AAPS PharmSciTech

, Volume 15, Issue 5, pp 1189–1196 | Cite as

A 5,7-Dimethoxyflavone/Hydroxypropyl-β-Cyclodextrin Inclusion Complex with Anti-Butyrylcholinesterase Activity

  • Supachai Songngam
  • Mongkol Sukwattanasinitt
  • Krisana Siralertmukul
  • Pattara Sawasdee
Research Article

Abstract

This study aimed to improve the water solubility of 5,7-dimethoxyflavone (5,7-DMF) isolated from Kaempferia parviflora by complexation with 2-hydroxypropyl-β-cyclodextrin (HPβ-CD). The phase solubility profile of 5,7-DMF in the presence of HPβ-CD was classified as AL-type and indicated a 1:1 mole ratio. Differential scanning colorimetry, X-ray diffraction, NMR and SEM analyses supported the formation of a 5,7-DMF/HPβ-CD inclusion complex involving the A ring of 5,7-DMF inside the HPβ-CD cavity. This is the first example of CD inclusion with the A ring of non-hydroxyl flavones. The stability and binding constants of the complexes were determined using the phase solubility and UV-vis absorption spectroscopy, respectively. The water solubility of 5,7-DMF was increased 361.8-fold by complexation with HPβ-CD and overcame the precipitation problem observed in aqueous buffers, such as during in vitro anti-butyrylcholinesterase activity assays. The 1:1 mole ratio of the 5,7-DMF/HPβ-CD complex showed a 2.7-fold higher butyrylcholinesterase inhibitory activity (in terms of the IC50 value) compared to the non-complexed compound.

KEY WORDS

5,7-dimethoxyflavone butyrylcholinesterase inhibitory activity hydroxypropyl-β-cyclodextrin inclusion complex water solubility 

Notes

Acknowledgments

This work was financially supported by the Higher Education Research Promotion and National Research University Project of Thailand, the Office of the Higher Education Commission (FW645A), National Research University project of CHE(AM1077I), the Special Task Force for Activating Research (STAR) from the Centenary Academic Development Project, Chulalongkorn University, and the Program of Center of Excellence Network from Nanotechnology Center (NANOTEC), NSTDA, Ministry of Science and Technology, Thailand. The authors are also grateful for English corrections by Robert Butcher of the Publication Counseling Unit, Faculty of Science, Chulalongkorn University.

Supplementary material

12249_2014_157_MOESM1_ESM.docx (591 kb)
ESM 1 (DOCX 591 kb)

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Copyright information

© American Association of Pharmaceutical Scientists 2014

Authors and Affiliations

  • Supachai Songngam
    • 1
  • Mongkol Sukwattanasinitt
    • 2
  • Krisana Siralertmukul
    • 3
  • Pattara Sawasdee
    • 2
  1. 1.Petrochemical and Polymer Science Program, Faculty of ScienceChulalongkorn UniversityBangkokThailand
  2. 2.Department of Chemistry, Faculty of ScienceChulalongkorn University and Nanotec-CU Center of Excellence on Food and AgricultureBangkokThailand
  3. 3.Metallurgy and Materials Science Research InstituteChulalongkorn UniversityBangkokThailand

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