Inclusion complexes of quercetin with three β-cyclodextrins derivatives at physiological pH: Spectroscopic study and antioxidant activity

Liu, Min; Dong, Lijie; Chen, Aiju; Zheng, Yan; Sun, Dezhi; Wang, Xu; Wang, Bingquan

doi:10.1016/j.saa.2013.07.008

Cited by 64 publications

(38 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The significant downfield shifts were observed for 17-20 carbons of the ω-chain as the α-CD concentration increased. In addition, as shown in Table 2(B), the shift changes of the ω-chain (C18, 19,20) in the binary PGF 2α /α-CD system were similar to those in the ternary PGF 2α /α-CD/β-CD system. This suggests that α-CD interacts preferentially with the ω-chain and the pre-existing β-CD does not significantly interfere with the interaction of α-CD with the ω-chain.…”

supporting

confidence: 58%

“…5A). When α-CD was added, the additional correlation peaks ap- peared between the ω-chain protons (H17, 18,19,20) of PGF 2α and the H3′ and H5′ protons of α-CD (Fig. 5B).…”

mentioning

confidence: 96%

“…Many studies of CD inclusion complex formations have been conducted to improve physicochemical properties of drugs, such as poor water solubility, [7][8][9][10] degradation upon heating [11][12][13][14][15] or by light irradiation, [16][17][18][19] and oxidation. 20) However, most of these studies have examined the effect of a single type of CD. Only a few reports focus on the effect of two types of CDs.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Formation of the Ternary Inclusion Complex of Limaprost with α- and β-Cyclodextrins in Aqueous Solution

Inoue

Sekiya

Yamamoto

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

The inclusion mode of Limaprost in the presence of α-and β-cyclodextrins (CDs) was investigated to gain insight into the stabilization mechanism of Limaprost-alfadex upon the addition of β-CD in the solid state. The inclusion sites of α-and β-CDs were studied by NMR spectroscopic and kinetic methods. With the addition of α-and β-CDs, displacements in 13 C chemical shifts of prostaglandin F 2α (PGF 2α ) were observed in the ω-chain and the five-membered ring, respectively, of the drug. Similar shift changes were observed with the addition of both α-and β-CDs. In two-dimensional (2D) 1 H-NMR spectra, intermolecular correlation peaks were observed between protons of PGF 2α and protons of both α-and β-CDs, suggesting that PGF 2α interacts with α-and β-CDs to form a ternary complex by including the ω-chain with the former CD and the five-membered ring with the latter. In kinetic studies in aqueous solution, Limaprost was degraded to 17S,20-dimethyl-trans-Δ 2 -PGA 1 (11-deoxy-Δ 10 ) and 17S,20-dimethyl-trans-Δ 2 -8-iso-PGE 1 (8-iso). The addition of α-CD promoted the dehydration to 11-deoxy-Δ 10 , while β-CD promoted the isomerization to 8-iso, under these conditions. In the presence of both α-and β-CDs, dehydration and isomerization were also accelerated, supporting the formation of the ternary Limaprost/α-CD/β-CD complex.Key words Limaprost alfadex; α-cyclodextrin; β-cyclodextrin; ternary inclusion complex; NMR spectroscopy; kinetics α-, β-and γ-Cyclodextrins (CDs) are cyclic oligosaccharides in which six, seven and eight D-glucose units, respectively, are linked by α-1,4 glycosidic bonds.

show abstract

supporting

confidence: 58%

“…5A). When α-CD was added, the additional correlation peaks ap- peared between the ω-chain protons (H17, 18,19,20) of PGF 2α and the H3′ and H5′ protons of α-CD (Fig. 5B).…”

mentioning

confidence: 96%

mentioning

confidence: 99%

See 1 more Smart Citation

Formation of the Ternary Inclusion Complex of Limaprost with α- and β-Cyclodextrins in Aqueous Solution

Inoue

Sekiya

Yamamoto

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…The antioxidant activity was measured by the scavenging of the stable free-radical DPPH, which showed a characteristic absorbance peak at 517 nm in ethanol. The addition of an antioxidant resulted in a decrease in the absorbance proportional to the concentration and antioxidant activity of the compound itself [ 40 , 41 ].…”

Section: Methodsmentioning

confidence: 99%

Studies on the Inclusion Complexes of Daidzein with β-Cyclodextrin and Derivatives

Chen

et al. 2017

Molecules

View full text Add to dashboard Cite

The inclusion complexes between daidzein and three cyclodextrins (CDs), namely β-cyclodextrin (β-CD), methyl-β-cyclodextrin (Me-β-CD, DS = 12.5) and (2-hydroxy)propyl-β-cyclodextrin (HP-β-CD, DS = 4.2) were prepared. The effects of the inclusion behavior of daidzein with three kinds of cyclodextrins were investigated in both solution and solid state by methods of phase-solubility, XRD, DSC, SEM, 1H-NMR and 2D ROESY methods. Furthermore, the antioxidant activities of daidzein and daidzein-CDs inclusion complexes were determined by the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) method. The results showed that daidzein formed a 1:1 stoichiometric inclusion complex with β-CD, Me-β-CD and HP-β-CD. The results also showed that the solubility of daidzein was improved after encapsulating by CDs. 1H-NMR and 2D ROESY analyses show that the B ring of daidzein was the part of the molecule that was most likely inserted into the cavity of CDs, thus forming an inclusion complex. Antioxidant activity studies showed that the antioxidant performance of the inclusion complexes was enhanced in comparison to the native daidzein. It could be a potentially promising way to develop a new formulation of daidzein for herbal medicine or healthcare products.

show abstract

“…and the complex is formed through a dimensional fit between the host cavity and the guest drug. 6 The host-guest binding mode of the complex was proposed using solid and liquid high-resolution NMR spectroscopy. 21 To overcome these limitations, we synthesized mono-6-deoxy-6-aminoethylamino-β-cyclodextrin (Et-β-CD), and utilized it as the solubilization agent for the hardly soluble flavonoid QUE.…”

Section: Introductionmentioning

confidence: 99%

Enhancement of Solubility and Bioavailability of Quercetin by Inclusion Complexation with the Cavity of Mono‐6‐deoxy‐6‐aminoethylamino‐β‐cyclodextrin

Park

Choi

Cho

et al. 2017

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

Quercetin (QUE) has a wide range of health benefits; however, its application is limited due to its low solubility. We synthesized mono-6-deoxy-6-aminoethylamino-β-cyclodextrin (Et-β-CD) to overcome this limitation. The solubility of QUE was increased 35.1-fold compared with QUE, by its complexation with Et-β-CD. Changes in physicochemical properties following successful complexation were investigated using field emission scanning electron microscope, differential scanning calorimetry, and Fourier transform infrared spectroscopy. The complexation behavior of QUE and Et-β-CD in aqueous solution was monitored by 1 H nuclear magnetic resonance (NMR), 2D rotating frame nuclear overhauser, and diffusion-ordered spectroscopy. The molecular docking simulation showed that the oblong shaped QUE is suitable for the formation of a stable complex with a characteristic cavity of Et-β-CD. Furthermore, the antioxidant activity and photostability of QUE was also improved after its complexation with Et-β-CD. From these results, we suggest that the characteristic elliptical cavity of Et-β-CD can be utilized for other hardly soluble drug molecules, which can expand the development of drug delivery systems.

show abstract

Inclusion complexes of quercetin with three β-cyclodextrins derivatives at physiological pH: Spectroscopic study and antioxidant activity

Cited by 64 publications

References 36 publications

Formation of the Ternary Inclusion Complex of Limaprost with α- and β-Cyclodextrins in Aqueous Solution

Formation of the Ternary Inclusion Complex of Limaprost with α- and β-Cyclodextrins in Aqueous Solution

Studies on the Inclusion Complexes of Daidzein with β-Cyclodextrin and Derivatives

Enhancement of Solubility and Bioavailability of Quercetin by Inclusion Complexation with the Cavity of Mono‐6‐deoxy‐6‐aminoethylamino‐β‐cyclodextrin

Contact Info

Product

Resources

About