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Related Experiment Video

Updated: Dec 17, 2025

Synthesis and Calibration of Phosphorescent Nanoprobes for Oxygen Imaging in Biological Systems
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Fluorogenic Probe Using a Mislow-Evans Rearrangement for Real-Time Imaging of Hydrogen Peroxide.

Dianne Pham1, Upamanyu Basu1, Ivanna Pohorilets1

  • 1Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA, 15260, USA.

Angewandte Chemie (International Ed. in English)
|June 26, 2020
PubMed
Summary

Researchers developed a novel fluorogenic probe for rapid, real-time detection of hydrogen peroxide (H2 O2 ). This new chemical probe enables faster imaging of H2 O2 in biological systems, advancing wound healing research.

Keywords:
fluorescent probeoxidationperoxidesseleniumsigmatropic rearrangement

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Area of Science:

  • Biochemistry
  • Chemical Biology
  • Cell Biology

Background:

  • Hydrogen peroxide (H2 O2 ) is a key signaling molecule in biological processes like wound healing and inflammation.
  • Existing small-molecule probes for H2 O2 imaging are slow, requiring minutes for detection.
  • Protein-based probes offer rapid H2 O2 imaging but have limitations.

Purpose of the Study:

  • To develop a novel, fast-acting fluorogenic probe for selective detection of hydrogen peroxide.
  • To enable real-time imaging of endogenous H2 O2 in biological systems.
  • To overcome the kinetic limitations of existing small-molecule H2 O2 probes.

Main Methods:

  • A new fluorogenic probe was designed to undergo a [2,3]-sigmatropic rearrangement (seleno-Mislow-Evans rearrangement) with H2 O2.
  • The probe acts as a nucleophile, reacting rapidly with H2 O2 followed by acetal hydrolysis.
  • Real-time imaging was performed in endothelial cells and a zebrafish wound healing model.

Main Results:

  • The probe produces a green fluorescent signal within seconds of reacting with H2 O2.
  • Real-time imaging of H2 O2 in endothelial cells was achieved in as little as 8 seconds.
  • The probe successfully visualized H2 O2 dynamics during zebrafish wound healing.

Conclusions:

  • A novel nucleophilic fluorogenic probe enables unprecedented real-time imaging of H2 O2.
  • This probe overcomes the slow kinetics of previous small-molecule probes.
  • The developed probe offers a promising platform for endogenous H2 O2 detection in various biological contexts.