Organic salt versus salt cocrystal: thermal behavior, structural and photoluminescence investigations

Crişan, Manuela; Petric, Mihaela; Vlase, Gabriela; Vlase, Titus; Siminel, Anatolii V.; Bourosh, Paulina N.; Croitor, Lilia

doi:10.1007/s10973-020-10438-y

Cited by 7 publications

(5 citation statements)

References 42 publications

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“…However, DSC thermograms of S2 and S3 showed a melting point lower than the melting point of coformers and the decomposition temperature of PXD101. The thermodynamic stability of these crystals is of the order S1 > S4 > S3 > S2 based on the values of their melting points, 35 which is consistent with the melting point sequence of the coformers (TPH, INA, INH, and L-Pro).…”

Section: Conformation and Packing Similarity Analysis As Shown In Figurementioning

confidence: 99%

Solubility Enhancement of Anticancer Drug Belinostat via the Co-crystallization Strategy: Synthesis, Characterization, and Antitumor Activity In Vitro Evaluation

Ouyang

Cao

et al. 2022

Crystal Growth & Design

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Belinostat (PXD101), a biopharmaceutical classification system II (BCSII) drug approved for treating refractory T-cell lymphoma, is currently administered by intravenous injection. To improve patient compliance, the development of oral formulations of PXD101 has attracted attention. Because the solubility and dissolution rate of active pharmaceutical ingredients can affect the therapeutic effect of the oral formulations, this work explores solid-state form modification of PXD101 by co-crystallization with four coformers, namely, theophylline, isonicotinamide (INA), isoniazid (INH), and l-proline (l-Pro) to solve the problem of poor water solubility. The four cocrystals were obtained on the basis of N–H···O, O–H···O, and O–H···N synthons. All the four obtained multicomponent crystals were characterized by powder X-ray diffraction (PXRD) and thermal analysis, meanwhile, crystal structure determination was performed by single-crystal XRD. The results of CrystalCMP show the similar packing patterns of PXD101-INA and PXD101-INH cocrystals. The data analysis from powder dissolution experiments suggested that the apparent solubility of the obtained multicomponent crystals is 1.14–2.22 times more than that of PXD101, and PXD101-l-Pro shows a completely different dissolution behavior from that of the other three cocrystals. Finally, 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay experiments demonstrated that the PXD101-INA cocrystal can significantly inhibit the proliferation of Michigan Cancer Foundation-7 (MCF-7) cells even at a low concentration (0.01 μM). Such results shed light on the potential value of multicomponent crystals in the further development of pharmaceutical products.

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Section: Conformation and Packing Similarity Analysis As Shown In Figurementioning

confidence: 99%

Solubility Enhancement of Anticancer Drug Belinostat via the Co-crystallization Strategy: Synthesis, Characterization, and Antitumor Activity In Vitro Evaluation

Ouyang

Cao

et al. 2022

Crystal Growth & Design

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“…In addition, there are limited reports of crystals composed of three or more organic components, from which the cases of solid solution are excluded. [27][28][29][30][31][32][33][34][35][36][37][38][39][40] Thus, in this study, we systematically prepared crystals composed of three πconjugated species, which would be basic building-blocks of functional materials for electronics and photonics.…”

Section: Introductionmentioning

confidence: 99%

“…However, general combination of the components appropriate for forming the cocrystals and arrangement of each component in the cocrystals have not been sufficiently investigated. In addition, there are limited reports of crystals composed of three or more organic components, from which the cases of solid solution are excluded [27–40] . Thus, in this study, we systematically prepared crystals composed of three π‐conjugated species, which would be basic building‐blocks of functional materials for electronics and photonics.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Structures of Multicomponent Crystals Composed of Heteroaromatic Cations, p‐Toluenesulfonate Anion, and Aromatic Hydrogen‐Bond Donors

Uno,

Yamakado,

Okada

et al. 2024

Asian J Org Chem

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Cocrystals with three π‐components, which were a π‐cation, a π‐anion acting as a hydrogen‐bonding acceptor, and a π‐molecule acting as a hydrogen‐bonding donor, were prepared by the solution‐growth methods. The first and second components were ion pairs of 1‐methylpyridinium or 1‐methylquinolinium p‐toluenesulfonate derivatives, and the third components were dihydric phenol derivatives, like hydroquinone, 1,4‐naphthalenediol, 4,4’‐biphenol, and 1,1’‐bi‐2‐naphthol, or benzoic acid derivatives with hydroxy or amino group at the para position. Among 23 cocrystals found from 35 possible combinations of five ion‐pairs and seven hydrogen‐bonding donors, 20 cocrystals were investigated by the X‐ray crystallographic analyses. Some of them also contained solvent molecules. In these cocrystals, hydrogen‐bonding sequences composed of p‐toluenesulfonate and the hydrogen‐bonding donors were observed, and ionic bonds between the first and second components and hydrogen bonds between the second and third components were found to be responsible for three‐π‐component cocrystals. When the cations were 4‐cyanopyridinium or quinolinium derivatives, the cocrystals showed charge‐transfer absorption bands due to electronic interaction between the cations and the hydrogen‐bonding donors. To the mixture of quinolinium p‐toluenesulfonate and 1,1’‐bi‐2‐naphthol forming the three‐π‐component cocrystals, tetrathiafulvalene were added to form four‐π‐component cocrystals with ethanol or water molecules.

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“…6,7 The most popular methods are liquid-assisted grinding (LAG) [8][9][10] and slow crystallization from a solution or from a mixture of solvents. [11][12][13] Moreover, each method has its own limitations. 14 Mechanochemical methods can lead to an undesirable transition of a mixture to an amorphous state.…”

Section: Introductionmentioning

confidence: 99%

Thermal method usage features for multicomponent crystal screening

et al. 2022

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Organic salt versus salt cocrystal: thermal behavior, structural and photoluminescence investigations

Cited by 7 publications

References 42 publications

Solubility Enhancement of Anticancer Drug Belinostat via the Co-crystallization Strategy: Synthesis, Characterization, and Antitumor Activity In Vitro Evaluation

Solubility Enhancement of Anticancer Drug Belinostat via the Co-crystallization Strategy: Synthesis, Characterization, and Antitumor Activity In Vitro Evaluation

Preparation and Structures of Multicomponent Crystals Composed of Heteroaromatic Cations, p‐Toluenesulfonate Anion, and Aromatic Hydrogen‐Bond Donors

Thermal method usage features for multicomponent crystal screening

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