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

作者:Sun, Xiaolong; Xu, Qingling; Kim, Gyoungmi; Flower, Stephen E.; Lowe, John P.; Yoon, Juyoung*; Fossey, John S.; Qian, Xuhong; Bull, Steven D.; James, Tony D.
来源:Chemical Science, 2014, 5(9): 3368-3373.
DOI:10.1039/c4sc01417k

摘要

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 o-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 o-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.