Synthesis of lipophosphoramidyl-cyclodextrins and their supramolecular properties

The synthesis of lipophosphoramidyl-beta-CD was obtained by an Atherton-Todd (AT) reaction that involved dioleylphosphite and either functionalized permethylated or native beta-cyclodextrin. This AT reaction that produced dioleylphosphoramide by making use of the amino group grafted on cyclodextrin, was optimized for these cyclic oligosaccharides. These new amphiphilic compounds were fully characterized, and their self-assembling properties were investigated: the mean size diameter and poly-dispersity measured by Dynamic Light Scattering (DLS) were affected by the nature of the aqueous media and the temperature of storage. The encapsulation properties of these nanoparticles have been evaluated using carboxyfluorescein and scopolamine derivatives as model of guests. (C) 2011 Elsevier Masson SAS. All rights reserved.