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.
Copyright © 2011 Elsevier Ltd. All rights reserved.
MeSH terms
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Animals
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology
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Hemagglutinin Glycoproteins, Influenza Virus / chemistry
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Hemagglutinin Glycoproteins, Influenza Virus / metabolism
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Humans
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Hydrophobic and Hydrophilic Interactions
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Influenza A Virus, H1N1 Subtype / drug effects
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Influenza A Virus, H1N1 Subtype / enzymology
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Influenza A Virus, H1N1 Subtype / metabolism
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Influenza A Virus, H3N2 Subtype / drug effects
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Influenza A Virus, H3N2 Subtype / enzymology
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Influenza A Virus, H3N2 Subtype / metabolism
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Influenza A virus / drug effects*
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Influenza A virus / enzymology
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Influenza A virus / metabolism
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N-Acetylneuraminic Acid / chemical synthesis
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N-Acetylneuraminic Acid / chemistry*
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N-Acetylneuraminic Acid / pharmacology
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Neuraminidase / antagonists & inhibitors
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Neuraminidase / metabolism
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Polymers / chemical synthesis*
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Polymers / chemistry
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Polymers / pharmacology
Substances
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Antiviral Agents
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Hemagglutinin Glycoproteins, Influenza Virus
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Polymers
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Neuraminidase
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N-Acetylneuraminic Acid