title: Preparation and supramolecular properties of unadulterated glycosyl liposomes from a bis(alpha-D-mannopyranosyl)-[60]fullerene conjugate.
abstract: The bis(alpha-D-mannopyranosyl)-[60]fullerene conjugate 3 was prepared by thermal coupling of C60 and either 2-azidoethyl 2,3,4,6-tetra-O-acetyl- or 2,3;4,6-di-O-isopropylidene-alpha-D-mannopyranoside (Scheme). Compound 3 was found to readily self-assemble. Dynamic-light-scattering (DLS) and atomic-force microscopy (AFM) experiments supported that the amphiphilic compound gives rise to nano-sized supramolecular structures during sugar deprotection (Ac-group removal) performed in MeOH/CH2Cl2 solution. Encapsulation studies with an aqueous suspension of 3 showed that the self-assembling structure envelopes Ba2+ and the fluorescent dye Acridine Red during its formation, which indicates that it resembles a bilayer vesicle or an unadulterated liposome with an inner hollow space. In addition to this notable property, the unique molecular geometry of the spatially arranged mannosyl surface residues of 3 gives rise to strong binding of the carbohydrate-recognizing lectin Con A. Hence, the polar amphiphilic end of 3 mimics the structure of 3,6-branched tri-alpha-D-mannoside (6; Fig. 3), a natural ligand of the Con A protein.
authors.affiliation: Molecular Design & Engineering, Graduate School of Engineering, Nagoya University Chikusa-ku, Nagoya 464-8603, Japan.
authors.forename: Haruhito
authors.initials: H
authors.lastname: Kato
authors.forename: Noboru
authors.initials: N
authors.lastname: Kaneta
authors.forename: Susumu
authors.initials: S
authors.lastname: Nii
authors.forename: Kazukiyo
authors.initials: K
authors.lastname: Kobayashi
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Fukui
authors.forename: Hisanori
authors.initials: H
authors.lastname: Shinohara
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Nishida
mesh_terms: D001464:Barium / Q000737:chemistry; D003208:Concanavalin A / Q000737:chemistry; D037741:Fullerenes / Q000737:chemistry*; D008081:Liposomes / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D012235:Rhodamines / Q000737:chemistry
chemical_list: D037741:Fullerenes; D008081:Liposomes; D012235:Rhodamines; C032527:acridine red; D003208:Concanavalin A; D001464:Barium