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Coumarin Triazabutadienes for Fluorescent Labeling of Proteins.

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.

SUBMITTER: Shadmehr M

PROVIDER: S-EPMC6457986 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Coumarin Triazabutadienes for Fluorescent Labeling of Proteins.

Shadmehr Mehrdad M Davis Garrett J GJ Mehari Bereketab T BT Jensen Stephanie M SM Jewett John C JC

Chembiochem : a European journal of chemical biology 20181115 24

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 ...[more]

PMID: 30341988

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