Synthesis and drug complexation studies with β-cyclodextrins fluorinated on the primary face

Three fluorinated beta-cyclodextrin derivatives, namely 5, 9 and 12, were prepared with the hope that the fluorine reporter group may assist in direct evaluation of the complexation properties of these potential drug carriers. Two of the synthesized derivatives, the previously reported monofluoro-beta-cyclodextrin 9 and the novel trifluoroethylthio-beta-cyclodextrin 12, displayed reasonable aqueous solubility and thus were suitable for drug-cyclodextrin complexation studies. Preliminary NMR results (H-1 and F-19) on the host-guest complex formation of both of these cyclodextrin derivatives with amantidine, a therapeutic agent employed in the treatment of Influenza A infections, are also presented.