A Native-Chemical-Ligation-Based Turn-on Fluorescent Probe for Selective Detection of Cysteine

Selective and quantitative detection of biological thiols such as cysteine, homocysteine, and glutathione is often necessary because abnormal levels of such thiols can cause some diseases. Here, we report that bis(pentafluorophenyl) 1,4-benzenedicarbothionic acid diester can serve as a turn-on fluorescent probe for selective detection of cysteine vis-a-vis homocysteine and glutathione. When cysteine was added to a mixture of the diester and a sodium phosphate buffer solution with THF (60 vol%), which is non-fluorescent, the mixture became green-fluorescent. In contrast, addition of homocysteine or glutathione did not make the mixture fluorescent. A native-chemical-ligation-based mechanism is proposed.