Amphiphilic N-glycosyl-thiocarbamoyl cyclodextrins: synthesis, self-assembly, and fluorimetry of recognition by Lens culinaris lectin.
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.
McNicholas
Simone
S
Centre for Synthesis and Chemical Biology of the Conway Institute, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
Rencurosi
Anna
A
Lay
Luigi
L
Mazzaglia
Antonino
A
Sturiale
Luisa
L
Perez
Marta
M
Darcy
Raphael
R
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*
D003505:Cyclodextrins; D037121:Plant Lectins; D011506:Proteins; D047392:beta-Cyclodextrins; C033619:lentil lectin