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Issue 29, 2013
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Incorporation of a calixarene-based glucose functionalised bolaamphiphile into lipid bilayers for multivalent lectin recognition

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Abstract

The synthesis, characterization and inclusion in liposomes of a glucosylated bolaamphiphile built on a calix[4]arene scaffold are described. The new glucocalixarene bolaamphiphile destabilizes bilayers of saturated lipids whereas it rigidifies those of unsaturated lipids, thus reducing leakage of calcein from the liposome internal aqueous compartment. Moreover, from fluorescence and turbidimetry experiments it was found that the glucose units of bolaamphiphile 1 functionalised liposomes allow a specific multivalent interaction with the tetrameric glucose binding protein Concanavalin A. These results therefore represent a novel strategy to functionalise liposomes with saccharides, exploiting multivalent glycosylated ligands to be used in the preparation of drug delivery systems potentially able to target specific lectins.

Graphical abstract: Incorporation of a calixarene-based glucose functionalised bolaamphiphile into lipid bilayers for multivalent lectin recognition

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Publication details

The article was received on 12 Apr 2013, accepted on 17 May 2013 and first published on 20 May 2013


Article type: Paper
DOI: 10.1039/C3OB40732B
Citation: Org. Biomol. Chem., 2013,11, 4811-4817
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    Incorporation of a calixarene-based glucose functionalised bolaamphiphile into lipid bilayers for multivalent lectin recognition

    S. Aleandri, A. Casnati, L. Fantuzzi, G. Mancini, G. Rispoli and F. Sansone, Org. Biomol. Chem., 2013, 11, 4811
    DOI: 10.1039/C3OB40732B

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