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

Abstract

Hydrogen peroxide (H O ) has been recognized as one of the most significant ROS (reactive oxygen species) in human health and disease. Because of the intrinsic attributes of H O -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 H O 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 H O . New H O 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 H O in living cells. In particular, starvation-induced H O 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 H O functions in biological phenomena.

Fluorogenic Probe Using a Mislow–Evans Rearrangement for Real‐Time Imaging of Hydrogen Peroxide

“…Generally, chemical probes for H 2 O 2 detect endogenously produced H 2 O 2 later times (ca. 30 min) . In the zebrafish tail wounding model, we observed the rapid generation of H 2 O 2 near the wound site in real time using selenide 1 , recapitulating the results using a protein‐based probe …”

“…When these probes were applied in biological systems, it took ca. 30 min to produce fluorescence signals …”

Sensors, Imaging Agents, and Theranostics to Help Understand and Treat Reactive Oxygen Species Related Diseases

“…The probe was able to image H 2 O 2 stimulated by phorbol myristate acetate (PMA) in RAW 264.7 cells ( Figure ). Duan and co‐workers developed a photostable probe based on an arylboronic ester for the imaging of A549 cells, while Yang and co‐workers reported a new “turn‐on” probe based on the tandem Payne/Dakin reaction, enabling the fluorescence imaging of H 2 O 2 in RAW264.7 microphages. The in vivo imaging of H 2 O 2 was realized by Liu and co‐workers .…”

Enzyme and AIEgens Modulated Solid‐State Nanochannels: In Situ and Noninvasive Monitoring of H2O2 Released from Living Cells

“…Herein, we take one of the reactive oxygen species (ROS), hydrogen peroxide (H 2 O 2 ), as a model target to establish an in situ and noninvasive functionalized solid‐state nanochannels device . This new strategy aims to detect H 2 O 2 released from living cells based on functionalized solid‐state nanochannels without living cells insertion procedure.…”

“…Herein, we take one of the reactive oxygen species (ROS), hydrogen peroxide (H 2 O 2 ), as a model target to establish an in situ and noninvasive functionalized solid-state nanochannels device. [56][57][58][59][60] This new strategy aims to detect H 2 O 2 released from living cells based on functionalized solid-state nanochannels without living cells insertion procedure. Aggregationinduced emission luminogens (AIEgens, a class of luminogens, which are emitting strong fluorescence in aggregated state) with enzyme-responsive linkage property were utilized in this strategy.…”