Complexes of Ibuprofen Thiazolidin-4-One Derivatives with β-Cyclodextrin: Characterization and In Vivo Release Profile and Biological Evaluation
Generally, NSAIDs are weakly soluble in water and contain both hydrophilic and hydrophobic groups. One of the most widely used NSAIDs is ibuprofen, which has a poor solubility and high permeability profile. By creating dynamic, non-covalent, water-soluble inclusion complexes, cyclodextrins (CDs) can...
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| Format: | Article |
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MDPI AG
2023-10-01
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| Series: | Pharmaceutics |
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| Online Access: | https://www.mdpi.com/1999-4923/15/10/2492 |
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| author | Ioana Mirela Vasincu Maria Apotrosoaei Florentina Lupascu Andreea-Teodora Iacob Simona-Eliza Giusca Irina-Draga Caruntu Narcisa-Laura Marangoci Anca Roxana Petrovici Gabriela Dumitrita Stanciu Bogdan-Ionel Tamba Bianca-Stefania Profire Alin-Viorel Focsa Mariana Pinteala Lenuta Profire |
| author_facet | Ioana Mirela Vasincu Maria Apotrosoaei Florentina Lupascu Andreea-Teodora Iacob Simona-Eliza Giusca Irina-Draga Caruntu Narcisa-Laura Marangoci Anca Roxana Petrovici Gabriela Dumitrita Stanciu Bogdan-Ionel Tamba Bianca-Stefania Profire Alin-Viorel Focsa Mariana Pinteala Lenuta Profire |
| author_sort | Ioana Mirela Vasincu |
| collection | DOAJ |
| description | Generally, NSAIDs are weakly soluble in water and contain both hydrophilic and hydrophobic groups. One of the most widely used NSAIDs is ibuprofen, which has a poor solubility and high permeability profile. By creating dynamic, non-covalent, water-soluble inclusion complexes, cyclodextrins (CDs) can increase the dissolution rate of low aqueous solubility drugs, operating as a drug delivery vehicle, additionally contributing significantly to the chemical stability of pharmaceuticals and to reducing drug-related irritability. In order to improve the pharmacological and pharmacokinetics profile of ibuprofen, new thiazolidin-4-one derivatives of ibuprofen (<b>4b</b>, <b>4g</b>, <b>4k</b>, <b>4m</b>) were complexed with <b>β-CD</b>, using co-precipitation and freeze-drying. The new <b>β-CD</b> complexes (<b>β-CD-4b</b>, <b>β-CD-4g</b>, <b>β-CD-4k</b>, <b>β-CD-4m</b>) were characterized using scanning electronic microscopy (SEM), differential scanning calorimetry (DSC), X-ray diffraction and a phase solubility test. Using the AutoDock-VINA algorithm included in YASARA-structure software, we investigated the binding conformation of ibuprofen derivatives to <b>β-CD</b> and measured the binding energies. We also performed an in vivo biological evaluation of the ibuprofen derivatives and corresponding <b>β-CD</b> complexes, using analgesic/anti-inflammatory assays, as well as a release profile. The results support the theory that <b>β-CD</b> complexes (<b>β-CD-4b</b>, <b>β-CD-4g</b>, <b>β-CD-4k</b>, <b>β-CD-4m</b>) have a similar effect to ibuprofen derivatives (<b>4b</b>, <b>4g</b>, <b>4k</b>, <b>4m</b>). Moreover, the <b>β-CD</b> complexes demonstrated a delayed release profile, which provides valuable insights into the drug-delivery area, focused on ibuprofen derivatives. |
| first_indexed | 2024-03-10T20:57:28Z |
| format | Article |
| id | doaj.art-41f03abcc9ed449582e6c7ad6a7fd350 |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-03-10T20:57:28Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj.art-41f03abcc9ed449582e6c7ad6a7fd3502023-11-19T17:45:18ZengMDPI AGPharmaceutics1999-49232023-10-011510249210.3390/pharmaceutics15102492Complexes of Ibuprofen Thiazolidin-4-One Derivatives with β-Cyclodextrin: Characterization and In Vivo Release Profile and Biological EvaluationIoana Mirela Vasincu0Maria Apotrosoaei1Florentina Lupascu2Andreea-Teodora Iacob3Simona-Eliza Giusca4Irina-Draga Caruntu5Narcisa-Laura Marangoci6Anca Roxana Petrovici7Gabriela Dumitrita Stanciu8Bogdan-Ionel Tamba9Bianca-Stefania Profire10Alin-Viorel Focsa11Mariana Pinteala12Lenuta Profire13Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaDepartment of Morphofunctional Sciences, Faculty of Medicine, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaDepartment of Morphofunctional Sciences, Faculty of Medicine, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaCentre of Advanced Research in Bionanoconjugates and Biopolymers, “Petru Poni“ Institute of Macromolecular Chemistry, 41A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaCentre of Advanced Research in Bionanoconjugates and Biopolymers, “Petru Poni“ Institute of Macromolecular Chemistry, 41A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaAdvanced Research and Development Center for Experimental Medicine (CEMEX) “Prof. Ostin C. Mungiu”, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaAdvanced Research and Development Center for Experimental Medicine (CEMEX) “Prof. Ostin C. Mungiu”, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaDepartment of Internal Medicine, Faculty of Medicine, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaDepartment of Drug Industry and Pharmaceutical Biotechnology, Faculty of Pharmacy, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaCentre of Advanced Research in Bionanoconjugates and Biopolymers, “Petru Poni“ Institute of Macromolecular Chemistry, 41A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, “Grigore T. Popa” University of Medicine and Pharmacy from Iasi, 16 University Street, 700115 Iasi, RomaniaGenerally, NSAIDs are weakly soluble in water and contain both hydrophilic and hydrophobic groups. One of the most widely used NSAIDs is ibuprofen, which has a poor solubility and high permeability profile. By creating dynamic, non-covalent, water-soluble inclusion complexes, cyclodextrins (CDs) can increase the dissolution rate of low aqueous solubility drugs, operating as a drug delivery vehicle, additionally contributing significantly to the chemical stability of pharmaceuticals and to reducing drug-related irritability. In order to improve the pharmacological and pharmacokinetics profile of ibuprofen, new thiazolidin-4-one derivatives of ibuprofen (<b>4b</b>, <b>4g</b>, <b>4k</b>, <b>4m</b>) were complexed with <b>β-CD</b>, using co-precipitation and freeze-drying. The new <b>β-CD</b> complexes (<b>β-CD-4b</b>, <b>β-CD-4g</b>, <b>β-CD-4k</b>, <b>β-CD-4m</b>) were characterized using scanning electronic microscopy (SEM), differential scanning calorimetry (DSC), X-ray diffraction and a phase solubility test. Using the AutoDock-VINA algorithm included in YASARA-structure software, we investigated the binding conformation of ibuprofen derivatives to <b>β-CD</b> and measured the binding energies. We also performed an in vivo biological evaluation of the ibuprofen derivatives and corresponding <b>β-CD</b> complexes, using analgesic/anti-inflammatory assays, as well as a release profile. The results support the theory that <b>β-CD</b> complexes (<b>β-CD-4b</b>, <b>β-CD-4g</b>, <b>β-CD-4k</b>, <b>β-CD-4m</b>) have a similar effect to ibuprofen derivatives (<b>4b</b>, <b>4g</b>, <b>4k</b>, <b>4m</b>). Moreover, the <b>β-CD</b> complexes demonstrated a delayed release profile, which provides valuable insights into the drug-delivery area, focused on ibuprofen derivatives.https://www.mdpi.com/1999-4923/15/10/2492ibuprofen derivativesβ-cyclodextrinrelease profileanalgesic assays |
| spellingShingle | Ioana Mirela Vasincu Maria Apotrosoaei Florentina Lupascu Andreea-Teodora Iacob Simona-Eliza Giusca Irina-Draga Caruntu Narcisa-Laura Marangoci Anca Roxana Petrovici Gabriela Dumitrita Stanciu Bogdan-Ionel Tamba Bianca-Stefania Profire Alin-Viorel Focsa Mariana Pinteala Lenuta Profire Complexes of Ibuprofen Thiazolidin-4-One Derivatives with β-Cyclodextrin: Characterization and In Vivo Release Profile and Biological Evaluation Pharmaceutics ibuprofen derivatives β-cyclodextrin release profile analgesic assays |
| title | Complexes of Ibuprofen Thiazolidin-4-One Derivatives with β-Cyclodextrin: Characterization and In Vivo Release Profile and Biological Evaluation |
| title_full | Complexes of Ibuprofen Thiazolidin-4-One Derivatives with β-Cyclodextrin: Characterization and In Vivo Release Profile and Biological Evaluation |
| title_fullStr | Complexes of Ibuprofen Thiazolidin-4-One Derivatives with β-Cyclodextrin: Characterization and In Vivo Release Profile and Biological Evaluation |
| title_full_unstemmed | Complexes of Ibuprofen Thiazolidin-4-One Derivatives with β-Cyclodextrin: Characterization and In Vivo Release Profile and Biological Evaluation |
| title_short | Complexes of Ibuprofen Thiazolidin-4-One Derivatives with β-Cyclodextrin: Characterization and In Vivo Release Profile and Biological Evaluation |
| title_sort | complexes of ibuprofen thiazolidin 4 one derivatives with β cyclodextrin characterization and in vivo release profile and biological evaluation |
| topic | ibuprofen derivatives β-cyclodextrin release profile analgesic assays |
| url | https://www.mdpi.com/1999-4923/15/10/2492 |
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