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

被引：27
|
作者：
Abranches, P. A. S. [1 ]
Varejao, E. V. V. [1 ]
da Silva, C. M. [2 ]
de Fatima, A. [2 ]
Magalhaes, T. F. F. [3 ]
da Silva, D. L. [3 ]
de Resende-Stoianoff, M. A. [3 ]
Reis, S. [4 ]
Nascimento, C. S., Jr. [4 ]
de Almeida, W. B. [5 ]
Figueiredo, I. M. [6 ]
Fernandes, S. A. [1 ]
机构：
[1] Univ Fed Vicosa, CCE, Dept Quim, BR-36570900 Vicosa, MG, Brazil
[2] Univ Fed Minas Gerais, ICEx, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil
[3] Univ Fed Minas Gerais, ICB, Dept Microbiol, BR-31270901 Belo Horizonte, MG, Brazil
[4] Univ Fed Sao Joao Del Rei, Dept Ciencias Nat DCNAT, BR-36301160 Sao Joao Del Rei, MG, Brazil
[5] Univ Fed Fluminense, Inst Quim, Dept Quim Inorgan, LQC, BR-24020141 Niteroi, RJ, Brazil
[6] Univ Fed Alagoas, Inst Quim & Biotecnol, BR-57072900 Maceio, AL, Brazil
来源：
RSC ADVANCES | 2015年 / 5卷 / 55期
关键词：
NUCLEAR-MAGNETIC-RESONANCE; P-SULFONIC ACID; STUDYING TRANSLATIONAL DIFFUSION; BETA-CYCLODEXTRINS; NMR; GUEST; ASPERGILLOSIS; EXCHANGE; ARENES; TOOL;
D O I：
10.1039/c5ra05423k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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 H-1 NMR spectroscopy and TGA experiments. The complexes' stoichiometry, apparent binding constants (K-a) and the complexed populations (%p(bound)), were determined, using H-1 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.
引用
收藏
页码：44317 / 44325
页数：9
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