Exploring calixarene-based clusters for efficient functional presentation of Streptococcus pneumoniae saccharides.
Calixarenes
Multivalent ligands
Saccharide antigens
Serotype 19F
Streptococcus pneumoniae
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
12 2019
12 2019
Historique:
received:
18
07
2019
revised:
17
09
2019
accepted:
19
09
2019
pubmed:
7
10
2019
medline:
21
10
2020
entrez:
7
10
2019
Statut:
ppublish
Résumé
Calixarenes are promising scaffolds for an efficient clustered exposition of multiple saccharide antigenic units. Herein we report the synthesis and biological evaluation of a calix[6]arene functionalized with six copies of the trisaccharide repeating unit of Streptococcus pneumoniae (SP) serotype 19F. This system has demonstrated its ability to efficiently inhibit the binding between the native 19F capsular polysaccharide and anti-19F antibodies, despite a low number of exposed saccharide antigens, well mimicking the epitope presentations in the polysaccharide. The calix[6]arene mobile scaffold has been selected for functionalization with SP 19F repeating unit after a preliminary screening of four model glycocalixarenes, functionalized with N-acetyl mannosamine, and differing in the valency and/or conformational properties. This work is a step forward towards the development of new fully synthetic calixarenes comprising small carbohydrate antigens as potential carbohydrate-based vaccine scaffolds.
Identifiants
pubmed: 31586712
pii: S0045-2068(19)31141-1
doi: 10.1016/j.bioorg.2019.103305
pii:
doi:
Substances chimiques
Antibodies, Bacterial
0
Carbohydrates
0
Epitopes
0
Phenols
0
calix(6)arene
0
Calixarenes
130036-26-9
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
103305Informations de copyright
Copyright © 2019 Elsevier Inc. All rights reserved.