A novel fluorescent probe for discrimination of Cys from GSH: inspiration from chemical ligation

作者：Zhang, Lili; Li, Mimi; Zhao, Chunchang; Gu, Xianfeng^*

来源：Tetrahedron Letters, 2016, 57(5): 578-581.

DOI：10.1016/j.tetlet.2015.12.093

• Cysteine
• Glutathione
• Fluorescent probe
• Chemical ligation

A novel fluorescent probe for discriminating cysteine (Cys) and glutathione (GSH) has been developed inspired by chemical ligation. The probe is able to react rapidly with Cys or GSH by nucleophilic aromatic substitution. In the case of Cys, the first produced sulfur-substituted BODIPY is unstable and undergoes a subsequent intramolecular displacement affording an amino-substituted BODIPY through a five membered cyclic transition stat. This irreversible aromatic hydrocarbon transfer from sulfur to nitrogen atoms is mostly like the well-known chemical ligation process. In comparison, the bulkiness of GSH sharply hinders such an aromatic hydrocarbon transfer process. Based on these reactions, the distinct fluorescence responses to Cys and GSH were achieved, and the probe can be used for the detection of Cys over GSH in living cells.

• 出版日期2016-2-3
• 单位复旦大学; 华东理工大学