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J Am Chem Soc. 2012 Nov 21;134(46):18928-31. doi: 10.1021/ja309079f. Epub 2012 Nov 8.

BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine.

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Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, PR China.


We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol-halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.

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