Utility of cyclodextrins in the formulation of genistein

Daruházi, Ágnes Emma; Szente, Lajos; Balogh, Balázs; Mátyus, Péter; Béni, Szabolcs; Takacs, Michael; Gergely, András; Horváth, Péter; Szöke, Éva; Lemberkovics, Éva

doi:10.1016/j.jpba.2008.06.007

Cited by 40 publications

(15 citation statements)

References 19 publications

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“…Inclusion complexes of cyclodextrins with nonpolar drugs represent a topic of high interest in pharmaceutical research, for providing the possibility to increase the water solubility, stability and bioavailability of the guest drugs [14,17,28,29]. Genistein bioavailability can be increased by complexation with CDs [30]. Zhao et al [31] found an enhanced bioavailability of soy isoflavones by complexation with two commercially available dendrimers.…”

Section: Resultsmentioning

confidence: 99%

Changes in the anti-inflammatory activity of soy isoflavonoid genistein versus genistein incorporated in two types of cyclodextrin derivatives

Danciu

Şoica

Csányi

et al. 2012

Chemistry Central Journal

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BackgroundThe isoflavonoid genistein represents the major active compound from soybean, the vegetal product from Glycine max (Fabaceae). The aim of this study is to prove that genistein was incorporated in two semisynthetic cyclodextrins, beta-cyclodextrin derivatives: hydroxypropyl-beta-cyclodextrin and randomly-methylated-beta-cyclodextrin as well as to compare the anti-inflammatory activity of genistein with that of genistein incorporated in these two types of semisynthetic cyclodextrins.ResultsThe animal studies were conducted on 8-week old C57BL/6 J female mice. Inflammation was induced in both ears of each mouse by topical application of 10 micrograms 12-O-tetradecanoylphorbol-3-acetate dissolved in 0.1 ml solvent (acetone : dimethylsulfoxide in a molar ratio 9:1). Thirty minutes later treatment was applied. The inflammatory reaction was correlated with increased values in ear thickness. Treatment with genistein and genistein incorporated in the two cyclodextrins led to decreased values for ear thickness. Better anti-inflammatory action was found for the complexes of genistein. Both haematoxylin-eosin analysis and CD45 marker expression are in agreement with these findings.ConclusionsResults allow concluding that genistein is an active anti-inflammatory phytocompound and its complexation with hydrophilic beta-cyclodextrin derivatives leads to a stronger anti-inflammatory activity.

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Section: Resultsmentioning

confidence: 99%

Changes in the anti-inflammatory activity of soy isoflavonoid genistein versus genistein incorporated in two types of cyclodextrin derivatives

Danciu

Şoica

Csányi

et al. 2012

Chemistry Central Journal

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“…[18] From the classical simulation, it seems that the structure of the complex is stabilized by the presence of H-bonds involving the phenolic OH and the C O groups of Gen and some OH groups of β-CD (Fig. 9).…”

Section: Resultsmentioning

confidence: 99%

“…For nutraceutical and pharmaceutical purposes, it needs to be solubilized to provide sufficient concentration of available monomeric form of the drug. [7,8] Cyclodextrins (CDs) are a group of structurally related macrocyclic oligosaccharides built up from 6, 7, or 8 glucopyranose units called α, β, and γ -CD, respectively. [9] Their special molecular structure, hydrophobic internal cavity, and hydrophilic external surface give them the remarkable property of acting as molecular hosts in the formation of inclusion complexes with various guest molecules with suitable polarity and dimension via noncovalent host-guest interactions like Van der Waals, hydrophobic, and hydrogen bonding.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, based on molecular modeling investigations and on the results of phase-solubility studies, a correlation between the size of the CD cavity and the inclusion of Gen was found. [18] Two-dimensional rotating-frame nuclear Overhauser effect spectroscopy experiments gave a clear explanation about the interacting moieties. In particular, the 4-hydroxyphenyl ring penetrated from the wider rim side into the β-CD cavity.…”

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The effect of hydrogen bond on the vibrational dynamics of genistein free and complexed with β‐cyclodextrins

Crupi

Majolino

Paciaroni

et al. 2010

J Raman Spectroscopy

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Inclusion, or host-guest, complexes are supramolecular assemblies in which two or more molecules hold together and organize by means of intermolecular noncovalent bonds. In the pharmaceutical field, inclusion complexation of drugs with unsubstituted and derivative β-cyclodextrins (β-CDs) has proven to be a successful method to improve the dissolution of water insoluble drugs. Genistein (Gen), an isoflavone constituent of Onodis spinosae radix, turned out to be a suitable guest molecule for the encapsulation into β-CD, resulting in a significant improvement of its aqueous solubility. In the present study, the modifications of the vibrational spectrum of Gen caused by its inclusion into β-CDs cavity have been characterized by means of Raman scattering experiments. These changes have been interpreted by comparing the experimental data with the vibrational wavenumbers and Raman intensities obtained by simulation for the free and complexed guest molecule. Following this strategy, we have obtained a deeper understanding of the host-guest interactions involved in the formation and stabilization of the complexes, with particular regard to the role played by the guest chemical groups, as well as to disentangle the effects directly related to the complexation process from those ascribed to other factors, such as formation of intra-and intermolecular hydrogen bonds.

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“…In a recent report, Daruházi et al 14 found that solely genistein B-ring would be included into the β-CD cavity and the mode of insertion would occur from the wider rim side (H-5 proton).…”

Section: Characterization Of Solid Complex and Corresponding Physicalmentioning

confidence: 99%

Improvement of genistein content in solid genistein/-cyclodextrin complexes β

et al. 2010

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Recebido em 17/3/09; aceito em 7/9/09; publicado na web em 23/2/10 Genistein:β-cyclodextrin complexes with high drug loading (19.22%) were prepared by freeze-drying and characterized by differential scanning calorimetry and hydrogen nuclear magnetic resonance spectroscopy. The spatial configuration of the complex was proposed by means of 2D-NOESY experiment combined with molecular modeling. According to the results obtained, the interaction of genistein with β-cyclodextrin in a 1:1 complex is supposed to occur mainly through the insertion of the guest A-ring in cyclodextrin cavity, without rule out the possibility of inclusion through the B-ring, as previously reported in the literature.

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Utility of cyclodextrins in the formulation of genistein

Cited by 40 publications

References 19 publications

Changes in the anti-inflammatory activity of soy isoflavonoid genistein versus genistein incorporated in two types of cyclodextrin derivatives

Changes in the anti-inflammatory activity of soy isoflavonoid genistein versus genistein incorporated in two types of cyclodextrin derivatives

The effect of hydrogen bond on the vibrational dynamics of genistein free and complexed with β‐cyclodextrins

Improvement of genistein content in solid genistein/-cyclodextrin complexes β

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