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Solubility enhancement of kinetin through host–guest interactions with cucurbiturils

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Abstract

We explored the use of cucurbiturils to form inclusion complexes to overcome the solubility problems of kinetin, a plant cytokinin. Inclusion complexes between kinetin and Q[7], TMeQ[6] and HMeQ[6] in aqueous solution and in solid state were investigated by phase solubility studies, 1H NMR and IR. The effects of pH and temperature on complex stability were also investigated. Phase solubility studies showed that kinetin solubility increased in a linear fashion as a function of Q[7] and TMeQ[6] concentrations. However, kinetin solubility increased first, then decreased as the HMeQ[6] concentration increased, and the maximum solubility of kinetin was achieved at 4.95 mM in HMeQ[6]. The solubility of kinetin as well as the stability constant of its complex with Q[7] were affected by the pH of the medium. The thermodynamic parameters of the complex formation were also determined, and it showed that the formation of the inclusion complexes between kinetin and Q[7] was enthalpy controlled, suggesting that hydrophobic and van der Waals interactions were the main driving forces. Moreover, we found that the size of the cavity of cucurbituril played an important role in the association process. The formation of inclusion complexes between Q[7], TMeQ[6] and HMeQ[6] with kinetin was confirmed by 1H NMR, and IR spectroscopy showed the presence of inclusion complexes in solid state. Our results demonstrated that the complexation of kinetin with Q[n] could be used to improve the solubility of kinetin in aqueous solution.

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Acknowledgments

We acknowledge the support of the National Natural Science Foundation of China (NSFC; No. 20662003, 20767001) and the International Collaborative Project of Guizhou Province.

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Authors and Affiliations

  1. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, 550025, P.R. China

    Ying Huang, Sai-Feng Xue, Zhu Tao, Qian-Jiang Zhu, Hong Zhang, Jing-Xiang Lin & Da-Hai Yu

  2. Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025, P.R. China

    Ying Huang

  3. Institute of Applied Chemistry, Guizhou University, Guiyang, 550025, P.R. China

    Zhu Tao

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  1. Ying Huang
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  2. Sai-Feng Xue
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  4. Qian-Jiang Zhu
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  5. Hong Zhang
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Correspondence to Sai-Feng Xue.

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Huang, Y., Xue, SF., Tao, Z. et al. Solubility enhancement of kinetin through host–guest interactions with cucurbiturils. J Incl Phenom Macrocycl Chem 61, 171–177 (2008). https://doi.org/10.1007/s10847-008-9410-z

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  • DOI: https://doi.org/10.1007/s10847-008-9410-z

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