Diaminonaphthalene Boronic Acid (DANBA): New Approach for Peroxynitrite Sensing Site

Abstract

Abstract Selective detection of reactive oxygen species (ROS) is vital for studying their role in brain diseases. Fluorescence probes can distinguish ONOO − species from other ROS; however, their selectivity toward ONOO − species depends on the ONOO − recognition group. Aryl‐boronic acids and esters, which are common ONOO − recognition groups, are not selective for ONOO − over H 2 O 2 . In this study, we developed a diaminonaphthalene (DAN)‐protected boronic acid as a new ONOO − recognition group that selectively reacts with ONOO − over H 2 O 2 and other ROS. Three DAN‐protected boronic acid (DANBA)‐based fluorophores that emit fluorescence over visible to near‐infrared (NIR) regions, Cou‐BN , BVP‐BN , and HDM‐BN , and their aryl‐boronic acid‐based counterparts ( Cou‐BO , BVP‐BO , and HDM‐BO ), were developed. The DANBA‐based probes exhibited enhanced selectivity toward ONOO − over that of their control group, as well as universality in solution assays and in vitro experiments with PC12 cells. The NIR‐emissive HDM‐BN was optimized to delineate in vivo ONOO − levels in mouse brains with Parkinson's disease. This DAN‐protected boronic acid belongs to a new generation of recognition groups for developing ONOO − probes, and this strategy could be extended to other common hydroxyl‐containing dyes to detect ONOO − levels in complex biological systems and processes.