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

초록

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 H2O2. In this study, we developed a diaminonaphthalene (DAN)-protected boronic acid as a new ONOO- recognition group that selectively reacts with ONOO- over H2O2 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. Diaminonaphthalene (DAN)-protected boronic acid (DANBA) proved to be a universal and highly selective recognition group for ONOO- over H2O2 and other reactive oxygen species, overcoming the long-standing issues of aryl-boronic acid-based probes. DANBA can be combined with diverse hydroxyl-containing fluorophores to obtain ONOO- sensing probes with different spectral emissions. A DANBA and malononitrile fluorophore-based probe detected subtle changes in the ONOO- levels of mouse brains with Parkinson's disease. image

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