Solubilization of ibuprofen with β-cyclodextrin derivatives: Energetic and structural studies

Cagno, Massimiliano Pio di; Stein, Paul C.; Škalko‐Basnet, Nataša; Brandl, Martin; Bauer‐Brandl, Annette

doi:10.1016/j.jpba.2011.02.022

Cited by 56 publications

(38 citation statements)

References 13 publications

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“…[20,21] Dexibuprofen is pharmaceutical enantiomer of ibuprofen with lesser side effects. [20,21] Dexibuprofen is pharmaceutical enantiomer of ibuprofen with lesser side effects.…”

Section: Introductionmentioning

confidence: 99%

Hydroxypropyl‐β‐cyclodextrin hybrid nanogels as nano‐drug delivery carriers to enhance the solubility of dexibuprofen: Characterization, in vitro release, and acute oral toxicity studies

2017

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The purpose of this study was to develop and characterize hydroxypropyl-βcyclodextrin (HPβCD) hybrid nanogels for solubility enhancement of lipophilic drug, dexibuprofen. HPβCD hybrid nanogels were designed by chemical crosslinking of hydroxypropyl-β-cyclodextrin with 2-acrylamido-2-methyl propane sulfonic acid (AMPS) via free radical polymerization. Loading efficiency, solubilization, zetasizer, FESEM Fourier transform infrared (FTIR), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), powder X-ray diffraction (PXRD), and in vitro drug release analysis were performed for characterization of hybrid nanogels. Efficient solubilization of dexibuprofen has been observed by HPβCD hybrid nanogels. FTIR, TGA, and DSC studies confirmed the formation of new hybrid nanogels and complexation of dexibuprofen with nanogels. XRD analysis revealed loss of dexibuprofen crystallinity in hybrid nanogels. Highly porous and amorphous nanogels showed a significant dexibuprofen release in aqueous medium. In toxicity studies, no significant changes in behavioral, physiological, biochemical, or histopathological parameters of animals endorsed that developed formulations are nontoxic and biocompatible. K E Y W O R D Samorphous, differential scanning calorimetry, drug delivery systems, Fourier transform infrared, hostguest systems, hybrid nanogels, hydroxypropyl-β-cyclodextrin, nanotechnology, radical polymerization, thermal gravimetric analysis, toxicity studies

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“…[20,21] Dexibuprofen is pharmaceutical enantiomer of ibuprofen with lesser side effects. [20,21] Dexibuprofen is pharmaceutical enantiomer of ibuprofen with lesser side effects.…”

Section: Introductionmentioning

confidence: 99%

Hydroxypropyl‐β‐cyclodextrin hybrid nanogels as nano‐drug delivery carriers to enhance the solubility of dexibuprofen: Characterization, in vitro release, and acute oral toxicity studies

2017

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“…Several studies performed by other authors showed the feasibility of the various processes of complexation in the inclusion complex formation between IB and βCD. The different results corroborated the inclusion complex formation and showed that the particles characteristics were dependent of the complexation methods [8][9][10][11][12][13]. These characteristics (shape, size distribution, crystalline or amorphous state) can influence the processing of the solid dosage form and subsequently the release of the drug in water.…”

Section: Introductionmentioning

confidence: 58%

Release profile of ibuprofen in β-cyclodextrin complexes from two different solid dosage forms

et al. 2012

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The objective of this work was to develop solid dosage forms using powders containing inclusion complexes (ibuprofen with β-cyclodextrin) which were used to produce tablets (direct compression without additional excipients) and pellets (extrusion/spheronization) from wet mass containing 40% (w/w) of microcrystalline cellulose. The pellets also demonstrated that during preparation of the wet mass, the inclusion process occurred in a same yield that when pre-complexation was used. The particles characteristics were evaluated after being obtained through different complexation methods. The results showed that the tensile strength and profile dissolution were as expected for both dosage forms. Tablets containing inclusion complexes showed higher solubility when compared with a reference formulation and with two commercial formulations. The ibuprofen released from the two pellets formulations didn't show relevant differences between them. The drug released was analyzed considering different dissolution parameters. The advantages of these new methodologies can be summarized as: (a) tablets were produced at a lower cost for the total process; and (b) in the pellet´s preparation there was no need of the previous complexation method resulting in a decrease in time and energy required.

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“…Several new types of research found the binding free energy between ibuprofen and β-CD was stronger than a complex of HP-β-CD and ibuprofen. [77,78] However, Mura get the HP-β-CD-solubilizing effectiveness for ibuprofen was more powerful than β-CD in aqueous solution. [78] Núñez-Agüero applied MM-GBSA method for enthalpy calculation of ibuprofen/β-CD complex.…”

Section: Quantum Mechanicsmentioning

confidence: 99%

Computer‐aided drug design to explore cyclodextrin therapeutics and biomedical applications

Abdolmaleki

Ghasemi

2017

Chem Biol Drug Des

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Cyclodextrin (CD) is a subset of the macrocyclic structural class, which is an important class of small organic agents that are useful functional excipients. They have wide range application possibilities in different fields of sciences such as material preparation, medicine, analytical chemistry, and separation processes. They are used widely in pharmaceutical formulations and drug delivery for increasing the water solubility of low soluble drugs and drug candidates. Due to the ring structure, they behave differently than smaller molecules and may be capable of hitting new classes of targets. A macrocyclic molecule presents varied functionality and stereochemical complexity in a pre-organized conformation of the ring structure. This can result in high selectivity and affinity for protein targets while conserving enough bioavailability to arrive at intracellular locations. Regardless of these valuable features, and the verified success of several marketed macrocycle drugs isolated from natural compounds, this class has been little explored in drug development. This study describes some of the key features of the CDs therapeutic discovery. Also, the application of computational chemistry approaches such as QSAR/QSPR, molecular docking, and molecular/quantum mechanics for modeling of CD-drug system is reviewed briefly. K E Y W O R D Sbioavailability, computational, cyclodextrin, drug design, drug discovery, macrocyclic, therapeutic

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Solubilization of ibuprofen with β-cyclodextrin derivatives: Energetic and structural studies

Cited by 56 publications

References 13 publications

Hydroxypropyl‐β‐cyclodextrin hybrid nanogels as nano‐drug delivery carriers to enhance the solubility of dexibuprofen: Characterization, in vitro release, and acute oral toxicity studies

Hydroxypropyl‐β‐cyclodextrin hybrid nanogels as nano‐drug delivery carriers to enhance the solubility of dexibuprofen: Characterization, in vitro release, and acute oral toxicity studies

Release profile of ibuprofen in β-cyclodextrin complexes from two different solid dosage forms

Computer‐aided drug design to explore cyclodextrin therapeutics and biomedical applications

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