Issue 29, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
12 Apr 2013
Accepted
17 May 2013
First published
20 May 2013

Org. Biomol. Chem., 2013,11, 4811-4817

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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