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Pham, Dianne; Basu, Upamanyu; Pohorilets, Ivanna; St Croix, Claudette M.; Watkins, Simon C.; Koide, Kazunori (, Angewandte Chemie International Edition)Abstract Hydrogen peroxide (H2O2) mediates the biology of wound healing, apoptosis, inflammation, etc. H2O2has 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 H2O2require 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 H2O2, 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 H2O2produced in endothelial cells in 8 seconds (much earlier than previously shown) and H2O2in a zebrafish wound healing model. This work may provide a platform for endogenous H2O2detection in real time with chemical probes.more » « less
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Garner, Amanda L.; St Croix, Claudette M.; Pitt, Bruce R.; Leikauf, George D.; Ando, Shin; Koide, Kazunori (, Nature Chemistry)null (Ed.)
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