Abstract
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.
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