A fluorogenic probe for the catalyst-free detection of azide-tagged molecules

Frédéric Friscourt, Christoph J Fahrni, Geert-Jan Boons

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Fluorogenic reactions in which non- or weakly fluorescent reagents produce highly fluorescent products can be exploited to detect a broad range of compounds including biomolecules and materials. We describe a modified dibenzocyclooctyne that under catalyst-free conditions undergoes fast strain-promoted cycloadditions with azides to yield strongly fluorescent triazoles. The cycloaddition products are more than 1000-fold brighter compared to the starting cyclooctyne, exhibit large Stokes shift, and can be excited above 350 nm, which is required for many applications. Quantum mechanical calculations indicate that the fluorescence increase upon triazole formation is due to large differences in oscillator strengths of the S(0) ↔ S(1) transitions in the planar C(2v)-symmetric starting material compared to the symmetry-broken and nonplanar cycloaddition products. The new fluorogenic probe was successfully employed for labeling of proteins modified by an azide moiety.

Original languageEnglish
Pages (from-to)18809-15
Number of pages7
JournalJournal of the American Chemical Society
Volume134
Issue number45
DOIs
Publication statusPublished - 14 Nov 2012
Externally publishedYes

Keywords

  • Azides
  • Cyclization
  • Fluorescent Dyes
  • Molecular Structure
  • Quantum Theory
  • Triazoles

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