Recent Advances in Fluorescent Probes for Biothiols

doi:10.6023/cjoc202006046

Abstract

Biothiols, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play an important role in life activities, and the fluctuation of their concentrations is closely related to many diseases. Therefore, it is of great importance to detect the content of biothiols. Among all varieties of techniques, the fluorescent probe demonstrates tremendous advantages ascribed to its good sensitivity, high temporal-spatial resolution, noninvasiveness and visualization. Taking advantage of the commonality and differences among the three thiols, namely, the similar reactive groups of sulfhydryl group and amino group, and the different molecular size, nucleophilicity, steric hindrance and intracellular contents, various recognition mechanisms, such as Michael addition, aromatic nucleophilic reaction and concerted addition and cyclization reaction, are all implemented to realize the specific detection of biothiols. The research progress of thiol fluorescent probes in recent three years is reviewed. The fluorescent probes that can selectively respond to biothiols as well as to Cys, Hcy and GSH are systemically analyzed and summarized. The molecular design, recognition mechanism, fluorescence properties and imaging applications are emphasized,, and the application of biothiol fluorescent probe on monitoring life activities is preliminary introduced. In addition, a perspective of future development in this area is also presented.

Key words: biothiol, fluorescent probe, cysteine, homocysteine, glutathione, advance

Cite this article

Li Chen, Junbo Li, Dugang Chen. Recent Advances in Fluorescent Probes for Biothiols[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 611-623.

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Fig. & Tab. 18

Figure 1. Molecular structures of three biothiols

Figure 2. Schematic illustration of the fluorescent probe

Figure 3. Common biothiol fluorescent probes 1~4

Figure 4. Common biothiol fluorescent Probes 5 and 6

Figure 5. Common biothiol fluorescent probes 7 and 8

Figure 6. Probe 9 with aldehyde as the recognition site for Cys detection

Figure 7. Probes 10 and 11 with aldehyde as the recognition site for Cys detection

Figure 8. Probes 12 and 13 based on Michael addition mechanism for Cys detection

Figure 9. Probes 14~16 based on addition-cyclization mechanism for Cys detection

Figure 10. Probes 17~25 based on addition-cyclization mechanism for Cys detection

Figure 11. Probe 26 based on FRET for Cys detection

Figure 12. Probe 27 based on aromatic substitution-rearrangement reaction for Cys detection

Figure 13. Probe 28 based on aromatic substitution-rearrangement reaction for Cys detection

Figure 14. Probes 29~31 for specific detection of Hcy

Figure 15. GSH Probes 32~34 based on Michael addition

Figure 16. GSH probe 35 based on nucleophilic aromatic substitution

Figure 17. GSH Probes 36 and 37 based on nucleophilic aromatic substitution

Figure 18. GSH Probes 38 and 39

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