Preparation and Characterization of Quercetin and Rutin Cyclodextrin Inclusion Complexes

Sri, K. Vijaya; Kondaiah, A.; Ratna, J. Vijaya; Akula, Annapurna

doi:10.1080/03639040601150195

Cited by 84 publications

(56 citation statements)

References 18 publications

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“…These events were also observed in the DSC curve obtained for β-cyclodextrin (Fig. 4a), where another endothermic event took place at approximately 220°C corresponding to an irreversible transformation process within the β-cyclodextrin molecule (16). The DSC curve obtained for quercetin/β-cyclodextrin solid complex prepared in aqueous solution followed by spraydrying (Fig.…”

Section: Differential Scanning Calorimetrymentioning

confidence: 71%

“…The quercetin/β-cyclodextrin solid complex prepared in aqueous solution followed by spray-drying presented amorphous particles with shrunken spherical shape (Fig. 7d), a (12), and Sri et al (16), which employed X-ray powder diffractometry to demonstrate that drug/cyclodextrin solid complexes exist in amorphous state. However, our study could not suggest an interaction between quercetin and β-cyclodextrin, because it was impossible to differentiate between the morphology of solid complex and that of the isolated compounds.…”

Section: Scanning Electron Microscopymentioning

confidence: 99%

“…Many studies assessing quercetin/cyclodextrin complexes (11)(12)(13)(14)16,17) using the phase-solubility technique do not mention the exact amount of quercetin added to cyclodextrin solutions; neither do they inform the influence of the operating conditions employed, such as temperature and stirring time. This lack of information about the influence temperature, stirring time, and excess amount of quercetin on quercetin/β-cyclodextrin complexation in aqueous media was the motivation of our investigation employing a 2 3 factorial design.…”

Section: Factorial Designmentioning

confidence: 99%

“…Some studies have shown that the association of quercetin with cyclodextrins to form inclusion complexes improves the aqueous solubility (5,(11)(12)(13)(14)(15)(16)(17) and dissolution rate (16) of the flavonoid. Most quercetin/β-cyclodextrin solid complexes are prepared in liquid media, (aqueous solution submitted to freeze-drying (12,14,18), co-evaporation (11,16), or thin layer (11) methods) or semisolid media (kneading method (11,14,16,19)).…”

Section: Introductionmentioning

confidence: 99%

“…Most quercetin/β-cyclodextrin solid complexes are prepared in liquid media, (aqueous solution submitted to freeze-drying (12,14,18), co-evaporation (11,16), or thin layer (11) methods) or semisolid media (kneading method (11,14,16,19)). However, no study to date has used a factorial design to assess the influence of operating conditions such as temperature, stirring time, and excess amount of quercetin on the complexation of quercetin with β-cyclodextrin.…”

Section: Introductionmentioning

confidence: 99%

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Quercetin/β-Cyclodextrin Solid Complexes Prepared in Aqueous Solution Followed by Spray-drying or by Physical Mixture

et al. 2009

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Abstract. The present study was designed to investigate the influence of operating conditions (temperature, stirring time, and excess amount of quercetin) on the complexation of quercetin with β-cyclodextrin using a 2 3 factorial design. The highest aqueous solubility of quercetin was reached under the conditions 37°C/24 h/6 mM of quercetin. The stoichiometric ratio (1:1) and the apparent stability constant (Ks=230 M −1 ) of the quercetin/β-cyclodextrin complex were determined using phase-solubility diagrams. The semi-industrial production of a 1:1 quercetin/β-cyclodextrin solid complex was carried out in aqueous solution followed by spray-drying. Although the yield of the spray-drying process was adequate (77%), the solid complex presented low concentration of quercetin (0.14%, w/w) and, thus, low complexation efficiency. The enhancement of aqueous solubility of quercetin using this method was limited to 4.6-fold in the presence of 15 mM of β-cyclodextrin. Subsequently, an inclusion complex was prepared via physical mixture of quercetin with β-cyclodextrin (molar ratio of 1:1 and quercetin concentration of 23% (w/w)) and characterized using infrared spectroscopy, differential scanning calorimetry, nuclear magnetic resonance spectroscopy, and scanning electron microscopy analyses. The enhancement of aqueous solubility of quercetin using this method was 2.2-fold, similar to that found in the complex prepared in aqueous solution before the spray-drying process (2.5-fold at a molar ratio of 1:1, i.e., 6 mM of quercetin and 6 mM of β-cyclodextrin).

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Section: Differential Scanning Calorimetrymentioning

confidence: 71%

Section: Scanning Electron Microscopymentioning

confidence: 99%

Section: Factorial Designmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quercetin/β-Cyclodextrin Solid Complexes Prepared in Aqueous Solution Followed by Spray-drying or by Physical Mixture

et al. 2009

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Phytochemicals

2017

Cyclodextrins

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Gold nanoparticles–conjugated quercetin induces apoptosis via inhibition of EGFR/PI3K/Akt–mediated pathway in breast cancer cell lines (MCF‐7 and MDA‐MB‐231)

Solaimuthu

Mukherjee

Das

et al. 2017

Cell Biochemistry & Function

150

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Epidermal growth factor plays a major role in breast cancer cell proliferation, survival, and metastasis. Quercetin, a bioactive flavonoid, is shown to exhibit anticarcinogenic effects against various cancers including breast cancer. Hence, the present study was designed to evaluate the effects of gold nanoparticles-conjugated quercetin (AuNPs-Qu-5) in MCF-7 and MDA-MB-231 breast cancer cell lines. Borohydride reduced AuNPs were synthesized and conjugated with quercetin to yield AuNPs-Qu-5. Both were thoroughly characterized by several physicochemical techniques, and their cytotoxic effects were assessed by MTT assay. Apoptotic studies such as DAPI, AO/EtBr dual staining, and annexin V-FITC staining were performed. AuNPs and AuNPs-Qu-5 were spherical with crystalline nature, and the size of particles range from 3.0 to 4.5 nm. AuNPs-Qu-5 exhibited lower IC value compared to free Qu. There was a considerable increase in apoptotic population with increased nuclear condensation seen upon treatment with AuNPs-Qu-5. To delineate the molecular mechanism behind its apoptotic role, we analysed the proteins involved in apoptosis and epidermal growth factor receptor (EGFR)-mediated PI3K/Akt/GSK-3β signalling by immunoblotting and immunocytochemistry. The pro-apoptotic proteins (Bax, Caspase-3) were found to be up regulated and anti-apoptotic protein (Bcl-2) was down regulated on treatment with AuNPs-Qu-5. Additionally, AuNPs-Qu-5 treatment inhibited the EGFR and its downstream signalling molecules PI3K/Akt/mTOR/GSK-3β. In conclusion, administration of AuNPs-Qu-5 in breast cancer cell lines curtails cell proliferation through induction of apoptosis and also suppresses EGFR signalling. AuNPs-Qu-5 is more potent than free quercetin in causing cancer cell death, and hence, this could be a potential drug delivery system in breast cancer therapy.

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Preparation and Characterization of Quercetin and Rutin Cyclodextrin Inclusion Complexes

Cited by 84 publications

References 18 publications

Quercetin/β-Cyclodextrin Solid Complexes Prepared in Aqueous Solution Followed by Spray-drying or by Physical Mixture

Quercetin/β-Cyclodextrin Solid Complexes Prepared in Aqueous Solution Followed by Spray-drying or by Physical Mixture

Phytochemicals

Gold nanoparticles–conjugated quercetin induces apoptosis via inhibition of EGFR/PI3K/Akt–mediated pathway in breast cancer cell lines (MCF‐7 and MDA‐MB‐231)

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