A superior preparation method for daidzein-hydroxypropyl-β-cyclodextrin complexes with improved solubility and dissolution: Supercritical fluid process

Pan, Hao; Wang, Han-Bing; Yu, Yi-Bin; Cheng, Bing-Chao; Wang, Xiao-Yu; Li, Ying

doi:10.1515/acph-2017-0005

Abstract

Advantages of the supercritical fluid (SCF) process compared to the conventional solution stirring method (CSSM) in the preparation of daidzein-hydroxypropyl-β-cyclodextrin (HPβCD) complexes were investigated. Formation of daidzein/ HPβCD inclusion complexes was confirmed by Fourier transformed-infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), X-ray diffraction (XRD) and scanning electron microscopy (SEM). Particle size, inclusion yield, drug solubility and dissolution of daidzein/HPβCD complexes were evaluated. Compared to CSSM, the SCF process resulted in higher inclusion yield and higher solubility. Also, extended dissolution of daidzein from the SCF processed HPβCD inclusion complexes was observed, with only 22.94 % released in 45 min, compared to its rapid release from those prepared by CSSM, with 98.25 % drug release in 15 min. This extended release of daidzein from SCF prepared inclusion complexes was necessary to avoid drug precipitation and improve drug solubilisation in the gastrointestinal tract. The results showed that the SCF process is a superior preparation method for daidzein-hydroxypropyl-β-cyclodextrin complexes.

References

1. S. Soumyakrishnan, T. Divya, S. Kalayarasan, N. Sriram and G. Sudhandiran, Daidzein exhibits anti-fibrotic effect by reducing the expressions of Proteinase activated receptor 2 and TGFbeta1/ Smad mediated inflammation and apoptosis in Bleomycin-induced experimental pulmonary fibrosis, Biochimie 103 (2014) 23-36; DOI: 10.1016/j.biochi.2014.04.005.10.1016/j.biochi.2014.04.00524769130
Search in Google Scholar Back to article
2. B. Pahari, B. Sengupta, S. Chakraborty, B. Thomas, D. McGowan and P. K. Sengupta, Contrasting binding of fisetin and daidzein in gamma-cyclodextrin nanocavity, J. Photochem. Photobiol. B. 118 (2013) 33-41; DOI: 10.1016/j.jphotobiol.2012.10.010.10.1016/j.jphotobiol.2012.10.010355358923177044
Search in Google Scholar Back to article
3. X. Dong, W. Xu, R. A. Sikes and C. Wu, Combination of low dose of genistein and daidzein has synergistic preventive effects on isogenic human prostate cancer cells when compared with individual soy isoflavone, Food. Chem. 141 (2013) 1923-1933; DOI: 10.1016/j.foodchem.2013.04.109.10.1016/j.foodchem.2013.04.10923870911
Search in Google Scholar Back to article
4. H. J. Park, Y. K. Jeon, D. H. You and M. J. Nam, Daidzein causes cytochrome c-mediated apoptosis via the Bcl-2 family in human hepatic cancer cells, Food. Chem. Toxicol. 60 (2013) 542-549; DOI: 10.1016/j.fct.2013.08.022.10.1016/j.fct.2013.08.02223959101
Search in Google Scholar Back to article
5. B. S. Pan, Y. Y. Kuo, T. Y. Chen and Y. C. Liu, Anti-oxidative and anti-inflammatory activities of two different species of a Chinese herb I-Tiao-Gung, Life Sci. 77 (2005) 2830-2839; DOI: 10.1016/j. lfs.2005.05.027.
Search in Google Scholar Back to article
6. M. H. Park, J. W. Ju, M. J. Park and J. S. Han, Daidzein inhibits carbohydrate digestive enzymes in vitro and alleviates postprandial hyperglycemia in diabetic mice, Eur. J.Pharmacol. 712 (2013) 48-52; DOI: 10.1016/j.ejphar.2013.04.047.10.1016/j.ejphar.2013.04.04723669248
Search in Google Scholar Back to article
7. H. J. Oh, Y. G. Kang, T. Y. Na, H. J. Kim, J. S. Park, W. J. Cho and M. O. Lee, Identification of daidzein as a ligand of retinoic acid receptor that suppresses expression of matrix metalloproteinase-9 in HaCaT cells, Mol. Cell. Endocrin. 376 (2013) 107-113; DOI: 10.1016/j.mce.2013.06.015.10.1016/j.mce.2013.06.01523791815
Search in Google Scholar Back to article
8. Y. Ma, X. Zhao, J. Li and Q. Shen, The comparison of different daidzein-PLGA nanoparticles in increasing its oral bioavailability, Int. J. Nanomed. 7 (2012) 559-570; DOI: 10.2147/IJN.S27641.10.2147/IJN.S27641327743622346351
Search in Google Scholar Back to article
9. T. Loftsson and D. Duchêne, Cyclodextrins and their pharmaceutical applications, Int. J. Pharm. 329 (2007) 1-11; DOI: 10.1016/j.ijpharm.2006.10.044.10.1016/j.ijpharm.2006.10.04417137734
Search in Google Scholar Back to article
10. T. Loftsson and M. E. Brewster, Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization, J. Pharm. Sci. 85 (1996) 1017-1025; DOI: 10.1021/js950534b.10.1021/js950534b8897265
Search in Google Scholar Back to article
11. F. K. Yatsu, L. S. Koester, I. Lula, J. J. Passos and R. Sinisterra, Multiple complexation of cyclodextrin with soy isoflavones present in an enriched fraction, Carbohyd. Polym. 98 (2013) 726-735; DOI: 10.1016/j.carbpol.2013.06.062.10.1016/j.carbpol.2013.06.06223987405
Search in Google Scholar Back to article
12. F. K. Yatsu, L. S. Koester, I. Lula, J. J. Passos, R. Sinisterra and V. L. Bassani, Cyclodextrin-based pharmaceutics: past, present and future, Nat. Rev. Drug. Discov. 3 (2004) 1023-1035; DOI: 10.1038/ nrd1576.10.1038/nrd157615573101
Search in Google Scholar Back to article
13. S. W. Jun, M. S. Kim, J. S. Kim, H. J. Park, S. Lee, J. S. Woo and S. J. Hwang, Preparation and characterization of simvastatin/hydroxypropyl-beta-cyclodextrin inclusion complex using supercritical antisolvent (SAS) process, Eur. J. Pharm. Biopharm. 66 (2007) 413-421; DOI: 10.1016/j. ejpb.2006.11.013.
Search in Google Scholar Back to article
14. Q. L. Zhu, T. Guo, D. N. Xia, X. Y. Li, C. L. Zhu, H. Y. Li, D. F. Ouyang, J. W. Zhang and Y. Gan, Pluronic F127-modified liposome-containing tacrolimus-cyclodextrin inclusion complexes: improved solubility, cellular uptake and intestinal penetration, J. Pharm. Pharmacol. 65 (2013) 1107-1117; DOI: 10.1111/jphp.12074.10.1111/jphp.1207423837579
Search in Google Scholar Back to article
15. Q. L. Zhu, X. Y. Li, D. N. Xia, H. Z. Yu, D. Chen, W. W. Fan and Y. Gan, Lipid-based formulations for oral drug delivery: effects on drug absorption and metabolism, Curr. Drug. Metab. 16 (2015) 200-210; DOI: 10.2174/138920021603150812121453.10.2174/13892002160315081212145326279327
Search in Google Scholar Back to article
16. L. M. Ensign, C. Richard and H. Justin, Oral drug delivery with polymeric nanoparticles: the gastrointestinal mucus barriers, Adv. Drug Deliv. Rev. 64 (2012) 557-570; DOI: 10.1016/j.addr.2011.12.009. 10.1016/j.addr.2011.12.009332227122212900
Search in Google Scholar Back to article

A superior preparation method for daidzein-hydroxypropyl-β-cyclodextrin complexes with improved solubility and dissolution: Supercritical fluid process

Abstract

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