Monodisperse Sequence-Controlled α-l-Fucosylated Glycooligomers and Their Multivalent Inhibitory Effects on LecB

Macromol Biosci. 2018 Dec;18(12):e1800337. doi: 10.1002/mabi.201800337. Epub 2018 Nov 8.

Abstract

The opportunistic bacterium Pseudomonas aeruginosa, often exhibiting multiresistance against conventional antibiotics, expresses the lectin LecB that is suspected to be an important factor during biofilm formation via interactions with cell-surface presented carbohydrate ligands such as the blood group antigens. Therefore, carbohydrate-based ligands interfering with LecB binding have the potential to lead to new anti-biofilm and anti-adhesion therapies. This study explores in vitro binding potencies of glycomimetic ligands containing up to six α-l-fucose ligands on a monodisperse, sequence-controlled oligoamide scaffold interacting with LecB. Surface plasmon resonance (SPR) and a modified enzyme-linked lectin assay (mELLA) revealed an increasing affinity to LecB with increasing fucose valency. Furthermore, fucosylated glycooligomers were shown to inhibit the formation of P. aeruginosa biofilm up to 20%. Overall these results show the potential of fucosylated oligoamides to be further developed as inhibitors of LecB binding and biofilm formation.

Keywords: LecB; fucose; glycomacromolecules; multivalent inhibitor; solid phase synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Bacterial Adhesion / drug effects
  • Biofilms / drug effects*
  • Biofilms / growth & development
  • Blood Group Antigens / chemistry
  • Blood Group Antigens / metabolism
  • Carbohydrate Sequence
  • Fucose / chemistry*
  • Glycosylation
  • Lectins / antagonists & inhibitors*
  • Lectins / chemistry
  • Lectins / metabolism
  • Ligands
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / pharmacology
  • Protein Binding / drug effects
  • Pseudomonas aeruginosa / chemistry
  • Pseudomonas aeruginosa / drug effects*
  • Pseudomonas aeruginosa / growth & development
  • Pseudomonas aeruginosa / metabolism

Substances

  • Anti-Bacterial Agents
  • Blood Group Antigens
  • LecB protein, Pseudomonas aeruginosa
  • Lectins
  • Ligands
  • Oligosaccharides
  • Fucose