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

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Abstract

Inclusion complexes of three different lengths of polyamine modified β-cyclodextrins (β-CDs) (hosts 1–3) 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 1–3 with BC are present. The binding ability of hosts 1–3 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 1–3/BC were satisfactory, making it possible candidates for application in herbal medicine and as healthcare products.

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References

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

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Acknowledgements

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

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, 650500, People’s Republic of China

    Jiaojiao Du, Lijuan Zhao, Songlin Yang, Yurong Huang, Shaoming Chi, Qiong Ruan, Ping Zheng, Rong Hu & Yan Zhao

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  1. Jiaojiao Du
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  2. Lijuan Zhao
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Correspondence to Yan Zhao.

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Du, J., Zhao, L., Yang, S. et al. Preparation, characterization, solubilization and antioxidant activity of polyamine modified β-cyclodextrins with baicalein inclusion complexes. J Incl Phenom Macrocycl Chem 93, 203–213 (2019). https://doi.org/10.1007/s10847-018-0871-4

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