title: Targeted liposomes: convenient coupling of ligands to preformed vesicles using "click chemistry".
abstract: An efficient and convenient chemoselective conjugation method based on "click chemistry" was developed for coupling ligands to the surface of preformed liposomes. It can be performed under mild conditions in aqueous buffers; the use of a water soluble Cu(I) chelator, such as bathophenanthrolinedisulfonate, was essential to obtain good yields in reasonable reaction times. A model reaction was achieved in which, in a single step, an unprotected alpha-D-mannosyl derivative carrying a spacer arm functionalized with an azide group was conjugated to the surface of vesicles presenting a synthetic lipid carrying a terminal alkyne function. When liposomes composed of saturated phospholipids were used, the reaction conditions developed in the present work did not damage the membranes as measured by the absence of leakage of entrapped 5,6-carboxyfluorescein. Moreover, as assessed by agglutination experiments using concanavalin A, the mannose residues were perfectly accessible on the surface of the targeted vesicles.
authors.affiliation: Institut Gilbert Laustriat, UMR 7175 CNRS/Université Louis Pasteur (Strasbourg I), Département de Chimie Bioorganique, Faculté de Pharmacie, 74 route du Rhin, 67400 Illkirch, France.
authors.forename: Fatouma
authors.initials: F
authors.lastname: Said Hassane
authors.forename: Benoît
authors.initials: B
authors.lastname: Frisch
authors.forename: Francis
authors.initials: F
authors.lastname: Schuber
mesh_terms: D001386:Azides / Q000737:chemistry; D008024:Ligands; D008081:Liposomes / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry; D008956:Models, Chemical
chemical_list: D001386:Azides; D008024:Ligands; D008081:Liposomes; D008358:Mannose