Synthesis of an amphiphilic tetraantennary mannosyl conjugate and incorporation into liposome carriers.
We have synthesized a novel conjugate (Man(4)K(3)DOG) composed of a tetramannosyl head group connected, via a polyethylene glycol spacer, to a lipid moiety. This amphiphilic molecule was easily incorporated into the bilayers of liposomes. As expected from the clustering effect, such multivalent mannose residues when exposed on the surface of the vesicles showed much higher binding affinity for Concanavalin A than their monomannosyl analogue. Mannosylated liposomes prepared with the tetravalent antenna could be promising carriers for e.g., loading dendritic cells with antigens for vaccination purposes.
Espuelas
Socorro
S
Laboratoire de Chimie Bioorganique, UMR 7514 CNRS/ULP, Université Louis Pasteur, Faculté de Pharmacie, 74 route du Rhin, 67400-Illkirch, France
Haller
Philippe
P
Schuber
Francis
F
Frisch
Benoît
B
D003208:Concanavalin A / Q000737:chemistry; D004337:Drug Carriers / Q000138:chemical synthesis*; D004563:Electrochemistry; D005990:Glycerol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D008051:Lipid Bilayers; D008055:Lipids / Q000737:chemistry; D008081:Liposomes; D008358:Mannose / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D010316:Particle Size; D011092:Polyethylene Glycols
D004337:Drug Carriers; D007202:Indicators and Reagents; D008051:Lipid Bilayers; D008055:Lipids; D008081:Liposomes; C482469:Man(4)K(3)DOG; D009844:Oligosaccharides; D003208:Concanavalin A; D011092:Polyethylene Glycols; D005990:Glycerol; D008358:Mannose