Solubilizing steroidal drugs by β-cyclodextrin derivatives

Schwarz, Dennis H.; Engelke, Annegret; Wenz, Gerhard

doi:10.1016/j.ijpharm.2017.07.046

Cited by 54 publications

(29 citation statements)

References 61 publications

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“…The cone inner walls are formed by the hydrophobic carbon backbones of the glucopyranose units, generating a hydrophobic interior. This particular structure supports the use of CDs as solubilizers of poorly water-soluble chemicals [6][7][8].…”

Section: Introductionsupporting

confidence: 62%

Synthesis and characterization of a new cyclodextrin derivative with improved properties to design oral dosage forms

Garcı́a

Priotti

Codina

et al. 2018

Drug Deliv. and Transl. Res.

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This work aimed to synthesize a novel β-cyclodextrin derivative, itaconyl-β-cyclodextrin to evaluate whether albendazole inclusion complexes with the new β-cyclodextrin derivative-improved albendazole dissolution efficiency and its anthelminthic activity. The new derivative was thoroughly evaluated and characterized, and an average degree of substitution of 1.4 per cyclodextrin molecule was observed. Albendazole:itaconyl-β-cyclodextrin complexes were prepared by spray drying procedures and investigated using phase solubility diagrams, dissolution efficiency, X-ray diffraction, differential scanning calorimetry, Fourier transform infrared, scanning electronic microscopy, mass spectrometry, and nuclear magnetic resonance spectroscopy. Phase solubility diagrams and mass spectrometry studies showed that the inclusion complex was formed in an equimolar ratio. Stability constant values were 602 M −1 in water, and 149 M −1 in HCl 0.1 N. Nuclear magnetic resonance experiments of the inclusion complex showed correlation signals between the aromatic and propyl protons of albendazole and the itaconyl-βcyclodextrin inner protons. The studies indicated solid structure changes of albendazole included in itaconyl-β-cyclodextrin. The maximum drug release was reached at 15 min, and the inclusion complex solubility was 88-fold higher than that of the pure drug. The in vitro anthelmintic activity assay showed that the complex was significantly more effective than pure albendazole.

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Section: Introductionsupporting

confidence: 62%

Synthesis and characterization of a new cyclodextrin derivative with improved properties to design oral dosage forms

Garcı́a

Priotti

Codina

et al. 2018

Drug Deliv. and Transl. Res.

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“…Among steroidal drugs, PDN is well known for its capability to undergo complexation with γ-CD [ 6 , 19 ]. The dried γ-CDHSAs’ membranes were immersed in an aqueous solution (PBS) of PDN (0.22 mg mL −1 ) at 25 °C for drug loading.…”

Section: Resultsmentioning

confidence: 99%

“…Polyvinyl alcohol (PVA) hydrogels [ 15 , 16 , 17 ], dicarboxylic acids (DCAs) [ 18 ] and cyclodextrins (CDs) [ 19 , 20 ] are commonly used as biomaterials because they have a high biocompatibility and are FDA-approve. CDs were selected because they are able to form inclusion complexes (host-guest type) with several classes of compounds including hydrophobic drugs.…”

Section: Introductionmentioning

confidence: 99%

Rational Design, Synthesis and Evaluation of γ-CD-Containing Cross-Linked Polyvinyl Alcohol Hydrogel as a Prednisone Delivery Platform

et al. 2018

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This study describes the in-silico rational design, synthesis and evaluation of cross-linked polyvinyl alcohol hydrogels containing γ-cyclodextrin (γ-CDHSAs) as platforms for the sustained release of prednisone (PDN). Through in-silico studies using semi-empirical quantum mechanical calculations, the effectiveness of 20 dicarboxylic acids to generate a specific cross-linked hydrogel capable of supporting different amounts of γ-cyclodextrin (γ-CD) was evaluated. According to the interaction energies calculated with the in-silico studies, the hydrogel made from PVA cross-linked with succinic acids (SA) was shown to be the best candidate for containing γ-CD. Later, molecular dynamics simulation studies were performed in order to evaluate the intermolecular interactions between PDN and three cross-linked hydrogel formulations with different proportions of γ-CD (2.44%, 4.76% and 9.1%). These three cross-linked hydrogels were synthesized and characterized. The loading and the subsequent release of PDN from the hydrogels were investigated. The in-silico and experimental results showed that the interaction between PDN and γ-CDHSA was mainly produced with the γ-CDs linked to the hydrogels. Thus, the unique structures and properties of γ-CDHSA demonstrated an interesting multiphasic profile that could be utilized as a promising drug carrier for controlled, sustained and localized release of PDN.

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“…Native or non-substituted CDs and their hydroxy-propyl derivatives have been used as pharmaceutical excipients to increase drug solubility, improve chemical stability, reduce toxicity and transport molecules to specific sites [19,20,21,22,23]. Importantly, drug/CD complexation increases the aqueous solubility of poorly soluble drugs without altering their properties [24]; as a result, CDs have been used in over 40 marketed products to date.…”

Section: Introductionmentioning

confidence: 99%

Nepafenac-Loaded Cyclodextrin/Polymer Nanoaggregates: A New Approach to Eye Drop Formulation

2019

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The topical administration route is commonly used for targeting therapeutics to the eye; however, improving the bioavailability of drugs applied directly to the eye remains a challenge. Different strategies have been studied to address this challenge. One of them is the use of aggregates that are formed easily by self-assembly of cyclodextrin (CD)/drug complexes in aqueous solution. The aim of this study was to design a new eye drop formulation based on aggregates formed between CD/drug complexes. For this purpose, the physicochemical properties of the aggregates associated with six CDs and selected water-soluble polymers were analysed. Complex formation was studied using differential scanning calorimetry (DSC), Fourier-transform infrared spectroscopy (FT-IR) and 1H nuclear magnetic resonance spectroscopy (1H-NMR). Results showed that HPβCD performed best in terms of solubilization, while γCD performed best in terms of enhancing nanoaggregate formation. Formation of inclusion complexes was confirmed by DSC, FT-IR and 1H-NMR studies. A mixture of 15% (w/v) γCD and 8% (w/v) HPβCD was selected for formulation studies. It was concluded that formulations with aggregate sizes less than 1 µm and viscosity around 10–19 centipoises can be easily prepared using a mixture of CDs. Formulations containing polymeric drug/CD nanoaggregates represent an interesting strategy for enhanced topical delivery of nepafenac.

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Solubilizing steroidal drugs by β-cyclodextrin derivatives

Cited by 54 publications

References 61 publications

Synthesis and characterization of a new cyclodextrin derivative with improved properties to design oral dosage forms

Synthesis and characterization of a new cyclodextrin derivative with improved properties to design oral dosage forms

Rational Design, Synthesis and Evaluation of γ-CD-Containing Cross-Linked Polyvinyl Alcohol Hydrogel as a Prednisone Delivery Platform

Nepafenac-Loaded Cyclodextrin/Polymer Nanoaggregates: A New Approach to Eye Drop Formulation

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