59 research outputs found

    Syntheses of Α-D-galactosamine neoglycolipids

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    Influence of a neoglycolipid and its PEO-lipid moiety on the organization of phospholipid monolayers

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    International audienceThe surface properties of the neoglycolipid (GlcNAcE(3)G(28)) and of its PEO-lipid (E(3)G(28)) moiety mixed with phospholipids (dipalmitoylphosphatidylcholine, DPPC; distearoylphosphatidylcholine, DSPC; diarachidoylphosphatidylcholine, DAPC; and dibehenoylphosphatidylcholine, DBPC) were studied in Langmuir monolayers at various mixture compositions and surface pressures. The pi-A isotherms of the pure compounds revealed that because of the presence of the sugar group in its molecule, GlcNAcE3G28 collapsed at a higher surface pressure and occupied a larger molecular area than the PEO-lipid moiety. It was also observed that the presence of the PEO-lipid (E3G28) in the mixtures triggered a strong alteration of both phospholipid pi-A isotherm profiles and surface diffraction spectra, an indication that the disordering of the initially structured phospholipid monolayers took place. Unlike E3G28, GlcNAcE(3)G(28) did not disorganize phospholipid monolayers but generated a partial segregation of the film-forming components. The calculated excess free energies of mixing (Delta G(exc)) for GlcNAcE(3)G(28)-phospholipid mixtures enabled us to predict the stability of such systems

    Self-organizing properties of natural and related synthetic glycolipids

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    In this article we report on the syntheses, self-organizing properties, and structures of a variety of cerebrosides and related synthetic glycolipids. The thermotropic and lyotropic liquid crystalline properties of the materials were evaluated in detail. All of the families of materials studied exhibited columnar mesophases. In the dry state the aliphatic chains were found to be located on the exterior of the columns, whereas in the wet state the reverse was the case with the polar headgroups on the exterior. Thus, the aliphatic chains act almost like hydrocarbon solvents in the dry state

    Self-organization of synthetic cholesteryl oligoethyleneglycol glycosides in water

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    International audienceLectin−sugar recognition systems are of interest in the pharmaceutical field, especially for the development of drug carriers, tailored for selective delivery. This paper deals with the anhydrous and aqueous self-organization properties of a synthetic cholesteryl oligoethyleneglycol glycoside with the aim of their incorporation in liposomes. Successive phases (lamellar, R3m, Im3m, micelles) have been described depending on water content and temperature. As a result of the presence of sugar residues and their hydration ability, this glycolipid shows a large range of packing parameter with increasing water content. However, because of oligoethyleneglycol spacer, a slight dehydration has been observed with increasing temperature from 20 to 60 °C
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