A simple fluorescent probe for sensing cysteine over homocysteine and glutathione based on PET

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2017-02, Vol.173, p.918-923
• Main Authors: Fan, Wenlong, Huang, Ximing, Shi, Xiaomin, Wang, Zhuo, Lu, Zhengliang, Fan, Chunhua, Bo, Qibing
• Format: Article
• Language: English
• Subjects: Bioimaging; Cysteine; Fluorescence; Probe; Selectivity
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2016.10.060

A big challenge is the discrimination of sulfhydryl-containing amino acids due to their structural similarity. We designed and synthesized a simple fluorescent probe 3 for specific detection of cysteine based on photo-induced electron transfer (PET). The acrylate and BODIPY moieties in probe 3 act as a reaction site and reporter group, respectively. So the synergistic effect of the substituent groups endows probe 3 very strong green fluorescence at 525nm (λex=500nm). The cleavage reaction induced by cysteine leads to acrylate hydrolysis, and thereby triggers PET on, which effectively quench the fluorescence of 3. Probe 3 exhibited a rapid response towards cysteine over homocysteine and glutathione. Probe 3 is successfully applied for sensing and imaging cysteine in vitro or in vivo cells with low cytotoxicity. [Display omitted] •A simple fluorescent probe for specific detection of cysteine based on PET was developed.•The acrylate and BODIPY moieties in the probe act as a reaction site and reporter group, respectively.•The synergistic effect of the substituent groups endows the probe very strong green fluorescence at 525nm (λex=500nm).•The probe is successfully applied for sensing and imaging cysteine in vitro or in vivo cells with low cytotoxicity.