Thiazolylaminomannosides as potent antiadhesives of type 1 piliated Escherichia coli isolated from Crohn's disease patients

J Med Chem. 2013 Jul 11;56(13):5395-406. doi: 10.1021/jm400723n. Epub 2013 Jun 24.

Abstract

Adherent-invasive Escherichia coli (AIEC) have previously been shown to induce gut inflammation in patients with Crohn's disease (CD). We developed a set of mannosides to prevent AIEC attachment to the gut by blocking the FimH bacterial adhesin. The crystal structure of the FimH lectin domain in complex with a lead thiazolylaminomannoside highlighted the preferential position for pharmacomodulations. A small library of analogues showing nanomolar affinity for FimH was then developed. Notably, AIEC attachment to intestinal cells was efficiently prevented by the most active compound and at around 10000-fold and 100-fold lower concentrations than mannose and the potent FimH inhibitor heptylmannoside, respectively. An ex vivo assay performed on the colonic tissue of a transgenic mouse model of CD confirmed this antiadhesive potential. Given the key role of AIEC in the chronic intestinal inflammation of CD patients, these results suggest a potential antiadhesive treatment with the FimH inhibitors developed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adhesins, Escherichia coli / metabolism
  • Animals
  • Antigens, CD / genetics
  • Antigens, CD / metabolism
  • Bacterial Adhesion / drug effects*
  • Binding Sites
  • Caco-2 Cells
  • Cell Adhesion Molecules / genetics
  • Cell Adhesion Molecules / metabolism
  • Colon / drug effects
  • Colon / metabolism
  • Colon / microbiology
  • Crohn Disease / microbiology*
  • Escherichia coli / metabolism
  • Escherichia coli / physiology*
  • Fimbriae Proteins / antagonists & inhibitors
  • Fimbriae Proteins / metabolism
  • Fimbriae, Bacterial / physiology
  • GPI-Linked Proteins / genetics
  • GPI-Linked Proteins / metabolism
  • Host-Pathogen Interactions / drug effects
  • Humans
  • Intestines / drug effects
  • Intestines / microbiology
  • Jurkat Cells
  • Mannosides / chemical synthesis
  • Mannosides / chemistry
  • Mannosides / pharmacology*
  • Mice
  • Mice, Transgenic
  • Models, Chemical
  • Molecular Structure
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology

Substances

  • Adhesins, Escherichia coli
  • Antigens, CD
  • CEACAM6 protein, human
  • Cell Adhesion Molecules
  • GPI-Linked Proteins
  • Mannosides
  • Thiazoles
  • fimH protein, E coli
  • Fimbriae Proteins

Associated data

  • PDB/3ZL1
  • PDB/3ZL2