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Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands
B. Bertolotti, B. Oroszová, I. Sutkeviciute, L. Kniežo, F. Fieschi, K. Parkan, Z. Lovyová, M. Kašáková, J. Moravcová,
Jazyk angličtina Země Nizozemsko
Typ dokumentu časopisecké články
- MeSH
- biomimetika MeSH
- fukosa chemie MeSH
- glykosidy chemická syntéza chemie MeSH
- lektiny typu C chemie metabolismus MeSH
- lidé MeSH
- mannosa chemie MeSH
- molekulární struktura MeSH
- molekuly buněčné adheze chemie metabolismus MeSH
- receptory buněčného povrchu chemie metabolismus MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
The discovery of effective ligands for DC-SIGN receptor is one of the most challenging concepts of antiviral drug design due to the importance of this C-type lectin in infection processes. DC-SIGN recognizes mannosylated and fucosylated oligosaccharides but glycosidic linkages are accessible to both chemical and enzymatic degradations. To avoid this problem, the synthesis of stable glycoside mimetics has attracted increasing attention. In this work we establish for the first time mono- and divalent C-glycosides based on d-manno and l-fuco configurations as prospective DC-SIGN ligands. In particular, the l-fucose glycomimetics were more active than the respective d-mannose ones. The highest affinity was assessed for simple 1,4-bis(α-l-fucopyranosyl)butane (SPR: IC50 0.43 mM) that displayed about twice higher activity than natural ligand Le(x). Our results make C-glycosides attractive candidates for multivalent presentations.
CEA IBS F 38044 Grenoble France
CNRS IBS F 38044 Grenoble France
University Grenoble Alpes Institut de Biologie Structurale F 38044 Grenoble France
Citace poskytuje Crossref.org
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