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Fluorogenic Cyclopropenones for Multicomponent, Real-Time Imaging.

Tyler K Heiss1, Robert S Dorn1, Andrew J Ferreira1

  • 1Department of Chemistry, University of California, Irvine, California 92697, United States.

Journal of the American Chemical Society
|April 20, 2022
PubMed
Summary
This summary is machine-generated.

New fluorogenic bioorthogonal reactions using cyclopropenones and phosphines enable real-time biomolecule visualization in live cells. This high signal-turn-on chemistry is ideal for cellular imaging and tracking biological targets.

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Area of Science:

  • Chemical Biology
  • Bioorthogonal Chemistry
  • Molecular Imaging

Background:

  • Fluorogenic bioorthogonal reactions are crucial for real-time biomolecule visualization.
  • Existing methods often lack compatibility with live cells due to cross-reactivity or low signal enhancement.
  • There is a need for novel chemistries with high signal-to-noise ratios for cellular imaging.

Purpose of the Study:

  • To develop a novel fluorogenic bioorthogonal reaction for live-cell imaging.
  • To create a reaction with high signal turn-on and minimal cross-reactivity.
  • To enable multicolor, real-time imaging applications.

Main Methods:

  • Development of cyclopropenone reporters and phosphine partners for a bioorthogonal reaction.
  • Investigation of the reaction mechanism involving regioselective activation and cyclization.
  • Evaluation of probe performance in vitro and within live cells.
  • Assessment of compatibility with other fluorogenic reactions for multicomponent imaging.

Main Results:

  • A new fluorogenic reaction between cyclopropenones and phosphines was established, forming coumarin products.
  • The reaction demonstrated a signal turn-on of over 1600-fold, one of the highest reported.
  • The developed bioorthogonal motifs were successfully validated in vitro and in cellular environments.
  • The chemistry proved compatible with other fluorogenic reactions, enabling simultaneous imaging.

Conclusions:

  • The cyclopropenone-phosphine reaction offers a highly efficient and sensitive method for bioorthogonal chemistry.
  • This reaction significantly advances the capabilities for real-time biomolecule tracking in native cellular settings.
  • The developed chemistry is a valuable tool for expanding the scope of live-cell imaging and multicomponent analyses.