title: Synthesis and biological evaluation of sialic acid derivatives containing a long hydrophobic chain at the anomeric position and their C-5 linked polymers as potent influenza virus inhibitors.
abstract: Conversions of the C-5 acetamide group in sialic acid into two kinds of C=C double bond substituents were accomplished under Shotten-Baumann conditions. The polymerizable glycomonomers also contain a hydrophobic chain or hydroxyl group at the anomeric position. Radical polymerizations of the fully protected glycomonomers were carried out with acryl amide in the presence of ammonium persulfate (APS) and N,N,N',N'-tetramethylethylenediamine (TEMED), followed by deprotection to furnish water-soluble glycopolymers. The activities of the deprotected glycopolymers and glycomonomers against human influenza viruses (H1N1 and H3N2) and avian influenza virus (H5N3) were evaluated. Biological evaluations showed that the glycomonomers containing a long hydrophobic chain at the anomeric position had both hemagglutination and neuraminidase inhibitory activities.
authors.affiliation: Division of Material Science, Graduate School of Science and Engineering, Saitama University, Sakura, Saitama 338-8570, Japan.
authors.forename: Kaori
authors.initials: K
authors.lastname: Suzuki
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Koyama
authors.forename: Sangchai
authors.initials: S
authors.lastname: Yingsakmongkon
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Suzuki
authors.forename: Ken
authors.initials: K
authors.lastname: Hatano
authors.forename: Koji
authors.initials: K
authors.lastname: Matsuoka
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019267:Hemagglutinin Glycoproteins, Influenza Virus / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D009980:Influenza A virus / Q000187:drug effects* / Q000201:enzymology / Q000378:metabolism; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D009439:Neuraminidase / Q000037:antagonists & inhibitors / Q000378:metabolism; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000998:Antiviral Agents; D019267:Hemagglutinin Glycoproteins, Influenza Virus; D011108:Polymers; D009439:Neuraminidase; D019158:N-Acetylneuraminic Acid