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高等学校化学研究 ›› 2017, Vol. 33 ›› Issue (5): 736-741.doi: 10.1007/s40242-017-7096-8

• Articles • 上一篇    下一篇

Effects of Inclusion of Chrysin in Cucurbit[8]uril on Its Stability, Solubility and Antioxidant Potential

XU Zhiling1,2, LIAN Xiaowei1,2, LI Mengjie2, ZHANG Xiaodong2, WANG Yi2, TAO Zhu2, ZHANG Qianjun2   

  1. 1. Research and Development Center of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. China;. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, College of Chemistry and Chemical Engineering, Guizhou University, Guiyang 550025, P. R. China
  • 收稿日期:2017-03-16 修回日期:2017-06-05 出版日期:2017-10-01 发布日期:2017-06-21
  • 通讯作者: TAO Zhu,E-mail:gzutao@263.net;ZHANG Qianjun,qianjunzhang@126.com E-mail:gzutao@263.net;qianjunzhang@126.com
  • 基金资助:

    Supported by the National Natural Science Foundation of China(No.21272045).

Effects of Inclusion of Chrysin in Cucurbit[8]uril on Its Stability, Solubility and Antioxidant Potential

XU Zhiling1,2, LIAN Xiaowei1,2, LI Mengjie2, ZHANG Xiaodong2, WANG Yi2, TAO Zhu2, ZHANG Qianjun2   

  1. 1. Research and Development Center of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. China;. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, College of Chemistry and Chemical Engineering, Guizhou University, Guiyang 550025, P. R. China
  • Received:2017-03-16 Revised:2017-06-05 Online:2017-10-01 Published:2017-06-21
  • Contact: TAO Zhu,E-mail:gzutao@263.net;ZHANG Qianjun,qianjunzhang@126.com E-mail:gzutao@263.net;qianjunzhang@126.com
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.21272045).

摘要:

The host-guest interaction between cucurbit[8]uril(Q[8]) and chrysin(CHR) has been studied by means of 1H NMR, mass spectrometry(MS), differential thermal analysis(DTA), and UV-Vis spectrophotometry. The results show that CHR forms a 1:1 inclusion complex with Q[8], with a binding constant of CHR with Q[8] by UV absorption being 5.4×106. Phase solubility experiments show a 5.13-fold increase in the solubility of CHR through interaction with Q[8]{c(Q[8])=10-4 mol/L}. A study of the evolution of UV absorption spectra with time shows that Q[8]significantly increases the stability of CHR. The antioxidant activity of CHR-Q[8] has been tested by the ABTS method. The CHR-Q[8] inclusion complex shows a better scavenging effect towards the ABTS radical than CHR, with respective IC50 values of 1.05×10-6 and 3.07×10-6 mol/L. In vitro release studies have shown that CHR-Q[8] has a sustained release effect.

关键词: Chrysin, Cucurbit[8]uril, Inclusion complex, Solubility, Stability, Antioxidant activity

Abstract:

The host-guest interaction between cucurbit[8]uril(Q[8]) and chrysin(CHR) has been studied by means of 1H NMR, mass spectrometry(MS), differential thermal analysis(DTA), and UV-Vis spectrophotometry. The results show that CHR forms a 1:1 inclusion complex with Q[8], with a binding constant of CHR with Q[8] by UV absorption being 5.4×106. Phase solubility experiments show a 5.13-fold increase in the solubility of CHR through interaction with Q[8]{c(Q[8])=10-4 mol/L}. A study of the evolution of UV absorption spectra with time shows that Q[8]significantly increases the stability of CHR. The antioxidant activity of CHR-Q[8] has been tested by the ABTS method. The CHR-Q[8] inclusion complex shows a better scavenging effect towards the ABTS radical than CHR, with respective IC50 values of 1.05×10-6 and 3.07×10-6 mol/L. In vitro release studies have shown that CHR-Q[8] has a sustained release effect.

Key words: Chrysin, Cucurbit[8]uril, Inclusion complex, Solubility, Stability, Antioxidant activity