Complexation of 3α,7α,12α-trihydroxy-5β-cholan-24-amine by β- and γ-cyclodextrins

The binding constants, standard molar enthalpy, Gibbs free energy, and entropy changes were determined for the formation of inclusion complexes between 3α,7α,12α- trihydroxy-5β-cholan-24-amine, C₂₄NH2, and β-cyclodextrin and γ-cyclodextrin. The stoichiometry of both complexes is 1:1 in agreement with previously reported results for other trihydroxy bile salts. The equilibrium constant values for the formation of the inclusion complex are similar as well. The structure of the C₂₄NH2/γ-cyclodextrin complex was studied by ROESY experiments. These results suggest that B, C and Drings of the steroid skeleton, as well as the side chain, interact with the cyclodextrin cavity, while the A ring of the steroid nucleus remains outside the cavity.