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.
Yang
Xiao-Feng
XF
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
Su
Zhuan
Z
Liu
Chenghai
C
Qi
Haiping
H
Zhao
Minglei
M
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