Citation: Lun Song, Li-Min Ma, Qian Sun, Wei-Bing Zhang, Min-Bo Lan, Jun-Hong Qian. Discrimination of biothiols in different media with NBD-F as the probe[J]. Chinese Chemical Letters, ;2016, 27(03): 330-334. doi: 10.1016/j.cclet.2015.12.012 shu

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

Lun Song ^a ,
Li-Min Ma ^a ,
Qian Sun ^a ,
Wei-Bing Zhang ^a ,
Min-Bo Lan ^a,, ,
Jun-Hong Qian ^a,b,,

a.
a. Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China;
b.
b. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Min-Bo Lan, Jun-Hong Qian,
Received Date: 17 July 2015
Available Online: 13 September 2015
Fund Project: This work was financially supported by Shanghai Municipal Natural Science Foundation(No.15ZR1409000) andtheopen fundof Shanghai Key Laboratory of Chemical Biology (No.SKLCB-2013-03). (No.15ZR1409000)

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 SDSmicelles). 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.
- NBD-F,
- Biothiols,
- Surfactant micelles,
- Fluorescent probe
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