Synthesis and properties of isocannabinoid and cholesterol derivatized rhamnosurfactants: application to liposomal targeting of keratinocytes and skin

The usefulness of vesicles to cargo material depends on the design of new ligands able to incorporate easily inside the bilayer and also to direct the vesicles to the targeted site. Therefore, the synthesis of two new rhamnose-bearing surfactants is described. The hydrophobic part consists of cholesterol (in compound 3) and citrylidene phloroglucinol (in compound 6). The ability of these two rhamnolipids to incorporate into a DPPC membrane and to form aggregates is investigated, respectively, by differential scanning calorimetry and by surface tension measurements. Those two new surfactants were incorporated in fluorescent liposomes to study their interactions with keratinocytes and skin sections. Intraliposomal delivery to keratinocytes was observed in both cases, even if the kinetics of delivery were different according to the rhamnosurfactant used. Skin sections were stained by both liposomal formulations, and different interactions between the liposomes and skin cells according to the surfactant used were noted.