Chemical Research in Chinese Universities ›› 2020, Vol. 36 ›› Issue (5): 804-809.doi: 10.1007/s40242-020-0005-6

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Study on the Interaction and Properties of Cucurbit[8]uril with Oroxin B

XIE Jun, ZENG Zhishu, TAO Zhu, ZHANG Qianjun   

  1. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, College of Chemistry and Chemical Engineering, Guizhou University, Guiyang 550025, P. R. China
  • Received:2020-01-06 Revised:2020-02-14 Online:2020-10-01 Published:2020-10-01
  • Contact: ZHANG Qianjun E-mail:qianjunzhang@126.com

Abstract: The interaction between cucurbit[8]uril(Q[8]) and oroxin B(ORB) was investigated by UV-visible(UV-Vis) spectroscopy, isothermal titration calorimetry(ITC), mass spectrum(MS) and nuclear magnetic resonance(NMR) spectroscopy. The results showed that ORB formed a 2:1 inclusion complex with Q[8] with a binding constant of 8.266×105 L2·mol-2. ORB had good scavenging ability for 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulphonate)(ABTS) free radicals(IC50=5.74 μmol/L) and the addition of Q[8] did not significantly affect the antioxidant activity of ORB(IC50=5.76 μmol/L). A phase solubility experiment revealed a 1.86-fold increase in the solubility of ORB when c(Q[8])=100 μmol/L. In vitro drug release experiments showed that the release rate for ORB@Q[8] complex was lower than that of ORB in artificial intestinal juice, and higher than that of ORB in artificial gastric juice.

Key words: Cucurbit[8]uril, Oroxin B, Inclusion complex, Solubility, Antioxidant activity