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Proc Natl Acad Sci U S A. 2013 Feb 12;110(7):2466-71. doi: 10.1073/pnas.1222183110. Epub 2013 Jan 28.

Cell-permeable probe for identification and imaging of sialidases.

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1
Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.

Abstract

Alkyne-hinged 3-fluorosialyl fluoride (DFSA) containing an alkyne group was shown to be a mechanism-based target-specific irreversible inhibitor of sialidases. The ester-protected analog DFSA (PDFSA) is a membrane-permeable precursor of DFSA designed to be used in living cells, and it was shown to form covalent adducts with virus, bacteria, and human sialidases. The fluorosialyl-enzyme adduct can be ligated with an azide-annexed biotin via click reaction and detected by the streptavidin-specific reporting signals. Liquid chromatography-mass spectrometry/mass spectrometry analysis on the tryptic peptide fragments indicates that the 3-fluorosialyl moiety modifies tyrosine residues of the sialidases. DFSA was used to demonstrate influenza infection and the diagnosis of the viral susceptibility to the anti-influenza drug oseltamivir acid, whereas PDFSA was used for in situ imaging of the changes of sialidase activity in live cells.

PMID:
23359711
PMCID:
PMC3574955
DOI:
10.1073/pnas.1222183110
[Indexed for MEDLINE]
Free PMC Article
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