Gelation switch of polyamorphic indomethacin depending on the thermal procedure

Shen, Pei; Zhang, Chunfeng; Hu, Enshi; Pang, Zunting; Gao, Yuan; Qian, Shuai; Zhang, Jianjun; Wei, Yuanfeng; Heng, Weili

doi:10.1016/j.ejpb.2022.07.008

Cited by 6 publications

(4 citation statements)

References 35 publications

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“…As illustrated in Figure S2a, all RDF plots exhibited peaks at 1.7–2.1 Å, suggesting the formation of hydrogen bond interactions between these sites [ i.e. , (HON)–H33···O2–(HON), (HON)–H34···O1–(HON), and (HON)–H33/H34···O1–(Men)] in the HON–Men system. , Nevertheless, the peak intensities of HON–Men interactions (10.2–11.5) were much greater than those of pure components (HON–HON: 4.5–4.7), suggesting that the HON molecules mainly interacted with Men through hydrogen bonds in the binary mixtures. , These molecular cluster units were further self-associated through homoassociated and heteroassociated interactions to form extensive hydrogen bonding networks and large clusters …”

Section: Resultsmentioning

confidence: 99%

Structural Self-Destruction of Deep Eutectic Solvents Induced the Formation of Unusual Diamond-Shaped Crystals of Honokiol and Its Mechanistic Study

Huang

Heng

et al. 2023

Crystal Growth & Design

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Deep eutectic solvents (DESs), as one type of modern green solvent, have gained increasing interest in regulating the crystallization process. Crystal habit is one of the crucial physical properties affecting product processing and the quality of pharmaceutical preparations. Here, a highly unusual diamondshaped crystal of honokiol (HON, a natural bioactive compound with multiple pharmacological activities) was discovered from volatile HON-based DES. In non-DES solvents, HON grows as hexagonal crystals with the same growth mode along the opposite directions of the nonpolar b-axis. In contrast, the (010) face along the b-axis disappeared in volatile DESs, breaking the original crystal symmetry. Surface tension analysis revealed that the volatilization of co-formers (i.e., menthol and camphor in this work) in the DES destroyed its hydrogen bond network, generating two crystallization environments for HON. Primary trapezoidal HON crystals formed in the hole environment after evaporation of coformers at an early stage. The (010) face of trapezoidal crystal continuously grows in the molecular cluster environment due to its highest roughness and preferential adsorption with DESs and finally disappears to form diamond-shaped crystals. Furthermore, the diamond-shaped crystals show improved dissolution behavior and powder flowability compared to the hexagonal crystals. This study clarifies the DES supramolecular structure changes caused by its component volatilization and its regulating mechanism on the HON crystallization process, which might provide a new route and guidance for the crystal morphology modification of organic small molecules.

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Section: Resultsmentioning

confidence: 99%

Structural Self-Destruction of Deep Eutectic Solvents Induced the Formation of Unusual Diamond-Shaped Crystals of Honokiol and Its Mechanistic Study

Huang

Heng

et al. 2023

Crystal Growth & Design

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“…Amorphous IMC was prepared by the melt quenching method according to our previous study. 39 In detail, the γ form of crystalline IMC (D 90 : 51.63 ± 3.47 μm, Figure S1) was melted at 175 °C for 3 min using a muffle furnace (StableTemp Muffle Furnaces, Coleparmer, USA) and then quickly quenched in liquid nitrogen. The collected resultant solid was gently ground by a mortar and pestle and passed through a sieve of mesh 60 in a glovebox.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Switch between Cocrystal and Coamorphous Forms Depending on Thermal Modulation of Hot-Melt Extrusion

Shen

Zhang

et al. 2023

Mol. Pharmaceutics

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Cocrystal (CC) and coamorphous (CM) techniques have become green technologies to improve the solubility and bioavailability of water-soluble drugs. In this study, hot-melt extrusion (HME) was employed to produce CC and CM formulations of indomethacin (IMC) and nicotinamide (NIC) due to its advantages like solvent-free and large-scale manufacturing. Interestingly, for the first time, IMC−NIC CC and CM were selectively prepared depending on the barrel temperatures of HME at a constant screw speed of 20 rpm and a feed rate of 1.0 g/min. IMC−NIC CC was obtained at 105−120 °C, IMC−NIC CM was produced at 125−150 °C, and the mixture of CC and CM was obtained between 120 and 125 °C (like a door switch of CC and CM). SS NMR combined with RDF and E bind calculations revealed the formation mechanisms of CC and CM, where strong interactions between heteromeric molecules formed at lower temperatures favored periodic molecular organization of CC, whereas discrete and weak interactions formed at higher temperatures promoted disordered molecular arrangement of CM. Additionally, IMC−NIC CC and CM showed enhanced dissolution and stability over crystalline/amorphous IMC. This study provides an easyto-operate and environmentally friendly strategy for the flexible regulation of CC and CM formulations with different properties through modulation of the barrel temperature of HME.

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“…For instance, Zhang, Qian, Heng et al found that in case of indomethacin (IMC) and nicotinamide (NIC), the temperature 105−120 °C allowed a co-crystal to be obtained, whereas the temperature 125−150 °C provided a co-amorphous solid dispersion. 147 The authors concluded that at low temperatures, the system had high viscosity and slow molecular diffusion, which resulted in a system with low diffusivity and high homogeneity that favored the formation of strong interactions. In the case of higher temperatures, the system was characterized by lower viscosity and faster molecular diffusion, which led to the creation of discrete and weak intermolecular interactions between the components.…”

Section: Co-crystallization and Co-amorphization As Strategies For Im...mentioning

confidence: 99%

New Perspectives for Antihypertensive Sartans as Components of Co-crystals and Co-amorphous Solids with Improved Properties and Multipurpose Activity

Turek,

Różycka-Sokołowska,

Owsianik

et al. 2023

Mol. Pharmaceutics

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Gelation switch of polyamorphic indomethacin depending on the thermal procedure

Cited by 6 publications

References 35 publications

Structural Self-Destruction of Deep Eutectic Solvents Induced the Formation of Unusual Diamond-Shaped Crystals of Honokiol and Its Mechanistic Study

Structural Self-Destruction of Deep Eutectic Solvents Induced the Formation of Unusual Diamond-Shaped Crystals of Honokiol and Its Mechanistic Study

Switch between Cocrystal and Coamorphous Forms Depending on Thermal Modulation of Hot-Melt Extrusion

New Perspectives for Antihypertensive Sartans as Components of Co-crystals and Co-amorphous Solids with Improved Properties and Multipurpose Activity

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