Host-guest interaction of β-cyclodextrin with isomeric ursolic acid and oleanolic acid: physicochemical characterization and molecular modeling study
Yuan Huang
Peng Quan
Yongwei Wang
Dongsheng Zhang
Mingwan Zhang
Rui Li
Nan Jiang
摘要：Ursolic acid (UA) and oleanolic acid (OA) are insoluble drugs.The objective of this study was to encapsulate them into β-cyclodextrin (β-CD) and compare the solubility and intermolecular force of β-CD with the two isomeric triterpenic acids.The host-guest interaction was explored in liquid and solid state by ultraviolet-visible absorption,1H NMR,phase solubility analysis,and differential scanning calorimetry,X-ray powder diffractometry,and molecular modeling studies.Both experimental and theoretical studies revealed that β-CD formed 1∶1 water soluble inclusion complexes and the complexation process was nattrally favorable.In addition,the overall results suggested that ring E with a carboxyl group of the drug was encapsulated into the hydrophobic CD nanocavity.Therefore,a clear different inclusion behavior was observed,and UA exhibited better affinity to β-CD compared with OA in various media due to little steric interference,which was beneficial to form stable inclusion complex with β-CD and increase its water solubility effectively.
机标关键词：oleanolic acidursolic aciddifferential scanning calorimetryinclusion complexesmolecular modelingwater solubilitycarboxyl groupwater soluble
分类号：R965(药理学)
资助基金：grants from the National Natural Science Foundation of China(21303086)the Natural Science Foundation of Jiangsu Province(BK20130884)the Research Fund for Doctoral Program of Higher Education (20123234120012)
论文发表日期：2017-01-01
在线出版日期：2025-08-15（本平台首次上网日期，不代表文献的发表时间）
页数：13( 395-407 )
英文信息