Inclusion Mechanism and Heat Stability of the Complex of 4'-Hydroxychalcone and Hydroxypropyl-&amp;#946;-Cyclodextrin

Guo, Yancheng; Chen, Yuzhen; Ma, Haile

doi:10.4314/tjpr.v13i12.3

Cited by 6 publications

(3 citation statements)

References 10 publications

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“…The TG/DSC analysis was conducted for each sample with a Q600 TG/DSC system (TA Instruments, USA) according to a previous method [12]. And the operation conditions were as following: dynamic atmosphere of nitrogen (99.999 %) at 100 mL/min and heating rate of 20 °C /min from 50 to 500 °C, with sample mass of about 10 mg.…”

Section: Thermogravimetric/differential Scanning Calorimetry Measuremmentioning

confidence: 99%

Preparation and Characterization of a Complex of Paeonol and Hydroxypropyl-β-cyclodextrin

Chen¹,

Xu²,

Li³

et al. 2015

Trop. J. Pharm Res

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Purpose: To improve the solubility of paeonol in water by complexing with hydroxypropyl-β-cyclodextrin (HP-β-CD) and also to characterize the physicochemical properties of the complex.Methods: The complex of paeonol and HP-β-CD was prepared by freeze-drying method. Its physicochemical properties were studied by phase-solubility method, ultraviolet-visible spectrometry (UV), infrared spectrometry (IR), scanning electron microscopy (SEM), x-ray diffractometry (XRD) and thermogravimetric/differential scanning calorimetry (TG/DSC).Results: The phase-solubility results showed that paeonol formed a 1:1 stoichiometric complex with HP-β-CD while UV and IR spectra suggested that HP-β-CD and paeonol in the complex interacted by a non-covalent bond. SEM and XRD indicate that the heat stability of paeonol was significantly improved by complexing with HP-β-CD.Conclusion: Paeonol can be efficiently complexed with HP-β-CD to form a complex by freeze-drying method. The aqueous solubility and heat stability of paeonol is significantly improved by complexation HP-β-CD.Keywords: Paeonol, Hydroxypropyl-β-cyclodextrin, Complexation, Aqueous solubility, Heat stability

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Section: Thermogravimetric/differential Scanning Calorimetry Measuremmentioning

confidence: 99%

Preparation and Characterization of a Complex of Paeonol and Hydroxypropyl-β-cyclodextrin

Chen¹,

Xu²,

Li³

et al. 2015

Trop. J. Pharm Res

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“…3), K s can be determined as 22 M −1 , which is low but still in normal range reported for β-CDs (10 1 and 10 5 • M −1 ) [24]. A common method for the identification of complexes of drugs and CDs is DSC [25][26][27]. The melting, boiling, or sublimation point of a complexed substance shifts or disappears, lacking a separate consistent solid phase [28].…”

Section: Resultsmentioning

confidence: 82%

Development and Characterization of the Neuroregenerative Xanthohumol C/Hydroxypropyl-β-cyclodextrin Complex Suitable for Parenteral Administration

et al. 2019

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The chroman-like chalcone Xanthohumol C, originally found in hops, was demonstrated to be a potent neuroregenerative and neuroprotective natural product and therefore constitutes a strong candidate for further pharmaceutical research. The bottleneck for in vivo experiments is the low water solubility of this chalcone. Consequently, we developed and validated a suitable formulation enabling in vivo administration. Cyclodextrins were used as water-soluble and nontoxic complexing agents, and the complex of Xanthohumol C and 2-hydroxypropyl-β-cyclodextrin was characterized using HPLC, HPLC-MS, NMR, and differential scanning calorimetry. The water solubility of Xanthohumol C increases with increasing concentrations of cyclodextrin. Using 50 mM 2-hydroxypropyl-β-cyclodextrin, solubility was increased 650-fold. Furthermore, in vitro bioactivity of Xanthohumol C in free and complexed form did not significantly differ, suggesting the release of Xanthohumol C from 2-hydroxypropyl-β-cyclodextrin. Finally, a small-scaled in vivo experiment in a rat model showed that after i. p. administration of the complex, Xanthohumol C can be detected in serum, the brain, and the cerebrospinal fluid at 1 and 6 h post-administration. Mean (± SD) Xanthohumol C serum concentrations after 1, 6, and 12 h were determined as 463.5 (± 120.9), 61.9 (± 13.4), and 9.3 (± 0.8) ng/mL upon i. v., and 294.3 (± 22.4), 45.5 (± 0.7), and 13 (± 1.0) ng/mL after i. p. application, respectively. Accordingly, the formulation of Xanthohumol C/2-hydroxypropyl-β-cyclodextrin is suitable for further in vivo experiments and further pharmaceutical research aiming for the determination of its neuroregenerative potential in animal disease models.

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“…The title compound has an s-cis conformation with electron conjugation between the central chain and the attached rings as can be seen in Figure 1A. Classical and recent methods were used in the synthesis of 1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one, including the use of different heteropolyacid catalysts and water as a green solvent [11,12]. Like many other types of chalcones, 1-(4-Hydroxyphenyl)-3-phenylprop-2en-1-one has been integrated as starting materials in the synthesis of a set of heterocyclic compounds such as quinolinones, isoxazoles, thiadiazines, and benzofuranones [13,14].…”

Section: Introductionmentioning

confidence: 99%

Density Functional Theory and Molecular Docking Investigations of the Chemical and Antibacterial Activities for 1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one

et al. 2021

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The present investigation informs a descriptive study of 1-(4-Hydroxyphenyl) -3-phenylprop-2-en-1-one compound, by using density functional theory at B3LYP method with 6-311G** basis set. The oxygen atoms and π-system revealed a high chemical reactivity for the title compound as electron donor spots and active sites for an electrophilic attack. Quantum chemical parameters such as hardness (η), softness (S), electronegativity (χ), and electrophilicity (ω) were yielded as descriptors for the molecule’s chemical behavior. The optimized molecular structure was obtained, and the experimental data were matched with geometrical analysis values describing the molecule’s stable structure. The computed FT-IR and Raman vibrational frequencies were in good agreement with those observed experimentally. In a molecular docking study, the inhibitory potential of the studied molecule was evaluated against the penicillin-binding proteins of Staphylococcus aureus bacteria. The carbonyl group in the molecule was shown to play a significant role in antibacterial activity, four bonds were formed by the carbonyl group with the key protein of the bacteria (three favorable hydrogen bonds plus one van der Waals bond) out of six interactions. The strong antibacterial activity was also indicated by the calculated high binding energy (−7.40 kcal/mol).

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Inclusion Mechanism and Heat Stability of the Complex of 4'-Hydroxychalcone and Hydroxypropyl-β-Cyclodextrin

Cited by 6 publications

References 10 publications

Preparation and Characterization of a Complex of Paeonol and Hydroxypropyl-β-cyclodextrin

Preparation and Characterization of a Complex of Paeonol and Hydroxypropyl-β-cyclodextrin

Development and Characterization of the Neuroregenerative Xanthohumol C/Hydroxypropyl-β-cyclodextrin Complex Suitable for Parenteral Administration

Density Functional Theory and Molecular Docking Investigations of the Chemical and Antibacterial Activities for 1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one

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