A fluorescent probe for the efficient discrimination of Cys, Hcy and GSH based on different cascade reactions

• Published in: Biosensors & bioelectronics Vol. 90; pp. 117 - 124
• Main Authors: Li, Ying, Liu, Weimin, Zhang, Panpan, Zhang, Hongyan, Wu, Jiasheng, Ge, Jiechao, Wang, Pengfei
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 15.04.2017
• Subjects: Biosensing Techniques; Biotechnology; Biothiols; Cascade chemical reactions; Cascade reactions; Cell imaging; Cells (biology); Coumarin; Coumarins - chemistry; Cysteine - isolation & purification; Discrimination; Excitation; Fluorescence; Fluorescent Dyes - chemistry; Fluorescent probe; Glutathione - isolation & purification; Homocysteine - isolation & purification; Humans; Imaging; Nitriles - chemistry; Wavelengths; Biothiols; Cell imaging; Cascade reactions; Coumarin; Fluorescent probe
• ISSN: 0956-5663; 1873-4235
• DOI: 10.1016/j.bios.2016.11.021

A fluorescent probe (1) for distinguishing amongst biothiols, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), is developed based on different cascade reactions. The key design feature of fluorescent probe 1 is the integration of two potential reaction groups for the thiol and amino groups of biothiols in one molecule. By reacting with the halogen atom and α, β-unsaturated malonitrile in probe 1, Cys, Hcy and GSH can generate a total of three main products with distinct photophysical properties. Probe 1 shows a strong fluorescence turn-on response to Cys with blue–green emission by using an excitation wavelength of 390nm. At an excitation wavelength of 500nm, probe 1 responds to GSH over Cys and Hcy and emits strong orange fluorescence. The discrimination of biothiols can be demonstrated by cell imaging experiments, indicating that probe 1 can be a useful tool for the selective imaging of Cys and GSH in living cells. [Display omitted] •We designed a fluorescent probe (1) by integrating two reactive groups into coumarin.•Probe 1 can differentiate Cys and GSH based on different cascade reactions.•Probe 1 can be a useful tool for the selective detection of Cys and GSH in living cells.