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Binding behaviors of scutellarin with α-, β-, γ-cyclodextrins and their derivatives

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Abstract

A series of cyclodextrin/scutellarin inclusion complexes were prepared from α-cyclodextrin, β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin with scutellarin (SCU), and their inclusion complexation behaviors, such as stoichiometry, complex stability constants and inclusion mode, were investigated by means of UV/Vis spectroscopy, 1H NMR and 2D NMR. The results showed that the SCU could be efficiently encapsulated in the cyclodextrin cavity in aqueous solution to produce complexes that were more soluble than free SCU. The enhanced binding ability of cyclodextrins towards SCU was discussed from the viewpoint of the size/shape-fit and multiple recognition mechanism between host and guest.

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References

  1. Zhang, W.D., Chen, W.S., Wang, Y.H., Yang, G.J., Kong, D.Y., Li, H.T.: Studies on the flavone glycosides from the extract of Erigeron breviscapus. Chin. Traditional Herb. Drugs. 31, 565–568 (2000)

    Google Scholar 

  2. Zhang, J., Li, X.S., Zhang, W.D.: Recent progress on pharmacologic activity and chemical components of breviscapine. J. Pharm. Pract. 20, 103–107 (2002)

    Google Scholar 

  3. Deng, T.F.: Clinical application of breviscapine injection in Chinese patients. China Pharm. 11, 728–730 (2002)

    Google Scholar 

  4. Si, S.L., Xu, L.Y.: Clinical application of breviscapine formulations. Chin. J. Clin. Pharm. 13, 408–410 (2004)

    Google Scholar 

  5. Ju, W.Z., Chun, J.H., Tan, R.X., Xiong, N.N.: Study on metabolites of scutellarin in gastrointestinal tract by UPLC-MS/MS method. Chin. J. Clin. Pharmacol. Ther. 11, 292–295 (2006)

    Google Scholar 

  6. Jiang, X.H., Li, S.H., Lan, K., Yang, J.Y., Zhou, J.: Study on the pharmacokinetics of scutellarin in dogs. Acta. Pharm. Sinica. 38, 371–373 (2003)

    Google Scholar 

  7. Liu, Y.M., Lin, A.H., Chen, H., Zeng, F.D.: Study on pharmacokinetics of scutellarin in rabbits. Acta. Pharm. Sinica. 38, 775–778 (2003)

    CAS  Google Scholar 

  8. Ge, Q.-H., Zhou, Z., Zhi, X.J., Ma, L.L.: Pharmacokinetics and absolute bioavailability of breviscapine in Beagle dogs. Chin. J. Pharm. 34, 618–620 (2003)

    CAS  Google Scholar 

  9. Hong, H., Liu, G.Q.: Protection against hydrogen peroxide-induced cytotoxicity in PC12 cells by scutellarin. Life Sci. 74, 2959–2973 (2004)

    Article  CAS  Google Scholar 

  10. David, G., Yian, H.L., Eng, S.O.: Inhibitory effects of a chemically standardized extract from scutellaria barbata in human colon cancer cell lines, LoVo. J. Agric. Food Chem. 53, 8197–8204 (2005)

    Article  CAS  Google Scholar 

  11. Shuai, J., Dong, W.W.: Experimental research of PKC inhibitor. Erigeron breviscapus on the ischemic/reperfusional brain injury. Chin. Pharmacol. Bull. 14, 75–77 (1998)

    CAS  Google Scholar 

  12. Szejtli, J.: Cyclodextrin Technology, pp. 450–455. Kluwer Academic Publisher, Dordrecht (1988)

    Google Scholar 

  13. Uekama, K., Hirayama, F., Irie, T.: Cyclodextrin drug carrier systems. Chem. Rev. 98, 2045–2076 (1998)

    Article  CAS  Google Scholar 

  14. Loftsson, T., Järvinen, T.: Cyclodextrins in ophthalmic drug delivery. Adv. Drug Deliv. Rev. 36, 59–79 (1999)

    Article  Google Scholar 

  15. Loftsson, T., Brewster, M.E.: Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J. Pharm. Sci. 85, 1017–1025 (1996)

    Article  CAS  Google Scholar 

  16. Inoue, Y., Yamamoto, K., Wada, T., Everitt, S., Gao, X.M., Hou, Z.J., Tong, L.H., Jiang, S.K., Wu, H.M.: Inclusion complexation of (cyclo)alkanes and (cyclo)alkanols with 6-O-modified cyclodextrins. J. Chem. Soc. Perkin Trans. 2, 1807–1816 (1998)

    Google Scholar 

  17. Liu, Y., Li, B., Wada, T., Inoue, Y.: Novel O-Phenylenediseleno bridged Bis(β-cyclodextrin)s complexes with Platinum(IV) and Palladium(II) Ions. Supramol. Chem. 10, 279–285 (1999)

    Article  CAS  Google Scholar 

  18. Reinhardt, R., Richter, M., Mager, P.P.: Investigation of the conformational behaviour of permethylated cyclodextrins by molecular modelling. Carbohydrate Res. 291, 1–9 (1996)

    Article  CAS  Google Scholar 

  19. Kano, K., Nishiyabu, R., Asada, T., Kuroda, Y.: Static and dynamic behavior of 2:1 inclusion complexes of cyclodextrins and charged porphyrins in aqueous organic media. J. Am. Chem. Soc. 124, 9937–9944 (2002)

    Article  CAS  Google Scholar 

  20. Yi, Z.-P., Chen, H.-L., Huang, Z.-Z., Huang, Q., Yu, J.-S.: Contributions of weak interactions to the inclusion complexation of 3-hydroxynaphthalene-2-carboxylic acid and its analogues with cyclodextrins. J. Chem. Soc. Perkin Trans. 2, 121–127 (2000)

    Google Scholar 

  21. Linares, M., de Bertorello, M.M., Longhi, M.: Solubilization of naphthoquinones by complexation with hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 159, 13–18 (1997)

    Article  CAS  Google Scholar 

  22. Liu, Y., Chen, C.-S., Chen, Y., Lin, J.: Inclusion complexes of azadirachtin with native and methylated cyclodextrins: solubilization and binding ability. Bioorg. Med. Chem. 13, 4037–4042 (2005)

    Article  CAS  Google Scholar 

  23. de Araújo, M.V.G.: Sulfadiazine/hydroxypropyl-β-cyclodextrin host–guest system: characterization, phase-solubility and molecular modeling. Bioorg. Med. Chem. 16, 5788–5794 (2008)

    Article  CAS  Google Scholar 

  24. Correia, I., Bezzenine, N., Ronzani, N., Platzer, N., Beloeil, J.-C., Doan, B.-T.: Study of inclusion complexes of acridine with β- and (2,6-di-O-methyl)-β-cyclodextrin by use of solubility diagrams and NMR spectroscopy. J. Phys. Org. Chem. 15, 647–659 (2002)

    Article  CAS  Google Scholar 

  25. Montassier, P., Duchêne, D., Poelman, M.C.: Inclusion complexes of tretinoin with cyclodextrins. Int. J. Pharm. 153, 199–209 (1997)

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the Opening Foundation of State Key Laboratory of Elemento-Organic Chemistry of Nankai University (0607 and 0704), which is gratefully acknowledged.

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Correspondence to Jun Lin or Yu Liu.

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Yang, B., Yang, LJ., Lin, J. et al. Binding behaviors of scutellarin with α-, β-, γ-cyclodextrins and their derivatives. J Incl Phenom Macrocycl Chem 64, 149–155 (2009). https://doi.org/10.1007/s10847-009-9547-4

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