Chemoselective ratiometric imaging of protein S-sulfenylation

Here we report a ratiometric fluorescent probe for chemoselective conjugation to sulfenic acids in living cells. Our approach couples an α-fluoro-substituted dimedone to an aminonaphthalene fluorophore (F-DiNap), which upon sulfenic acid conjugation is locked as the 1,3-diketone, changing the fluoro...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017-06, Vol.53 (53), p.7385-7388
Main Authors: Tom, Christopher T M B, Crellin, John E, Motiwala, Hashim F, Stone, Matthew B, Davda, Dahvid, Walker, William, Kuo, Yu-Hsuan, Hernandez, Jeannie L, Labby, Kristin J, Gomez-Rodriguez, Lyanne, Jenkins, Paul M, Veatch, Sarah L, Martin, Brent R
Format: Article
Language:English
Subjects:
Cells (biology)
Chemical compounds
Conjugation
Couples
Equivalence
Fluorescence
Imaging
Proteins
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Summary:Here we report a ratiometric fluorescent probe for chemoselective conjugation to sulfenic acids in living cells. Our approach couples an α-fluoro-substituted dimedone to an aminonaphthalene fluorophore (F-DiNap), which upon sulfenic acid conjugation is locked as the 1,3-diketone, changing the fluorophore excitation. F-DiNap reacts with S-sulfenylated proteins at equivalent rates to current probes, but the α-fluorine substitution blocks side-reactions with biological aldehydes.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc02285a