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

2 Scopus citations

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)
Pages (from-to)2550-2552
Number of pages3
JournalChemBioChem
Volume19
Issue number24
DOIs
StatePublished - Dec 18 2018

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Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

Cite this

Shadmehr, M., Davis, G. J., Mehari, B. T., Jensen, S. M., & Jewett, J. C. (2018). Coumarin Triazabutadienes for Fluorescent Labeling of Proteins. ChemBioChem, 19(24), 2550-2552. https://doi.org/10.1002/cbic.201800599