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Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa
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 P...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7865631/ https://www.ncbi.nlm.nih.gov/pubmed/33494330 http://dx.doi.org/10.3390/molecules26030542 |
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author | Illyés, Tünde Zita Malinovská, Lenka Rőth, Erzsébet Tóth, Boglárka Farkas, Bence Korsák, Marek Wimmerová, Michaela Kövér, Katalin E. Csávás, Magdolna |
author_facet | Illyés, Tünde Zita Malinovská, Lenka Rőth, Erzsébet Tóth, Boglárka Farkas, Bence Korsák, Marek Wimmerová, Michaela Kövér, Katalin E. Csávás, Magdolna |
author_sort | Illyés, Tünde Zita |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7865631 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-78656312021-02-07 Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa Illyés, Tünde Zita Malinovská, Lenka Rőth, Erzsébet Tóth, Boglárka Farkas, Bence Korsák, Marek Wimmerová, Michaela Kövér, Katalin E. Csávás, Magdolna Molecules Article 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. MDPI 2021-01-21 /pmc/articles/PMC7865631/ /pubmed/33494330 http://dx.doi.org/10.3390/molecules26030542 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Illyés, Tünde Zita Malinovská, Lenka Rőth, Erzsébet Tóth, Boglárka Farkas, Bence Korsák, Marek Wimmerová, Michaela Kövér, Katalin E. Csávás, Magdolna Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa |
title | Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa |
title_full | Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa |
title_fullStr | Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa |
title_full_unstemmed | Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa |
title_short | Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa |
title_sort | synthesis of tetravalent thio- and selenogalactoside-presenting galactoclusters and their interactions with bacterial lectin pa-il from pseudomonas aeruginosa |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7865631/ https://www.ncbi.nlm.nih.gov/pubmed/33494330 http://dx.doi.org/10.3390/molecules26030542 |
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