title: Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain.
abstract: A series of neoglycoconjugates derived from deoxynojirimycin has been prepared by click connection with functionalised adamantanes. They have been assayed as glycosidase inhibitors, as inhibitors of the glycoenzymes relevant to the treatment of Gaucher disease, as well as correctors of the defective ion-transport protein involved in cystic fibrosis. We have demonstrated that it is possible to selectively either strongly inhibit ER-α-glucosidases and ceramide glucosyltransferase or restore the activity of CFTR in CF-KM4 cells by varying the length of the alkyl chain linking DNJ and adamantane.
authors.affiliation: CNRS and Univ. Paris Sud, Glycochimie Moléculaire et Macromoléculaire, ICMMO, UMR 8182, Orsay, F-91405, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Ardes-Guisot
authors.forename: Dominic S
authors.initials: DS
authors.lastname: Alonzi
authors.forename: Gabriele
authors.initials: G
authors.lastname: Reinkensmeier
authors.forename: Terry D
authors.initials: TD
authors.lastname: Butters
authors.forename: Caroline
authors.initials: C
authors.lastname: Norez
authors.forename: Frédéric
authors.initials: F
authors.lastname: Becq
authors.forename: Yousuke
authors.initials: Y
authors.lastname: Shimada
authors.forename: Shinpei
authors.initials: S
authors.lastname: Nakagawa
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
authors.forename: Boris
authors.initials: B
authors.lastname: Vauzeilles
mesh_terms: D017485:1-Deoxynojirimycin / Q000737:chemistry*; D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry*; D002460:Cell Line; D002851:Chromatography, High Pressure Liquid; D057930:Click Chemistry; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D006001:Glycoconjugates / Q000737:chemistry*; D018922:HL-60 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D051381:Rats; D054852:Small Molecule Libraries / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D006001:Glycoconjugates; D054852:Small Molecule Libraries; D017485:1-Deoxynojirimycin