Synthesis of S-linked NeuAc-α(2-6)-di-LacNAc bearing liposomes for H1N1 influenza virus inhibition assays

Bioorg Med Chem. 2018 May 15;26(9):2262-2270. doi: 10.1016/j.bmc.2018.02.012. Epub 2018 Feb 12.

Abstract

S-NeuAc-α(2-6)-di-LacNAc (5) was efficiently synthesized by a [2+2] followed by a [1+4] glycosylation, and later conjugated with 1,2-dilauroyl-sn-glycero-3-phosphoethanolamine (DLPE) to form both single-layer and multi-layer homogeneous liposomes in the presence of dipalmitoyl phosphatidylcholine (DPPC) and cholesterol. These liposomes were found to be weak inhibitors in both the influenza virus entry assay and the hemagglutination inhibition assay. The single layer liposome was found to more efficiently interfere with the entry of the H1N1 influenza virus into MDCK cells than the multilayer liposome containing 5.

Keywords: Hemagglutinin; Influenza; Liposome; Sialic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / pharmacology*
  • Cholesterol / chemistry
  • Dogs
  • Glycosylation
  • Hemagglutinin Glycoproteins, Influenza Virus / metabolism
  • Influenza A Virus, H1N1 Subtype / drug effects
  • Liposomes / chemistry*
  • Madin Darby Canine Kidney Cells
  • Oligosaccharides / chemical synthesis
  • Oligosaccharides / chemistry*
  • Phosphatidylethanolamines / chemistry
  • Virus Internalization / drug effects
  • Zanamivir / pharmacology*

Substances

  • Antiviral Agents
  • Hemagglutinin Glycoproteins, Influenza Virus
  • Liposomes
  • Oligosaccharides
  • Phosphatidylethanolamines
  • 1,2-dilauroylphosphatidylethanolamine
  • Cholesterol
  • Zanamivir