Complexes of fluconazole with sodium p-sulfonatocalix[n]arenes: characterization, solubility and antifungal activity

P. A. S. Abranches; E. V. V. Varejão; C. M. da Silva; Â. de Fátima; T. F. F. Magalhães; D. L. da Silva; M. A. de Resende-Stoianoff; S. Reis; C. S. Nascimento; W. B. de Almeida; I. M. Figueiredo; S. A. Fernandes

doi:10.1039/C5RA05423K

Complexes of fluconazole with sodium p-sulfonatocalix[n]arenes: characterization, solubility and antifungal activity†

P. A. S. Abranches,^a E. V. V. Varejão,^a C. M. da Silva,^b Â. de Fátima,^b T. F. F. Magalhães,^c D. L. da Silva,^c M. A. de Resende-Stoianoff,^c S. Reis,^d C. S. Nascimento, Jr.,^d W. B. de Almeida,^e I. M. Figueiredo^f and S. A. Fernandes*^a

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^a Departamento de Química, CCE, Universidade Federal de Viçosa, Viçosa, MG, Brazil
E-mail: santonio@ufv.br, sefernandes@gmail.com
Tel: +55 31 3899 3071

^b Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil

^c Departamento de Microbiologia, ICB, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil

^d Departamento de Ciências Naturais (DCNAT), Universidade Federal de São João Del-Rei, São João Del Rei, MG, Brazil

^e Laboratório de Química Computacional (LQC), Departamento de Química Inorgânica, Instituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Centro, Niterói, RJ, Brazil

^f Instituto de Química e Biotecnologia, Universidade Federal de Alagoas, Maceió, AL, Brazil

Abstract

Aiming at providing new formulations capable of improving the biopharmaceutical properties of fluconazole, we studied the formation of host–guest complexes of this antifungal agent with water-soluble sodium p-sulfonatocalix[4]arene and sodium p-sulfonatocalix[6]arene. The formation of inclusion complexes was first investigated using ¹H NMR spectroscopy and TGA experiments. The complexes' stoichiometry, apparent binding constants (K_a) and the complexed populations (%p_bound), were determined, using ¹H NMR data. The topology of the complexes were assessed by 1D ROESY experiments, and the data were corroborated by semi-empirical and DFT calculations. The activity of the fluconazole-calix[n]arene complexes against clinically relevant fungal species was investigated. Finally, the effect of complexation on the solubility of fluconazole was investigated using the phase-solubility method of Higuchi and Connors.

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Complexes of fluconazole with sodium p-sulfonatocalix[n]arenes: characterization, solubility and antifungal activity†

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Complexes of fluconazole with sodium p-sulfonatocalix[n]arenes: characterization, solubility and antifungal activity

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