Coumarin Triazabutadienes for Fluorescent Labeling of Proteins

Mehrdad Shadmehr, Garrett J. Davis, Bereketab T. Mehari, Stephanie M. Jensen, John C Jewett

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The use of small-molecule fluorophores to label proteins with minimal perturbation in response to an external stimulus is a powerful tool to probe chemical and biochemical environments. Herein, we describe the use of a coumarin-modified triazabutadiene that can deliver aryl diazonium ions to fluorescently label proteins by tyrosine-selective modification. The labeling can be triggered by low-pH-induced liberation of the diazonium species, thus making the fluorophore especially useful in labeling biochemical surroundings such as those found within the late endosome. Additionally, we show that a variety of coumarin triazabutadienes might also be prone to releasing their diazonium cargo after irradiation with UV light.

Original languageEnglish (US)
JournalChemBioChem
DOIs
StateAccepted/In press - Jan 1 2018

Fingerprint

Fluorophores
Labeling
Labels
Endosomes
Ultraviolet Rays
Ultraviolet radiation
Tyrosine
Proteins
Irradiation
Ions
Molecules
coumarin

Keywords

  • electrophilic substitution
  • fluorescent probes
  • protecting groups
  • protein modifications
  • substituent effects

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

Cite this

Coumarin Triazabutadienes for Fluorescent Labeling of Proteins. / Shadmehr, Mehrdad; Davis, Garrett J.; Mehari, Bereketab T.; Jensen, Stephanie M.; Jewett, John C.

In: ChemBioChem, 01.01.2018.

Research output: Contribution to journalArticle

Shadmehr, Mehrdad ; Davis, Garrett J. ; Mehari, Bereketab T. ; Jensen, Stephanie M. ; Jewett, John C. / Coumarin Triazabutadienes for Fluorescent Labeling of Proteins. In: ChemBioChem. 2018.
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