First cocrystal of esculetin: Simultaneously optimized in vitro/vivo properties and antioxidant effect

Liu, Fang; Li, Jinyang; Han, Chao; Wang, Jun‐Hao; Tong, Shuo; Wang, Xuekun; Li, Yan‐Tuan; Sun, Wenjun

doi:10.1016/j.ejps.2023.106469

Cited by 3 publications

(6 citation statements)

References 40 publications

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“…However, at present, there are very few studies on the solubility of esculetin, and only some studies have mentioned information about the solubility of esculetin. Moon pointed out that due to the low solubility of fishskin in water and ethanol, coupled with extensive phase II metabolism, esculetin is rapidly eliminated from the human body, thus affecting the medicinal value of esculetin; Zuo mentioned that esculetin’s poor water solubility may limit its therapeutic effect; Liu found that the low esculetin solubility, which resulted in low oral absorption and bioavailability, prevents the antioxidant activity of esculetin from fully releasing in vivo, thereby hampering its clinical application.…”

Section: Introductionmentioning

confidence: 99%

“…9 However, at present, there are very few studies on the solubility of esculetin, and only some studies have mentioned information about the solubility of esculetin. Moon out that due to the low solubility of fishskin in water and ethanol, coupled with extensive phase II metabolism, esculetin is rapidly eliminated from the human body, thus affecting the medicinal value of esculetin; Zuo 11 mentioned that esculetin's poor water solubility may limit its therapeutic effect; Liu 12 found that the low esculetin solubility, which resulted in low oral absorption and bioavailability, prevents the antioxidant activity of esculetin from fully releasing in vivo, thereby hampering its clinical application. According to the above research, it is clear that esculetin has been widely used; it proves efficacious not only in addressing intestinal disorders, protecting the liver, easing mucus-related problems and asthma, and showcasing antioxidant, antibacterial, and anti-inflammatory attributes but also exhibits effectiveness in diverse medical conditions.…”

Section: Introductionmentioning

confidence: 99%

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Solubility Determination and Thermodynamic Model Analysis of Esculetin in Different Solvents from 273.15 to 318.15 K

Yang,

Yan,

Huang

et al. 2024

J. Chem. Eng. Data

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Esculetin is derived from the leaves of lemons of Rutaceae and the bark of bittersweet ash, belladonna, mandala, and Rehmannia plants. In this research, the solubility of esculetin in ten solvents such as ethyl acetate, isobutyl alcohol, water, methanol, acetonitrile, n-propyl alcohol, isopropyl alcohol, n-butanol, ethanol, and acetone was determined by utilizing static equilibrium-high performance liquid chromatography (HPLC) under standard atmospheric pressure conditions and temperatures in the range of 273.15 to 318.15 K. Among the above ten pure solvents, water displayed the least solubility, while methanol exhibited the highest solubility. At the same temperature (T = 273.15 ∼ 318.15 K), the solubility of esculetin increased with the increase of the molar ratio of soluble solvents. Similarly, when the temperature increases (T = 273.15 ∼ 318.15 K), the solubility of the three binary solvents increases under the condition of a constant molar ratio. The above results suggest that the main factor affecting the solubility of esculetin in the solvent may be the polarization/bipolarity of the solvent. The experimental data was fitted by five thermodynamic models (the Buchowski−Ksiazaczak λh model, the Modified Apelblat model, the Jouyban−Acree model, the SUN model, and the CNIBS/R-K model), and the relative average deviation and root-mean-square deviation of the data were calculated, which proved that the correlation of the solubility data and the five models was relatively good. XRD and DSC were used to detect the crystal form and stability of esculetin during the experiment.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solubility Determination and Thermodynamic Model Analysis of Esculetin in Different Solvents from 273.15 to 318.15 K

Yang,

Yan,

Huang

et al. 2024

J. Chem. Eng. Data

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“…[1][2][3][4] A cocrystal is composed of two or more molecules present in the same crystalline lattice, principally via hydrogen-bond interactions under ambient conditions. [1][2][3][4] The formation of cocrystals using an active pharmaceutical ingredient (API) with inactive substances (called coformer), such as inactive drug molecules or solubilizing agents, can provide better pharmaceutical properties for the API and allow for the design of drug delivery systems. [5,6] Cocrystals have been increasingly recognized as an attractive alternative for solid forms of drug products.…”

Section: Introductionmentioning

confidence: 99%

“…Nowadays, the preparation of cocrystal compounds has significantly become a modern research field for the production of new shapes of pharmaceutically active compounds. [1][2][3][4] A cocrystal is composed of two or more molecules present in the same crystalline lattice, principally via hydrogen-bond interactions under ambient conditions. [1][2][3][4] The formation of cocrystals using an active pharmaceutical ingredient (API) with inactive substances (called coformer), such as inactive drug molecules or solubilizing agents, can provide better pharmaceutical properties for the API and allow for the design of drug delivery systems.…”

Section: Introductionmentioning

confidence: 99%

X‐Ray Crystallography and Antimicrobial Activity of Synthetic Cyanoguanidinophenytoin Cocrystals

Mabied,

Moustafa,

Abdelhamid

et al. 2024

ChemistrySelect

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A novel series of 1 : 1 cocrystals of 2‐cyanoguanidinophenytoin (CNG‐DPH) with primary, secondary, and tertiary aliphatic amines has been presented through this work. The antimicrobial activities of all new CNG‐DPH‐amine cocrystals were studied. The existence of cocrystals has been proven through crystal structure results. The 5‐Oxo‐4,4‐diphenylimidazolidin‐2‐ylidenecyanamide‐piperidine cocrystal (10) is located in an orthorhombic crystal system, and the cocrystal is connected via the N−H−N hydrogen bond between the cyanide group and the piperidine molecule. Hirshfeld surface analysis authenticated supramolecular contacts. Ring puckering analysis revealed a chair stereochemistry at the 6‐membered piperidine. The crystal packing has been stabilized through intermolecular forces, hydrogen bonds, and interactions within the gravity center of rings (Cg). The antimicrobial activities of the newly synthesized compounds were only effective against Gram‐positive bacteria, demonstrating that the antibacterial spectrum of these compounds was restricted. In vitro cytotoxicity of the synthesized cocrystals was assessed in normal cells, giving the highest half‐maximal inhibitory concentration (IC50) ratio (637.63 μg/ml) and the lowest value (181.98 μg/ml).

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“…5,8 Cocrystallization is an effective strategy for modifying the physicochemical properties of such natural medicines. 2,5,9 Cocrystallization is highly complex and can be influenced by various factors, such as weak intermolecular interactions and spatial site-barrier effects. 3,10 Currently, the prevailing view suggests that cocrystal formation depends on the development of weak intermolecular interactions between the active pharmaceutical ingredient (API) and the cocrystal forming factor (CCF).…”

Section: Introductionmentioning

confidence: 99%

Uncovering Cocrystal Formation and Competition Mechanism of Polyhydroxy Natural Products: Cases of Quercetin, Hesperidin, Resveratrol, and Curcumin

Li,

Chen,

Zhou

et al. 2024

Crystal Growth & Design

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Understanding drug cocrystal formation and its competitive mechanism is important for improving the physicochemical properties of drugs. In this article, the cocrystal formation of polyhydroxy natural products and their competitive mechanisms are discussed through experimental screening and theoretical calculations. The formation conditions and types of cocrystals were determined based on efficient screening experiments of polyhydroxy natural product cocrystals. To investigate the difficulty and stability of cocrystal formation, competitive cocrystal experiments of polyhydroxy natural products were carried out simultaneously. By simulation of the electrostatic potential surface of molecules and the Hirshfeld surface of crystals, the mode of hydrogen bonding within the crystals was determined. The strength of hydrogen bonding was assessed based on the intermolecular interactions and energy framework within the crystal structure. A “substitution model” was constructed based on experimental results and theoretical calculations, which is of great significance for the prediction and design of natural product cocrystals and provides a feasible solution for improving the physicochemical properties of drugs.

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First cocrystal of esculetin: Simultaneously optimized in vitro/vivo properties and antioxidant effect

Cited by 3 publications

References 40 publications

Solubility Determination and Thermodynamic Model Analysis of Esculetin in Different Solvents from 273.15 to 318.15 K

Solubility Determination and Thermodynamic Model Analysis of Esculetin in Different Solvents from 273.15 to 318.15 K

X‐Ray Crystallography and Antimicrobial Activity of Synthetic Cyanoguanidinophenytoin Cocrystals

Uncovering Cocrystal Formation and Competition Mechanism of Polyhydroxy Natural Products: Cases of Quercetin, Hesperidin, Resveratrol, and Curcumin

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