An arylboronate-based fluorescent probe for selective and sensitive detection of peroxynitrite and its applications for fluorescence imaging in living cells

Peroxynitrite (ONOO-) is an extremely reactive oxygen species in biological systems, and can react with a wide variety of molecular targets including proteins, lipids, and nucleic acids, eventually resulting in mitochondria dysfunction and cell death. In this work, we designed and synthesized a new arylboronate-based fluorescent probe, which could detect ONOO- with a big fluorescence off-on ratio (155-fold), fast response rate (50 s), high sensitivity (detection limit:0.83 nM), and excellent selectivity over a series of biologically relevant reactive oxygen species as well as anions, cations, and biothiols. The sensing mechanism has proved to be the ONOO--triggered covalent assembly of a bright iminocourmarin fluorophore. With the probe, the stimulation-induced ONOO- in RAW264.7 murine macrophages as well as the endogenous ONOO- in endothelial cells after oxygen-glucose deprivation (OGD) has been successfully visualized. (C) 2016 Elsevier B.V. All rights reserved.