Supramolecular host-guest interactions of pseudoginsenoside F11 with β- and γ-cyclodextrin: Spectroscopic/spectrometric and computational studies

Abstract Pseudoginsenoside F11 (PF11) was described considering its complexation capabilities with β- and γ-cyclodextrin. A merged computational/experimental approach was used, and it was found that the PF11 molecule form a stable inclusion complex with the γ-cyclodextrin, with an association constant of 1.66 × 104 M−1, while it is not able to form an analogously one with the β-cyclodextrin. Nuclear magnetic resonance spectroscopy (1H NMR, 2D ROESY, and DOSY) and mass spectrometry experiments were used for the study and characterization of the supramolecular complex revealing the effective inclusion of the PF11 in the γ-cyclodextrin cavity. The thermodynamic parameters and the geometry of the PF11/cyclodextrin inclusion complex were studied by molecular dynamics simulations and semi-empirical calculations. The results of this study might lead the way for new PF11/γ-cyclodextrin formulations with advanced bioavailability and targeting.