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.

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

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

Abstract

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.

Links

GA15-17572S, research and development project

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

Investor: Czech Science Foundation

90043, large research infrastructures

Name: CIISB

Citovat

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.

@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 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. \textit{Molecules}. Mayer und Muller, 2019, vol.~24, No~12, p.~1-17. ISSN~1420-3049. Available from: https://dx.doi.org/10.3390/molecules24122262.

Detailed Information on Publication Record