Investigation of the Binding Affinity of a Broad Array of
L-Fucosides with Six Fucose-Specific Lectins of Bacterial and
Fungal Origin

J 2019

Investigation of the Binding Affinity of a Broad Array of L-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin

THAI LE, Son, Lenka MALINOVSKÁ, Michaela VAŠKOVÁ, Erika MEZO, Viktor KELEMEN et. al.

Základní údaje

Originální název

Investigation of the Binding Affinity of a Broad Array of L-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin

Autoři

THAI LE, Son, Lenka MALINOVSKÁ (203 Česká republika, domácí), Michaela VAŠKOVÁ (203 Česká republika), Erika MEZO (348 Maďarsko), Viktor KELEMEN (348 Maďarsko), Anikó BORBÁS (348 Maďarsko), Petr HODEK (203 Česká republika), Michaela WIMMEROVÁ (203 Česká republika, garant, domácí) a Magdolna CSÁVÁS (348 Maďarsko)

Vydání

Molecules, Mayer und Muller, 2019, 1420-3049

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.267

Kód RIV

RIV/00216224:14740/19:00107484

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.3390/molecules24122262

UT WoS

000473816900068

Klíčová slova anglicky

l-fucosides; multivalency; lectins; glycoclusters; hemagglutination; cystic fibrosis

Štítky

CF BIC, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 27. 10. 2024 15:05, Ing. Martina Blahová

Anotace

V originále

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.

Návaznosti

GA15-17572S, projekt VaV

Název: Glykoklastry kalix[4]aren/C-oligosacharidy pro studium selektivity interakcí s lektiny

Investor: Grantová agentura ČR, Glykoklastry kalix[4]aren/C-oligosacharidy pro studium selektivity interakcí s lektiny

90043, velká výzkumná infrastruktura

Název: CIISB

Citovat

THAI LE, Son, Lenka MALINOVSKÁ, Michaela VAŠKOVÁ, Erika MEZO, Viktor KELEMEN, Anikó BORBÁS, Petr HODEK, Michaela WIMMEROVÁ a 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, roč. 24, č. 12, s. 1-17. ISSN 1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules24122262.

@article{1543778,
   author = {Thai Le, Son and Malinovská, Lenka and Vašková, Michaela and Mezo, Erika and Kelemen, Viktor and Borbás, Anikó and Hodek, Petr and Wimmerová, Michaela and Csávás, Magdolna},
   article_number = {12},
   doi = {http://dx.doi.org/10.3390/molecules24122262},
   keywords = {l-fucosides; multivalency; lectins; glycoclusters; hemagglutination; cystic fibrosis},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   title = {Investigation of the Binding Affinity of a Broad Array of L-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin},
   url = {https://www.mdpi.com/1420-3049/24/12/2262},
   volume = {24},
   year = {2019}
}

TY  - JOUR
ID  - 1543778
AU  - Thai Le, Son - Malinovská, Lenka - Vašková, Michaela - Mezo, Erika - Kelemen, Viktor - Borbás, Anikó - Hodek, Petr - Wimmerová, Michaela - Csávás, Magdolna
PY  - 2019
TI  - Investigation of the Binding Affinity of a Broad Array of L-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin
JF  - Molecules
VL  - 24
IS  - 12
SP  - 1-17
EP  - 1-17
PB  - Mayer und Muller
SN  - 14203049
KW  - l-fucosides
KW  - multivalency
KW  - lectins
KW  - glycoclusters
KW  - hemagglutination
KW  - cystic fibrosis
UR  - https://www.mdpi.com/1420-3049/24/12/2262
L2  - https://www.mdpi.com/1420-3049/24/12/2262
N2  - 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.
ER  -

THAI LE, Son, Lenka MALINOVSKÁ, Michaela VAŠKOVÁ, Erika MEZO, Viktor KELEMEN, Anikó BORBÁS, Petr HODEK, Michaela WIMMEROVÁ a Magdolna CSÁVÁS. Investigation of the Binding Affinity of a Broad Array of L-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin. \textit{Molecules}. Mayer und Muller, 2019, roč.~24, č.~12, s.~1-17. ISSN~1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules24122262.

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