Inclusion complexes of fluconazole with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin in aqueous solution: preparation, characterization and a structural insight

Li, Jing; Zhang, Shuo; Zhou, Yan; Guan, Su; Zhang, Lei

doi:10.1007/s10847-016-0598-z

Cited by 38 publications

(37 citation statements)

References 30 publications

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“…A nuclear magnetic resonance (NMR) spectroscopic study was published in order to evaluate the complexation of fluconazole with β-CD, and the results confirmed the formation of an inclusion complex in aqueous solution [23,24]. Complexes of BFZ and miconazole prepared with different CDs by various methods such as kneading, co-evaporation, and physical mixing were characterized by Fourier transform infrared spectroscopy (FTIR) and DSC studies, and the effect of complexationon the dissolution rate of BFZ was studied [25,26].…”

Section: карактеризација на инклузиони комплекси меѓу бифоназол и разmentioning

confidence: 90%

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Kelemen

Csillag

Hancu

et al. 2017

Maced. J. Chem. Chem. Eng.

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The aim of this study is to confirm the formation of inclusion complexes between bifonazole (BFZ) and different cyclodextrin (CD) derivatives. BFZ, an imidazole antifungal derivative, is a very hydrophobic compound, which is a major drawback in obtaining topical pharmaceutical formulations with optimal bioavailability. CDs may increase local drug delivery by enhancing the drug release and/or permeation. Several native and derivatized CD derivatives were tested in the experiments. The binary systems between BFZ and CDs were prepared in two molar ratios by physical mixing methods. The physicochemical properties of these complexes were studied by differential scanning calorimetry (DSC), Fourier transform infrared (FTIR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy methods. The results showed favorable molecular interaction between the components in solid state and in solution. 1 H NMR-CD titrations and molecular modeling study showed that the most stable complex was obtained when using γ-CD. The Job's method and 2D NMR spectroscopy support the 2 : 1 stoichiometry of the BFZ : γ-CD complex.Keywords: bifonazole; cyclodextrins; differential scanning calorimetry; Fourier transform infrared spectroscopy; H NMR-CD titrations КАРАКТЕРИЗАЦИЈА НА ИНКЛУЗИОНИ КОМПЛЕКСИ МЕЃУ БИФОНАЗОЛ И РАЗЛИЧНИ ЦИКЛОДЕКСТРИНИ ВО ЦВРСТА СОСТОЈБА И ВО РАСТВОРЦелта на ова истражување е да се потврди образувањето на инклузиони комплекси меѓу бифоназол (BFZ) и различни циклодекстрински (CD) деривати. BFZ, кој претставува имидазолски фунгициден дериват, е силно хидрофобно соединение, што претставува голем недостаток при добивање топични фармацевтски препарати со оптимална биорасположливост. CD може да ја зголеми локалната испорака на лекот со подобрување на ослободувањето и/или пропустливоста на лекот. Експериментално беа тестирани неколку нативни и дериватизирани CD. Бинарните системи меѓу BFZ и CD беа подготвени во два моларни односа со методи на физичко мешање. Физичкохемиските својства на овие комплекси беа испитувани со диференцијална скенирачка калориметрија (DSC), Фуриеова трансформна инфрацрвена (FTIR) спектроскопија и со нуклеарно-магнетни резонантни спектроскопски методи. Резултатите покажуваат позитивна молекулска интеракција меѓу компонентите во цврста фаза и во раствор. Титрациите на 1 H NMR-CD и испитувањето со молекулско моделирање покажуваат дека најстабилен комплекс се добива со

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Section: карактеризација на инклузиони комплекси меѓу бифоназол и разmentioning

confidence: 90%

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Kelemen

Csillag

Hancu

et al. 2017

Maced. J. Chem. Chem. Eng.

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“…The initial 3.3 % Flu sample mass loss in Figure a between 35 and 125 °C corresponds to the removal of the extraction solvent; the second mass loss (1.04 %), before Flu fusion begins, occurs between 125 and 242 °C, and can be attributed to total desolvation; at 242 °C, the crystallization of the compound begins, which melts and disintegrates at 375 °C. After that, the final weight loss is attributed to residues of the Flu precursors . The DSC curve for Flu in the same figure displayed an endothermic band (desolvation) at 90 °C; the process also presents two exothermic peaks at temperatures that correlate with the decomposition of Flu and the organic residues.…”

Section: Resultsmentioning

confidence: 86%

“…After that, the final weightl oss is attributed to residues of the Flu precursors. [52] The DSC curve for Flu in the same figure displayed an endothermicb and (desolvation) at 90 8C; the process also presents two exothermic peaks at temperatures that correlate with the decomposition of Flu and the organic residues.F igure 6b depicts the TGA/DSC of the SBA15 sample. Although the total loss of materiald uring the process was 10.6 %, consistent with the results of Ramanjaneya and Chennakesavulu, [53] the TGA line reveals three weight losses at temperatureso f3 5-200, 200-500, and 500-900 8C.…”

Section: Materials Characterizationmentioning

confidence: 73%

SBA15–Fluconazole as a Protective Approach Against Mild Steel Corrosion: Synthesis, Characterization, and Computational Studies

et al. 2018

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A SBA15–Fluconazole composite (SBA15‐Flu) was prepared to formulate a self‐healing coating for mild steel. The composite was obtained by dispersing SBA15 in a methanolic solution containing Fluconazole (Flu). The materials were characterized by using different techniques. Electrochemical impedance spectroscopy (EIS) was used for protective behavior evaluation of the coatings on mild steel substrates in an electrolytic solution prepared from sodium chloride and ammonium sulfate. The EIS results indicate that the inhibitor trapped in the SiO2 matrix is released when it comes into contact the aggressive solution, thus protecting the metal. To understand the inhibitor release mechanism, docking studies were used to model the SBA15‐Flu complex, which allowed us to further determine polar and non‐polar contributions to the binding free energy. An analysis of the electron density within the quantum theory of atoms in molecules and the non‐covalent interaction index frameworks were also carried out for the most favorable models of SBA15‐Flu. The results indicate that the liberation rate of the Flu molecules is mainly determined by the formation of strong O−H⋅⋅⋅O, O−H⋅⋅⋅N, and O−H⋅⋅⋅F hydrogen bonds.

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“…Low aqueous solubility often results in poor therapeutic outcome. Different solubility techniques were used to enhance its solubility, namely: solid dispersion (Sayeed et al, 2016), use of cyclodextrins (Yurtdas et al 2011;Li et al 2016;Ahad et al, 2011) and cocrystal formation with dicarboxylic acid (Kastelic et al, 2010). However, no literature reveals formation of FLC-ILs.…”

Section: * Corresponding Authormentioning

confidence: 99%

Synthesis and physicochemical studies of fluconazole ionic liquids

2017

J App Pharm Sci

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Active pharmaceutical ingredient (API) based ionic liquids (ILs) were synthesized by combination of cationic fluconazole (FLC) and anionic ascorbic acid. The solid form of the low water soluble API was converted into its liquid salt form to improve physicochemical properties and evaluate biological activity. ILs were synthesized in different molar ratios of FLC-ascorbic acid (1:1 and 1: 2.5) by applying solvent evaporation method with methanol as the solvent. The analytical evidences for the formation of ILs were generated and confirmed by differential scanning calorimetry (DSC), Fourier transformation-infrared spectroscopy (FTIR) and X-ray powder diffractometry (XRPD). The solubility and dissolution of 1:1 and 1:2.5 ILs were significantly improved as compared to FLC alone, supported by decreased log P values. The improvement of physicochemical properties of IL 1:1 was found to be reliable as compared to the IL 1: 2.5. The antifungal activity of IL 1:1 was retained against Candida albicans. However, increasing the molar ratio of ascorbic acid resulted in reduction of activity.

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Inclusion complexes of fluconazole with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin in aqueous solution: preparation, characterization and a structural insight

Cited by 38 publications

References 30 publications

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

SBA15–Fluconazole as a Protective Approach Against Mild Steel Corrosion: Synthesis, Characterization, and Computational Studies

Synthesis and physicochemical studies of fluconazole ionic liquids

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