Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F16%3A43901664" target="_blank" >RIV/60461373:22330/16:43901664 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.carres.2016.09.005" target="_blank" >http://dx.doi.org/10.1016/j.carres.2016.09.005</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.carres.2016.09.005" target="_blank" >10.1016/j.carres.2016.09.005</a>
Alternative languages
Result language
angličtina
Original language name
Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands
Original language description
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(alpha-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. (C) 2016 Elsevier Ltd. All rights reserved.
Czech name
—
Czech description
—
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Carbohydrate Research
ISSN
0008-6215
e-ISSN
—
Volume of the periodical
435
Issue of the periodical within the volume
29.11.2016
Country of publishing house
BE - BELGIUM
Number of pages
12
Pages from-to
7-18
UT code for WoS article
000389399200002
EID of the result in the Scopus database
2-s2.0-84988515876