A thiol-selective fluorogenic probe based on the cleavage of 4-methylumbelliferyl-2',4',6'-trinitropheyl ether.
A new fluorescent probe 1,4-methylumbelliferyl-2',4',6'-trinitropheyl ether (Probe 1) was designed and synthesized. Probe 1 was a nonfluorescent compound and was synthesized via the one-step reaction of 4-methylumbelliferone (4-MU) with 1-chloro-2,4,6-trinitrobenzene. Upon mixing with biothiols under neutral aqueous conditions, the 2,4,6-trinitrophenyl group of 1 was efficiently removed, and the emissive free dye 4-MU was released, hence leading to a dramatic increase in fluorescence emission of the reaction mixture. A good linear relationship was obtained from 0.1 to 4.0 micromol L(-1) for cysteine (Cys), from 0.1 to 3.0 micromol L(-1) for homocysteine (Hcy), and from 0.2 to 3.0 micromol L(-1) for glutathione (GSH), respectively. The detection limits of Cys, Hcy, and GSH were 24.3, 35.6, and 26.8 nmol L(-1), respectively. Furthermore, probe 1 was highly selective for biothiols without the interference of some biologically relevant analytes and has been applied to detecting biothiols in human serum samples.
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Institute of Analytical Science, Department of Chemistry, Northwest University, Xi'an 710069, China. xfyang@nwu.edu.cn
Xiao-Feng
XF
Yang
Zhuan
Z
Su
Chenghai
C
Liu
Haiping
H
Qi
Minglei
M
Zhao
D004987:Ethers / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D013050:Spectrometry, Fluorescence / Q000379:methods*; D013438:Sulfhydryl Compounds / Q000032:analysis* / Q000138:chemical synthesis*
D004987:Ethers; D005456:Fluorescent Dyes; D013438:Sulfhydryl Compounds