Facile Synthesis of β-Cyclodextrin-Dextran Polymers by “Click” Chemistry

Abstract

Three series of novel water-soluble beta-cyclodextrin-dextran polymers have been prepared by "click" chemistry. The polymers were synthesized from alkyne-modified dextrans (AMDs) onto which mono-6-O-deoxy-monoazido-betaCD (N3betaCD) was grafted by a copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The polymers have been characterized by NMR spectroscopy and size exclusion chromatography (SEC). The binding properties have been characterized by isothermal titration calorimetry (ITC) and show excellent accessibility of the betaCDs.

Size‐Controlled Nanoassemblies Based on Cyclodextrin‐Modified Dextrans

“…[25] We showed that the excellent binding properties of these polymers are due to a high accessibility of the bCD cavities. Association constants as high as with bCD were determined at 25 8C in 0.05 mol Á L À1 NaCl solution (K % 1.2 Â 10 5 -2.05 Â 10 5 mol Á L À1 ).…”

“…The substitution degree was obtained by 1 H NMR in deuterated dimethyl sulfoxide (DMSO) from the ratio of the integration of the Ada protons (d ¼ 1.6-2.0) and of the integration of the anomeric and hydroxylic protons (d ¼ 4.4-5.0). The synthesis of the bCD grafted dextrans was recently reported [25] with their characterization [ 1 H NMR in deuterated water (Bruker DRX600) and size-exclusion chromatography]. The degree of substitution, the bCD content, and the number of bCD per chain are given in Table 2.…”

“…[25] The two series of polymers differ by the spacer arm between the bCD moieties and the dextran backbone, either ether or ester for the D70GPbCD or D70HXbCD series, respectively. Structure of the polymers is given in Figure 1.…”

“…Welldefined bCD polymers, prepared by click grafting bCD units onto dextran chains, were reported by our groups recently and will be used for this study. [25] The bCD units are linked to the polymer backbones via spacer arms which ensure flexibility and accessibility for host/guest associations. As corresponding counterpart, guest polymers are made of a dextran backbone with adamantyl (Ada) pending groups.…”

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“…Cavasol R W7, with a molar substitution (per anhydro glucose unit) of 1.6-1.9 was a gift from Wacker Chemie AG (Burghausen, Germany). The water-soluble and biocompatible polymeric CDs have CDs as a part of the backbone [18][19][20] and were synthesized at the Section of Chemistry, Department of Biotechnology, Chemistry and Environmental Engineering, Aalborg University (Aalborg, Denmark) and used as received. The representative structure of the (-CD-PEG polymer is shown in Figure 1.…”