Biological hydrogen peroxide detection with aryl boronate and benzil BODIPY-based fluorescent probes

Abstract The detection of hydrogen peroxide (H 2 O 2 ) using fluorescent probes is critical to the study of oxidative stress in biological environments. Two important sensing architectures for detecting H 2 O 2 , aryl boronates and benzils, are compared here using novel boron-dipyrromethene (BODIPY) fluorescent probes. The aryl boronate PeroxyBODIPY-1 ( PB1 ) and benzil-based nitrobenzoylBODIPY ( NbzB ) were synthesised from a common BODIPY intermediate in order to compare sensitivity and selectivity to H 2 O 2 . The aryl boronate PB1 gives the highest change in fluorescence on reaction with H 2 O 2 while the benzil NbzB exhibits exclusive selectivity for H 2 O 2 over other reactive oxygen species (ROS). Both proved to be cell-permeable, with PB1 being able to detect H 2 O 2 in denuded bovine oocytes. The strengths of these aryl boronate and benzil probes can now be exploited concurrently to elucidate biological mechanisms of H 2 O 2 production and oxidative stress.