Simple synthesis of sialyllactose-carrying polystyrene and its binding with influenza virus.
Glycoconjugate polystyrenes bearing sialyllactose moieties were prepared via a simple method from a mixture of alpha2-6 and a2-3 linked sialyllactose isomers of bovine milk origin. The reducing end of sialyllactose was converted to an amino function with ammonium hydrogen carbonate and then coupled with p-vinylbenzoyl chloride. The resulting styrene derivative substituted with sialyllactose via an amide linkage was polymerized with ammonium peroxodisulfate and N,N,N',N-tetramethylethylenediamine in water at 30 degrees C. The interaction of the glycopolymer with influenza A and B viruses was investigated by three different methods. The glycopolymer inhibited the hemagglutination of influenza A virus (PR/8/34) and its activity was 10(3) times higher than that of the oligosaccharide itself. The cytopathic effect of virus-infected MDCK (Madine-Darby canine kidney) cells was inhibited by the glycopolymer. The homopolymer showed 10(2) times higher inhibitory activity than naturally-occurring fetuin. It was also found that various viruses could be trapped by the glycopolymer adsorbed on a polystyrene surface. The inhibitory and trapping activities of the glycopolymers were correlated with the sialyl linkage specificities of the virus strains.
Tsuchida
A
A
Graduate School of Engineering, Nagoya University, Japan.
Kobayashi
K
K
Matsubara
N
N
Muramatsu
T
T
Suzuki
T
T
Suzuki
Y
Y
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002460:Cell Line; D004285:Dogs; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019267:Hemagglutinin Glycoproteins, Influenza Virus / Q000187:drug effects; D007785:Lactose / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009975:Orthomyxoviridae / Q000187:drug effects / Q000378:metabolism*; D011137:Polystyrenes / Q000138:chemical synthesis* / Q000737:chemistry; D012794:Sialic Acids / Q000737:chemistry*
D000998:Antiviral Agents; D006001:Glycoconjugates; D019267:Hemagglutinin Glycoproteins, Influenza Virus; D011137:Polystyrenes; D012794:Sialic Acids; C000020:N-acetylneuraminoyllactose; D007785:Lactose