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Preparation, characterization, solubilization and antioxidant activity of polyamine modified β-cyclodextrins with baicalein inclusion complexes

  • Jiaojiao Du
  • Lijuan Zhao
  • Songlin Yang
  • Yurong Huang
  • Shaoming Chi
  • Qiong Ruan
  • Ping Zheng
  • Rong Hu
  • Yan Zhao
Original Article
  • 14 Downloads

Abstract

Inclusion complexes of three different lengths of polyamine modified β-cyclodextrins (β-CDs) (hosts 13) with baicalein (BC) were prepared by a solution stirring method, and characterized by UV–Vis spectroscopy, proton nuclear magnetic resonance, scanning electron microscopy, thermogravimetric analysis, and X-ray diffractometry. The results demonstrated that 1:1 inclusion complexes of hosts 13 with BC are present. The binding ability of hosts 13 towards BC increased according to the sequence H1 > H2 > H3, which was in good agreement with the decreasing chain lengths of these hosts. When compared to BC, the inclusion complexes produced 508-, 451- and 323-fold enhancement in water solubility, respectively. At low concentrations, inclusion complexes 1/BC and 3/BC were observed with a better capacity of scavenging when compared to that of free BC. These findings reflected that the complexation strengthened the antioxidant activity of BC. Moreover, the solubility in water and resistance to oxidation of hosts 13/BC were satisfactory, making it possible candidates for application in herbal medicine and as healthcare products.

Keywords

Antioxidant activity Baicalein Inclusion complexes Polyamine modified β-cyclodextrins Solubility 

Notes

Acknowledgements

This work was supported by the National Natural Science Foundations (Nos. 21362046 and 21062030), which are gratefully acknowledged.

References

  1. 1.
    Shen, Y.C., Chiou, W.F., Chou, Y.C., Chen, C.F.: Mechanisms in mediating the anti-inflammatory effects of baicalin and baicalein in human leukocytes. Eur. J. Pharmacol. 465, 171–181 (2003).  https://doi.org/10.1016/S0014-2999(03)01378-5 CrossRefPubMedGoogle Scholar
  2. 2.
    Wu, J.A., Attele, A.S., Zhang, L., Yuan, C.S.: Anti-HIV activity of medicinal herbs: usage and potential development. Am. J. Chin. Med. 29, 69–81 (2001).  https://doi.org/10.1142/S0192415X01000083 CrossRefPubMedGoogle Scholar
  3. 3.
    Lee, H.Z., Leung, H.W., Lai, M.Y., Wu, C.H.: Baicalein induced cell cycle arrest and apoptosis in human lung squamous carcinoma CH27 cells. Anticancer Res. 25, 959–964 (2005).  https://doi.org/10.1097/00006534-200009040-00020 CrossRefPubMedGoogle Scholar
  4. 4.
    Shimizu, I.: Sho-saiko-to: Japanese herbal medicine for protection against hepatic fibrosis and carcinoma. J. Gastroenterol. Hepatol. 15, 84–90 (2000).  https://doi.org/10.1046/j.1440-1746.2000.02138.x CrossRefGoogle Scholar
  5. 5.
    Kimata, M., Shichijo, M., Miura, T., Serizawa, I., Inagaki, N., Nagai, H.: Effects of luteolin, quercetin and baicalein on immunoglobulin E-mediated mediator release from human cultured mast cells. Clin. Exp. Allergy 30, 501–508 (2000).  https://doi.org/10.1046/j.1365-2222.2000.00768.x CrossRefPubMedGoogle Scholar
  6. 6.
    Kim, D.H., Jeon, S.J., Son, K.H., Jung, J.W., Lee, S., Yoon, B.H., Lee, J.J., Cho, Y.W., Cheong, J.H., Ko, K.H., Ryu, J.H.: The ameliorating effect of oroxylin A on scopolamine-induced memory impairment in mice. Neurobiol. Learn. Mem. 87, 536–546 (2007).  https://doi.org/10.1016/j.nlm.2006.11.005 CrossRefPubMedGoogle Scholar
  7. 7.
    Gao, Z., Huang, K., Yang, X., Xu, H.: Free radical scavenging and antioxidant activities of flavonoids extracted from the radix of Scutellaria baicalensis Georgi. Biochim. Biophys. Acta BBA 1472, 643–650 (1999).  https://doi.org/10.1016/S0304-4165(99)00152-X CrossRefPubMedGoogle Scholar
  8. 8.
    Shao, Z.H., Vanden Hoek, T.L., Qin, Y., Becker, L.B., Schumacker, P.T., Li, C.Q., Dey, L..,Barth, E., Halpern, H., Rosen, G.M., Yuan, C.S.: Baicalein attenuates oxidant stress in cardiomyocytes. Am. J. Physiol. Heart Circ. Physiol. 282, H999–H1006 (2002).  https://doi.org/10.1152/ajpheart.00163.2001 CrossRefPubMedGoogle Scholar
  9. 9.
    Gao, Z.H., Huang, K.X., Xu, H.B.: Protective effects of flavonoids in the roots of Scutellaria baicalensis Georgi against hydrogen peroxide-induced oxidative stress in HS-SY5Y cells. Pharmacol. Res. 43, 173–178 (2001).  https://doi.org/10.1006/phrs.2000.0761 CrossRefPubMedGoogle Scholar
  10. 10.
    Liu, J., Qiu, L., Gao, J., Jin, Y.: Preparation, characterization and in vivo evaluation of formulation of baicalein with hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 312, 137–143 (2006).  https://doi.org/10.1016/j.ijpharm.2006.01.011 CrossRefPubMedGoogle Scholar
  11. 11.
    Zhou, Y., Dong, W., Ye, J., Hao, H., Zhou, J., Wang, R., Liu, Y.: A novel matrix dispersion based on phospholipid complex for improving oral bioavailability of baicalein: preparation, in vitro and in vivo evaluations. Drug Deliv. 24, 720–728 (2017).  https://doi.org/10.1080/10717544.2017.1311968 CrossRefPubMedGoogle Scholar
  12. 12.
    Misiuk, W.: Investigation of inclusion complex of HP-γ-cyclodextrin with ceftazidime. J. Mol. Liq. 224, 387–392 (2016).  https://doi.org/10.1016/j.molliq.2016.10.009 CrossRefGoogle Scholar
  13. 13.
    Li, W., Lu, B., Sheng, A., Yang, F., Wang, Z.: Spectroscopic and theoretical study on inclusion complexation of beta-cyclodextrin with permethrin. J. Mol. Struct. 981, 194–203 (2010).  https://doi.org/10.1016/j.molstruc.2010.08.008 CrossRefGoogle Scholar
  14. 14.
    Li, J., Han, L., Chao, J.: Preparation and characterization of the inclusion complex of baicalein with γ-cyclodextrin: an antioxidant ability study. J. Incl. Phenom. Macrocycl. Chem. 73, 247–254 (2012).  https://doi.org/10.1007/s10847-011-0048-x CrossRefGoogle Scholar
  15. 15.
    Zhou, Q.N., Wei, X.H., Dou, W., Chou, G.X., Wang, Z.H.: Preparation and characterization of inclusion complexes formed between baicalein and cyclodextrins. Carbohyd. Polym. 95, 733–739 (2013).  https://doi.org/10.1016/j.carbpol.2013.02.038 CrossRefGoogle Scholar
  16. 16.
    Gu, J., Chi, S.M., Zhao, Y., Zheng, P., Ruan, Q., Zhu, H.Y.: Inclusion complexes of coenzyme Q10 with polyamine-modified β-cyclodextrins: characterization, solubilization, and inclusion mode. Helv. Chim. Acta 94, 1608–1617 (2011).  https://doi.org/10.1002/hlca.201100026 CrossRefGoogle Scholar
  17. 17.
    Liu, Y., Chen, G.S., Zhang, H.Y., Cao, D.X., Yuan, Y.J.: Inclusion complexation and solubilization of paclitaxel by bridged bis(β-cyclodextrin)s containing a tetraethylenepentaamino spacer. J. Med. Chem. 46, 4634–4637 (2003).  https://doi.org/10.1021/jm034148f CrossRefPubMedGoogle Scholar
  18. 18.
    Meo, P.L., D’Anna, F., Gruttadauria, M., Riela, S., Noto, R.: Synthesis and characterization of new polyamino-cyclodextrin materials. Carbohydr. Res. 347, 32–39 (2012).  https://doi.org/10.1016/j.carres.2011.10.029 CrossRefPubMedGoogle Scholar
  19. 19.
    Liu, Y., Fan, X., Gao, L.: Synthesis and characterization of β-cyclodextrin based functional monomers and its copolymers with N-isopropylacrylamide. Macromol. Biosci. 3, 715–719 (2003).  https://doi.org/10.1002/mabi.200300052 CrossRefGoogle Scholar
  20. 20.
    Tabushi, I., Shimizu, N., Sugimoto, T., Shiozuka, M., Yamamura, K.: Cyclodextrin flexibly capped with metal ion. J. Am. Chem. Soc. 99, 7100–7102 (1977).  https://doi.org/10.1021/ja00463a073 CrossRefGoogle Scholar
  21. 21.
    Landy, D., Tetart, F., Truant, E., Surpateanu, G.: Development of a competitive continuous variation plot for the determination of inclusion compounds stoichiometry. J. Incl. Phenom. Macrocycl. Chem. 57(1–4), 409–413 (2007).  https://doi.org/10.1007/s10847-006-9226-7 CrossRefGoogle Scholar
  22. 22.
    Yang, L.J., Wang, S.H., Zhou, S.Y., Zhao, F., Chang, Q., Li, M.Y., Chen, W., Yang, X.D.: Supramolecular system of podophyllotoxin and hydroxypropyl-β-cyclodextrin: characterization, inclusion mode, docking calculation, solubilization, stability and cytotoxic activity. Mater. Sci. Eng. C 76, 1136 (2017).  https://doi.org/10.1016/j.msec.2017.03.197 CrossRefGoogle Scholar
  23. 23.
    Wang, L., Li, S., Tang, P., Yan, J., Xu, K., Li, H.: Characterization and evaluation of synthetic riluzole with β-cyclodextrin and 2,6-di-O-methyl-β-cyclodextrin inclusion complexes. Carbohydr. Polym. 129, 9–16 (2015).  https://doi.org/10.1016/j.carbpol.2015.04.046 CrossRefPubMedGoogle Scholar
  24. 24.
    Xu, W.T., Zhang, F.F., Luo, Y.B., Ma, L.Y., Kou, X.H., Huang, K.L.: Antioxidant activity of a water-soluble polysaccharide purified from Pteridium aquilinum. Carbohydr. Res. 344, 217–222 (2009).  https://doi.org/10.1016/j.carres.2008.10.021 CrossRefPubMedGoogle Scholar
  25. 25.
    Guo, M., Perez, C., Wei, Y.B., Rapoza, E., Su, G., Bou-Abdallahb, F., Chasteenb, N.D.: Iron-binding properties of plant phenolics and cranberry’s bio-effects. Dalton Trans. 43(43), 4951 (2007)CrossRefGoogle Scholar
  26. 26.
    Benesi, H.A., Hidebrand, J.H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703–2707 (1949).  https://doi.org/10.1021/ja01176a030 CrossRefGoogle Scholar
  27. 27.
    Tangm, P.X., Li, S.S., Wang, L.L., Yang, H.Q., Yan, J., Li, H.: Inclusion complexes of chlorzoxazone with β- and hydroxypropyl-β-cyclodextrin: characterization, dissolution, and cytotoxicity. Carbohydr. Polym. 131, 297–305 (2015).  https://doi.org/10.1016/j.carbpol.2015.05.055 CrossRefGoogle Scholar
  28. 28.
    Ren, S.H., Zhang, J.Q., Yan, H.H., Zheng, X., Zhu, H.Y., Jin, Y., Lin, J.: Preparation, characterization, molecular docking and in vitro evaluation of two novel morin hydrate/CD inclusion complexes. J. Incl. Phenom. Macrocycl. Chem. 85, 317–328 (2016).  https://doi.org/10.1007/s10847-016-0631-2 CrossRefGoogle Scholar
  29. 29.
    Aytac, Z., Ipek, S., Durgun, E., Uyar, T.: Antioxidant electrospun zein nanofibrous web encapsulating quercetin/cyclodextrin inclusion complex. J. Mater. Sci. 53, 1527–1539 (2018).  https://doi.org/10.1007/s10853-017-1580-x CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  1. 1.College of Chemistry and Chemical EngineeringYunnan Normal UniversityKunmingPeople’s Republic of China

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