A water-soluble boronate-based fluorescent probe for the selective detection of peroxynitrite and imaging in living cells

Abstract

A water-soluble boronate-based fluorescent probe was evaluated for the detection of peroxynitrite (ONOO⁻) in the presence of a monosaccharide. The enhanced fluorescence of the probe when bound with D-fructose was switched off in the presence of peroxynitrite. In contrast, other reactive oxygen/nitrogen species (ROS/RNS) led to only slight fluorescence decreases due to protection by an internal N–B interaction. The interaction of the probe with D-fructose not only strengthens the fluorescence signal, but also protects the boronic acid from oxidation by other ROS/RNS. Therefore, under conditions generating various ROS/RNS, the boronate-based saccharide complex preferentially reacts with peroxynitrite. The probe was used in cell imaging experiments for the detection of endogenous and exogenous peroxynitrite. The sensor displays good “on–off” responses towards peroxynitrite, both in RAW 264.7 cells and HeLa cells.