Document Detail

Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity.
MedLine Citation:
PMID:  20889348     Owner:  NLM     Status:  In-Process    
New fluorescently-labelled sp(2)-iminosugars based on the 5N,6S-[N'-(4-aminobutyl)iminomethylidene]-6-thionojirimycin skeleton have been synthesized as photoprobes to monitor glycosidase binding. Dansyl, dapoxyl and coumarin fluorophores were appended to the terminal amino group at the N'-substituent by either sulfonamide or amide bridging reaction. All the conjugates behaved as strong (low micromolar to nanomolar) and selective inhibitors of β-glucosidases (almonds and bovine liver) and naringinase, in agreement with the inhibition pattern previously encountered for related iso(thio)urea-type bicyclic sp(2)-iminosugars. The presence of the fluorescent probe allows real-time and continuous monitoring of β-glucosidase inhibition by fluorescence resonance energy transfer (FRET), taking advantage of the intrinsic tryptophan-associated fluorescence of the protein.
Matilde Aguilar-Moncayo; M Isabel García-Moreno; Arnold E Stütz; José M García Fernández; Tanja M Wrodnigg; Carmen Ortiz Mellet
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-09-07
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  18     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-10-18     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  7439-45     Citation Subset:  IM    
Copyright Information:
Copyright © 2010 Elsevier Ltd. All rights reserved.
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, E-41012 Sevilla, Spain.
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