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J Am Chem Soc. 2014 Sep 10;136(36):12520-3. doi: 10.1021/ja504156a. Epub 2014 Aug 21.

A mitochondria-targetable fluorescent probe for dual-channel NO imaging assisted by intracellular cysteine and glutathione.

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School of Chemistry and Chemical Engineering and ‡Institute of Biotechnology, Shanxi University , Taiyuan 030006, China.


A mitochondria-specific fluorescent probe for NO (1) was synthesized by the direct conjugation of a pyronin dye with one of the amino groups of o-phenylenediamino (OPD). The probe could selectively detect NO over dehydroascorbic acid (DHA), ascorbic acid (AA), and methylglyoxal (MGO) as well as the reactive oxygen/nitrogen species (ROS/RNS) with the significant off-on response due to the production of a red-emission triazole 2. In the presence of cysteine/glutathione (Cys/GSH), 2 could be further transformed into a green-emission aminopyronin 4 and a red-emission thiopyronin 5, respectively. Assisted by intracellular Cys and GSH, the probe demonstrated its potential to monitor mitochondrial NO in a dual-channel mode.

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