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A 4-Methylumbelliferone-based fluorescent probe for the sensitive detection of captopril

Journal of Fluorescence, ISSN: 1053-0509, Vol: 19, Issue: 4, Page: 593-599
2009
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Article Description

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 with a detection limit of 2.2 ng mL (3σ). 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. © 2008 Springer Science+Business Media, LLC.

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