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Issue 16, 2014
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A near-infrared fluorescent sensor for selective detection of cysteine and its application in live cell imaging

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Abstract

Biological thiols, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play important roles in maintaining the appropriate redox status of biological systems. The discrimination between them is of great importance because of their different biological roles. Herein, we present a new near-infrared (NIR) fluorescent sensor Cy-NO2 for selective detection of Cys over Hcy/GSH. The nitrothiophenol group is introduced to quench the fluorescence through photo-induced electron transfer (PET). The sensor undergoes displacement of nitrothiophenol with thiol to turn on the fluorescence. The amino groups of Cys/Hcy further replace the thiolate to form amino-substituted products, which exhibit dramatically different photophysical properties compared to the sulfur-substituted product from the reaction with GSH. By means of more rapid intramolecular displacement of sulfur with the amino group of Cys than Hcy, the discrimination of Cys is achieved. Moreover, Cy-NO2 was successfully applied for bioimaging Cys in living cells.

Graphical abstract: A near-infrared fluorescent sensor for selective detection of cysteine and its application in live cell imaging

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Supplementary files

Article information


Submitted
28 Nov 2013
Accepted
14 Jan 2014
First published
14 Jan 2014

RSC Adv., 2014,4, 8360-8364
Article type
Paper

A near-infrared fluorescent sensor for selective detection of cysteine and its application in live cell imaging

Y. Guan, L. Niu, Y. Chen, L. Wu, C. Tung and Q. Yang, RSC Adv., 2014, 4, 8360
DOI: 10.1039/C3RA47116K

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