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Coumarin Triazabutadienes for Fluorescent Labeling of Proteins
Author(s) -
Shadmehr Mehrdad,
Davis Garrett J.,
Mehari Bereketab T.,
Jensen Stephanie M.,
Jewett John C.
Publication year - 2018
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800599
Subject(s) - fluorophore , coumarin , chemistry , fluorescence , tyrosine , fluorescent labelling , biophysics , endosome , aryl , combinatorial chemistry , biochemistry , organic chemistry , biology , intracellular , physics , quantum mechanics , alkyl
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.