Inclusion compound formulation of hirsutenone with beta-cyclodextrinInclusion compound formulation of hirsutenone with beta-cyclodextrin
- Authors
- Ahn, B.K.; Lee, S.G.; Kim, S.R.; Lee, D.H.; Oh, M.H.; Lee, M.W.; Choi, Y.W.
- Issue Date
- Dec-2013
- Publisher
- 한국약제학회
- Keywords
- Cyclodextrin; Hirsutenone; Inclusion complex; Solvent evaporation; Stability
- Citation
- Journal of Pharmaceutical Investigation, v.43, no.6, pp 453 - 459
- Pages
- 7
- Journal Title
- Journal of Pharmaceutical Investigation
- Volume
- 43
- Number
- 6
- Start Page
- 453
- End Page
- 459
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/19920
- DOI
- 10.1007/s40005-013-0089-9
- ISSN
- 2093-5552
2093-6214
- Abstract
- Inclusion complexation with β-cyclodextrin (β-CD) was performed to improve the stability of hirsutenone (HST), a naturally occurring immunomodulator that is labile in aqueous solutions. HST-β-CD inclusion complexes were prepared using a solvent evaporation method. Briefly, solutions of HST (dissolved in isopropyl alcohol) and β-CD (dissolved in distilled water) were mixed and evaporated under vacuum by using a rotary evaporator. Phase solubility studies of the product revealed 1:1 or 1:2 complex formation, with an apparent stability constant of 249.2 M-1. Differential scanning calorimetry showed a shift of endothermic peaks and nuclear magnetic resonance spectra displayed shift changes in H-3,5,6 protons, located inside the β-CD cavity, in inclusion complexes. These data provided strong evidence for inclusion complex formation. Characterization using infrared spectroscopy was hindered because of interfering β-CD vibrations. Inclusion complex stability was evaluated in the solid and aqueous solution states. Rate constants (×10-2, day-1) of HST and HST-β-CD were 13.2 and 9.79, respectively, in an aqueous solution at 25 °C; the corresponding values in the solid state were 0.14 and 0.18. The present study therefore showed successful formation of HST-β-CD, but the stability of HST within this inclusion compound was not markedly improved. © 2013 The Korean Society of Pharmaceutical Sciences and Technology.
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