Fluorogenic Probe Using a Mislow–Evans Rearrangement for Real‐Time Imaging of Hydrogen Peroxide
Dianne Pham, Upamanyu Basu, Ivanna Pohorilets, Claudette M. St. Croix, Simon C. Watkins, Kazunori Koide
Abstract
Abstract Hydrogen peroxide (H 2 O 2 ) mediates the biology of wound healing, apoptosis, inflammation, etc. H 2 O 2 has been fluorometrically imaged with protein‐ or small‐molecule‐based probes. However, only protein‐based probes have afforded temporal insights within seconds. Small‐molecule‐based electrophilic probes for H 2 O 2 require many minutes for a sufficient response in biological systems. Here, we report a fluorogenic probe that selectively undergoes a [2,3]‐sigmatropic rearrangement (seleno‐Mislow‐Evans rearrangement) with H 2 O 2 , followed by acetal hydrolysis, to produce a green fluorescent molecule in seconds. Unlike other electrophilic probes, the current probe acts as a nucleophile. The fast kinetics enabled real‐time imaging of H 2 O 2 produced in endothelial cells in 8 seconds (much earlier than previously shown) and H 2 O 2 in a zebrafish wound healing model. This work may provide a platform for endogenous H 2 O 2 detection in real time with chemical probes.