BODIPY-based selenides as fluorescent probes for rapid, sensitive and mitochondria-specific detection of hypochlorous acid†
Hypochlorous acid (HClO) is a powerful microbicidal agent in the innate immue system; however, abnormal HClO levels can cause tissue damage and many diseases. Thus, it is vitally important to develop facile, rapid and accurate analytical methods for the detection of HClO/ClO− in vitro and in vivo. In this work, we have constructed three meso-substituted BODIPY selenides with different hydrocarbyl groups (ethyl for BSe-Et, benzyl for BSe-Bz and phenyl for BSe-Ph) as fluorescent probes for the detection of HClO/ClO−. All three non-fluorescent probes can sense HClO/ClO− to form fluorescent selenoxides by blocking the photo-induced electron transfer process. Their sensing properties display a clear relationship with the structure of the hydrocarbyl. The sensing reactivity is heavily dependent on the electron-donating ability of hydrocarbyls, with the order of the response time as BSe-Et (2 s) < BSe-Bz (5 s) ≪ BSe-Ph (>100 s). Both BSe-Et and BSe-Bz afford a large fluorescence response and very low detection limits (0.3 nM and 0.8 nM), and BSe-Bz displays a higher selectivity over BSe-Et. Finally, as a representative, BSe-Bz was successfully applied to the detection of exo- and endogenous HClO in living cells, and demonstrated to be a mitochondria-localized fluorescent probe.