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. 2020 Sep 28;59(40):17435-17441.
doi: 10.1002/anie.202007104. Epub 2020 Aug 6.

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

Dianne Pham  1 , Upamanyu Basu  1 , Ivanna Pohorilets  1 , Claudette M St Croix  2 , Simon C Watkins  2 , Kazunori Koide  1
Affiliations

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

Dianne Pham et al. Angew Chem Int Ed Engl. .

Abstract

Hydrogen peroxide (H2 O2 ) mediates the biology of wound healing, apoptosis, inflammation, etc. H2 O2 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 H2 O2 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 H2 O2 , 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 H2 O2 produced in endothelial cells in 8 seconds (much earlier than previously shown) and H2 O2 in a zebrafish wound healing model. This work may provide a platform for endogenous H2 O2 detection in real time with chemical probes.

Keywords: fluorescent probe; oxidation; peroxides; selenium; sigmatropic rearrangement.

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References

    1. None
    1. C. C. Winterbourn, Nat. Chem. Biol. 2008, 4, 278-286;
    1. H. Sies, D. P. Jones, Nat. Rev. Mol. Cell Biol. 2020, https://doi.org/10.1038/s41580-020-0230-0233.
    1. J. R. Stone, S. Yang, Antioxid. Redox Signaling 2006, 8, 243-270.
    1. None

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