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.
Barragan-Montero
Véronique
V
Laboratoire de Chimie Biomoléculaire, UMR 5032, Université Montpellier II, ENSCM, 8, rue de l'Ecole Normale, 34296 Montpellier cedex 5, France. vbarragan@univ-montp2.fr
Winum
Jean-Yves
JY
Molès
Jean-Pierre
JP
Juan
Emmanuelle
E
Clavel
Caroline
C
Montero
Jean-Louis
JL
D002152:Calorimetry, Differential Scanning; D002186:Cannabinoids / Q000737:chemistry*; D002448:Cell Adhesion; D002478:Cells, Cultured; D002784:Cholesterol / Q000737:chemistry*; D006801:Humans; D015603:Keratinocytes / Q000378:metabolism*; D008081:Liposomes / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D009928:Organ Specificity; D012867:Skin / Q000166:cytology / Q000378:metabolism*; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry*
D002186:Cannabinoids; D008081:Liposomes; D013501:Surface-Active Agents; D002784:Cholesterol