Synthesis of a calix[4]arene derivative exposing multiple units of fucose and preliminary investigation as a potential broad-spectrum antibiofilm agent

Carbohydr Res. 2019 Apr 1:476:60-64. doi: 10.1016/j.carres.2019.03.005. Epub 2019 Mar 13.

Abstract

Calix[4]arene derivative (1), bearing four α-l-C-fucosyl units linked via a flexible spacer, and a monomeric analogous (2) bearing a single moiety of fucose, were synthesized. Compounds 1 and 2 were assayed for antibiofilm activity against Pseudomonas aeruginosa (Gram-) and Staphylococcus epidermidis (Gram+). The macrocyclic compound 1 showed very high percentage of biofilm inhibition against two different bacterial strains while compound 2, which does not possess a macrocyclic structure, showed only moderate biofilm inhibition against P. aeruginosa and no biofilm inhibition against S. epidermidis. The fucose multivalent derivative could be a new broad-spectrum antibiofilm agent.

Keywords: Bacterial biofilm inhibition; Fucosyl-calix[4]arene derivative; Fucosyl-phenetidine derivative; Pseudomonas aeruginosa; Staphylococcus epidermidis.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Biofilms / drug effects*
  • Biofilms / growth & development
  • Calixarenes / chemical synthesis*
  • Calixarenes / chemistry
  • Calixarenes / pharmacology*
  • Chemistry Techniques, Synthetic
  • Fucose / chemistry*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Phenols / pharmacology*
  • Pseudomonas aeruginosa / drug effects
  • Pseudomonas aeruginosa / physiology
  • Staphylococcus epidermidis / drug effects
  • Staphylococcus epidermidis / physiology

Substances

  • Anti-Bacterial Agents
  • Phenols
  • calix(4)arene
  • Calixarenes
  • Fucose