Anticrystal Engineering of Ketoprofen and Ester Local Anesthetics: Ionic Liquids or Deep Eutectic Mixtures?
Ionic liquids (ILs) and deep eutectic mixtures (DEMs) are potential solutions to the problems of low solubility, polymorphism, and low bioavailability of drugs. The aim of this work was to develop and investigate ketoprofen (KET)-based ILs/DEMs containing an ester local anesthetic (LA): benzocaine (...
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| Format: | Article |
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MDPI AG
2020-04-01
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| Series: | Pharmaceutics |
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| Online Access: | https://www.mdpi.com/1999-4923/12/4/368 |
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| author | Anita Umerska Klaudia Bialek Julija Zotova Marcin Skotnicki Lidia Tajber |
| author_facet | Anita Umerska Klaudia Bialek Julija Zotova Marcin Skotnicki Lidia Tajber |
| author_sort | Anita Umerska |
| collection | DOAJ |
| description | Ionic liquids (ILs) and deep eutectic mixtures (DEMs) are potential solutions to the problems of low solubility, polymorphism, and low bioavailability of drugs. The aim of this work was to develop and investigate ketoprofen (KET)-based ILs/DEMs containing an ester local anesthetic (LA): benzocaine (BEN), procaine (PRO) and tetracaine (TET) as the second component. ILs/DEMs were prepared via a mechanosynthetic process that involved the mixing of KET with an LA in a range of molar ratios and applying a thermal treatment. After heating above the melting point and quench cooling, the formation of supercooled liquids with Tgs that were dependent on the composition was observed for all KET-LA mixtures with exception of that containing 95 mol% of BEN. The KET-LA mixtures containing either ≥ 60 mol% BEN or 95 mol% of TET showed crystallization to BEN and TET, respectively, during either cooling or second heating. KET decreased the crystallization tendency of BEN and TET and increased their glass-forming ability. The KET-PRO systems showed good glass-forming ability and did not crystallize either during the cooling or during the second heating cycle irrespective of the composition. Infrared spectroscopy and molecular modeling indicated that KET and LAs formed DEMs, but in the KET-PRO systems small quantities of carboxylate anions were present. |
| first_indexed | 2024-03-10T20:24:30Z |
| format | Article |
| id | doaj.art-bf276c79f5c74662a769ddba66a433c0 |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-03-10T20:24:30Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj.art-bf276c79f5c74662a769ddba66a433c02023-11-19T21:55:03ZengMDPI AGPharmaceutics1999-49232020-04-0112436810.3390/pharmaceutics12040368Anticrystal Engineering of Ketoprofen and Ester Local Anesthetics: Ionic Liquids or Deep Eutectic Mixtures?Anita Umerska0Klaudia Bialek1Julija Zotova2Marcin Skotnicki3Lidia Tajber4School of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, College Green, Dublin 2, IrelandSchool of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, College Green, Dublin 2, IrelandSchool of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, College Green, Dublin 2, IrelandSchool of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, College Green, Dublin 2, IrelandSchool of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, College Green, Dublin 2, IrelandIonic liquids (ILs) and deep eutectic mixtures (DEMs) are potential solutions to the problems of low solubility, polymorphism, and low bioavailability of drugs. The aim of this work was to develop and investigate ketoprofen (KET)-based ILs/DEMs containing an ester local anesthetic (LA): benzocaine (BEN), procaine (PRO) and tetracaine (TET) as the second component. ILs/DEMs were prepared via a mechanosynthetic process that involved the mixing of KET with an LA in a range of molar ratios and applying a thermal treatment. After heating above the melting point and quench cooling, the formation of supercooled liquids with Tgs that were dependent on the composition was observed for all KET-LA mixtures with exception of that containing 95 mol% of BEN. The KET-LA mixtures containing either ≥ 60 mol% BEN or 95 mol% of TET showed crystallization to BEN and TET, respectively, during either cooling or second heating. KET decreased the crystallization tendency of BEN and TET and increased their glass-forming ability. The KET-PRO systems showed good glass-forming ability and did not crystallize either during the cooling or during the second heating cycle irrespective of the composition. Infrared spectroscopy and molecular modeling indicated that KET and LAs formed DEMs, but in the KET-PRO systems small quantities of carboxylate anions were present.https://www.mdpi.com/1999-4923/12/4/368ionic liquidsdeep eutectic mixturesketoprofennon-steroidal anti-inflammatory drugs (NSAIDs)local anestheticsprocaine |
| spellingShingle | Anita Umerska Klaudia Bialek Julija Zotova Marcin Skotnicki Lidia Tajber Anticrystal Engineering of Ketoprofen and Ester Local Anesthetics: Ionic Liquids or Deep Eutectic Mixtures? Pharmaceutics ionic liquids deep eutectic mixtures ketoprofen non-steroidal anti-inflammatory drugs (NSAIDs) local anesthetics procaine |
| title | Anticrystal Engineering of Ketoprofen and Ester Local Anesthetics: Ionic Liquids or Deep Eutectic Mixtures? |
| title_full | Anticrystal Engineering of Ketoprofen and Ester Local Anesthetics: Ionic Liquids or Deep Eutectic Mixtures? |
| title_fullStr | Anticrystal Engineering of Ketoprofen and Ester Local Anesthetics: Ionic Liquids or Deep Eutectic Mixtures? |
| title_full_unstemmed | Anticrystal Engineering of Ketoprofen and Ester Local Anesthetics: Ionic Liquids or Deep Eutectic Mixtures? |
| title_short | Anticrystal Engineering of Ketoprofen and Ester Local Anesthetics: Ionic Liquids or Deep Eutectic Mixtures? |
| title_sort | anticrystal engineering of ketoprofen and ester local anesthetics ionic liquids or deep eutectic mixtures |
| topic | ionic liquids deep eutectic mixtures ketoprofen non-steroidal anti-inflammatory drugs (NSAIDs) local anesthetics procaine |
| url | https://www.mdpi.com/1999-4923/12/4/368 |
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