Bistetrazine-Cyanines as Double-Clicking Fluorogenic Two-Point Binder or Crosslinker Probes

Attila Kormos, Christine Koehler, Eszter A. Fodor, Zsófia R. Rutkai, Madison E. Martin, G. Mező, Edward A. Lemke, P. Kele

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Fluorogenic probes can be used to minimize the background fluorescence of unreacted and nonspecifically adsorbed reagents. The preceding years have brought substantial developments in the design and synthesis of bioorthogonally applicable fluorogenic systems mainly based on the quenching effects of azide and tetrazine moieties. The modulation power exerted by these bioorthogonal motifs typically becomes less efficient on more conjugated systems; that is, on probes with redshifted emission wavelength. To reach efficient quenching, that is, fluorogenicity, even in the red range of the spectrum, we present the synthesis, fluorogenic, and conjugation characterization of bistetrazine-cyanine probes with emission maxima between 600 and 620nm. The probes can bind to genetically altered proteins harboring an 11-amino acid peptide tag with two appending cyclooctyne motifs. Moreover, we also demonstrate the use of these bistetrazines as fluorogenic, covalent cross-linkers between monocyclooctynylated proteins.

Original languageEnglish
JournalChemistry - A European Journal
DOIs
Publication statusAccepted/In press - Jan 1 2018

Fingerprint

Binders
Quenching
Proteins
Azides
Peptides
Amino acids
Fluorescence
Modulation
Amino Acids
Wavelength

Keywords

  • Bioorthogonal
  • Dyes/pigments
  • Fluorescence
  • Fluorogenic probes
  • Noncanonical amino acid
  • Peptides

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Bistetrazine-Cyanines as Double-Clicking Fluorogenic Two-Point Binder or Crosslinker Probes. / Kormos, Attila; Koehler, Christine; Fodor, Eszter A.; Rutkai, Zsófia R.; Martin, Madison E.; Mező, G.; Lemke, Edward A.; Kele, P.

In: Chemistry - A European Journal, 01.01.2018.

Research output: Contribution to journalArticle

Kormos, Attila ; Koehler, Christine ; Fodor, Eszter A. ; Rutkai, Zsófia R. ; Martin, Madison E. ; Mező, G. ; Lemke, Edward A. ; Kele, P. / Bistetrazine-Cyanines as Double-Clicking Fluorogenic Two-Point Binder or Crosslinker Probes. In: Chemistry - A European Journal. 2018.
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AU - Martin, Madison E.

AU - Mező, G.

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