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  • Title: Characterization, phase solubility and molecular modeling of alpha-cyclodextrin/pyrimethamine inclusion complex.
    Author: de Araujo MV, Macedo OF, Nascimento Cda C, Conegero LS, Barreto LS, Almeida LE, da Costa NB, Gimenez IF.
    Journal: Spectrochim Acta A Mol Biomol Spectrosc; 2009 Feb; 72(1):165-70. PubMed ID: 19019728.
    Abstract:
    An inclusion complex between the dihydrofolate reductase inhibitor pyrimethamine (PYR) and alpha-cyclodextrin (alpha-CD) was prepared and characterized. From the phase-solubility diagram, a linear increase of PYR solubility was verified as a function of alpha-CD concentration, suggesting the formation of a soluble complex. A 1:1 host-guest stoichiometry can be proposed according to the Job's plot, obtained from the difference of PYR fluorescence intensity in the presence and absence of alpha-CD. Differential scanning calorimetry (DSC) measurements provided additional evidences of complexation such as the absence of the endothermic peak assigned to the melting of the drug. The inclusion mode characterized by two-dimensional (1)H NMR spectroscopy (ROESY) involves penetration of the p-chlorophenyl ring into the alpha-CD cavity, in agreement to the orientation optimized by molecular modeling methods.
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