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Closed Access item Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity

Authors:Aguilar Moncayo, Matilde
García Moreno, María Isabel
Stütz, Arnold E.
García-Fernández, José Manuel
Wrodnigg, Tanja M.
Ortiz-Mellet, Carmen
Keywords:Glycosidase inhibitors, Fluorescence resonance energy transfer, FRET, Iminosugars, Photolabeling
Issue Date:1-Oct-2010
Publisher:Elsevier
Citation:Bioorganic and Medicinal Chemistry Letters 18(21): 7439-7445 (2010)
Abstract: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.
Description:7 páginas, 3 figuras, 1 tabla
Publisher version (URL):http://dx.doi.org/10.1016/j.bmc.2010.09.003
URI:http://hdl.handle.net/10261/36183
ISSN:0960-894X
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Appears in Collections:(IIQ) Artículos

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