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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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Publication details

The article was received on 28 Nov 2013, accepted on 14 Jan 2014 and first published on 14 Jan 2014


Article type: Paper
DOI: 10.1039/C3RA47116K
Citation: RSC Adv., 2014,4, 8360-8364
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    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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