Chem. J. Chinese Universities ›› 2014, Vol. 35 ›› Issue (6): 1224.doi: 10.7503/cjcu20130966

• Organic Chemistry • Previous Articles     Next Articles

Encapsulation of Cytarabine in Cucurbit[7]uril and Its Effects on Stability of the Drug

HUANG Ying1,2, SONG Guixian2, TANG Qing1, WANG Juan2, TAO Zhu1, XUE Saifeng2,*(), ZHANG Jianxin3,*()   

  1. 1. The Engineering and Research Center for Southwest Bio-Pharmaceutical Resources, Ministry of Education,2. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province,3. The Key Laboratory of Chemistry for Nature Products of Gui Zhou Province and Chinese Academy of Science,Guizhou University, Guiyang 550025, China
  • Received:2013-09-30 Online:2014-06-10 Published:2013-12-05
  • Contact: XUE Saifeng,ZHANG Jianxin E-mail:sfxue@gzu.edu.cn;zjxnmr@126.com
  • Supported by:
    † Supported by the the National Natural Science Foundation of China(No.21202026), the National Major Scienpngic Instruments Development Project, China(No.2011YQ120035), the International Cooperation Projects of Science and Technology Agency of Guizhou Province, China(No.20127003), the “Chun-Hui” Fund of Ministry of Education, China(No.Z2011034) and the Young Talent Development Project of Guizhou Province, China(No.2012154)

Abstract:

The interaction of cucurbit[7]uril(Q[7]) with cytarabine(Ara-C) in different proton forms were studied by ultraviolet absorption spectroscopy and 1H NMR technique in details. Complexation by Q[7] has also been investigated to cause pKa shifts and stability of drug. The results showed that Q[7] encapsulated the Ara-C and shifted its pKa value by down to 0.3 units. Ara-C in different proton forms with Q[7] informed 1∶1 inclusion complexes, and the formation constants were (9.48±0.29)×103 L/mol and (6.30±0.04)×103 L/mol for the Q[7]-Ara-C+ system and Q[7]-Ara-C system, respectively. Moreover, The formation of inclusion complexes between Q[7] with Ara-C was confirmed by 1H NMR, the pyrimidine moiety of Ara-C were entrapped in the cavity of the host and the D-ribose ring was likely located at the outside cucurbituril cavity. In addition, stability studies were investigated by initial uniform rate experiment. The results revealed that complexation of Ara-C with Q[7] offers a major improvement in drug stability.

Key words: Cytarabine, Cucurbit[7]uril, Inclusion complex, Stability

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