Co-grinding Effect on Crystalline Zaltoprofen with β-cyclodextrin/Cucurbit[7]uril in Tablet Formulation

Li, Shanshan; Lin, Xiang; Xu, Kailin; He, Jiawei; Yang, Hongqin; Li, Hui

doi:10.1038/srep45984

Cited by 13 publications

(10 citation statements)

References 37 publications

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“…After the completion of the grinding process, the sample was formed into a pellet using a hydraulic press. The spectra were measured in the transmission mode. For the sample of the complex of βCD and the guest (compound Fc-1–Fc-5 or Ada-1 ): the grinding-induced liquid-assisted method was applied for the complex preparation. − To the mixture of 5.0 × 10 –3 mmol of the guest and 5.0 × 10 –3 mmol of βCD (complex stoichiometry 1:1), 5 μL of pure water was added, and the solid was intensively grinded for 25 min. At first, the mixture had a form of slurry, but after the grinding process, it became a dry solid.…”

Section: Methodsmentioning

confidence: 99%

Supramolecular Interactions between β-Cyclodextrin and the Nucleobase Derivatives of Ferrocene

Kasprzak

Koszytkowska‐Stawińska

Nowicka

et al. 2019

J. Org. Chem.

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Novel conjugates of ferrocene with uracil, 5-fluorouracil, tegafur, or acyclovir are reported. Their synthesis involved (i) the azide–alkyne 1,3-dipolar cycloaddition or (ii) the formation of the ester linkage. For the first time, we present an in-depth insight into the supramolecular interactions between β-cyclodextrin and ferrocene-nucleobase derivatives. Spectroscopic and voltammetric analyses performed within this work suggested that the ferrocene or adamantane unit of the conjugates interacted with the β-cyclodextrin’s inner cavity. The methods applied for the supramolecular studies included 1H–1H ROESY NMR, 1H NMR titration, Fourier-transform infrared spectroscopy, cyclic voltammetry, fluorescence spectra titration, and 1H DOSY NMR. 1H DOSY NMR was also employed to evaluate the apparent binding constants for all the complexes. The ferrocene–acyclovir conjugate Fc-5 featured the highest apparent binding constant value among all the complexes tested.

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Section: Methodsmentioning

confidence: 99%

Supramolecular Interactions between β-Cyclodextrin and the Nucleobase Derivatives of Ferrocene

Kasprzak

Koszytkowska‐Stawińska

Nowicka

et al. 2019

J. Org. Chem.

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“…The ZPF polymorph, Form I showed an aqueous solubility of 0.019 mg/mL and was found in agreement with the solubility of 0.018 mg/mL, reported earlier by Li and coworkers. 34 The ZPF polymorph, Form II shows a 3-fold increase in the solubility (0.060 mg/mL) compared to Form I. The polymorph solubility data also correlates with the computed lattice energy differences, i.e., the more stable polymorph (Form I) is less soluble than the metastable polymorph, Form II.…”

Section: ■ Results and Discussionmentioning

confidence: 72%

“…Li et al recently reported the crystal structure of the anhydrous crystalline form (Form I) of zaltoprofen. 34 They also studied the effect of cogrinding of ZPF with β-cyclodextrin and cucurbit [7]uril on its solubility, dissolution rates, and compressibility properties. Herein, we report a new metastable polymorph (Form II) and three new cocrystals of nonsteroidal anti-inflammatory drug zaltoprofen identified from the rational coformer screening approach.…”

Section: ■ Introductionmentioning

confidence: 99%

Computational Screening of Multicomponent Solid Forms of 2-Aryl-Propionate Class of NSAID, Zaltoprofen, and Their Experimental Validation

Dash

Thakur

2020

Crystal Growth & Design

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A rational coformer screening methodology was adopted to identify new multicomponent solid preformulations of the 2-aryl propionate class of nonsteroidal anti-inflammatory drugs. The coformer screening was performed using a modified molecular electrostatic potential based site−pair interaction energy computations used in conjunction with the free energy of cocrystal formation calculations to attain better predictability. The computational results were validated against the available experimental data and used for optimizing the cocrystal screening methodology for the drug zaltoprofen. A new polymorph and three new cocrystal forms of zaltoprofen were reported in the study, which exhibits up to four times enhancement in the drug solubility than that of the marketed form. We also report one new salt and two new cocrystals of (+)-ibuprofen, a drug from the same 2-aryl propionate family. In hindsight, we propose incorporating secondary heteromeric interactions formed by homo/heterodimer in the calculations of site−pair interaction energy differences for improving the predictability of the molecular electrostatic potential (MESP) based screening.

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“…Standard methods for obtaining API complexes with CDs in solid form can be quite laborious and time consuming. For example, cogrinding of APIs with CDs is usually carried out in high-energy mills for one hour or longer [55][56][57][58]. On the basis of the results reported in this work, it should be possible to use low-energy cogrinding, which is desirable due to the simplicity and reduced production time.…”

Section: Discussionmentioning

confidence: 90%

Caffeine-Cyclodextrin Complexes as Solids: Synthesis, Biological and Physicochemical Characterization

Szmeja

Gubica

Ostrowski

et al. 2021

IJMS

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Mechanochemical and in-solution synthesis of caffeine complexes with α-, β-, and γ-cyclodextrins was optimized. It was found that short-duration, low-energy cogrinding, and evaporation (instead of freeze-drying) are effective methods for the formation and isolation of these complexes. The products obtained, their pure components, and their mixtures were examined by powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), FT-IR and Raman spectroscopy. Moreover, molecular modeling provided an improved understanding of the association process between the guest and host molecules in these complexes. The complexes were found to exhibit high toxicity in zebrafish (Danio rerio) embryos, in contrast to pure caffeine and cyclodextrins at the same molar concentrations. HPLC measurements of the caffeine levels in zebrafish embryos showed that the observed cytotoxicity is not caused by an increased caffeine concentration in the body of the organism, as the concentrations are similar regardless of the administered caffeine form. Therefore, the observed high toxicity could be the result of the synergistic effect of caffeine and cyclodextrins.

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Co-grinding Effect on Crystalline Zaltoprofen with β-cyclodextrin/Cucurbit[7]uril in Tablet Formulation

Cited by 13 publications

References 37 publications

Supramolecular Interactions between β-Cyclodextrin and the Nucleobase Derivatives of Ferrocene

Supramolecular Interactions between β-Cyclodextrin and the Nucleobase Derivatives of Ferrocene

Computational Screening of Multicomponent Solid Forms of 2-Aryl-Propionate Class of NSAID, Zaltoprofen, and Their Experimental Validation

Caffeine-Cyclodextrin Complexes as Solids: Synthesis, Biological and Physicochemical Characterization

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