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Derivatives of coumarin, containing oxidant-sensitive boronate group, were recently developed for fluorescent detection of inflammatory oxidants. Here, we report the synthesis and the characterization of 3-(2-benzothiazolyl)-7-coumarin boronic acid pinacol ester ( BC-BE ) as a fluorescent probe for the detection of peroxynitrite (ONOO - ), with high stability and a fast response time. The BC-BE probe hydrolyzes in phosphate buffer to 3-(2-benzothiazolyl)-7-coumarin boronic acid ( BC-BA ) which is stable in the solution even after a prolonged incubation time (24 h). BC-BA is slowly oxidized by H 2 O 2 to form the phenolic product, 3-benzothiazol-2-yl-7-hydroxy-chromen-2-one ( BC-OH ). On the other hand, the BC-BA probe reacts rapidly with ONOO - . The ability of the BC-BA probe to detect ONOO - was measured using both authentic ONOO - and the system co-generating steady-state fluxes of O 2  •  - and • NO. BC-BA is oxidized by ONOO - to BC-OH . However, in this reaction 3-benzothiazol-2-yl-chromen-2-one ( BC-H ) is formed in the minor pathway, as a peroxynitrite-specific product. BC-OH is also formed in the reaction of BC-BA with HOCl, and subsequent reaction of BC-OH with HOCl leads to the formation of a chlorinated phenolic product, which could be used as a specific product for HOCl. We conclude that BC-BA shows potential as an improved fluorescent probe for the detection of peroxynitrite and hypochlorite in biological settings. Complementation of the fluorescence measurements by HPLC-based identification of oxidant-specific products will help to identify the oxidants detected.

Novel Boronate Probe Based on 3-Benzothiazol-2-yl-7-hydroxy-chromen-2-one for the Detection of Peroxynitrite and Hypochlorite