Investigation of the binding affinity of a broad array of L-fucosides with six fucose-specific lectins of bacterial and fungal origin

Son Thai Le, Lenka Malinovska, Michaela Vašková, Erika Mezo, Viktor Kelemen, A. Borbás, Petr Hodek, Michaela Wimmerová, Magdolna Csávás

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Article number2262
JournalMolecules
Volume24
Issue number12
DOIs
Publication statusPublished - Jun 18 2019

Fingerprint

Alkynes
Azides
alkynes
Lectins
affinity
sulfation
Click Chemistry
Ligands
Glycosylation
monosaccharides
ligands
Glycoconjugates
pseudomonas
Fucose
Monosaccharides
Hemagglutination
cells
Sulfhydryl Compounds
thiols
Dimers

Keywords

  • Cystic fibrosis
  • Glycoclusters
  • Hemagglutination
  • L-fucosides
  • Lectins
  • Multivalency

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Investigation of the binding affinity of a broad array of L-fucosides with six fucose-specific lectins of bacterial and fungal origin. / Le, Son Thai; Malinovska, Lenka; Vašková, Michaela; Mezo, Erika; Kelemen, Viktor; Borbás, A.; Hodek, Petr; Wimmerová, Michaela; Csávás, Magdolna.

In: Molecules, Vol. 24, No. 12, 2262, 18.06.2019.

Research output: Contribution to journalArticle

Le, ST, Malinovska, L, Vašková, M, Mezo, E, Kelemen, V, Borbás, A, Hodek, P, Wimmerová, M & Csávás, M 2019, 'Investigation of the binding affinity of a broad array of L-fucosides with six fucose-specific lectins of bacterial and fungal origin', Molecules, vol. 24, no. 12, 2262. https://doi.org/10.3390/molecules24122262
Le, Son Thai ; Malinovska, Lenka ; Vašková, Michaela ; Mezo, Erika ; Kelemen, Viktor ; Borbás, A. ; Hodek, Petr ; Wimmerová, Michaela ; Csávás, Magdolna. / Investigation of the binding affinity of a broad array of L-fucosides with six fucose-specific lectins of bacterial and fungal origin. In: Molecules. 2019 ; Vol. 24, No. 12.
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