A 4-methylumbelliferone-based fluorescent probe for the sensitive detection of captopril.
A highly sensitive fluorogenic probe for captopril, 4-methylumbelliferyl-2, 4-dinitrobenzenesulfonate (4-MUDNBS), was designed and synthesized. 4-MUDNBS is a nonfluorescent compound and was synthesized via the one-step reaction of 4-methylumbelliferone (4-MU) with 2,4-dinitrobenzenesulfonyl chloride. Upon mixing with captopril in basic solution, the 2,4-dinitrobenzenesulfonyl group of 4-MUDNBS was efficiently removed and highly fluorescent 4-MU was released, hence leading to the dramatic fluorescence increase of the reaction solution. The fluorescence intensity is linear with captopril concentration in the range 3.0-500 ng mL(-1) with a detection limit of 2.2 ng mL(-1) (3sigma). The effect of substituents on the benzenesulfonyl moiety of the probe is discussed, and the presence of electronegative groups is favorable for the thiolate-induced cleavage reaction. The proposed method has been successfully applied to the captopril determination in pharmaceutical preparations.
Wang
Liping
L
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.
Yang
Xiao-Feng
XF
Zhao
Minglei
M
D001557:Benzenesulfonates / Q000138:chemical synthesis / Q000737:chemistry*; D002216:Captopril / Q000032:analysis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D006923:Hymecromone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D012680:Sensitivity and Specificity; D013056:Spectrophotometry, Ultraviolet; D013997:Time Factors
C543680:4-methylumbelliferyl-2, 4-dinitrobenzenesulfonate; D001557:Benzenesulfonates; D005456:Fluorescent Dyes; D006923:Hymecromone; D002216:Captopril