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Título : Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity
Autor : Aguilar Moncayo, Matilde, García Moreno, María Isabel, Stütz, Arnold E., García-Fernández, José Manuel, Wrodnigg, Tanja M., Ortiz-Mellet, Carmen
Palabras clave : Glycosidase inhibitors
Fluorescence resonance energy transfer
Fecha de publicación : 1-Oct-2010
Editor: Elsevier
Resumen: New fluorescently-labelled sp2-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 sp2-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.
Descripción : 7 páginas, 3 figuras, 1 tabla
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ISSN: 0960-894X
DOI: 10.1016/j.bmc.2010.09.003
Citación : Bioorganic and Medicinal Chemistry Letters 18(21): 7439-7445 (2010)
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