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  • ISSN 1674-8301
  • CN 32-1810/R
Volume 31 Issue 5
Aug.  2017
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Yuan Huang, Peng Quan, Yongwei Wang, Dongsheng Zhang, Mingwan Zhang, Rui Li, Nan Jiang. Host-guest interaction of β-cyclodextrin with isomeric ursolic acid and oleanolic acid: physicochemical characterization and molecular modeling study[J]. The Journal of Biomedical Research, 2017, 31(5): 395-407. DOI: 10.7555/JBR.31.20160073
Citation: Yuan Huang, Peng Quan, Yongwei Wang, Dongsheng Zhang, Mingwan Zhang, Rui Li, Nan Jiang. Host-guest interaction of β-cyclodextrin with isomeric ursolic acid and oleanolic acid: physicochemical characterization and molecular modeling study[J]. The Journal of Biomedical Research, 2017, 31(5): 395-407. DOI: 10.7555/JBR.31.20160073
shu

Host-guest interaction of β-cyclodextrin with isomeric ursolic acid and oleanolic acid: physicochemical characterization and molecular modeling study

  • 1.

    Department of Pharmacy, Affiliated Wuxi Peoples Hospital, Nanjing Medical University, Wuxi, Jiangsu 214023, China

  • 2.

    Department of Pharmaceutical Sciences, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China

  • 3.

    School of Pharmacy, Nanjing Medical University, Nanjing, Jiangsu 211166, China

  • 4.

    Department of Colorectal Surgery, The First Affiliated Hospital of Nanjing Medical University, Nanjing, Jiangsu 210029, China

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This work was supported by grants from the National Natural Science Foundation of China (21303086), the Natural Science Foundation of Jiangsu Province (BK20130884), and the Research Fund for Doctoral Program of Higher Education (20123234120012). We thank the High Performance Computing Center at Shanghai

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  • Received Date: July 14, 2016
  • Revised Date: September 19, 2016
    Graphical Abstract
    • Abstract
  • 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, 1 H 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 naturally 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.
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