title: Amphiphilic N-glycosyl-thiocarbamoyl cyclodextrins: synthesis, self-assembly, and fluorimetry of recognition by Lens culinaris lectin.
abstract: Amphiphilic beta-cyclodextrins have been synthesized bearing hexylthio, dodecylthio, and hexadecylthio chains at the 6-positions and glycosylthiocarbamoyl-oligo(ethylene glycol) units at the 2-positions. The glycosyl residues (alpha-D-mannosyl and beta-L-fucosyl) are intended for cell-targeting. Self-assembly of these new amphiphilic glycosylated cyclodextrins in water to form vesicles was investigated by dynamic light scattering and transmission electron microscopy. Selective binding of the hexylthio assemblies to a protein receptor (Lens culinaris lectin) was confirmed by fluorescence spectroscopy.
authors.affiliation: Centre for Synthesis and Chemical Biology of the Conway Institute, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
authors.forename: Simone
authors.initials: S
authors.lastname: McNicholas
authors.forename: Anna
authors.initials: A
authors.lastname: Rencurosi
authors.forename: Luigi
authors.initials: L
authors.lastname: Lay
authors.forename: Antonino
authors.initials: A
authors.lastname: Mazzaglia
authors.forename: Luisa
authors.initials: L
authors.lastname: Sturiale
authors.forename: Marta
authors.initials: M
authors.lastname: Perez
authors.forename: Raphael
authors.initials: R
authors.lastname: Darcy
mesh_terms: D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry; D016503:Drug Delivery Systems; D006031:Glycosylation; D027806:Lens Plant / Q000378:metabolism; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D046529:Microscopy, Electron, Transmission; D008956:Models, Chemical; D008968:Molecular Conformation; D037121:Plant Lectins / Q000737:chemistry*; D011506:Proteins / Q000737:chemistry; D012542:Scattering, Radiation; D013050:Spectrometry, Fluorescence; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D003505:Cyclodextrins; D037121:Plant Lectins; D011506:Proteins; D047392:beta-Cyclodextrins; C033619:lentil lectin