Simultaneously enhancing the <i>in vitro</i>/<i>in vivo</i> performances of acetazolamide using proline as a zwitterionic coformer for cocrystallization

Song, Yu; Wang, Ling-Yang; Liu, Fang; Wu, Zhi‐Yong; Yan, Cui‐Wei

doi:10.1039/c9ce00270g

Cited by 37 publications

(30 citation statements)

References 54 publications

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“…However, many of the bioactive ingredients of CTM are poorly soluble, leading to low oral bioavailability and delivery problems. Specifically for PUE, the oral bioavailability is only about 7% [ 32 , 33 , 34 , 35 ], and the dominant drug uptake at present is through intravenous injection. Thus, in the current study, the co-crystallization method using L-proline (PRO) as the partner excipient is employed to improve the water solubility of PUE.…”

Section: Resultsmentioning

confidence: 99%

“…In this work, we demonstrate that the solubility of PUE can be readily improved via its co-crystallization with L-proline (PRO, Scheme 1 ). PRO is well-known to exhibit good potential for co-crystal formation due to the presence of both hydrogen-bonding donor and acceptor sites in the molecule [ 32 , 33 , 34 ]. Two different phases of PUE-PRO co-crystals, namely the solvate-free form [PUE][PRO] ( I ) and the solvated form [PUE] 2 [PRO]∙EtOH∙(H 2 O) 2 ( II ), have been prepared under different crystallization conditions and characterized spectroscopically.…”

Section: Introductionmentioning

confidence: 99%

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Enhancing the Physiochemical Properties of Puerarin via L-Proline Co-Crystallization: Synthesis, Characterization, and Dissolution Studies of Two Phases of Pharmaceutical Co-Crystals

Inam

Liu

Wang

et al. 2021

IJMS

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Puerarin (PUE) is a Chinese traditional medicine known to enhance glucose uptake into the insulin cells to downregulate the blood glucose levels in the treatment of type II diabetes. Nevertheless, the bioavailability of pristine PUE is limited due to its poor solubility and low intestinal permeability. In this work, we demonstrate that the solubility of PUE can be significantly enhanced via its co-crystallization with L-Proline (PRO). Two crystalline phases, namely, the solvate-free form [PUE][PRO] (I) and the solvated form [PUE]2[PRO]∙EtOH∙(H2O)2 (II) are isolated. These two phases are characterized by single-crystal X-ray diffraction (SCXRD), powder X-ray diffraction (PXRD), Fourier-transformed infrared (FT-IR) spectra, nuclear magnetic resonance (NMR), and thermogravimetric analysis in association with differential scanning calorimetry (TGA-DSC). The solubility and dissolution rate of both I and II in water, gastrointestinal tract at pH 1.2, and phosphate buffer at pH 6.8 indicates a nearly doubled increase as compared to the pristine PUE. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay of pristine PUE, I and II against murine colon cancer cell lines CT-26 and human kidney cell lines HEK-293 indicated that neither compound exhibits obvious cytotoxicity after 24 h. This work showcases that the readily available and biocompatible PRO can be a promising adjuvant to enhance the physicochemical properties of PUE toward orally administered drug formulation with improved pharmacokinetics.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enhancing the Physiochemical Properties of Puerarin via L-Proline Co-Crystallization: Synthesis, Characterization, and Dissolution Studies of Two Phases of Pharmaceutical Co-Crystals

Inam

Liu

Wang

et al. 2021

IJMS

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“…A search for cocrystal structures of PRO gave 148 hits. PRO has been used as a cocrystal former of various active pharmaceutical ingredients (Tilborg et al, 2013;Tumanova et al, 2018;Song et al, 2019). The most relevant cocrystal structure to this work is the cocrystal of RES and PRO (He et al, 2017; refcode PEBZEE).…”

Section: Database Surveymentioning

confidence: 99%

Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline

2020

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The hydrated and anhydrous 1:2 cocrystals of oxyresveratrol (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol; OXY; C14H12O4) and proline [(S)-pyrrolidine-2-carboxylic acid; PRO; C5H9NO2], namely, 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol bis[(S)-pyrrolidin-1-ium-2-carboxylate] monohydrate, C14H12O4·2C5H9NO2·H2O, and the anhydrous form, C14H12O4·2C5H9NO2, were obtained by crystallization at different temperatures. Both of them crystallize with orthorhombic (P212121) symmetry. The structures display N—H...O and O—H...O hydrogen-bonding interactions between PRO and PRO, OXY and OXY, and OXY and PRO. In the hydrated cocrystal, these types of contacts are also observed between the OXY, PRO and water molecules. A combination of these interactions leads to a three-dimensional supramolecular assembly in each case. Hirshfeld surfaces were used to gain further insight into the intermolecular interactions in the packing, including the relative percentage contributions of the significant intermolecular H...H and H...O/O...H contacts.

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“…Amino acids are Zwitterionic compounds that exist under the GRAS group with low hazardous to the biological system in comparison with other co-formers [31,32]. Moreover, their zwitterionic potentialities could form charge-assisted hydrogen bondings in cocrystal formation [33,34].…”

Section: Introductionmentioning

confidence: 99%

Rosuvastatin cocrystals: an attempt to modulate physicochemical parameters

Vemuri

Srinivas

2021

Futur J Pharm Sci

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Background The meager physicochemical properties like low solubility and low dissolution rate of rosuvastatin calcium remain as an obstruction for formulation development. In the present work, we explore the evolution of rosuvastatin cocrystal, which may offer the synergetic physico-chemical properties of the drug. Cocrystal crafting depends on two possible intermolecular interactions; heteromeric and the homomeric selection of compounds with complementary functional groups are contemplated as a possible cause of supramolecular synthons in cocrystal formation. Specifically, cocrystals of rosuvastatin with l-asparagine and l-glutamine with molar ratio (1:1) were fabricated by using slow solvent evaporation and slow evaporation techniques. Novel cocrystals of rosuvastatin-asparagine (RSC-C) and rosuvastatin-glutamine (RSC-G) cocrystals obtained by slow solvent evaporation were utilized for preliminary investigation and further scale-up was done by using the solvent evaporation technique. Results The novel cocrystals showed a new characteristic of powder X-ray diffraction, thermograms of differential scanning calorimetry, 1H liquid FT-NMR spectra, and scanning electron microscopy. These results signify the establishment of intermolecular interaction within the cocrystals. In both the novel cocrystals, rosuvastatin was determined to be engaged in the hydrogen bond interaction with the complementary functional groups of l-asparagine and l-glutamine. Compared with the pure rosuvastatin, RSC-C and RSC-G cocrystal showed 2.17-fold and 1.60-fold improved solubility respectively. The dissolution test showed that the RSC-C and RSC-G cocrystal exhibited 1.97-fold and 1.94-fold higher dissolution rate than the pure rosuvastatin in pH6.8 phosphate buffer respectively. Conclusion Modulation in the chemical environment, improvement in the solubility, and dissolution rate demonstrated the benefit of co-crystallization to improve the physicochemical properties of the drug. Graphical abstract

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Simultaneously enhancing the in vitro/in vivo performances of acetazolamide using proline as a zwitterionic coformer for cocrystallization

Abstract: The synthesized first acetazolamide zwitterionic cocrystal highlights simultaneously-increasing solubility and permeability of acetazolamide, which successfully translate into enhanced bioavailability.

Cited by 37 publications

References 54 publications

Enhancing the Physiochemical Properties of Puerarin via L-Proline Co-Crystallization: Synthesis, Characterization, and Dissolution Studies of Two Phases of Pharmaceutical Co-Crystals

Enhancing the Physiochemical Properties of Puerarin via L-Proline Co-Crystallization: Synthesis, Characterization, and Dissolution Studies of Two Phases of Pharmaceutical Co-Crystals

Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline

Rosuvastatin cocrystals: an attempt to modulate physicochemical parameters

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