Controlled self-assembly of carbohydrate conjugate rod-coil amphiphiles for supramolecular multivalent ligands

J Am Chem Soc. 2005 Nov 23;127(46):16333-7. doi: 10.1021/ja055999a.

Abstract

Carbohydrate conjugate rod-coil amphiphiles were synthesized and their self-assembling behavior in aqueous solution was investigated. These amphiphiles were observed to self-assemble into supramolecular structures that differ significantly depending on the molecular architecture. The rod-coil amphiphiles based on a short coil (1) self-assemble into a vesicular structure, while the amphiphiles with a long coil (2) show a spherical micellar structure. In contrast, 3, based on a twin-rod segment, was observed to aggregate into cylindrical micelles with twice the diameter of molecular length scale. As a means to determine the binding activity to protein receptors of these supramolecular objects, hemagglutination inhibition assay was performed. The experiments showed that the supramolecular architecture has a significant effect on the binding activity. In addition, incubation experiments with Escherichia coli showed that mannose-coated objects specifically bind to the bacterial pili of the ORN 178 strain. These results demonstrate that precise control of the nano-objects in shape and size by molecular design can provide control of the biological activities of the supramolecular materials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbohydrates / chemistry*
  • Carbohydrates / pharmacology
  • Cell Aggregation
  • Concanavalin A / pharmacology
  • Erythrocytes / cytology
  • Erythrocytes / drug effects
  • Ligands
  • Micelles
  • Microscopy, Electron, Transmission
  • Molecular Structure
  • Rabbits

Substances

  • Carbohydrates
  • Ligands
  • Micelles
  • Concanavalin A