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Thiol-selective fluorogenic probes for labeling and release.

Vu Hong1, Alexander A Kislukhin, M G Finn

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Journal of the American Chemical Society
|July 23, 2009
PubMed
Summary
This summary is machine-generated.

Researchers developed novel 7-oxanorbornadiene (OND) probes for selective and fluorogenic labeling of thiols in aqueous solutions. These probes offer high reactivity and enable sensitive detection of thiols in peptides and proteins.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Biochemistry

Background:

  • Thiol alkylation is crucial for protein labeling.
  • Existing methods may lack selectivity or require specific conditions.
  • Development of efficient and versatile thiol-reactive probes is needed.

Purpose of the Study:

  • To introduce a new class of 7-oxanorbornadiene (OND) based probes.
  • To achieve selective, fluorogenic labeling of thiols in aqueous solution at neutral pH.
  • To explore the cleavage mechanisms and versatility of the resulting adducts.

Main Methods:

  • Synthesis of 7-oxanorbornadiene (OND) derivatives with dansyl fluorophores.
  • Investigation of thiol addition kinetics and fluorescence enhancement.
  • Analysis of retro-Diels-Alder fragmentation and succinimide formation.
  • Chemoselective labeling of thiols in peptides and proteins.

Main Results:

  • OND probes exhibit high reactivity (40-200 M(-1) s(-1)) and selectivity towards thiols.
  • Fluorescence intensity increases up to 180-fold upon thiol addition.
  • Adducts allow for cleavage via retro-Diels-Alder or succinimide formation, enabling alcohol release.
  • Successful labeling of proteins and peptides with OND electrophiles.

Conclusions:

  • The OND framework provides a versatile platform for developing reactive and fluorogenic thiol probes.
  • These probes enable sensitive detection and labeling of thiols in biological systems.
  • The modular nature of OND linkers allows for further functionalization and attachment of other molecules.