A water-soluble BODIPY-based fluorescent probe for rapid and selective detection of hypochlorous acid in living cells.

We designed and synthesized 4,4-di-(4'-methylmercaptophenoxy)-8-(N-methylpyridinium-2-yl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (probe 1) as a water-soluble BODIPY derivative for rapid and selective detection of hypochlorous acid. The pyridinium-2-yl linked at the meso position of BODIPY core was used to maintain highly fluorescent nature and to increase water solubility. Methylmercaptophenoxy was selected as responsive site installed on the boron atom (to replace the fluorine atom) and induced the photoinduced electron-transfer (PeT) effect to quench the fluorescence of BODIPY. The probe exhibited 83.9 μg mL solubility in PBS (10 mM, pH 7.4), and possessed very low fluorescence (Φ = 0.0013). Upon addition of HClO, the probe could display a distinct response in 1 min and generate marked fluorescence enhancement by 100-fold due to the oxidation of thioether into sulfoxide to terminate PeT process. A limit of detection of 53 nM was calculated for HClO in the linear response range from 0 μM to 10 μM, and the probe was successfully applied to image HClO in living cells.