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

Abranches, P. A. S.; Varejão, Eduardo Vinícius Vieira; Silva, C. M. da; Fátima, Ângelo de; Magalhães, Thaís Furtado Ferreira; Silva, Danielle L. da; Stoianoff, Maria Aparecida de Resende; Reis, Filipa S.; Nascimento, Clébio S.; Almeida, Wagner B. De; Figueiredo, Isis M.; Fernandes, Sérgio Antônio

doi:10.1039/c5ra05423k

Cited by 27 publications

(22 citation statements)

References 54 publications

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“…Note that the numerical results without PCM differ from each other in Figures and because of the lack of BSSE corrections in Figure (PCM implementation in Gaussian09 excludes BSSE; hence, the comparison in Figure should be made without BSSE). The stabilization is consistent with other preceding reports using PCM. − Except for BCD, the trend over the conformations is qualitatively unchanged, for which the binding energies could roughly be corrected by a common scaling factor. A previous study on a host–guest system using β-cyclodextrin reported that their predictions using IEFPCM corrections could reproduce the most stable conformation that is experimentally observed in solution, thus supporting the present predictions.…”

Section: Resultssupporting

confidence: 89%

“…However, for the ab initio approach, it is impractical to completely consider the solvent effects from the feasibility viewpoint and computational costs. It is, therefore, practical to consider − such predictions made in vacuum as a rough estimation to provide a trend that is expected to be unchanged qualitatively even in a solution. In such cases, it is important to consider the extent of expectation that would be justified.…”

Section: Resultsmentioning

confidence: 99%

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Ab Initio Evaluation of Complexation Energies for Cyclodextrin-Drug Inclusion Complexes

2020

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We investigated the reliability of ab initio methods to predict the binding energies of molecular encapsulation complexes. Vast possibilities for the docking conformations were screened down to a couple of geometries using a semiempirical docking simulation. For the candidates, we applied density functional theory (DFT) with several exchange–correlation (XC) functionals to evaluate the binding energy. We carefully selected and compared the functionals to elucidate the role of the characteristic factors in achieving the XC effects. It is clarified that the improper combination in XC with D3 dispersion force correction leads to overbinding. For achieving a proper combination, the exchange interaction over the longer range to avoid the overbinding was found to be important.

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Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Ab Initio Evaluation of Complexation Energies for Cyclodextrin-Drug Inclusion Complexes

2020

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“…The constructed phase solubility curves could be classified as A L type, which suggested the formation of the 1:1 water-soluble ME-sulfonatocalix[4]naphthalene inclusion complex. This result might be attributed to the weak interaction forces including hydrogen bonding, π-π interactions, dipole-dipole interaction, or electrostatic interaction between hydrophobic cavity or hydroxyl groups of sulfonatecalix[4]naphthalene and drug aromatic rings, or other functional groups of the drug molecules [ 15 , 16 , 46 ]. The calculated stability constants (Ks) of ME-sulfonatocalix[4]naphthalene complex (1:1) at 25 ± 0.5 °C are presented in Table 1 .…”

Section: Resultsmentioning

confidence: 99%

Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam towards Enhancing Its Solubility and Dissolution Performance

et al. 2021

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The interaction between meloxicam and sulfonatocalix[4]naphthalene was investigated to improve the meloxicam solubility and its dissolution performance. Solubility behavior was investigated in distilled water (DW) and at different pH conditions. Besides, solid systems were prepared in a 1:1 molar ratio using coevaporate, kneading, and simple physical mixture techniques. Further, they were characterized by PXRD, FT-IR, DCS, and TGA. In vitro dissolution rate for coevaporate, kneaded, and physical mixture powders were also investigated. Solubility study revealed that meloxicam solubility significantly increased about 23.99 folds at phosphate buffer of pH 7.4 in the presence of sulfonatocalix[4]naphthalene. The solubility phase diagram was classified as AL type, indicating the formation of 1:1 stoichiometric inclusion complex. PXRD, FT-IR, DCS, and TGA pointed out the formation of an inclusion complex between meloxicam and sulfonatocalix[4]naphthalene solid powders prepared using coevaporate technique. In addition, in vitro meloxicam dissolution studies revealed an improvement of the drug dissolution rate. Furthermore, a significantly higher drug release (p ≤ 0.05) and a complete dissolution was achieved during the first 10 min compared with the other solid powders and commercial meloxicam product. The coevaporate product has the highest increasing dissolution fold and RDR10 in the investigated media, with average values ranging from 5.4–65.28 folds and 7.3–90.7, respectively. In conclusion, sulfonatocalix[4]naphthalene is a promising host carrier for enhancing the solubility and dissolution performance of meloxicam with an anticipated enhanced bioavailability and fast action for acute and chronic pain disorders.

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“…Cocrystallization can also be conceived to control the release of APIs through their inclusion into carriers, assembling host-guest complexes (Jones et al, 2006). Concerning the carriers, calix [n]arenes have been used extensively as hosts due to their versatile molecular backbone (de Fá tima et al, 2009;Dalgarno et al, 2006;Clark et al, 2007;Abranches et al, 2015). These compounds are made up of aromatic rings bonded through methylene bridges in a macrocyclic structure (Gutsche et al, 1981).…”

Section: Introductionmentioning

confidence: 99%

Exploring the structural landscape of 2-(thiophen-2-yl)-1,3-benzothiazole: high-Z′ packing polymorphism and cocrystallization with calix[4]tube

et al. 2019

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We report here for the first time a cocrystal of the so‐called neutral calix[4]tube, which is two tail‐to‐tail‐arranged and partially deprotonated tetrakis(carboxymethoxy)calix[4]arenes, including three sodium ions, with 2‐(thiophen‐2‐yl)‐1,3‐benzothiazole, namely trisodium bis(carboxymethoxy)bis(carboxylatomethoxy)calix[4]arene tris(carboxymethoxy)(carboxylatomethoxy)calix[4]arene–2‐(thiophen‐2‐yl)‐1,3‐benzothiazole–dimethyl sulfoxide–water (1/1/2/2), 3Na+·C36H30O122−·C36H31O12−·C11H7NS2·2C2H6OS·2H2O, which provides a new approach into the host–guest chemistry of inclusion complexes. Three packing polymorphs of the same benzothiazole with high Z′ (one with Z′ = 8 and two with Z′ = 4) were also discovered in the course of our desired cocrystallization. The inspection of these polymorphs and a previously known polymorph with Z′ = 2 revealed that Z′ increases as the strength of intermolecular contacts decreases. Also, these results expand the frontier of invoking calixarenes as a host for nonsolvent small molecules, besides providing knowledge on the rare formation of high‐Z′ packing polymorphs of simple molecules, such as the target benzothiazole.

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

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[n]arenes.

Cited by 27 publications

References 54 publications

Ab Initio Evaluation of Complexation Energies for Cyclodextrin-Drug Inclusion Complexes

Ab Initio Evaluation of Complexation Energies for Cyclodextrin-Drug Inclusion Complexes

Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam towards Enhancing Its Solubility and Dissolution Performance

Exploring the structural landscape of 2-(thiophen-2-yl)-1,3-benzothiazole: high-Z′ packing polymorphism and cocrystallization with calix[4]tube

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