Inclusion Complexes of Daidzein with Cyclodextrin-Based Metal–Organic Framework-1 Enhance Its Solubility and Antioxidant Capacity

Inoue, Yutaka; Yoshida, Masaaki; Ezawa, Toshinari; Tanikawa, Takashi; Arce, F.; See, Gerard Lee; Tomita, Junki; Suzuki, Mitsuaki; Oguchi, Tamio

doi:10.1208/s12249-021-02151-2

Cited by 11 publications

(6 citation statements)

References 29 publications

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“…CDs also increase the antioxidant activity of other biologically active compounds. Daidzein–CD–metal organic framework solid dispersion complexes prepared by the solvent evaporation method increased daidzein DPPH scavenging activity ~1.3 times [ 67 ]. In another study, DPPH radical-scavenging activity test indicated that the caffeic acid complexes with α-CD and with β-CD obtained by the ground mixture method had greater antioxidant activity than caffeic acid; additionally, greater results were obtained for the complex with α-CD [ 68 ].…”

Section: Discussionmentioning

confidence: 99%

Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid

et al. 2022

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Rosmarinic acid (RA) is a natural antioxidant with neuroprotective properties; however, its preventive and therapeutic use is limited due to its slight solubility and poor permeability. This study aimed to improve RA physicochemical properties by systems formation with cyclodextrins (CDs): hydroxypropyl-α-CD (HP-α-CD), HP-β-CD, and HP-γ-CD, which were prepared by the solvent evaporation (s.e.) method. The interactions between components were determined by X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC) and Fourier Transform infrared spectroscopy (FTIR). The sites of interaction between RA and CDs were suggested as a result of in silico studies focused on assessing the interaction between molecules. The impact of amorphous systems formation on water solubility, dissolution rate, gastrointestinal (GIT) permeability, and biological activity was studied. RA solubility was increased from 5.869 mg/mL to 113.027 mg/mL, 179.840 mg/mL, and 194.354 mg/mL by systems formation with HP-α-CD, HP-β-CD, and HP-γ-CD, respectively. During apparent solubility studies, the systems provided an acceleration of RA dissolution. Poor RA GIT permeability at pH 4.5 and 5.8, determined by parallel artificial membrane permeability assay (PAMPA system), was increased; RA–HP-γ-CD s.e. indicated the greatest improvement (at pH 4.5 from Papp 6.901 × 10−7 cm/s to 1.085 × 10−6 cm/s and at pH 5.8 from 5.019 × 10−7 cm/s to 9.680 × 10−7 cm/s). Antioxidant activity, which was determined by DPPH, ABTS, CUPRAC, and FRAP methods, was ameliorated by systems; the greatest results were obtained for RA–HP-γ-CD s.e. The inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) was increased from 36.876% for AChE and 13.68% for BChE to a maximum inhibition of the enzyme (plateau), and enabled reaching IC50 values for both enzymes by all systems. CDs are efficient excipients for improving RA physicochemical and biological properties. HP-γ-CD was the greatest one with potential for future food or dietary supplement applications.

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Section: Discussionmentioning

confidence: 99%

Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid

et al. 2022

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“…1 H– 1 H NOESY NMR measurements were performed to investigate the detailed intramolecular interactions of FD (SAC/αCD), FD (SAC/βCD), and FD (SAC/γCD) in solution (Figures – ). The 1 H– 1 H NOESY NMR measurement was used to infer the relative position of the inclusion complex because it can confirm the interaction between the guest molecule and the CD cavity . In FD (SAC/αCD), a cross peak was confirmed between the peak Hc (2.90 ppm) derived from the alkyl group (H) of SAC and the peak H-6 (3.75 ppm) derived from αCD (Figure b).…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H− 1 H NOESY NMR measurement was used to infer the relative position of the inclusion complex because it can confirm the interaction between the guest molecule and the CD cavity. 24 In FD (SAC/αCD), a cross peak was confirmed between the peak Hc (2.90 ppm) derived from the alkyl group (H) of SAC and the peak H-6 (3.75 ppm) derived from αCD (Figure 10b). Furthermore, a cross peak was confirmed between Ha (5.06 ppm) and Hb (5.69 ppm) of SAC and H-3 (3.81 ppm) and H-5 (3.66 ppm) derived from αCD (Figure 10c).…”

Section: Determination Of Inclusion Molar Ratio Between Sac and α β γ...mentioning

confidence: 88%

Preparation, Characterization, and In Vitro Evaluation of Inclusion Complexes Formed between S-Allylcysteine and Cyclodextrins

et al. 2022

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The present study prepared inclusion complexes of S -allylcysteine (SAC) and cyclodextrin (α, β, γ) by the freeze-drying (FD) method and verified the inclusion behavior of the solid dispersion. Also, the study investigated the effect of SAC/CD complex formation on liver tumor cells. Isothermal titration calorimetry (ITC) measurements confirmed the exothermic titration curve for SAC/αCD, suggesting a molar ratio of SAC/αCD = 1/1, but no exothermic/endothermic reaction was obtained for the SAC/βCD and SAC/γCD system. Powder X-ray diffraction (PXRD) results showed that the characteristic diffraction peaks of SAC and CDs disappeared in FD (SAC/αCD) and FD (SAC/γCD), indicated by a halo pattern. On the other hand, diffraction peaks originating from SAC and βCDs were observed in FD (SAC/βCD). Near-infrared (NIR) absorption spectroscopy results showed that CH and OH groups derived from SAC and OH groups derived from αCD and γCD cavity were shifted, suggesting complex formation due to intermolecular interactions occurring in SAC/αCD and SAC/γCD. Stability test results showed that the stability was maintained with FD (SAC/αCD) over FD (SAC/βCD) and FD (SAC/γCD). In 1 H– 1 H of NOESY NMR measurement, FD (SAC/αCD) was confirmed to have a cross peak at the CH group of the alkene of SAC and the proton (H-3, -5, -6) in the αCD cavity. In FD (SAC/γCD), a cross peak was confirmed at the alkyl group on the carbonyl group side of SAC and the proton (H-3) in the cavity of γCD. From the above, it was suggested that the inclusion mode of SAC is different on FD (SAC/CDs). The results of the hepatocyte proliferation inhibition test using HepG2 cells showed that FD (SAC/βCD) inhibited cell proliferation. On the other hand, FD (SAC/αCD) and FD (SAC/γCD) did not show a significant decrease in the number of viable cells. These results suggest that the difference in the inclusion mode may contribute to the stability and cell proliferation inhibition.

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“…Numerous pharmacological effects of DAI include anti-carcinogenesis [ 42 ], anti-inflammatory [ 43 ], antioxidant [ 44 ], anti-diabetic [ 45 ], cholesterol-lowering [ 46 ], and cardiovascular activity [ 47 , 48 ].…”

Section: Mechanism Of Action and Pharmacological Applications Of Daid...mentioning

confidence: 99%

Unveiling the Pharmacological and Nanotechnological Facets of Daidzein: Present State-of-the-Art and Future Perspectives

et al. 2023

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Herbal drugs have been attracting much scientific interest in the last few decades and nowadays, phytoconstituents-based research is in progress to disclose their unidentified medicinal potential. Daidzein (DAI) is the natural phytoestrogen isoflavone derived primarily from leguminous plants, such as the soybean and mung bean, and its IUPAC name is 4′,7-dihydroxyisoflavone. This compound has received great attention as a fascinating pharmacophore with remarkable potential for the therapeutic management of several diseases. Certain pharmacokinetic properties of DAI such as less aqueous solubility, low permeability, and poor bioavailability are major obstacles restricting the therapeutic applications. In this review, distinctive physicochemical characteristics and pharmacokinetics of DAI has been elucidated. The pharmacological applications in treatment of several disorders like oxidative stress, cancer, obesity, cardiovascular, neuroprotective, diabetes, ovariectomy, anxiety, and inflammation with their mechanism of action are explained. Furthermore, this review article comprehensively focuses to provide up-to-date information about nanotechnology-based formulations which have been investigated for DAI in preceding years which includes polymeric nanoparticles, solid lipid nanoparticles, nanostructured lipid carrier, polymer-lipid nanoparticles, nanocomplexes, polymeric micelles, nanoemulsion, nanosuspension, liposomes, and self-microemulsifying drug delivery systems.

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Inclusion Complexes of Daidzein with Cyclodextrin-Based Metal–Organic Framework-1 Enhance Its Solubility and Antioxidant Capacity

Cited by 11 publications

References 29 publications

Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid

Cyclodextrin Derivatives as Promising Solubilizers to Enhance the Biological Activity of Rosmarinic Acid

Preparation, Characterization, and In Vitro Evaluation of Inclusion Complexes Formed between S-Allylcysteine and Cyclodextrins

Unveiling the Pharmacological and Nanotechnological Facets of Daidzein: Present State-of-the-Art and Future Perspectives

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