Monte Carlo docking simulations of cyclomaltoheptaose and dimethyl cyclomaltoheptaose with paclitaxel Original Research Article

The molecular basis for the remarkable enhancement of the solubility of paclitaxel by O-dimethylcyclomaltoheptaose (DM-β-CD) over cyclomaltoheptaose (β-cyclodextrin, β-CD) was investigated with Monte Carlo docking–minimization simulation. As possible guests of inclusion complexation for the host cyclic oligosaccharides, two functional moieties of the suggested solution structure of paclitaxel were used where one is the C-3′N benzoyl moiety (B-ring) and the other is a hydrophobic (HP) cluster site among the C-3′ phenyl (C-ring), C-2 benzoate (A-ring), and C-4 acetoxy moieties. The energetic preference of inclusion complexation of DM-β-CD over β-CD was analyzed on the basis of more efficient partitioning process of DM-β-CD into the hydrophobic cluster site of the paclitaxel.