Comparative Study of Aryl O-, C-, and S-Mannopyranosides as Potential Adhesion Inhibitors toward Uropathogenic E. coli FimH.
Leila MousavifarGérard VergotenGuillaume CharronRené RoyPublished in: Molecules (Basel, Switzerland) (2019)
A set of three mannopyranoside possessing identical 1,1'-biphenyl glycosidic pharmacophore but different aglyconic atoms were synthesized using either a palladium-catalyzed Heck cross coupling reaction or a metathesis reaction between their corresponding allylic glycoside derivatives. Their X-ray structures, together with their calculated 3D structures, showed strong indicators to explain the observed relative binding abilities against E. coli FimH as measured by a improved surface plasmon resonance (SPR) method. Amongst the O-, C-, and S-linked analogs, the C-linked analog showed the best ability to become a lead candidate as antagonist against uropathogenic E. coli with a Kd of 11.45 nM.
Keyphrases
- escherichia coli
- high resolution
- biofilm formation
- molecular docking
- photodynamic therapy
- molecular dynamics
- risk assessment
- electron transfer
- magnetic resonance
- climate change
- staphylococcus aureus
- binding protein
- mass spectrometry
- pseudomonas aeruginosa
- molecular dynamics simulations
- transcription factor
- cell adhesion