Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from <i>Pseudomonas aeruginosa</i>
Tünde Zita Illyés,
Lenka Malinovská,
Erzsébet Rőth,
Boglárka Tóth,
Bence Farkas,
Marek Korsák,
Michaela Wimmerová,
Katalin E. Kövér,
Magdolna Csávás
Affiliations
Tünde Zita Illyés
Department of Organic Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
Lenka Malinovská
Central European Institute of Technology, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
Erzsébet Rőth
Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
Boglárka Tóth
Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
Bence Farkas
Department of Inorganic and Analytical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
Marek Korsák
Central European Institute of Technology, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
Michaela Wimmerová
Central European Institute of Technology, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
Katalin E. Kövér
Department of Inorganic and Analytical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
Magdolna Csávás
Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
Synthesis of tetravalent thio- and selenogalactopyranoside-containing glycoclusters using azide-alkyne click strategy is presented. Prepared compounds are potential ligands of Pseudomonas aeruginosa lectin PA-IL. P. aeruginosa is an opportunistic human pathogen associated with cystic fibrosis, and PA-IL is one of its virulence factors. The interactions of PA-IL and tetravalent glycoconjugates were investigated using hemagglutination inhibition assay and compared with mono- and divalent galactosides (propargyl 1-thio- and 1-seleno-β-d-galactopyranoside, digalactosyl diselenide and digalactosyl disulfide). The lectin-carbohydrate interactions were also studied by saturation transfer difference NMR technique. Both thio- and seleno-tetravalent glycoconjugates were able to inhibit PA-IL significantly better than simple d-galactose or their intermediate compounds from the synthesis.
