Drug–Drug Cocrystallization Simultaneously Improves Pharmaceutical Properties of Genistein and Ligustrazine

Li, Xuejiao; Liu, Xinna; Song, Jian; Wang, Chenguang; Li, Jinhui; Liu, Lianchao; He, Xin; Zhao, Xinghua; Sun, Changquan Calvin

doi:10.1021/acs.cgd.1c00229

Cited by 19 publications

(15 citation statements)

References 47 publications

(69 reference statements)

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“…In addition, the results of TG (Figure 7) indicated that the first weight loss of 24.7% from 160 to 254 • C was reckoned as the loss of the PPZ molecule, whose theoretical weight percentage was 25.3%. To our knowledge, PPZ has a low boiling point of about 146.0 • C. Based on this evidence, it could be predicted that the cocrystal decomposed at 235.47 • C, and PPZ was sublimated with the elevation of temperature, whose phenomenon was similar to the thermodynamic characteristics of solvent compounds and reported in previous studies [25,31,32]. Additionally, it could be found that there was no mass loss to be observed in the test temperature range below the melting point of the DAI-PPZ cocrystal, which indicated that the cocrystal of DAI-PPZ did not contain water or solvents.…”

Section: Thermal Analysissupporting

confidence: 81%

A Novel Cocrystal of Daidzein with Piperazine to Optimize the Solubility, Permeability and Bioavailability of Daidzein

Wang,

Li,

et al. 2024

Molecules

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It is well known that daidzein has various significant medicinal values and health benefits, such as anti-oxidant, anti-inflammatory, anti-cancer, anti-diabetic, cholesterol lowering, neuroprotective, cardioprotective and so on. To our disappointment, poor solubility, low permeability and inferior bioavailability seriously limit its clinical application and market development. To optimize the solubility, permeability and bioavailability of daidzein, the cocrystal of daidzein and piperazine was prepared through a scientific and reasonable design, which was thoroughly characterized by single-crystal X-ray diffraction, powder X-ray diffraction, Fourier transform infrared spectroscopy, differential scanning calorimetry and thermogravimetric analysis. Combining single-crystal X-ray diffraction analysis with theoretical calculation, detailed structural information on the cocrystal was clarified and validated. In addition, a series of evaluations on the pharmacogenetic properties of the cocrystal were investigated. The results indicated that the cocrystal of daidzein and piperazine possessed the favorable stability, increased solubility, improved permeability and optimized bioavailability of daidzein. Compared with the parent drug, the formation of cocrystal, respectively, resulted in 3.9-, 3.1-, 4.9- and 60.8-fold enhancement in the solubility in four different media, 4.8-fold elevation in the permeability and 3.2-fold in the bioavailability of daidzein. Targeting the pharmaceutical defects of daidzein, the surprising elevation in the solubility, permeability and bioavailability of daidzein was realized by a clever cocrystal strategy, which not only devoted assistance to the market development and clinical application of daidzein but also paved a new path to address the drug-forming defects of insoluble drugs.

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Section: Thermal Analysissupporting

confidence: 81%

A Novel Cocrystal of Daidzein with Piperazine to Optimize the Solubility, Permeability and Bioavailability of Daidzein

Wang,

Li,

et al. 2024

Molecules

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“…The melting points ( T m s) of PFD, HES, and GEN are 109.6, 231.3, and 306.2 °C, respectively, which are all consistent with the reported data. 18,31,32 For the two cocrystal samples, the endothermic melting signals appear at 116.4 and 137.8 °C, respectively. TGA curves of PFD and the two cocrystals are given in Fig.…”

Section: Resultsmentioning

confidence: 99%

Pirfenidone–flavonoid cocrystals with reduced solubility and dissolution rate

Meng¹,

Li²,

Zhu³

et al. 2023

CrystEngComm

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“…The weight loss is very close to the BIP weight percentage in the NITRO–BIP cocrystal (24.7%), but the melting point of pure BIP is very low (about 70 °C), so, at 196.5 °C, its evaporation process should be considered completed. Nevertheless, it is well-known that cocrystallization can significantly affect the thermal stability of the coformer characterized by the higher volatility . Thus, it can be assumed that the first endo event, at 196.5 °C, is associated with the dissociation and release of BIP.…”

Section: Resultsmentioning

confidence: 99%

“…Nevertheless, it is wellknown that cocrystallization can significantly affect the thermal stability of the coformer characterized by the higher volatility. 58 Thus, it can be assumed that the first endo event, at 196.5 °C, is associated with the dissociation and release of BIP. The second weight loss step at 269.9 °C appears very near that of pure NITRO (272.9 °C), suggesting the sample was predominantly NITRO after the loss of BIP.…”

Section: Methodsmentioning

confidence: 99%

Cocrystals of Nitrofurantoin: How Coformers Can Modify Its Solubility and Permeability Across Intestinal Cell Monolayers

Segalina

Pavan

Ferretti

et al. 2022

Crystal Growth & Design

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Solubility and permeability of nitrofurantoin (NITRO) were compared with those of its cocrystals containing isoniazid (ISO), bipyridyl (BIP), or phenanthroline (PHE) as coformers, and their parent mixtures. NITRO dissolution profiles were evaluated via HPLC; we resorted to molecular dynamics (MD) simulations to rationalize the experimental data on the basis of nitrofurantoin−coformers and nitrofurantoin−water intermolecular interactions. Permeation studies were performed by using an in vitro model of the small intestine based on IEC-6 cells. The NITRO water solubility was reduced by its mixture with PHE and BIP but not with ISO. Cocrystallization with BIP induced a slight increase of NITRO solubility; cocrystallization with PHE induced its solubility decrease, even if lower than the physical mixture. The solubility changes were attributed to NITRO solvation shell alterations (MD simulations). Cocrystallization with ISO allowed an increase of the NITRO solubility in the first 30 min of the dissolution pattern. Permeation measurements showed that the NITRO− PHE mixture was detrimental for the monolayer integrity, whereas no alterations were induced by the cocrystal. No effects on NITRO permeability and monolayer integrity were observed either for NITRO−ISO or for NITRO−BIP mixtures. The NITRO− ISO cocrystal increased the NITRO permeability across the monolayer without reducing its integrity.

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Drug–Drug Cocrystallization Simultaneously Improves Pharmaceutical Properties of Genistein and Ligustrazine

Cited by 19 publications

References 47 publications

A Novel Cocrystal of Daidzein with Piperazine to Optimize the Solubility, Permeability and Bioavailability of Daidzein

A Novel Cocrystal of Daidzein with Piperazine to Optimize the Solubility, Permeability and Bioavailability of Daidzein

Pirfenidone–flavonoid cocrystals with reduced solubility and dissolution rate

Cocrystals of Nitrofurantoin: How Coformers Can Modify Its Solubility and Permeability Across Intestinal Cell Monolayers

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