Solubility enhancement of kinetin through host–guest interactions with cucurbiturils

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.