Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified β-cyclodextrin

Figueiras, Ana; Carvalho, Rui A.; Ribeiro, Laura; Torres‐Labandeira, Juan J.; Veiga, Francisco

doi:10.1016/j.ejpb.2007.03.005

Cited by 122 publications

(64 citation statements)

References 27 publications

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“…aromatic compounds, ferrocene, cholesterol, and adamantane groups (in the case of β-CD)), forming a diverse set of host-guest inclusion complexes through facile hydrophobic and van der Waals interactions. [5][6][7][8] Taking advantage of these highly defined CD-guest interactions, CDs have been widely utilized in separation technologies, food processing, and pharmaceutical formulations. 9,10 Nevertheless, thus far there have been no reports of the utilization of these facile non-covalent interactions to conjugate peptide sequences onto biomaterial surfaces for cell adhesion.…”

Section: Introductionmentioning

confidence: 99%

Modulation of Stem Cell Adhesion and Morphology via Facile Control over Surface Presentation of Cell Adhesion Molecules

Frith

Cooper-White

2013

Biomacromolecules

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ABSTRACT. To encourage cell adhesion on biomaterial surfaces in a more facile, safe, and lowcost fashion, we have demonstrated a non-covalent approach to spatially conjugate β-cyclodextrin (β-CD) modified peptide sequences onto self-assembled adamantane-terminated polystyrene-b-poly(ethylene oxide) (PS-PEO-Ada) films through inclusion complexing interactions between β-CDs and adamantane. By simply blending various ratios of unmodified PS-PEO with a newly synthesised PS-PEO-Ada, we produced PS polymer films that displayed 2 well-organized adamantine-decorated cylindrical PEO domains with varying average interdomain spacings ranging from 29 to 47 nm. The presence of the adamantane moiety at the terminal end of the PEO chain permitted rapid, and importantly, oriented attachment of β-CD functionalized peptides onto these surfaces. This one-step process not only converted these proven non-adherent PS-PEO surfaces into adherent surfaces, but also permitted precisely controlled presentation and surface distribution of the conjugated peptides. The utility of these surfaces as cell culture substrates was confirmed with human mesenchymal stem cells (hMSCs).We observed that with increasing PS-PEO-Ada content in the PEO cylindrical domains, these novel polymer films displayed improved cell attachment and spreading, with notable differences in hMSC morphology. We further confirmed that this novel PS-PEO-Ada surface provides a flexible platform for facile conjugation of mixtures of β-CDs functionalized with different peptides, specifically RGD and IKVAV peptides. The cell adhesion and spreading assays on these surfaces indicated that the morphologies of hMSCs can be easily manipulated, while no significant changes in cell attachment were observed. The 'lock-and-key' peptide conjugation technique presented in this work is applicable to any substrate that incorporates a moiety capable of forming inclusion complexes with α-, β-and γ-CDs, providing a facile and flexible method by which to construct peptide-conjugated biomaterial substrates for a multitude of applications in fields ranging from cell bioprocessing, regenerative medicine to cell-based assays.

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Section: Introductionmentioning

confidence: 99%

Modulation of Stem Cell Adhesion and Morphology via Facile Control over Surface Presentation of Cell Adhesion Molecules

Frith

Cooper-White

2013

Biomacromolecules

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“…BNZ characteristically takes the form of regular crystals, 27 while RMβCD and SBβCD are normally composed of amorphous particles. 8 In general, all the processed samples underwent changes in the morphology of the particles. The characteristics of the amorphous particles of the non-manipulated CDs were not observed.…”

Section: Scanning Electron Microscopy (Sem)mentioning

confidence: 99%

“…[6][7][8][9][10][11] The potential use of natural cyclodextrins (CDs) and their synthetic derivatives has been extensively studied as a way of improving certain drug properties, such as solubility, stability and/or bioavailability. The property of enhancing solubility may be explained by the formation of water-soluble inclusion complexes in which the hollow, truncated, cone-like CD structure encapsulates the hydrophobic drug molecules in the apolar interior.…”

Section: Introductionmentioning

confidence: 99%

Improving the solubility of the antichagasic drug benznidazole through formation of inclusion complexes with cyclodextrins

Sobrinho¹,

Soares²,

Labandeira³

et al. 2011

Quím. Nova

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Recebido em 12/11/10; aceito em 19/4/11; publicado na web em 17/6/11This study describes unpublished research on improving the solubility of benznidazole by the formation of an inclusion complex. The cyclodextrins selected were αCD, βCD, γCD, HPβCD, RMβCD and SBβCD. All complexes were obtained in solution, presenting 1:1 stoichiometry according to the phase solubility diagram. The highest association constants were obtained with RMβCD and SBβCD, being selected for attainment of solid state complexes. These were characterized using XRD, SEM and dissolution test. The data obtained suggest the formation of complexes and indicate that these may provide a promising alternative way of developing solid doses of drug with suitable biopharmaceutical properties.

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“…Conventional formulation approaches for water-solubility enhancement include co-grinding with surfactants, 8,9 formation of solid dispersions, 10,11 and inclusion complexes with hydrophilic cyclodextrins. [12][13][14][15] In addition to these techniques, particle size reduction to the nanometer range has also been utilized. [16][17][18] For instance, the use of a nanosuspension was able to overcome the low/erratic absorption problem associated with poorly water-soluble drugs after peroral, 19,20 transdermal, 21 ocular, or pulmonary 23 administration.…”

Section: Introductionmentioning

confidence: 99%

Particle size reduction to the nanometer range: a promising approach to improve buccal absorption of poorly water-soluble drugs

Rao¹,

Song²,

Peddie³

et al. 2011

IJN

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Poorly water-soluble drugs, such as phenylephrine, offer challenging problems for buccal drug delivery. In order to overcome these problems, particle size reduction (to the nanometer range) and cyclodextrin complexation were investigated for permeability enhancement. The apparent solubility in water and the buccal permeation of the original phenylephrine coarse powder, a phenylephrine–cyclodextrin complex and phenylephrine nanosuspensions were characterized. The particle size and particle surface properties of phenylephrine nanosuspensions were used to optimize the size reduction process. The optimized phenylephrine nanosuspension was then freeze dried and incorporated into a multi-layered buccal patch, consisting of a small tablet adhered to a mucoadhesive film, yielding a phenylephrine buccal product with good dosage accuracy and improved mucosal permeability. The design of the buccal patch allows for drug incorporation without the need to change the mucoadhesive component, and is potentially suited to a range of poorly water-soluble compounds.

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Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified β-cyclodextrin

Cited by 122 publications

References 27 publications

Modulation of Stem Cell Adhesion and Morphology via Facile Control over Surface Presentation of Cell Adhesion Molecules

Modulation of Stem Cell Adhesion and Morphology via Facile Control over Surface Presentation of Cell Adhesion Molecules

Improving the solubility of the antichagasic drug benznidazole through formation of inclusion complexes with cyclodextrins

Particle size reduction to the nanometer range: a promising approach to improve buccal absorption of poorly water-soluble drugs

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