ALKYL AND PERFLUOROALKYL GLYCOLIPID-BASED SUPRAMOLECULAR ASSEMBLIES

New amphiphilic agents with single or double-chain hydrogenated and/or fluorinated hydrophobic tails have been synthesized from natural disaccharides (lactose, maltose). The sugar moiety is intended to allow specific targeting of cell membrane sugar receptors. The introduction of a peptide moiety (Gly, Gly-Gly or Lys) between the hydrophilic head and the hydrophobic tail allows the adjustment of the hydrophilic-lipophilic balance (HLB). These amphiphiles are shown to form vesicles and other supramolecular assemblies readily. The morphology of these assemblies strongly depends on the component's molecular structure. Glycolipids with a single fluorinated chain produced disk-like assemblies; the double-tailed analogs led to multilayer vesicles. The impact of the amino acid linkage is considerable for the double-tailed compounds: multilamellar vesicles were readily obtained when one glycine residue was interposed between the carbohydrate and the hydrophobic double tail. With a glycyl-glycine spacer unilamellar vesicles were formed. With lysine, the glycolipid molecules formed mainly disk-like lamellar structures, tubules and helical superstructures along with a few vesicles.