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Relevant academic research and scientific papers

Binding affinity properties of dendritic glycosides based on a β-cyclodextrin core toward guest molecules and concanavalin A

The inclusion behavior and concanavalin A binding properties of hepta-antennated and newly synthesized tetradeca-antennated C-6-branched mannopyranosyl and glucopyrannosyl cyclomaltoheptaose (β-cyclodextrin) derivatives have been evaluated by isothermal titration microcalorimetry and enzyme-linked lectin assay (ELLA), respectively. The synthesis of three first-order dendrimers based on a β-cyclodextrin core containing 14 1-thio-β-D-glucose, 1-thio-β-mannose, and 1-thio-β-rhamnose residues was performed following a convergent approach and involving (1) preparation of a thiolated bis-branched glycoside building block and (2) attachment of the building block onto heptakis(6-deoxy-6-iodo)-β-cyclodextrin. Calorimetric titrations performed at 25 °C in buffered aqueous solution (pH 7.4) gave the affinity constants and the thermodynamic parameters for the inclusion complex formation of these β-cyclodextrin derivatives with guests sodium 8-anilino-1-naphthalensulfonate (ANS) and 2-naphthalenesulfonate. The host capability of the persubstituted β-cyclodextrins decreased with respect to the native β-CD when sodium 2-naphthalenesulfonate was used as a guest and improved when ANS was used as a guest molecule. Heptavalent mannoclusters based on β-CD cores enhance the lectin binding affinity due to the cluster effect; however, the increase of the valency from 7 to 14 ligands did not contribute to the improvement of the concanavalin A binding affinity. In addition, the synthesized hyperbranched mannoCDs lost completely the capability as a host molecules.

Dendritic galactosides based on a β-cyclodextrin core for the construction of site-specific molecular delivery systems: Synthesis and molecular recognition studies

In order to evaluate the ability of multivalent glycosides based on a β-cyclodextrin core as site-specific molecular carriers, a study on both the inclusion complexation behaviour and lectin binding affinity of branched and hyperbranched β-cyclodextrins is presented. A series of cluster galactosides constructed on β-cyclodextrin scaffolds containing seven 1-thio-β-lactose or β-lactosylamine bound to the macrocyclic core through different spacer arms were synthesised. In addition, the first synthesis of three first-order dendrimers based on a β-cyclodextrin core containing fourteen 1-thio-β-D-galactose, 1-thio-β-lactose and 1-thio-β-melibiose residues was performed. Calorimetric titrations performed at 25°C in buffered aqueous solution (pH 7.4) gave the affinity constants and the thermodynamic parameters for the complex formation of these β-cyclodextrin derivatives with guests sodium 8-anilino-1-naphthalenesulfonate (ANS) and 2-naphthalenesulfonate, and lectin from peanut (Arachis hypogaea) (PNA). The persubstitution of the primary face of the β-cyclodextrin with saccharides led to a slight increase of the binding constant values for the inclusion complexation with ANS relative to the native β-cyclodextrin. However, the increase of the steric congestion due to the presence of the saccharide residues on the narrow rim of the β-cyclodextrin may cause a decrease of the binding ability as shown for sodium 2-naphthalenesulfonate. The spacer arms are not passive elements and influence the host binding ability according to their chemical nature. PNA forms soluble cross-linked complexes with cluster galactosides and lactosides scaffolded on β-cyclodextrin but not with cluster galactopyranosylamines or melibiose. Both, perbranched and hyperbranched β-cyclodextrins, form stronger complexes with PNA than the monomeric analogues. However, the use of hyperbranched CDs does not contribute to the improvement of the complex stability relative to heptakis-glycocyclodextrin derivatives. Finally, a titration experiment with PNA and a complex formed by a heptakis lactose β-cyclodextrin derivative with sodium 2-naphthalenesulfonate showed the formation of a soluble cross-linked complex with stronger affinity constant and higher stoichiometry than those observed for the complex formation of PNA with the same heptakis-lactose β-cyclodextrin derivative, suggesting the formation of a three component complex.