Inclusion complexes of isoflavones with two commercially available dendrimers: Solubility, stability, structures, release behaviors, cytotoxicity, and anti-oxidant activities

Zhao, Chen; Wang, Yitong; Su, Yunzhang; Zhang, Hongfeng; Ding, Linfeng; Yan, Xiaofeng; Zhao, Di; Shao, Naimin; Ye, Xiyun; Cheng, Yiyun

doi:10.1016/j.ijpharm.2011.09.044

Cited by 39 publications

(15 citation statements)

References 43 publications

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“…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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“…In addition, daidzein has been studied due to its potential health effects, including chemoprevention of cardiovascular diseases, inhibitory effects on prostate cancer as well as an alternative for estrogen replacement therapy to prevent and treat osteoporosis . However, the oral bioavailability is low due to daidzein's poor aqueous solubility and low intestinal absorption, and its administration is a major challenge in pharmaceutical applications . Therefore, the development of daidzein loaded polymer microspheres can be considered a suitable approach to deliver daidzein to the site where it is required, for example incorporating such microspheres in bone tissue scaffolds.…”

Section: Introductionmentioning

confidence: 99%

“…[15][16][17][18][19][20][21] However, the oral bioavailability is low due to daidzein's poor aqueous solubility and low intestinal absorption, and its administration is a major challenge in pharmaceutical applications. 22 Therefore, the development of daidzein loaded polymer microspheres can be considered a suitable approach to deliver daidzein to the site where it is required, for example incorporating such microspheres in bone tissue scaffolds. One study has also highlighted the positive effects of purified daidzein in combination with calcium on bone mineral density (BMD) and biomechanical strength of cortical and cancellous bone in a mouse model.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of 45S5 bioactive glass‐based scaffolds loaded with PHBV microspheres with daidzein release function

Macías-Andrés

Aguilar-Reyes

et al. 2017

J Biomedical Materials Res

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Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV) microsphere loaded 45S5 bioactive glass (BG) based scaffolds with drug releasing capability have been developed. PHBV microspheres with a mean particle size 4 ± 2 μm loaded with daidzein were obtained by oil-in-water single emulsion solvent evaporation method and applied to the surface of BG scaffolds by dip coating technique. The morphology, in vitro bioactivity in simulated body fluid (SBF), mechanical properties and drug release kinetics of microsphere loaded scaffolds were studied. The microspheres were shown to be homogeneously dispersed on the scaffold surfaces. It was confirmed that hydroxyapatite crystals homogeneously grew not only on the surface of the scaffold but also on the surface of the microspheres within 3 days of immersion in SBF. The daidzein release from the microsphere loaded scaffolds lasted almost 1 month and was determined to be diffusion controlled. The microsphere loaded BG scaffolds with daidzein releasing capability obtained in this study are a candidate for bone tissue engineering. © 2017 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 105A: 1765-1774, 2017.

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“…However, besides being challenging to synthesize, these derivatives are still not soluble enough and/or show poorer biological activity than unmodified DAI. The second approach is to encapsulate DAI and related compounds in polymeric nanoparticles composed of, for example, hypromellose [36], carboxymethyl cellulose [37], zein [38], Eudragit E100-polyvinyl alcohol [39], poly(D,L)lactic acid [40], polymeric dendrimers [41,42], and polymeric microparticles composed of gelatin [43] or chitosan [44]. The third common approach is inclusion complexation of DAI with different cyclodextrins (CDs) and their derivatives, which was found to significantly improve its bioavailability, cellular membrane penetration, and therapeutic properties [45][46][47][48].…”

Section: Introductionmentioning

confidence: 99%

Improved Pharmacokinetics and Tissue Uptake of Complexed Daidzein in Rats

et al. 2020

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The pharmacokinetic profile and tissue uptake of daidzein (DAI) was determined in rat serum and tissues (lungs, eyes, brain, heart, spleen, fat, liver, kidney, and testes) after intravenous and intraperitoneal administration of DAI in suspension or complexed with ethylenediamine-modified γ-cyclodextrin (GCD-EDA/DAI). The absolute and relative bioavailability of DAI suspended (20 mg/kg i.v. vs. 50 mg/kg i.p.) and complexed (0.54 mg/kg i.v. vs. 1.35 mg/kg i.p.) was determined. After i.p. administration, absorption of DAI complexed with GCD-EDA was more rapid (tmax = 15 min) than that of DAI in suspension (tmax = 45 min) with a ca. 3.6 times higher maximum concentration (Cmax = 615 vs. 173 ng/mL). The i.v. half-life of DAI was longer in GCD-EDA/DAI complex compared with DAI in suspension (t0.5 = 380 min vs. 230 min). The volume of distribution of DAI given i.v. in GCD-EDA/DAI complex was ca. 6 times larger than DAI in suspension (38.6 L/kg vs. 6.2 L/kg). Our data support the concept that the pharmacokinetics of DAI suspended in high doses are nonlinear. Increasing the intravenous dose 34 times resulted in a 5-fold increase in AUC. In turn, increasing the intraperitoneal dose 37 times resulted in a ca. 2-fold increase in AUC. The results of this study suggested that GCD-EDA complex may improve DAI bioavailability after i.p. administration. The absolute bioavailability of DAI in GCD-EDA inclusion complex was ca. 3 times greater (F = 82.4% vs. 28.2%), and the relative bioavailability was ca. 21 times higher than that of DAI in suspension, indicating the need to study DAI bioavailability after administration by routes other than intraperitoneal, e.g., orally, subcutaneously, or intramuscularly. The concentration of DAI released from GCD-EDA/DAI inclusion complex to all the rat tissues studied was higher than after administration of DAI in suspension. The concentration of DAI in brain and lungs was found to be almost 90 and 45 times higher, respectively, when administered in complex compared to the suspended DAI. Given the nonlinear relationship between DAI bioavailability and the dose released from the GCD-EDA complex, complexation of DAI may thus offer an effective approach to improve DAI delivery for treatment purposes, for example in mucopolysaccharidosis (MPS), allowing the reduction of ingested DAI doses.

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Inclusion complexes of isoflavones with two commercially available dendrimers: Solubility, stability, structures, release behaviors, cytotoxicity, and anti-oxidant activities

Cited by 39 publications

References 43 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

Preparation and characterization of 45S5 bioactive glass‐based scaffolds loaded with PHBV microspheres with daidzein release function

Improved Pharmacokinetics and Tissue Uptake of Complexed Daidzein in Rats

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