THAI LE, Son, Lenka MALINOVSKÁ, Michaela VAŠKOVÁ, Erika MEZO, Viktor KELEMEN, Anikó BORBÁS, Petr HODEK, Michaela WIMMEROVÁ and Magdolna CSÁVÁS. Investigation of the Binding Affinity of a Broad Array of L-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin. Molecules. Mayer und Muller, 2019, vol. 24, No 12, p. 1-17. ISSN 1420-3049. Available from: https://dx.doi.org/10.3390/molecules24122262.
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Basic information
Original name Investigation of the Binding Affinity of a Broad Array of L-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin
Authors THAI LE, Son, Lenka MALINOVSKÁ (203 Czech Republic, belonging to the institution), Michaela VAŠKOVÁ (203 Czech Republic), Erika MEZO (348 Hungary), Viktor KELEMEN (348 Hungary), Anikó BORBÁS (348 Hungary), Petr HODEK (203 Czech Republic), Michaela WIMMEROVÁ (203 Czech Republic, guarantor, belonging to the institution) and Magdolna CSÁVÁS (348 Hungary).
Edition Molecules, Mayer und Muller, 2019, 1420-3049.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10400 1.4 Chemical sciences
Country of publisher Switzerland
Confidentiality degree is not subject to a state or trade secret
WWW URL
Impact factor Impact factor: 3.267
RIV identification code RIV/00216224:14740/19:00107484
Organization unit Central European Institute of Technology
Doi http://dx.doi.org/10.3390/molecules24122262
UT WoS 000473816900068
Keywords in English l-fucosides; multivalency; lectins; glycoclusters; hemagglutination; cystic fibrosis
Tags CF BIC, rivok
Tags International impact, Reviewed
Changed by Changed by: Mgr. Pavla Foltynová, Ph.D., učo 106624. Changed: 31/3/2020 21:40.
Abstract
Series of multivalent alpha-l-fucoside containing glycoclusters and variously decorated l-fucosides were synthesized to find potential inhibitors of fucose-specific lectins and study the structure-binding affinity relationships. Tri- and tetravalent fucoclusters were built using copper-mediated azide-alkyne click chemistry. Series of fucoside monomers and dimers were synthesized using various methods, namely glycosylation, an azide-alkyne click reaction, photoinduced thiol-en addition, and sulfation. The interactions between compounds with six fucolectins of bacterial or fungal origin were tested using a hemagglutination inhibition assay. As a result, a tetravalent, aplha-l-fucose presenting glycocluster showed to be a ligand that was orders of magnitude better than a simple monosaccharide for tested lectins in most cases, which can nominate it as a universal ligand for studied lectins. This compound was also able to inhibit the adhesion of Pseudomonas aeruginosa cells to human epithelial bronchial cells. A trivalent fucocluster with a protected amine functional group also seems to be a promising candidate for designing glycoconjugates and chimeras.
Links
GA15-17572S, research and development projectName: Glykoklastry kalix[4]aren/C-oligosacharidy pro studium selektivity interakcí s lektiny
Investor: Czech Science Foundation
LM2015043, research and development projectName: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)
Investor: Ministry of Education, Youth and Sports of the CR
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