Anisotropic Crystal Growth Inhibition by Polymeric Additives: Impact on Modulation of Naproxen Crystal Shape and Size

Poornachary, Sendhil K.; Chia, Vernissa Dilys; Yani, Yin; Han, Guangjun; Chow, Pui Shan; Tan, Reginald B. H.

doi:10.1021/acs.cgd.7b00802

Cited by 42 publications

(49 citation statements)

References 42 publications

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“…Copper/poly(ethylene oxide)/low density polyethylene composite [33] Guar gum, pectin, κ-carrageenan, gelatin, polyvinylpyrrolidone Thiamine chloride hydrochloride [34] Poly(acrylic acid), poly(N-vinyl pyrrolidone), poly(4-vinylphenol) Ibuprofen [46] Polymers functionalized from a parent batch of poly(chloromethylstyrene-co-styrene) Nabumetone [47] Functionalized poly(N-hydroxyethyl acrylamide) Ethenzamide [48] Hydroxypropylmethyl cellulose Felodipine [49] Alginate Lovastatin, indomethacin, itraconazole [50] Hydroxypropyl methylcellulose and methylcellulose polymers Griseofulvin [51] Hydroxypropyl methylcellulose, polyvinylpyrrolidone), Eudragit L-100 Griseofulvin, danazol [52] Different polymers of vinylpyrrolidone and a copolymer of vinylpyrrolidone and vinylacetate Sixteen drugs of different chemical nature [53] Polyvinylpyrrolidone Celecoxib [55,56] Nylon 6/6, polypropylene, polyvinylchloride paracetamol [59] Polyvinylpyrrolidone, hydroxypropyl methyl cellulose, Kollidone VA64 Indomethacin [65] Hydroxypropyl methylcellulose, polyvinylpyrrolidone Naproxen [68] Polyvinylpyrrolidone Naproxen [69] Polyvinylpyrrolidone Carvedilol [70] Poly(vinyl alcohol), polyethylene glycol Nitrendipine [71] Poly(ethylene imine) Eprosartan [75] Poly(N-isopropyl acrylamide) Nitrofurantoin [76] Hydroxypropylmethyl cellulose, copovidone Complex impurity [77] Polyvinylpolypyrrolidone K30 and K90, polyethyleneglycol 6000, polyethylene-polypropylene glycol 188 Pioglitazone [80] Poly(ethylene glycol)-block-poly(lactic acid) Tolazamide [81] Poly(ethylene glycol), poly(ethylene oxide)-poly(propylene oxide) triblock, hydroxypropyl cellulose, poly(acrylic acid), poly(ethylene imine), elastin-like peptide, chitosan…”

Section: Crystal Surface Screening/nucleation Inhibitionmentioning

confidence: 99%

“…Poornachary et al investigated the effects of polymeric additives HPMC and PVP used in pharmacy to stabilize crystalline suspensions on the growth kinetics of naproxen (non-steroidal anti-inflammatory drug [ 68 ]. The influence of PVP on the crystal growth of the drug was explained based on hydrophobic—hydrophilic intermolecular interactions occurring at the crystal—solution interface.…”

Section: Present and Future Perspectives Of Applications Of Crystallization Phenomena In The Presence Of Polymersmentioning

confidence: 99%

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Application of Polymers as a Tool in Crystallization—A Review

et al. 2021

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The application of polymers as a tool in the crystallization process is gaining more and more interest among the scientific community. According to Web of Science statistics the number of papers dealing with “Polymer induced crystallization” increased from 2 in 1990 to 436 in 2020, and for “Polymer controlled crystallization”—from 4 in 1990 to 344 in 2020. This is clear evidence that both topics are vivid, attractive and intensively investigated nowadays. Efficient control of crystallization and crystal properties still represents a bottleneck in the manufacturing of crystalline materials ranging from pigments, antiscalants, nanoporous materials and pharmaceuticals to semiconductor particles. However, a rapid development in precise and reliable measuring methods and techniques would enable one to better describe phenomena involved, to formulate theoretical models, and probably most importantly, to develop practical indications for how to appropriately lead many important processes in the industry. It is clearly visible at the first glance through a number of representative papers in the area, that many of them are preoccupied with the testing and production of pharmaceuticals, while the rest are addressed to new crystalline materials, renewable energy, water and wastewater technology and other branches of industry where the crystallization process takes place. In this work, authors gathered and briefly discuss over 100 papers, published in leading scientific periodicals, devoted to the influence of polymers on crystallizing solutions.

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Section: Crystal Surface Screening/nucleation Inhibitionmentioning

confidence: 99%

Section: Present and Future Perspectives Of Applications Of Crystallization Phenomena In The Presence Of Polymersmentioning

confidence: 99%

Application of Polymers as a Tool in Crystallization—A Review

et al. 2021

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“…They regarded the method as a promising way for the computer-aided design of desirable pharmaceutical crystal habits with rapid solvent screening. Poornachary et al [23] investigated the mechanism of additive inhibition on naproxen crystal growth by modeling the intermolecular interactions between the polymeric additive and the crystal surface and ascribed the phenomenon to solute diffusion control.…”

Section: Introductionmentioning

confidence: 99%

Solvent Effects on Catechol Crystal Habits and Aspect Ratios: A Combination of Experiments and Molecular Dynamics Simulation Study

et al. 2020

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This work could help to better understand the solvent effects on crystal habits and aspect ratio changes at the molecular level, which provide some guidance for solvent selection in industrial crystallization processes. With the catechol crystal habits acquired using both experimental and simulation methods in isopropanol, methyl acetate and ethyl acetate, solvent effects on crystal morphology were explored based on the modified attachment energy model. Firstly, morphologically dominant crystal faces were obtained with the predicted crystal habit in vacuum. Then, modified attachment energies were calculated by the molecular dynamics simulation to modify the crystal shapes in a real solvent environment, and the simulation results were in agreement with the experimental ones. Meanwhile, the surface properties such as roughness and the diffusion coefficient were introduced to analyze the solvent adsorption behaviors and the radial distribution function curves were generated to distinguish diverse types of interactions like hydrogen bonds and van der Waals forces. Results show that the catechol crystal habits were affected by the combination of the attachment energy, surface structures and molecular interaction types. Moreover, the changing aspect ratios of catechol crystals are closely related to the existence of hydrogen bonds which contribute to growth inhibition on specific faces.

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“…The AE model is generally an improvement on the BFDH model but still fails to consider the impacts of supersaturation, solvents, and additives. 13 , 14 They are often used in pharmaceutical crystallization to modify the crystal habit 15 − 17 or to stabilize metastable polymorph. 18 , 19 Therefore, a new modified attachment energy (MAE) model has been developed to show that the crystal aspect ratios were sensitive to the relative polarity of the solvents.…”

Section: Introductionmentioning

confidence: 99%

Structure and Morphology of Indole Analogue Crystals

Pisarek

Malińska

2020

ACS Omega

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Indole and six simple analogues were crystallized in different environments to study the crystal habit changes. All crystal structures were determined by X-ray diffraction experiments. Lattice energies based on DFT-D3 periodic calculations and framework analysis were used to define the most important intermolecular interactions in the crystal structures: N–H···π (−28 kJ/mol), hydrogen bonds (−34 kJ/mol), π···π stacking interactions (−18 kJ/mol), and dipole–dipole (−18 kJ/mol). As morphology is an important feature in many industrial applications, such as photovoltaic cells, electronic devices, and drug discovery, we predicted the crystal morphology of selected crystals using the BFDH and AE models. Facet character depends on the orientation of the molecules at the surface and is therefore sensitive to the variation of crystallization conditions such as solvent, method, and temperature. All indole derivatives tend to form plate crystals with the largest {002} facet. We showed that the morphological importance of the {002} facet increases, whereas the {011} facet decreases with solvent polarity for 5-nitroindole and 4-cyanindole crystals, resulting in a change of crystal habit from needle to plate and from plate to prism, respectively.

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Anisotropic Crystal Growth Inhibition by Polymeric Additives: Impact on Modulation of Naproxen Crystal Shape and Size

Cited by 42 publications

References 42 publications

Application of Polymers as a Tool in Crystallization—A Review

Application of Polymers as a Tool in Crystallization—A Review

Solvent Effects on Catechol Crystal Habits and Aspect Ratios: A Combination of Experiments and Molecular Dynamics Simulation Study

Structure and Morphology of Indole Analogue Crystals

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