The opportunistic Gram-negative bacterium Burkholderia cenocepacia causes lethal infections in cystic fibrosis patients. Multivalent mannoside derivatives were prepared as potential inhibitors of lectin BC2L-A, one of the virulence factors deployed by B. cenocepacia in the infection process. An (α1→2)-thio-linked mannobioside mimic bearing an azide functionalized aglycon was conjugated to different multivalent scaffolds such as propargylated calix[4]arenes, methyl gallate and pentaerythritol by azide-alkyne 1,3-dipolar cycloaddition. The interaction between the glycoclusters and the mannose binding BC2L-A lectin from B. cenocepacia was examined by isothermal microcalorimetry, surface plasmon resonance, inhibition of yeast agglutination and analytical ultracentrifugation.

Central European Institute of Technology Masaryk University Kamenice 5 625 00 Brno Czechia

Central European Institute of Technology Masaryk University Kamenice 5 625 00 Brno Czechia; National Centre for Biomolecular Research Faculty of Science Masaryk University Kotlářská 2 611 37 Brno Czechia

Department of Organic Chemistry University of Debrecen POB 20 H 410 Debrecen Hungary

Department of Pharmaceutical Chemistry University of Debrecen POB 78 H 4010 Debrecen Hungary

ICBMS Equipe CSAp Université Lyon 1 69622 Villeurbanne France

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Synthesis of β-d-galactopyranoside-Presenting Glycoclusters, Investigation of Their Interactions with Pseudomonas aeruginosa Lectin A (PA-IL) and Evaluation of Their Anti-Adhesion Potential

Microscopy examination of red blood and yeast cell agglutination induced by bacterial lectins