Discrimination of biothiols in different media with NBD-F as the probe

• Published in: Chinese chemical letters 2016-03, Vol.27 (3), p.330-334
• Main Authors: Song, Lun, Ma, Li-Min, Sun, Qian, Zhang, Wei-Bing, Lan, Min-Bo, Qian, Jun-Hong
• Format: Article
• Language: English
• Subjects: Biothiols; CTAB法; CTAB胶束; Fluorescent probe; NBD-F; SDS胶束; Surfactant micelles; 介质; 光谱响应; 同型半胱氨酸; 探针; 表面活性剂胶束
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2015.12.012

4-Fluoro-7-nitrobenzo-2-oxa-1,3-diazole（NBD-F） was employed as a colorimetric probe for differential detection of biothiols in different media. The spectral response and the selectivity of NBD-F toward thiols were significantly improved by surfactant micelles. Mercapto group exhibited high reactivity in all the solvents（including Tris–HCl buffer solution, CTAB and SDS micelles）. The 4-thioether derivatives of NBDF reacting with Cys and Hcy but not GSH could transfer to the corresponding 4-amino-substituents via intramolecular nucleophilic aromatic substitution, thus, GSH could be discriminated from Cys/Hcy. In CTAB micelles, the reaction product of NBD-F with Cys is non-fluorescent and it absorbs in longwavelength region. According to the spectral responses of NBD-F toward different low-molecularweight thiols, we could identify Cys, Hcy and GSH from each other.