Investigation of β-cyclodextrin–norfloxacin inclusion complexes. Part 2. Inclusion mode and stability studies

Mendes, Cassiana; Buttchevitz, Aline; Barison, Andersson; Ocampos, Fernanda Maria Marins; Bernardi, Luana; Oliveira, Paulo Renato de; Silva, Marcos Antônio Segatto

doi:10.1586/14787210.2015.982092

Cited by 12 publications

(3 citation statements)

References 19 publications

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“…Mendes et al [ 179 , 180 ] analysed different techniques of the preparation of norfloxacin ICs with β-CD, HP-β-CD, and γ-CD. The complex of norfloxacin and β-CD (1:1) obtained by kneading followed by freeze-drying led to increased drug solubility, as a result of the amorphous state attributed to the freeze-drying process and the inclusion of norfloxacin into the hydrophobic cavity.…”

Section: Quinolonesmentioning

confidence: 99%

“…Based on the NMR spectra, the geometric structure of the complex was proposed with the bicyclic moiety inserted into the CD through the wide rim. Norfloxacin/β-CD complex obtained by kneading followed by freeze-drying or spray-drying preserved the antibacterial activity of norfloxacin, as the drug was incorporated into the β-CD cavity, thus protecting it from humidity-induced or thermal degradation to the decarboxylated derivative of no pharmacological action [ 180 ].…”

Section: Quinolonesmentioning

confidence: 99%

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Cyclodextrin Inclusion Complexes with Antibiotics and Antibacterial Agents as Drug-Delivery Systems—A Pharmaceutical Perspective

Boczar

Michalska

2022

Pharmaceutics

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Cyclodextrins (CDs) are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits linked by α-1,4 glycosidic bonds. The shape of CD molecules is similar to a truncated cone with a hydrophobic inner cavity and a hydrophilic surface, which allows the formation of inclusion complexes with various molecules. This review article summarises over 200 reports published by the end of 2021 that discuss the complexation of CDs with antibiotics and antibacterial agents, including beta-lactams, tetracyclines, quinolones, macrolides, aminoglycosides, glycopeptides, polypeptides, nitroimidazoles, and oxazolidinones. The review focuses on drug-delivery applications such as improving solubility, modifying the drug-release profile, slowing down the degradation of the drug, improving biological membrane permeability, and enhancing antimicrobial activity. In addition to simple drug/CD combinations, ternary systems with additional auxiliary substances have been described, as well as more sophisticated drug-delivery systems including nanosponges, nanofibres, nanoparticles, microparticles, liposomes, hydrogels, and macromolecules. Depending on the desired properties of the drug product, an accelerated or prolonged dissolution profile can be achieved when combining CD with antibiotics or antimicrobial agents.

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Section: Quinolonesmentioning

confidence: 99%

Section: Quinolonesmentioning

confidence: 99%

Cyclodextrin Inclusion Complexes with Antibiotics and Antibacterial Agents as Drug-Delivery Systems—A Pharmaceutical Perspective

Boczar

Michalska

2022

Pharmaceutics

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“…Furthermore, the stability of NFX: β-CD complexes can be maintained with exposure to light, humidity and heat. 7,8 High-performance liquid chromatography (HPLC) is widely employed in the quantification of drugs in formulations and in studies on drug stability and dissolution as well as biological matrixes. The development of an analytical method involves the evaluation and optimization of the chromatographic conditions with subsequent validation.…”

Section: Introductionmentioning

confidence: 99%

Quantitative Analysis of Norfloxacin in β-Cyclodextrin Inclusion Complexes—Development and Validation of a Stability-indicating HPLC Method

et al. 2015

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The aim of this study was to develop and validate a simple liquid-chromatography method, with good accuracy, reproducibility and sensitivity, for the quantification of norfloxacin in β-cyclodextrin inclusion complexes. In the method validation, the parameters evaluated were linearity, limits of detection and quantification, specificity, accuracy, precision and robustness. The stability-indication property of the method was evaluated through studies on the degradation under stress conditions. A method employing a simple mobile phase consisting of phosphate buffer (pH 3.0) and acetonitrile (86:14 v/v) was developed. Fluorescence detection was employed to minimize the influence of degradation products, due to its high sensitivity, selectivity and specificity. The method was specific, linear in the concentration range of 1 -30 μg/mL, robust, precise and accurate. The proposed method was successfully applied in the determination of norfloxacin in inclusion complexes, thus aiding quality-control analysis in the future development of drug delivery systems.

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Computational investigation on the host–guest inclusion process of norfloxacin into β-cyclodextrin

et al. 2016

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A theoretical (1)H NMR spectroscopy and thermodynamic analysis of the host-guest inclusion process involving the norfloxacin (NFX) into β-cyclodextrin (β-CD) was carried out. DFT structure and stabilization energies were obtained in both gas and aqueous phases. We could establish that the complex formation is enthalpy driven, and the hydrogen bonds established between NFX and β-CD play a major role in the complex stabilization. Besides, a theoretical (1)H NMR analysis has shown to be a supplementary proceeding to predict appropriately the inclusion mode of norfloxacin molecule into the β-CD. In this work, a theoretical study of the NFX@β-CD complex is reported for the first time, seeking a deep understanding of topology and thermodynamics of the inclusion complex formation. Graphical Abstract Topology, thermodynamic and (1)H NMR analysis of NFX@β-CD host-guest complexes.

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Investigation of β-cyclodextrin–norfloxacin inclusion complexes. Part 2. Inclusion mode and stability studies

Abstract: The satisfactory stability indicates that the NFX/β-cyclodextrin complexes could be useful as an alternative to the existing NFX drug formulation.

Cited by 12 publications

References 19 publications

Cyclodextrin Inclusion Complexes with Antibiotics and Antibacterial Agents as Drug-Delivery Systems—A Pharmaceutical Perspective

Cyclodextrin Inclusion Complexes with Antibiotics and Antibacterial Agents as Drug-Delivery Systems—A Pharmaceutical Perspective

Quantitative Analysis of Norfloxacin in β-Cyclodextrin Inclusion Complexes—Development and Validation of a Stability-indicating HPLC Method

Computational investigation on the host–guest inclusion process of norfloxacin into β-cyclodextrin

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