Posaconazole/hydroxypropyl-β-cyclodextrin host–guest system: Improving dissolution while maintaining antifungal activity

Tang, Peixiao; Ma, Xiaoli; Wu, Di; Li, Shanshan; Xu, Kailin; Tang, Bin; Li, Hui

doi:10.1016/j.carbpol.2016.01.042

Cited by 49 publications

(24 citation statements)

References 32 publications

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“…albicans and maintain its antimicrobial activities, as previously observed in studies with Posaconazole/HPβCD [35]. Maintain the pharmaceutical effect of a drug while develop a novel drug formulation is the foundation of other applications [35]. It is not surprising that the MIC values were not changed, since at these concentrations (0.625 and 1.25 mg/mL), GA presents a good water solubility.…”

Section: Resultsmentioning

confidence: 70%

“…albicans ATCC 18804 and SC 5314 respectively, suggesting that the complexation process does not alter the antifungal activity of GA for planktonic C . albicans and maintain its antimicrobial activities, as previously observed in studies with Posaconazole/HPβCD [35]. Maintain the pharmaceutical effect of a drug while develop a novel drug formulation is the foundation of other applications [35].…”

Section: Resultsmentioning

confidence: 83%

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Gallic acid/hydroxypropyl-β-cyclodextrin complex: Improving solubility for application on in vitro/ in vivo Candida albicans biofilms

et al. 2017

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The aim of this study was to increase the solubility of gallic acid (GA) for the treatment of Candida albicans biofilm, which is very difficult to treat and requires high drug concentrations. Cyclodextrins (CDs) were used for this purpose. Complexes were evaluated by phase-solubility studies, prepared by spray drying and characterized by drug loading, scanning electron microscopy (SEM) and differential scanning calorimetry (DSC). The complexes were tested on C. albicans biofilm using in vitro and in vivo models. HPβCD formed soluble inclusion complexes with GA. The percentage of GA in GA/HPβCD was 10.8 ± 0.01%. The SEM and DSC analyses confirmed the formation of inclusion complexes. GA/HPβCD maintained the antimicrobial activity of the pure GA. GA/HPβCD was effective on C. albicans biofilms of 24 and 48h. The in vivo results showed an anti-inflammatory activity of GA/HPβCD with no difference in invading hypha counting among the groups. This study encourages the development of new antifungal agents.

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Section: Resultsmentioning

confidence: 70%

Section: Resultsmentioning

confidence: 83%

Gallic acid/hydroxypropyl-β-cyclodextrin complex: Improving solubility for application on in vitro/ in vivo Candida albicans biofilms

et al. 2017

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“…These changes in FTIR spectra suggest that the interaction between the 6CN10 and HP-β-CD does not occur by an inclusion process, which is generally observed only decrease in the intensity of the absorptions bands of the functional groups that are within the cyclodextrin cavity, or very close to the cavity. 28,29 Furthermore, no additional peaks were detected in the spectrum of 6CN10:HP-β-CD complex, indicating the absence of any chemical reactions between 6CN10 and HP-β-CD.…”

Section: Fourier Transform Infrared and Raman Spectroscopymentioning

confidence: 94%

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Eleamen¹,

Costa²,

Lima-Neto³

et al. 2016

Journal of the Brazilian Chemical Society

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This study aimed to prepare a complex of 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and 6CN10, a poorly water soluble 2-aminothiophene derivative with antifungal properties, by freeze-drying technique. The complex was characterized by thermal analysis, infrared/Raman spectroscopy, X-ray diffraction and scanning electron microscopy. In addition, we used the data of the phase solubility study, 1 H, and 2D NMR spectroscopy and molecular modeling in order to investigate the interactions between 6CN10 and HP-β-CD. The apparent solubility of 6CN10 with HP-β-CD increased more than 29 fold. The phase solubility assay in water at 25 ºC showed an A P -type curve, with an apparent stability constant K 1:1 and K 1:2 of 96 and 0.1989 M -1 , respectively. The results of IR, NMR and docking indicate that 6CN10 is able to form complexes with HP-β-CD (1:1 and 1:2 stoichiometric ratios), generating the formation of inclusion and preferably, non-inclusion complexes. The antifungal activity against Cryptococcus neoformans demonstrated the superior performance of the complex (46.66 μg mL -1 ) when compared with the free drug (166.66-333.33 μg mL -1 ). The present study provides useful information for the potential application of complexation with low soluble compounds and about the type of complex formation between 6CN10 and HP-β-CD.

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“…However, the aqueous solubility of β‐CD is limited because of the lack of substitutional groups in its glucopyranose unit. Therefore, hydroxypropyl‐β‐cyclodextrin (HP‐β‐CD) as a derivative of β‐CD has gained increasing attention due to its low toxicity, improved aqueous solubility, and flexible cavity (Dreassi et al., 2010; Liu et al., 2013; Tang et al., 2016). Previous studies found that polyphenols have high activity in cyclodextrin, thereby inhibiting polyphenol‐induced protein aggregation (Budryn, Zaczyńska, Rachwa‐Rosiak, & Oracz, 2015; Niccoli, Oliva, & Castronuovo, 2017; Roy, Dinda, Chaudhury, & Dasgupta, 2017).…”

Section: Introductionmentioning

confidence: 99%

Inclusion complexes of tea polyphenols with HP‐β‐cyclodextrin:Preparation, characterization, molecular docking, and antioxidant activity

Zhong

Lidan

et al. 2020

Journal of Food Science

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The purpose of this study was to prepare and characterize inclusion complexes between tea polyphenol (TP) and hydroxypropyl-β-cyclodextrin (HP-β-CD), and to evaluate their antioxidant properties. Freeze-drying was used to prepare the inclusion complex of TP/HP-β-CD at different component ratios (1:0.5, 1:1, and 1:2). The supermolecular structure of the TP/HP-β-CD complex was characterized by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), and scanning electron microscopy (SEM). Molecular docking was used to simulate the positions and interactions of the binding sites of TP/HP-β-CD inclusion complexes and target protein receptors. In addition, the effects of TP/HP-β-CD inclusion complexes on myofibrillar protein (MP) from lamb tripe were observed under oxidative conditions. Results showed that TP was encapsulated in the cavity of HP-β-CD to form an optimal complex with 1:2 molar ratio of stoichiometry, while the FTIR, TGA, and SEM studies also support the inclusion process. Molecular modeling results were systematically analyzed to determine the stability of inclusion complexes and protein. Furthermore, the addition of an appropriate concentration (5 to 105 µmol/g) of TP/HP-β-CD inclusion complex decreased the carbonyl content, hydrophobicity, and protein aggregation of MP from lamb tripe, whereas it increased the sulfhydryl content. This improved antioxidant activity and bioavailability of the inclusion complexes will be beneficial for its potential applications in food.Practical Application: Tea polyphenol was an antioxidant with potential for the field of food. In this study, the unstable properties of tea polyphenols were evaluated and were improved by inclusion of HP-β-cyclodextrin. The binding mode of the inclusion complex with protein was revealed via the molecular docking method, and the application of inclusion complex to control protein oxidation was studied. Results showed that the inclusion complex could effectively inhibit protein oxidation, which can provide a reference for the application of polyphenols in meat products and the improvement of protein properties.

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Posaconazole/hydroxypropyl-β-cyclodextrin host–guest system: Improving dissolution while maintaining antifungal activity

Cited by 49 publications

References 32 publications

Gallic acid/hydroxypropyl-β-cyclodextrin complex: Improving solubility for application on in vitro/ in vivo Candida albicans biofilms

Gallic acid/hydroxypropyl-β-cyclodextrin complex: Improving solubility for application on in vitro/ in vivo Candida albicans biofilms

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Inclusion complexes of tea polyphenols with HP‐β‐cyclodextrin:Preparation, characterization, molecular docking, and antioxidant activity

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