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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...

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Autores principales: Illyés, Tünde Zita, Malinovská, Lenka, Rőth, Erzsébet, Tóth, Boglárka, Farkas, Bence, Korsák, Marek, Wimmerová, Michaela, Kövér, Katalin E., Csávás, Magdolna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
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.
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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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