The specificity of carbohydrate-lectin interaction has been reported as an attractive strategy for drug delivery in cancer therapy because of the high levels of lectins in several human malignancies. A novel cationic glucosylated amphiphile was therefore synthesized, as a model system, to attribute specificity toward d-glucose receptors to liposome formulations. Fluorescence experiments demonstrated that the monomeric glucosylated amphiphile is capable of interacting with fluorescently labeled concanavalin A, a D-glucose specific plant lectin. The interaction of concanavalin A with liposomes composed of a phospholipid and the glucosylated amphiphile was demonstrated by agglutination observed by optical density and dynamic laser light scattering measurements, thus paving the way to the preparation of other glycosilated amphiphiles differing for the length of polyoxyethylenic spacer, the sugar moieties, and/or the length of the hydrophobic chain.
An absorption and circular dichroism spectroscopies investigation was carried out on the heteroaggregates formed in water upon the interaction of Chicago Sky Blue with four different cationic surfactants derived from ephedrine and pseudoephedrine and featuring hydrophobic tails of different length. The chirooptical features of the heteroaggregates indicate that hydrophobic interactions control the transcription of the chiral information from the surfactant to the supramolecular architectures they form with the dye. In fact, surfactants characterised by the same stereochemistry and by different length of the hydrophobic tails mediate the selection of the enantiomers of the same chiral topological arrangement
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