Association of aescin with β- and γ-cyclodextrins studied by DFT calculations and spectroscopic methods

Abstract

Background: Aescin, a natural mixture of saponins occurring in Aesculus hippocastanum, exhibits important flebotonic properties, being used in the treatment of chronic venous insufficiency in legs. The inclusion of aescin into cyclodextrins (CDs) is a technical solution for its incorporation into the textile of stockings, but details of the physicochemistry of these host-guest systems are lacking. This work investigates the inclusion of aescin into the cavities of two native cyclodextrins, β-CD and γ-CD.

Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study

“…The MβCD (e.g., 2,6-di- O -methyl-βCD; DMβCD) and the HPβCD derivatives exhibit higher aqueous solubility and lower toxicity than the unmodified βCD [21,22,23]. Several experimental and theoretical reports (both classical molecular dynamics (MD) and density functional theory (DFT)) have demonstrated that the water solubility, chemical stability, and anticancer activity of poorly soluble molecules are significantly improved by complexation with DMβCD and HPβCD derivatives [24,25,26,27,28]. However, the information on the inclusion complexes of MG with βCDs has never been previously reported.…”

The Role of Cyclodextrins in the Design and Development of Triterpene-Based Therapeutic Agents

“…Ramos et al studied the complexes formed by aescin, a mixture of triterpenic saponins extracted from the seeds of Aesculus hippocastanum (Hippocastanaceae), where β-aescin is the main component and represents a mixture of aescin Ia and Ib; its inclusion in β-CD and γ-CD was hypothesized to increase the bioavailability of the active compounds. Aescin formed 1:1 and 1:2 complexes with γ-CD and β-CD, respectively, thus suggesting that the larger γ-CD cavity may better accommodate the aescin molecule [ 101 ].…”