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Preparation and Supramolecular Properties of Unadulterated Glycosyl Liposomes from a Bis( α ‐ D ‐mannopyranosyl)[60]Fullerene Conjugate
Author(s) -
Kato Haruhito,
Kaneta Noboru,
Nii Susumu,
Kobayashi Kazukiyo,
Fukui Nobuyuki,
Shinohara Hisanori,
Nishida Yoshihiro
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590093
Subject(s) - chemistry , supramolecular chemistry , vesicle , amphiphile , conjugate , bilayer , liposome , aqueous solution , dynamic light scattering , acridine , crystallography , stereochemistry , nanoparticle , membrane , organic chemistry , nanotechnology , copolymer , polymer , crystal structure , mathematical analysis , biochemistry , materials science , mathematics
The bis( α ‐ D ‐mannopyranosyl)[60]fullerene conjugate 3 was prepared by thermal coupling of C 60 and either 2‐azidoethyl 2,3,4,6‐tetra‐ O ‐acetyl‐ or 2,3;4,6‐di‐ O ‐isopropylidene‐α‐ 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/CH 2 Cl 2 solution. Encapsulation studies with an aqueous suspension of 3 showed that the self‐assembling structure envelopes Ba 2+ 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‐ α ‐ D ‐mannoside ( 6 ; Fig. 3 ), a natural ligand of the Con A protein.