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Updated: Jun 27, 2026

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging
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Tetrazine-based cycloadditions: application to pretargeted live cell imaging.

Neal K Devaraj1, Ralph Weissleder, Scott A Hilderbrand

  • 1Center for Systems Biology, Massachusetts General Hospital/Harvard Medical School Boston, Massachusetts 02114, USA.

Bioconjugate Chemistry
|December 5, 2008
PubMed
Summary

Bioorthogonal chemistry enables precise live cell labeling. Tetrazines rapidly and selectively target cancer cells, showing promise for in vivo imaging applications.

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Microfluidic On-chip Capture-cycloaddition Reaction to Reversibly Immobilize Small Molecules or Multi-component Structures for Biosensor Applications
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Microfluidic On-chip Capture-cycloaddition Reaction to Reversibly Immobilize Small Molecules or Multi-component Structures for Biosensor Applications

Published on: September 23, 2013

Area of Science:

  • Bioorthogonal chemistry
  • Chemical biology
  • Bioconjugation

Background:

  • Bioorthogonal reactions are crucial for labeling biomolecules in living systems.
  • Tetrazine cycloadditions offer rapid, selective, and high-yielding reactions in aqueous environments.
  • Targeting specific cell receptors like Her2/neu is vital for cancer research and diagnostics.

Purpose of the Study:

  • To investigate the utility of bioorthogonal tetrazine cycloadditions for live cell labeling.
  • To assess the efficiency and selectivity of norbornene-tetrazine reactions in a biological context.
  • To evaluate the potential of this chemistry for pretargeted imaging of cancer cells.

Main Methods:

  • Utilized bioorthogonal tetrazine cycloaddition chemistry.
  • Modified monoclonal antibodies targeting Her2/neu receptors with norbornene.
  • Conjugated tetrazines to a near-infrared fluorochrome.
  • Performed labeling experiments on live human breast cancer cells in the presence of serum.

Main Results:

  • Achieved irreversible cycloaddition between tetrazines and norbornene.
  • Demonstrated selective and rapid labeling of Her2/neu receptors on cancer cells.
  • Confirmed the reaction's effectiveness in aqueous media and serum.
  • Showcased successful pretargeting and labeling of cancer cells.

Conclusions:

  • Bioorthogonal tetrazine cycloadditions are highly effective for live cell labeling.
  • This chemistry is suitable for in vitro labeling and pretargeted imaging.
  • The approach shows significant potential for in vivo pretargeted imaging modalities.