Controlled Self-Assembly of Carbohydrate Conjugate Rod−Coil Amphiphiles for Supramolecular Multivalent Ligands

• Published in: Journal of the American Chemical Society 2005-11, Vol.127 (46), p.16333-16337
• Main Authors: Kim, Byung-Sun, Hong, Dong-Je, Bae, Jinyoung, Lee, Myongsoo
• Format: Article
• Language: English
• Subjects: Animals; Biological and medical sciences; Carbohydrates - chemistry; Carbohydrates - pharmacology; Cell Aggregation; Concanavalin A - pharmacology; Disperse state. Micelles; Erythrocytes - cytology; Erythrocytes - drug effects; Fundamental and applied biological sciences. Psychology; Ligands; Micelles; Microscopy, Electron, Transmission; Molecular biophysics; Molecular Structure; Physico-chemical properties of biomolecules; Rabbits
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja055999a

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.