Biological thiols such as cysteine (Cys), glutathione (GSH), and homocysteine (Hcy) are known to play important roles in biosystems, the levels of which are closely related with diseases including cancer, matabolic diseases, and brain-related diseases. Therefore, the development of efficient biothiol sensing tools is highly desirable for chemical biology research. In this work, we disclose for the first time a turn-on fluorescent probe, Cys-P1, for the detection of Cys, which functions based on Cys-mediated O-phenyl benzothioate native chemical ligation (NCL). We observed that Cys-P1 shows fast responses as well as high selectivity towards Cys among amino acids, metal ions, and biothiols which might possibly be a source for interference. Moreover, we verified the generation of H2S gas as a side product, which would make possible Cys-P1 applied to H2S delivery system as well. Furthermore, the probe showed superior sensing ability for Cys in cancer cells with low cytotoxicity. Taken together, we believe our study will provide a new platform for Cys sensing and warrant further related biological applications.

Development of a benzothioate native chemical ligations-based cysteine-selective fluorescent probe

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.