Dendritic cell lectin-targeting sentinel-like unimolecular glycoconjugates to release an anti-HIV drug

J Am Chem Soc. 2014 Mar 19;136(11):4325-32. doi: 10.1021/ja4131565. Epub 2014 Mar 6.

Abstract

A series of cyclodextrin-based glycoconjugates, including glycoclusters and star glycopolymers, were synthesized via combination of CuAAC Huisgen coupling and copper-mediated living radical polymerization. These glycoconjugates showed high affinity binding to the human transmembrane lectin DC-SIGN and act as inhibitors to prevent the binding of HIV envelope protein gp120 to DC-SIGN at nanomolar concentrations. The star block glycopolymers showed high loading capacity of hydrophobic anticancer and anti-HIV drugs, indicating promising applications in HIV-therapeutic and smart drug delivery.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Binding Sites / drug effects
  • Cyclodextrins / chemistry*
  • Dendritic Cells / drug effects
  • Glycoconjugates / chemical synthesis
  • Glycoconjugates / chemistry
  • Glycoconjugates / pharmacology*
  • HIV / drug effects*
  • HIV Envelope Protein gp120 / antagonists & inhibitors*
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Polymerization
  • Structure-Activity Relationship

Substances

  • Anti-HIV Agents
  • Cyclodextrins
  • Glycoconjugates
  • HIV Envelope Protein gp120