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Bioorg Med Chem. 2010 Nov 1;18(21):7439-45. doi: 10.1016/j.bmc.2010.09.003. Epub 2010 Sep 7.

Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity.

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Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, E-41012 Sevilla, Spain.


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.

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