CONFORMATIONALLY MOBILE GLUCOSYLTHIOUREIDO-CALIX[6]- AND CALIX[8]ARENES: SYNTHESIS, AGGREGATION AND LECTIN BINDING

Francesco Sansone (1) , Laura Baldini (1) , Alessandro Casnati (2) , Rocco Ungaro (1)

1 Dipartimento di Chimica Organica e Industriale
2 Dipartimento di Chimica Organica e Industriale

Two new glucoclusters 2a and 2b, in which the sugar units are connected to the upper rim of methoxycalix[6]- and calix[8]arene derivatives via thiourea linkages, were synthesized and their aggregation properties in water studied by 1H NMR, Atomic Force Microscopy (AFM) and Dynamic Light Scattering (DLS). Small size aggregates (2-10 nm diameter) are formed by both macrocycles, which become much larger (200-300 nm) in the presence of a phosphate buffer, whereas other anions (Cl-, NO3-, SO4-) have no effect. The glycoclusters 2a and 2b interact with plasmid DNA but do not condense it, while in the presence of a glucose specific lectin such as Concanavalin A (ConA) agglutination occurs. The data obtained give useful insight into the mode of binding of calixarene- based glycoclusters with lectins.

Mots clés: Physical Sciences

Francesco Sansone, Laura Baldini, Alessandro Casnati, Rocco Ungaro. CONFORMATIONALLY MOBILE GLUCOSYLTHIOUREIDO-CALIX[6]- AND CALIX[8]ARENES: SYNTHESIS, AGGREGATION AND LECTIN BINDING. Supramolecular Chemistry, 2008, 20 (01-02), pp.161-168. ⟨10.1080/10610270701777344⟩. ⟨hal-00513524⟩