Synthesis of a cluster-forming sialylthio-D-galactose fullerene conjugate and evaluation of its interaction with influenza virus hemagglutinin and neuraminidase.
In order to obtain self assembling, multivalent ligand for influenza virus hemagglutinin α-N-acetylneuraminyl-(2-6)-D-galactopyranose has been synthesized and bonded to a water soluble fullerene derivative using 1,3-dipolar cycloaddition click reaction. The aggregating amphiphilic compound did not inhibit the influenza virus hemagglutinin, but it proved to be an inhibitor of its neuraminidase with a 50% inhibitory concentration of 81 μM.
Department of Pharmaceutical Chemistry, University of Debrecen, H-4010 Debrecen, Hungary.
Szilvia
S
Tollas
Department of Pharmaceutical Chemistry, University of Debrecen, H-4010 Debrecen, Hungary.
Ilona
I
Bereczki
Department of Pharmaceutical Chemistry, University of Debrecen, H-4010 Debrecen, Hungary.
Anikó
A
Borbás
Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, Hungary.
Gyula
G
Batta
Rega Institute for Medical Research, KU Leuven, B-3000 Leuven, Belgium.
Evelien
E
Vanderlinden
Rega Institute for Medical Research, KU Leuven, B-3000 Leuven, Belgium. Electronic address: lieve.naesens@rega.kuleuven.be.
Lieve
L
Naesens
Department of Pharmaceutical Chemistry, University of Debrecen, H-4010 Debrecen, Hungary. Electronic address: herczeghp@gmail.com.
Pál
P
Herczegh
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D037741:Fullerenes / Q000737:chemistry / Q000494:pharmacology*; D006388:Hemagglutinins / Q000378:metabolism*; D008024:Ligands; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009975:Orthomyxoviridae / Q000187:drug effects / Q000378:metabolism*; D013329:Structure-Activity Relationship
D001952:Bridged-Ring Compounds; D004187:Disaccharides; D037741:Fullerenes; D006388:Hemagglutinins; D008024:Ligands; D009439:Neuraminidase
Aggregation; Antiviral activity; Fullerene; Multivalent ligand; Sialic acid; Thiodisaccharide