Series of multivalent α-l-fucoside containing glycoclusters and variously decorated l-fucosides were synthesized to find potential inhibitors of fucose-specific lectins and study the structure-binding affinity relationships. Tri- and tetravalent fucoclusters were built using copper-mediated azide-alkyne click chemistry. Series of fucoside monomers and dimers were synthesized using various methods, namely glycosylation, an azide-alkyne click reaction, photoinduced thiol-en addition, and sulfation. The interactions between compounds with six fucolectins of bacterial or fungal origin were tested using a hemagglutination inhibition assay. As a result, a tetravalent, α-l-fucose presenting glycocluster showed to be a ligand that was orders of magnitude better than a simple monosaccharide for tested lectins in most cases, which can nominate it as a universal ligand for studied lectins. This compound was also able to inhibit the adhesion of Pseudomonas aeruginosa cells to human epithelial bronchial cells. A trivalent fucocluster with a protected amine functional group also seems to be a promising candidate for designing glycoconjugates and chimeras.
- Klíčová slova
- cystic fibrosis, glycoclusters, hemagglutination, l-fucosides, lectins, multivalency,
- MeSH
- bakteriální proteiny chemie metabolismus MeSH
- fukosa chemie metabolismus MeSH
- fungální proteiny chemie metabolismus MeSH
- hemaglutinace MeSH
- lektiny chemie metabolismus MeSH
- lidé MeSH
- testy inhibice hemaglutinace MeSH
- vazba proteinů MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- bakteriální proteiny MeSH
- fucose-binding lectin MeSH Prohlížeč
- fukosa MeSH
- fungální proteiny MeSH
- lektiny MeSH
