Bambus[4,6]urils as Dual Scaffolds for Multivalent Iminosugar Presentation and Ion Transport: Access to Unprecedented Glycosidase-Directed Anion Caging Agents.
CuAAC
DNJ
bambusuril
enzyme inhibition
iminosugars
multivalency
α-mannosidase
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
26 Jul 2022
26 Jul 2022
Historique:
received:
29
06
2022
revised:
19
07
2022
accepted:
21
07
2022
entrez:
28
7
2022
pubmed:
29
7
2022
medline:
30
7
2022
Statut:
epublish
Résumé
Bambusurils, BU[4] and BU[6], were used for the first time as multivalent scaffolds to link glycosidases inhibitors derived from 1-deoxynojirimycin (DNJ). Two linear DNJ ligands having six or nine carbon alkyl azido linkers or a trivalent DNJ dendron were grafted onto octapropargylated BU[4] and dodecapropargylated BU[6] using copper-catalyzed cycloaddition (CuAAC) to yield corresponding neoglycobambus[4] and neoglycobambus[6]urils bearing 8 to 24 iminosugars. The inhibition potencies of neoglycoBU[4], neoglycoBU[6] and neoglycoBU[6] caging anions were evaluated against Jack Bean α-mannosidase and compared to monovalent DNJ derivatives. Strong affinity enhancements per inhibitory head were obtained for the clusters holding trivalent dendrons with inhibitory constants in the nanomolar range (
Identifiants
pubmed: 35897947
pii: molecules27154772
doi: 10.3390/molecules27154772
pmc: PMC9330389
pii:
doi:
Substances chimiques
Anions
0
Enzyme Inhibitors
0
Imino Sugars
0
1-Deoxynojirimycin
19130-96-2
Glycoside Hydrolases
EC 3.2.1.-
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : University of Strasbourg
ID : no
Organisme : Centre National de la Recherche Scientifique
ID : no
Organisme : CEA
ID : no
Organisme : Chinese scholarship council
ID : no
Organisme : icFRC
ID : PCO-003-2016
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