A Double-Clicking Bis-Azide Fluorogenic Dye for Bioorthogonal Self-Labeling Peptide Tags

Orsolya Demeter, Eszter A. Fodor, Mihály Kállay, Gábor Mez, Krisztina Németh, Pál T. Szabó, Péter Kele

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Herein, we give the very first example for the development of a fluorogenic molecular probe that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. This proof-of-principle study reports on the synthesis and fluorogenic characterization of a new, double-quenched, bis-azide fluorogenic probe suitable for bioorthogonal two-point tagging of small peptide tags by double strain-promoted azide-alkyne cycloaddition. The presented probe exhibits remarkable increase in fluorescence intensity when reacted with bis-cyclooctynylated peptide sequences, which could also serve as possible self-labeling small peptide tag motifs. The first example of a fluorogenic molecular probe has been developed that combines the two-point binding specificity of biarsenical-based dyes with the robustness of bioorthogonal click-chemistry. The new, double-quenched, bis-azide fluorogenic probe can bind to small bis-cyclooctynylated peptide tags through a double strain-promoted click reaction (see figure; SPAAC=strain-promoted alkyne-azide cycloaddition). The probe exhibits remarkable increase in fluorescence intensity with peptide sequences that can serve as possible self-labeling small peptide tags.

Original languageEnglish
Pages (from-to)6382-6388
Number of pages7
JournalChemistry - A European Journal
Volume22
Issue number18
DOIs
Publication statusPublished - Apr 25 2016

Keywords

  • click chemistry
  • cycloaddition
  • dyes/pigments
  • fluorescent probes
  • peptides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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