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Chembiochem. 2010 Sep 24;11(14):2026-33. doi: 10.1002/cbic.201000192.

Fluorous iminoalditols: a new family of glycosidase inhibitors and pharmacological chaperones.

Author information

1
Glycogroup, Deparment of Organic Chemistry, Graz University of Technology, 8010 Graz, Austria.

Abstract

A collection of new reversible glycosidase inhibitors of the iminoalditol type featuring N-substituents containing perfluorinated regions has been prepared for evaluation of physicochemical, biochemical and diagnostic properties. The vast variety of feasible oligofluoro moieties allows for modular approaches to customised structures according to the intended applications, which are influenced by the fluorine content as well as the distance of the fluorous moiety from the ring nitrogen. The first examples, in particular in the D-galacto series, exhibited excellent inhibitory activities. A preliminary screen with two human cell lines showed that, at subinhibitory concentrations, they are powerful pharmacological chaperones enhancing the activities of the catalytically handicapped lysosomal D-galactosidase mutants associated with GM1 gangliosidosis and Morquio B disease.

PMID:
20715263
PMCID:
PMC3198847
DOI:
10.1002/cbic.201000192
[Indexed for MEDLINE]
Free PMC Article

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