title: 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.
authors.affiliation: Dipartimento di Chimica Università degli Studi di Roma Sapienza, P.le A. Moro 5, 00185 Roma, Italy.
authors.forename: S
authors.initials: S
authors.lastname: Aleandri
authors.forename: A
authors.initials: A
authors.lastname: Casnati
authors.forename: L
authors.initials: L
authors.lastname: Fantuzzi
authors.forename: G
authors.initials: G
authors.lastname: Mancini
authors.forename: G
authors.initials: G
authors.lastname: Rispoli
authors.forename: F
authors.initials: F
authors.lastname: Sansone
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D003208:Concanavalin A / Q000737:chemistry; D016503:Drug Delivery Systems; D005663:Furans / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D037102:Lectins / Q000737:chemistry*; D008051:Lipid Bilayers / Q000737:chemistry*; D008081:Liposomes / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D011728:Pyridones / Q000737:chemistry*
chemical_list: D005663:Furans; D037102:Lectins; D008051:Lipid Bilayers; D008081:Liposomes; D010636:Phenols; D011728:Pyridones; C543575:bolaamphiphile; C121325:calix(4)arene; D003208:Concanavalin A; D047250:Calixarenes; D005947:Glucose