst, P.; Won, M.; Lee, M.H. A Fluorescent Cy7-Mercaptopyridine for the Selective Detection of Glutathione over Homocysteine and Cysteine. Sensors 2018, 18, 2897.

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