Cocrystals of Praziquantel with Phenolic Acids: Discovery, Characterization, and Evaluation
Solvent-assisted grinding (SAG) and solution slow evaporation (SSE) methods are generally used for the preparation of cocrystals. However, even by using the same solvent, active pharmaceutical ingredient (API), and cocrystal coformer (CCF), the cocrystals prepared using the two methods above are som...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/6/2022 |
| _version_ | 1797444233957736448 |
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| author | Shiying Yang Qiwen Liu Weiwen Ji Qi An Junke Song Cheng Xing Dezhi Yang Li Zhang Yang Lu Guanhua Du |
| author_facet | Shiying Yang Qiwen Liu Weiwen Ji Qi An Junke Song Cheng Xing Dezhi Yang Li Zhang Yang Lu Guanhua Du |
| author_sort | Shiying Yang |
| collection | DOAJ |
| description | Solvent-assisted grinding (SAG) and solution slow evaporation (SSE) methods are generally used for the preparation of cocrystals. However, even by using the same solvent, active pharmaceutical ingredient (API), and cocrystal coformer (CCF), the cocrystals prepared using the two methods above are sometimes inconsistent. In the present study, in the cocrystal synthesis of praziquantel (PRA) with polyhydroxy phenolic acid, including protocatechuic acid (PA), gallic acid (GA), and ferulic acid (FA), five different cocrystals were prepared using SAG and SSE. Three of the cocrystals prepared using the SAG method have the structural characteristics of carboxylic acid dimer, and two cocrystals prepared using the SSE method formed cocrystal solvates with the structural characteristics of carboxylic acid monomer. For phenolic acids containing only one phenolic hydroxyl group (ferulic acid), when preparing cocrystals with PRA by using SAG and SSE, the same product was obtained. In addition, the weak molecular interactions that were observed in the cocrystal are explained at the molecular level by using theoretical calculation methods. Finally, the in vitro solubility of cocrystals without crystal solvents and in vivo bioavailability of PRA-FA were evaluated to further understand the influence on the physicochemical properties of API for the introduction of CCF. |
| first_indexed | 2024-03-09T13:08:42Z |
| format | Article |
| id | doaj.art-6f612e229e4b442484fb7eecdeabb9ce |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T13:08:42Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6f612e229e4b442484fb7eecdeabb9ce2023-11-30T21:44:47ZengMDPI AGMolecules1420-30492022-03-01276202210.3390/molecules27062022Cocrystals of Praziquantel with Phenolic Acids: Discovery, Characterization, and EvaluationShiying Yang0Qiwen Liu1Weiwen Ji2Qi An3Junke Song4Cheng Xing5Dezhi Yang6Li Zhang7Yang Lu8Guanhua Du9Beijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Drug Target and Screening Research, National Center for Pharmaceutical Screening, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Polymorphic Drugs, Center of Pharmaceutical Polymorphs, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaBeijing City Key Laboratory of Drug Target and Screening Research, National Center for Pharmaceutical Screening, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, ChinaSolvent-assisted grinding (SAG) and solution slow evaporation (SSE) methods are generally used for the preparation of cocrystals. However, even by using the same solvent, active pharmaceutical ingredient (API), and cocrystal coformer (CCF), the cocrystals prepared using the two methods above are sometimes inconsistent. In the present study, in the cocrystal synthesis of praziquantel (PRA) with polyhydroxy phenolic acid, including protocatechuic acid (PA), gallic acid (GA), and ferulic acid (FA), five different cocrystals were prepared using SAG and SSE. Three of the cocrystals prepared using the SAG method have the structural characteristics of carboxylic acid dimer, and two cocrystals prepared using the SSE method formed cocrystal solvates with the structural characteristics of carboxylic acid monomer. For phenolic acids containing only one phenolic hydroxyl group (ferulic acid), when preparing cocrystals with PRA by using SAG and SSE, the same product was obtained. In addition, the weak molecular interactions that were observed in the cocrystal are explained at the molecular level by using theoretical calculation methods. Finally, the in vitro solubility of cocrystals without crystal solvents and in vivo bioavailability of PRA-FA were evaluated to further understand the influence on the physicochemical properties of API for the introduction of CCF.https://www.mdpi.com/1420-3049/27/6/2022cocrystalpraziquantelphenolic acidsolubilityevaluation |
| spellingShingle | Shiying Yang Qiwen Liu Weiwen Ji Qi An Junke Song Cheng Xing Dezhi Yang Li Zhang Yang Lu Guanhua Du Cocrystals of Praziquantel with Phenolic Acids: Discovery, Characterization, and Evaluation Molecules cocrystal praziquantel phenolic acid solubility evaluation |
| title | Cocrystals of Praziquantel with Phenolic Acids: Discovery, Characterization, and Evaluation |
| title_full | Cocrystals of Praziquantel with Phenolic Acids: Discovery, Characterization, and Evaluation |
| title_fullStr | Cocrystals of Praziquantel with Phenolic Acids: Discovery, Characterization, and Evaluation |
| title_full_unstemmed | Cocrystals of Praziquantel with Phenolic Acids: Discovery, Characterization, and Evaluation |
| title_short | Cocrystals of Praziquantel with Phenolic Acids: Discovery, Characterization, and Evaluation |
| title_sort | cocrystals of praziquantel with phenolic acids discovery characterization and evaluation |
| topic | cocrystal praziquantel phenolic acid solubility evaluation |
| url | https://www.mdpi.com/1420-3049/27/6/2022 |
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