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

doi:10.1007/s40242-020-0005-6

高等学校化学研究 ›› 2020, Vol. 36 ›› Issue (5): 804-809.doi: 10.1007/s40242-020-0005-6

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

XIE Jun, ZENG Zhishu, TAO Zhu, ZHANG Qianjun

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:2020-01-06 修回日期:2020-02-14 出版日期:2020-10-01 发布日期:2020-10-01
通讯作者: ZHANG Qianjun E-mail:qianjunzhang@126.com

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

XIE Jun, ZENG Zhishu, TAO Zhu, ZHANG Qianjun

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

摘要/Abstract

摘要： 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.

关键词: Cucurbit[8]uril, Oroxin B, Inclusion complex, Solubility, Antioxidant activity

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

XIE Jun, ZENG Zhishu, TAO Zhu, ZHANG Qianjun. Study on the Interaction and Properties of Cucurbit[8]uril with Oroxin B[J]. 高等学校化学研究, 2020, 36(5): 804-809.

XIE Jun, ZENG Zhishu, TAO Zhu, ZHANG Qianjun. Study on the Interaction and Properties of Cucurbit[8]uril with Oroxin B[J]. Chemical Research in Chinese Universities, 2020, 36(5): 804-809.

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

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

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