title: Macrocyclic glycoclusters: from amphiphiles through nanoparticles to glycoviruses.
abstract: Macrocyclic glycocluster amphiphiles are intended to be a covalent-bundle mimic of clustering glycolipid motifs on the cell membrane. They are irreversibly micellized to give glycocluster nanoparticles (GNPs); their masked hydrophobicity endows them with remarkable saccharide specificities in the interactions with biological saccharide receptors. The GNPs also exhibit unprecedented hydrogen-bond capacities; they are agglutinated with Na(2)HPO(4) and assembled on plasmid DNA in a number-, size-, and shape-controlled manner to give artificial glycoviral particles capable of transfection. Thus, the intrinsic function of viruses, that is, cell invasion followed by gene expression, is also intrinsic to size-regulated (approximately 50 nm) glycoviruses. The growth of glycocluster amphiphiles through nanoparticles to glycoviruses reveals a hierarchical adhesion control of the saccharide clusters.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. aoyamay@sbchem.kyoto-u.ac.jp
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Aoyama
mesh_terms: D045744:Cell Line, Tumor; D004247:DNA / Q000737:chemistry / Q000235:genetics; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D046911:Macromolecular Substances; D008823:Micelles; D015394:Molecular Structure; D036103:Nanotechnology; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D010316:Particle Size; D010957:Plasmids / Q000737:chemistry / Q000235:genetics; D014780:Viruses / Q000737:chemistry*
chemical_list: D006027:Glycosides; D046911:Macromolecular Substances; D008823:Micelles; D009844:Oligosaccharides; D004247:DNA