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1,2‐Mannobioside Mimic: Synthesis, DC‐SIGN Interaction by NMR and Docking, and Antiviral Activity
Author(s) -
Reina José J.,
Sattin Sara,
Invernizzi Donatella,
Mari Silvia,
MartínezPrats Lorena,
Tabarani Georges,
Fieschi Franck,
Delgado Rafael,
Nieto Pedro M.,
Rojo Javier,
Bernardi Anna
Publication year - 2007
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200700047
Subject(s) - docking (animal) , dc sign , chemistry , disaccharide , lectin , in vivo , ligand (biochemistry) , combinatorial chemistry , in vitro , biochemistry , stereochemistry , biophysics , biology , immune system , receptor , dendritic cell , immunology , medicine , nursing , microbiology and biotechnology
The design and preparation of carbohydrate ligands for DC‐SIGN is a topic of high interest because of the role played by this C‐type lectin in immunity and infection processes. The low chemical stability of carbohydrates against enzymatic hydrolysis by glycosylases has stimulated the search for new alternatives more stable in vivo. Herein, we present a good alternative for a DC‐SIGN ligand based on a mannobioside mimic with a higher enzymatic stability than the corresponding disaccharide. NMR and docking studies have been performed to study the interaction of this mimic with DC‐SIGN in solution demonstrating that this pseudomannobioside is a good ligand for this lectin. In vitro studies using an infection model with Ebola pseudotyped virus demonstrates that this compound presents an antiviral activity even better than the corresponding disaccharide and could be an interesting ligand to prepare multivalent systems with higher affinities for DC‐SIGN with potential biomedical applications.