Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Carbohydrate Research

ISSN

0008-6215

e-ISSN

—

Svazek periodika

435

Číslo periodika v rámci svazku

29.11.2016

Stát vydavatele periodika

BE - Belgické království

Počet stran výsledku

12

Strana od-do

7-18

Kód UT WoS článku

000389399200002

EID výsledku v databázi Scopus

2-s2.0-84988515876