Interaction of Oxicam Derivatives with the Artificial Models of Biological Membranes—Calorimetric and Fluorescence Spectroscopic Study
The modified 1,2-benzothiazine analogues designed as new drug candidates and discussed in this paper are oxicam derivatives. Oxicams are a class of non-steroidal anti-inflammatory drugs (NSAIDs). Their biological target is cyclooxygenase (COX), a membrane protein associated with the phospholipid bil...
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| Format: | Article |
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MDPI AG
2022-08-01
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| Series: | Membranes |
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| Online Access: | https://www.mdpi.com/2077-0375/12/8/791 |
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| author | Jadwiga Maniewska Żaneta Czyżnikowska Berenika M. Szczęśniak-Sięga Krystyna Michalak |
| author_facet | Jadwiga Maniewska Żaneta Czyżnikowska Berenika M. Szczęśniak-Sięga Krystyna Michalak |
| author_sort | Jadwiga Maniewska |
| collection | DOAJ |
| description | The modified 1,2-benzothiazine analogues designed as new drug candidates and discussed in this paper are oxicam derivatives. Oxicams are a class of non-steroidal anti-inflammatory drugs (NSAIDs). Their biological target is cyclooxygenase (COX), a membrane protein associated with the phospholipid bilayer. In recent decades, it has been proven that the biological effect of NSAIDs may be closely related to their interaction at the level of the biological membrane. These processes are often complicated and the biological membranes themselves are very complex. Therefore, to study these mechanisms, simplified models of biological membranes are used. To characterize the interaction of six oxicam derivatives with DPPC, DMPC and EYPC, artificial models of biological membranes (multi-bilayers or liposomes), differential scanning calorimetry (DSC) and fluorescence spectroscopy techniques were applied. In spectroscopic measurements, two fluorescent probes (Laurdan and Prodan) localized in different membrane segments were used. All tested oxicam derivatives interacted with the lipid bilayers and may penetrate the artificial models of biological membranes. They intercalated into the lipid bilayers and were located in the vicinity of the polar/apolar membrane interface. Moreover, a good drug candidate should not only have high efficiency against a molecular target but also exhibit strictly defined ADMET parameters, therefore these activities of the studied compounds were also estimated. |
| first_indexed | 2024-03-09T12:57:42Z |
| format | Article |
| id | doaj.art-3d9361d521cc4b3eb6d3ff72edae5a39 |
| institution | Directory Open Access Journal |
| issn | 2077-0375 |
| language | English |
| last_indexed | 2024-03-09T12:57:42Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Membranes |
| spelling | doaj.art-3d9361d521cc4b3eb6d3ff72edae5a392023-11-30T21:57:34ZengMDPI AGMembranes2077-03752022-08-0112879110.3390/membranes12080791Interaction of Oxicam Derivatives with the Artificial Models of Biological Membranes—Calorimetric and Fluorescence Spectroscopic StudyJadwiga Maniewska0Żaneta Czyżnikowska1Berenika M. Szczęśniak-Sięga2Krystyna Michalak3Department of Medicinal Chemistry, Faculty of Pharmacy, Wroclaw Medical University, Borowska 211, 50-556 Wroclaw, PolandDepartment of Inorganic Chemistry, Faculty of Pharmacy, Wroclaw Medical University, Borowska 211a, 50-556 Wroclaw, PolandDepartment of Medicinal Chemistry, Faculty of Pharmacy, Wroclaw Medical University, Borowska 211, 50-556 Wroclaw, PolandDepartment of Biophysics and Neuroscience, Faculty of Medicine, Wroclaw Medical University, T. Chałubińskiego 3a, 50-368 Wroclaw, PolandThe modified 1,2-benzothiazine analogues designed as new drug candidates and discussed in this paper are oxicam derivatives. Oxicams are a class of non-steroidal anti-inflammatory drugs (NSAIDs). Their biological target is cyclooxygenase (COX), a membrane protein associated with the phospholipid bilayer. In recent decades, it has been proven that the biological effect of NSAIDs may be closely related to their interaction at the level of the biological membrane. These processes are often complicated and the biological membranes themselves are very complex. Therefore, to study these mechanisms, simplified models of biological membranes are used. To characterize the interaction of six oxicam derivatives with DPPC, DMPC and EYPC, artificial models of biological membranes (multi-bilayers or liposomes), differential scanning calorimetry (DSC) and fluorescence spectroscopy techniques were applied. In spectroscopic measurements, two fluorescent probes (Laurdan and Prodan) localized in different membrane segments were used. All tested oxicam derivatives interacted with the lipid bilayers and may penetrate the artificial models of biological membranes. They intercalated into the lipid bilayers and were located in the vicinity of the polar/apolar membrane interface. Moreover, a good drug candidate should not only have high efficiency against a molecular target but also exhibit strictly defined ADMET parameters, therefore these activities of the studied compounds were also estimated.https://www.mdpi.com/2077-0375/12/8/791DSCfluorescence spectroscopy1,2-benzothiazine derivativesoxicamspiroxicammodel membranes |
| spellingShingle | Jadwiga Maniewska Żaneta Czyżnikowska Berenika M. Szczęśniak-Sięga Krystyna Michalak Interaction of Oxicam Derivatives with the Artificial Models of Biological Membranes—Calorimetric and Fluorescence Spectroscopic Study Membranes DSC fluorescence spectroscopy 1,2-benzothiazine derivatives oxicams piroxicam model membranes |
| title | Interaction of Oxicam Derivatives with the Artificial Models of Biological Membranes—Calorimetric and Fluorescence Spectroscopic Study |
| title_full | Interaction of Oxicam Derivatives with the Artificial Models of Biological Membranes—Calorimetric and Fluorescence Spectroscopic Study |
| title_fullStr | Interaction of Oxicam Derivatives with the Artificial Models of Biological Membranes—Calorimetric and Fluorescence Spectroscopic Study |
| title_full_unstemmed | Interaction of Oxicam Derivatives with the Artificial Models of Biological Membranes—Calorimetric and Fluorescence Spectroscopic Study |
| title_short | Interaction of Oxicam Derivatives with the Artificial Models of Biological Membranes—Calorimetric and Fluorescence Spectroscopic Study |
| title_sort | interaction of oxicam derivatives with the artificial models of biological membranes calorimetric and fluorescence spectroscopic study |
| topic | DSC fluorescence spectroscopy 1,2-benzothiazine derivatives oxicams piroxicam model membranes |
| url | https://www.mdpi.com/2077-0375/12/8/791 |
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