Tandem Payne/Dakin Reaction: A New Strategy for Hydrogen Peroxide Detection and Molecular Imaging

Hydrogen peroxide (H₂ O₂ ) has been recognized as one of the most significant ROS (reactive oxygen species) in human health and disease. Because of the intrinsic attributes of H₂ O₂ -such as its low reactivity under physiological pH-it is exceedingly challenging to develop small-molecule fluorescent probes with high selectivity and sensitivity for visualization of H₂ O₂ in an intricate biological milieu. To address this gap, a rationally designed tandem Payne/Dakin reaction is reported that is specific to molecular recognition of H₂ O₂ . New H₂ O₂ probes based on this unique chemical strategy can be easily synthesized by a general coupling reaction, and the practical applicability of those probes has been confirmed by the visualization of endogenously produced H₂ O₂ in living cells. In particular, starvation-induced H₂ O₂ production in mouse macrophages has been detected by the novel probe in both confocal imaging and flow cytometry. This tandem Payne/Dakin reaction provides a basis for developing more sophisticated molecular tools to interrogate H₂ O₂ functions in biological phenomena.