Inclusion complex of 20(S)-protopanaxatriol with modified β-cyclodextrin: Characterization, solubility, and interaction with bovine serum albumin

• Published in: Analytical biochemistry 2022-09, Vol.653, p.114753-114753, Article 114753
• Main Authors: Yan, Jin, Li, Zhiwen, Zhu, Fangdao, Chi, Shaoming, Wang, Qin, Rong, Meizhu, Xie, Weiyou, Zhao, Yan
• Format: Article
• Language: English
• Subjects: 20(S)-Protopanaxatriol; Bovine albumin serum; Inclusion complex; Interaction; MD simulation; Modified β-cyclodextrin
• ISSN: 0003-2697; 1096-0309
• DOI: 10.1016/j.ab.2022.114753

20(S)-protopanaxatriol (PPT) is one of the ginsenosides isolated from Panax ginseng which have many pharmaceutical activities. However, the poor water solubility of PPT restrict its applications. Herein, a novel bridged-bis-[6-(3,3’-(ethylenedioxy) bis (propylamine))-6-deoxy-β-cyclodextrin] (EDBA-bis-β-CD) was designed and synthesized, and the inclusion complex (IC) of EDBA-bis-β-CD with PPT was successfully prepared in the solid state, and characterized by UV, 1H NMR, 2D ROESY, FT-IR, XRD and SEM and molecular modelling methods. The continuous variation method analysis indicated that the stoichiometry of the IC was 1:1. UV–vis spectral analysis demonstrated the binding constant Ks was 995.94 M-1, and the solubility study showed that the solubility of PPT improved 290 times. The interaction of the IC with bovine serum albumin (BSA) was investigated via fluorescence spectroscopy. The results indicated that fluorescence quenching of BSA by IC was static quenching. Thermodynamic studies showed that van der Waals forces and hydrogen bonding play significant roles in interaction. The esterase-like activity of BSA in the presence of IC showed that it reduce the esterase activity of BSA in a competitive manner. Furthermore, molecular docking and molecular dynamics simulations for EDBA-bis-β-CD/PPT and BSA/IC systems were generated to provide information on the stability and the forces in the binding. [Display omitted] •Inclusion complex (IC) of a novel modified β-CD with PPT was prepared and confirmed.•Solid IC was characterized with UV–vis, NMR, FT-IR, PXRD, and SEM.•The solubility of PPT improved 290 times after inclusion.•Interaction of IC with BSA was investigated via fluorescence spectroscopy and computational methods.•Inclusion process decreased the binding strength of PPT with BSA but not influence the binding mechanism.