Fluorogenic Probe Using a Mislow–Evans Rearrangement for Real-Time Imaging of Hydrogen Peroxide |
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| Authors: | Dianne Pham Upamanyu Basu Ivanna Pohorilets Claudette M St Croix Simon C Watkins Kazunori Koide |
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| Institution: | 1. Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA, 15260 USA;2. Center for Biologic Imaging, Department of Cell Biology, University of Pittsburgh, 3500 Terrace Street, Pittsburgh, PA, 15261 USA |
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| Abstract: | Hydrogen peroxide (H2O2) mediates the biology of wound healing, apoptosis, inflammation, etc. H2O2 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 H2O2 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 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 H2O2 produced in endothelial cells in 8 seconds (much earlier than previously shown) and H2O2 in a zebrafish wound healing model. This work may provide a platform for endogenous H2O2 detection in real time with chemical probes. |
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| Keywords: | fluorescent probe oxidation peroxides selenium sigmatropic rearrangement |
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