Synthesis of Various Glycopolymers Bearing Sialyllactose and the Effect of Their Molecular Mobility on Interaction with the Influenza Virus

Biomacromolecules. 2019 Jul 8;20(7):2763-2769. doi: 10.1021/acs.biomac.9b00515. Epub 2019 Jun 26.

Abstract

Synthetic glyco-ligands are promising candidates for effective nanomedicines against pathogens. Glycopolymers bearing sialyl-oligosaccharides interact with hemagglutinin present on the surface of influenza viruses. In designing new glycopolymers that further enhance the interaction with viruses, both static and dynamic properties of the glycopolymers should be considered. In this report, we evaluated the correlation between dynamic properties of glycopolymers and their interaction with the influenza virus. Glycopolymers with pendant sialyllactoses and various linker structures were synthesized, and their molecular mobility was determined by proton spin-spin relaxation time measurements. The molecular mobility of the glycounits increased as the length of the linker structures increased. Interestingly, glycopolymers with the medium-length linker structure exhibited the strongest interaction with the influenza virus, suggesting that optimal molecular mobility is required for maximizing multivalent interactions with the target.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Humans
  • Influenza, Human / drug therapy*
  • Influenza, Human / virology
  • Lactose / analogs & derivatives*
  • Lactose / chemistry
  • Lactose / pharmacology
  • Ligands
  • Nanomedicine
  • Oligosaccharides / chemistry
  • Oligosaccharides / pharmacology
  • Orthomyxoviridae / drug effects*
  • Orthomyxoviridae / pathogenicity
  • Polymers / chemical synthesis
  • Polymers / chemistry
  • Polymers / pharmacology*
  • Polysaccharides / chemical synthesis
  • Polysaccharides / chemistry
  • Sialic Acids / chemistry
  • Sialic Acids / pharmacology*

Substances

  • Ligands
  • Oligosaccharides
  • Polymers
  • Polysaccharides
  • Sialic Acids
  • N-acetylneuraminoyllactose
  • Lactose