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

Maricán, Adolfo; Ávila-Salas, Fabián; Valdés, Oscar; Wehinger, Sergio; Villaseñor, Jorge; Fuentealba, Natalia; Arenas-Salinas, Mauricio; Argandoña, Yerko; Carrasco-Sánchez, Verónica; Durán-Lara, Esteban F.

doi:10.3390/pharmaceutics10010030

Cited by 19 publications

(23 citation statements)

References 47 publications

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“…In view of these traits, many studies have shown that CDs and their derivatives as drug carriers or pharmaceutical formulations improve the stability, solubility, and bioavailability of drugs [51,52]. CD-based inclusion complexes or polymers have been widely investigated in drug-loading experiments, but they have certain drawbacks with inorganic/organic materials, such as low drug-loading capacity and burst release [53,54,55,56]. Inspired by these works, Smaldone et al [57] reported the first example of a cubic CD-MOF-K (called CD-MOF-1) that was prepared in aqueous media at ambient temperature and pressure.…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin-Based Metal-Organic Frameworks (CD-MOFs) in Pharmaceutics and Biomedicine

et al. 2018

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Metal-organic frameworks (MOFs) show promising application in biomedicine and pharmaceutics owing to their extraordinarily high surface area, tunable pore size, and adjustable internal surface properties. However, MOFs are prepared from non-renewable or toxic materials, which limit their real-world applications. Cyclodextrins (CDs) are a typical natural and biodegradable cyclic oligosaccharide and are primarily used to enhance the aqueous solubility, safety, and bioavailability of drugs by virtue of its low toxicity and highly flexible structure, offering a peculiar ability to form CD/drug inclusions. A sophisticated strategy where CD is deployed as a ligand to form an assembly of cyclodextrin-based MOFs (CD-MOFs) may overcome real-world application drawbacks of MOFs. CD-MOFs incorporate the porous features of MOFs and the encapsulation capability of CD for drug molecules, leading to outstanding properties when compared with traditional hybrid materials. This review focuses on the inclusion technology and drug delivery properties associated with CD-MOFs. In addition, synthetic strategies and currently developed uses of CD-MOFs are highlighted as well. Also, perspectives and future challenges in this rapidly developing research area are discussed.

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Section: Introductionmentioning

confidence: 99%

Cyclodextrin-Based Metal-Organic Frameworks (CD-MOFs) in Pharmaceutics and Biomedicine

et al. 2018

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“…These simulations were carried out in an isothermal–isobaric (NPT) ensemble for a period of 100 ns. To carry out relaxation of the system, the protocol implemented by default in the Desmond program was used (Marican et al ). The optimised potential for liquid simulations force field parameters were applied in all systems.…”

Section: Methodsmentioning

confidence: 99%

Simple approach for cleaning up 2,4,6‐trichloroanisole from alcoholic‐beverage‐reconstituted solutions using polymeric materials

Valdés

Maricán

Ávila-Salas

et al. 2019

Australian Journal of Grape and Wine Research

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Background and Aims 2,4,6‐Trichloroanisole (TCA) is a well‐recognised contaminant in the wine and whisky industries. In this work, several polymeric materials were tested through a hybrid strategy (computational and experimental studies) as potential fining agents for elimination of TCA. Methods and Results Sodium alginate, polyaniline emeraldine base (PANI‐EB), polyaniline emeraldine salt (PANI‐ES) and three cross‐linked derivatives of different generations (G3, G4 and G5) of polyamidoamine (PAMAM) were tested. Materials were characterised by Fourier transform infrared spectroscopy and thermogravimetric analysis. The amount of material and the interaction time needed to achieve TCA sorption were optimised in a screening study. The binding capacity of the materials was then determined in methanol‐reconstituted wine and whisky solutions to demonstrate their effectiveness. The proportion of TCA in wine retained by PANI‐ES, PANI‐EB and PAMAM‐G5‐CD was greater than 75%, and for whisky all polymers except PANI‐ES retained greater than 75% of TCA. The concentration of phenolic substances of both methanol‐reconstituted solutions was measured after treatment; most of the polymers had no impact on the concentration of phenolic substances. The intermolecular interactions between the polymeric materials and TCA were characterised by computational studies involving molecular dynamics simulations. Conclusions The polymers PAMAM G5‐CD and PANI‐EB retained the most TCA in reconstituted red wine and whisky solutions. Significance of the Study The provision of efficient materials for the removal of TCA will improve the purification processes employed in beverage production.

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“…The 3D geometries for each structure were optimized using Gaussian software version 16, revision A.03, Inc., Wallingford, CT, USA [29] at Density Functional Theory level using the B3LYP method and 6-311+G(d,p) as the selected basis set. The DCAs identified by Marican et al 2018 [17] were used in this study.…”

Section: Methodsmentioning

confidence: 99%

“…To model the 10:2 proportion of PVA:MA, the polymer matrix built with the 28 PVA chains (considering a total of 952 PVA monomers) was crosslinked incorporating 190 MA into the polymer matrix, of which 150 were covalently bonded to the –OH groups of PVA chains. The crosslinking procedure was performed according to previous work described by Marican et al (2018) and Avila-Salas et al (2018) [17,34]. Subsequently, LEAP program was used to covalently bonding 16 γ-CD molecules to the MAs that were linked to the PVA only by one end.…”

Section: Methodsmentioning

confidence: 99%

“…On the other hand, several mechanisms have been elucidated to describe drug release from polymer hydrogel systems including diffusion, swelling, and chemically controlled release (erosion by enzymatic degradation and pH-responsive) [16]. This property offered by hydrogels for drug delivery applications involves the chance for sustained release, which results in keeping an appropriate local concentration of bioactive compounds over a long period [17]. Moreover, it is very important that the formulation based on hydrogels be harmless (non-allergic, non-toxic and biocompatible) [18].…”

Section: Introductionmentioning

confidence: 99%

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Rational Development of a Novel Hydrogel as a pH-Sensitive Controlled Release System for Nifedipine

et al. 2018

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This work depicts the rational development (in-silico design, synthesis, characterization and in-vitro evaluation) of polyvinyl alcohol hydrogels (PVAH) cross-linked with maleic acid (MA) and linked to γ-cyclodextrin molecules (γ-CDPVAHMA) as systems for the controlled and sustained release of nifedipine (NFD). Through computational studies, the structural blocks (PVA chain + dicarboxylic acid + γ-CD) of 20 different hydrogels were evaluated to test their interaction energies (ΔE) with NFD. According to the ΔE obtained, the hydrogel cross-linked with maleic acid was selected. To characterize the intermolecular interactions between NFD and γ-CDPVAHMA, molecular dynamics simulation studies were carried out. Experimentally, three hydrogel formulations with different proportions of γ-CD (2.43%, 3.61% and 4.76%) were synthesized and characterized. Both loading and release of NFD from the hydrogels were evaluated at acid and basic pH. The computational and experimental results show that γ-CDs linked to the hydrogels were able to form 1:1 inclusion complexes with NFD molecules. Finally, γ-CDPVAHMA-3 demonstrated to be the best pH-sensitive release platform for nifedipine. Its effectiveness could significantly reduce the adverse effects caused by the anticipated release of NFD in the stomach of patients.

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

Cited by 19 publications

References 47 publications

Cyclodextrin-Based Metal-Organic Frameworks (CD-MOFs) in Pharmaceutics and Biomedicine

Cyclodextrin-Based Metal-Organic Frameworks (CD-MOFs) in Pharmaceutics and Biomedicine

Simple approach for cleaning up 2,4,6‐trichloroanisole from alcoholic‐beverage‐reconstituted solutions using polymeric materials

Rational Development of a Novel Hydrogel as a pH-Sensitive Controlled Release System for Nifedipine

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