Enhanced Bioavailability of Soy Isoflavones by Complexation with β-Cyclodextrin in Rats

Lee, Seung–Hyun; Kim, Young Heui; Yu, Heui-Jong; Cho, Nam-Suk; Kim, Tae Hyun; Kim, Dong-Chool; Chung, Chan-Bok; Hwang, Yong-Il; Kim, Ki Ho

doi:10.1271/bbb.70296

Cited by 45 publications

(34 citation statements)

References 32 publications

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“…The complexes of genistein with the natural beta-cyclodextrin proved a higher solubility and bioavailability compared to the drug alone [16]. Considering the rather low water solubility of natural β-CD, studies have been conducted on the complexation of genistein with derivatisedcyclodextrins [17].…”

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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“…The successful incorporation of Gen in native cyclodextrins: β- and γ-cyclodextrin was previously reported, while α-CD did not form a stable complex [23]. Furthermore, using animal models, enhanced bioavailability and better anti-inflammatory properties were detected for Gen:CD inclusion complexes [5,24]. …”

Section: Introductionmentioning

confidence: 85%

Genistein in 1:1 Inclusion Complexes with Ramified Cyclodextrins: Theoretical, Physicochemical and Biological Evaluation

Danciu

Şoica

Oltean

et al. 2014

IJMS

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Genistein is one of the most studied phytocompound in the class of isoflavones, presenting a notable estrogenic activity and in vitro and/or in vivo benefits in different types of cancer such as those of the bladder, kidney, lung, pancreatic, skin and endometrial cancer. A big inconvenience for drug development is low water solubility, which can be solved by using hydrophilic cyclodextrins. The aim of this study is to theoretically analyze, based on the interaction energy, the possibility of a complex formation between genistein (Gen) and three different ramified cyclodextrins (CD), using a 1:1 molar ratio Gen:CD. Theoretical data were correlated with a screening of both in vitro and in vivo activity. Proliferation of different human cancer cell lines, antimicrobial activity and angiogenesis behavior was analyzed in order to see if complexation has a beneficial effect for any of the above mentioned activities and if so, which of the three CDs is the most suitable for the incorporation of genistein, and which may lead to future improved pharmaceutical formulations. Results showed antiproliferative activity with different IC50 values for all tested cell lines, remarkable antimicrobial activity on Bacillus subtilis and antiangiogenic activity as revealed by CAM assay. Differences regarding the intensity of the activity for pure and the three Gen complexes were noticed as explained in the text. The data represent a proof that the three CDs can be used for furtherer research towards practical use in the pharmaceutical and medical field.

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“…Various pharmaceutical formulations such as polymeric micro-/nano-particles (Tang et al ., 2011), β-cyclodextrin complexes (Lee et al ., 2007), micellar systems (Kwon et al ., 2007), and self-nanoemulsifying drug delivery systems (Tripathi et al ., 2016) have been explored to improve dissolution behavior and oral bioavailability of genistein. Among them, SLPS have been suggested as a promising drug delivery system for enhancing the oral bioavailability of genistein because they can be fabricated to release the incorporated drugs in a controlled manner by varying the composition of the solid matrix, which is a critical determinant of oral bioavailability (Harde et al ., 2011).…”

Section: Discussionmentioning

confidence: 99%

Absorption Study of Genistein Using Solid Lipid Microparticles and Nanoparticles: Control of Oral Bioavailability by Particle Sizes

Kim

Barua

Kim

et al. 2017

Biomolecules & Therapeutics

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In this study, the effect of particle size of genistein-loaded solid lipid particulate systems on drug dissolution behavior and oral bioavailability was investigated. Genistein-loaded solid lipid microparticles and nanoparticles were prepared with glyceryl palmitostearate. Except for the particle size, other properties of genistein-loaded solid lipid microparticles and nanoparticles such as particle composition and drug loading efficiency and amount were similarly controlled to mainly evaluate the effect of different particle sizes of the solid lipid particulate systems on drug dissolution behavior and oral bioavailability. The results showed that genistein-loaded solid lipid microparticles and nanoparticles exhibited a considerably increased drug dissolution rate compared to that of genistein bulk powder and suspension. The microparticles gradually released genistein as a function of time while the nanoparticles exhibited a biphasic drug release pattern, showing an initial burst drug release, followed by a sustained release. The oral bioavailability of genistein loaded in solid lipid microparticles and nanoparticles in rats was also significantly enhanced compared to that in bulk powders and the suspension. However, the bioavailability from the microparticles increased more than that from the nanoparticles mainly because the rapid drug dissolution rate and rapid absorption of genistein because of the large surface area of the genistein-solid lipid nanoparticles cleared the drug to a greater extent than the genistein-solid lipid microparticles did. Therefore, the findings of this study suggest that controlling the particle size of solid-lipid particulate systems at a micro-scale would be a promising strategy to increase the oral bioavailability of genistein.

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Enhanced Bioavailability of Soy Isoflavones by Complexation with β-Cyclodextrin in Rats

Cited by 45 publications

References 32 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

Genistein in 1:1 Inclusion Complexes with Ramified Cyclodextrins: Theoretical, Physicochemical and Biological Evaluation

Absorption Study of Genistein Using Solid Lipid Microparticles and Nanoparticles: Control of Oral Bioavailability by Particle Sizes

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