A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes
Biological membranes are complex dynamic systems composed of a great variety of carbohydrates, lipids, and proteins, which together play a pivotal role in the protection of organisms and through which the interchange of different substances is regulated in the cell. Given the complexity of membranes...
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| Format: | Article |
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MDPI AG
2021-06-01
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| Series: | Membranes |
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| Online Access: | https://www.mdpi.com/2077-0375/11/6/449 |
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| author | Alberto Aragón-Muriel Yamil Liscano David Morales-Morales Dorian Polo-Cerón Jose Oñate-Garzón |
| author_facet | Alberto Aragón-Muriel Yamil Liscano David Morales-Morales Dorian Polo-Cerón Jose Oñate-Garzón |
| author_sort | Alberto Aragón-Muriel |
| collection | DOAJ |
| description | Biological membranes are complex dynamic systems composed of a great variety of carbohydrates, lipids, and proteins, which together play a pivotal role in the protection of organisms and through which the interchange of different substances is regulated in the cell. Given the complexity of membranes, models mimicking them provide a convenient way to study and better understand their mechanisms of action and their interactions with biologically active compounds. Thus, in the present study, a new Schiff base (<i>Bz-Im</i>) derivative from 2-(<i>m</i>-aminophenyl)benzimidazole and 2,4-dihydroxybenzaldehyde was synthesized and characterized by spectroscopic and spectrometric techniques. Interaction studies of (<i>Bz-Im</i>) with two synthetic membrane models prepared with 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and DMPC/1,2-dimyristoyl-sn-glycero-3-phosphoglycerol (DMPG) 3:1 mixture, imitating eukaryotic and prokaryotic membranes, respectively, were performed by applying differential scanning calorimetry (DSC). Molecular dynamics simulations were also developed to better understand their interactions. In vitro and in silico assays provided approaches to understand the effect of <i>Bz-Im</i> on these lipid systems. The DSC results showed that, at low compound concentrations, the effects were similar in both membrane models. By increasing the concentration of <i>Bz-Im</i>, the DMPC/DMPG membrane exhibited greater fluidity as a result of the interaction with <i>Bz-Im</i>. On the other hand, molecular dynamics studies carried out on the erythrocyte membrane model using the phospholipids POPE (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine), SM (N-(15Z-tetracosenoyl)-sphing-4-enine-1-phosphocholine), and POPC (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) revealed that after 30 ns of interaction, both hydrophobic interactions and hydrogen bonds were responsible for the affinity of <i>Bz-Im</i> for PE and SM. The interactions of the imine with POPG (1-Palmitoyl-2-Oleoyl-sn-Glycero-3-Phosphoglycerol) in the <i>E. coli</i> membrane model were mainly based on hydrophobic interactions. |
| first_indexed | 2024-03-10T10:22:38Z |
| format | Article |
| id | doaj.art-966f590a7066444582d9dd5f2ba03df8 |
| institution | Directory Open Access Journal |
| issn | 2077-0375 |
| language | English |
| last_indexed | 2024-03-10T10:22:38Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Membranes |
| spelling | doaj.art-966f590a7066444582d9dd5f2ba03df82023-11-22T00:17:47ZengMDPI AGMembranes2077-03752021-06-0111644910.3390/membranes11060449A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian MembranesAlberto Aragón-Muriel0Yamil Liscano1David Morales-Morales2Dorian Polo-Cerón3Jose Oñate-Garzón4Laboratorio de Investigación en Catálisis y Procesos (LICAP), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad del Valle, Cali 760031, ColombiaGrupo de Investigación en Química y Biotecnología (QUIBIO), Facultad de Ciencias Básicas, Universidad Santiago de Cali, Cali 760035, ColombiaInstituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Circuito Exterior, Coyoacán, Mexico D.F. 04510, MexicoLaboratorio de Investigación en Catálisis y Procesos (LICAP), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad del Valle, Cali 760031, ColombiaGrupo de Investigación en Química y Biotecnología (QUIBIO), Facultad de Ciencias Básicas, Universidad Santiago de Cali, Cali 760035, ColombiaBiological membranes are complex dynamic systems composed of a great variety of carbohydrates, lipids, and proteins, which together play a pivotal role in the protection of organisms and through which the interchange of different substances is regulated in the cell. Given the complexity of membranes, models mimicking them provide a convenient way to study and better understand their mechanisms of action and their interactions with biologically active compounds. Thus, in the present study, a new Schiff base (<i>Bz-Im</i>) derivative from 2-(<i>m</i>-aminophenyl)benzimidazole and 2,4-dihydroxybenzaldehyde was synthesized and characterized by spectroscopic and spectrometric techniques. Interaction studies of (<i>Bz-Im</i>) with two synthetic membrane models prepared with 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and DMPC/1,2-dimyristoyl-sn-glycero-3-phosphoglycerol (DMPG) 3:1 mixture, imitating eukaryotic and prokaryotic membranes, respectively, were performed by applying differential scanning calorimetry (DSC). Molecular dynamics simulations were also developed to better understand their interactions. In vitro and in silico assays provided approaches to understand the effect of <i>Bz-Im</i> on these lipid systems. The DSC results showed that, at low compound concentrations, the effects were similar in both membrane models. By increasing the concentration of <i>Bz-Im</i>, the DMPC/DMPG membrane exhibited greater fluidity as a result of the interaction with <i>Bz-Im</i>. On the other hand, molecular dynamics studies carried out on the erythrocyte membrane model using the phospholipids POPE (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine), SM (N-(15Z-tetracosenoyl)-sphing-4-enine-1-phosphocholine), and POPC (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) revealed that after 30 ns of interaction, both hydrophobic interactions and hydrogen bonds were responsible for the affinity of <i>Bz-Im</i> for PE and SM. The interactions of the imine with POPG (1-Palmitoyl-2-Oleoyl-sn-Glycero-3-Phosphoglycerol) in the <i>E. coli</i> membrane model were mainly based on hydrophobic interactions.https://www.mdpi.com/2077-0375/11/6/449model membranesmolecular dynamicscalorimetrySchiff baseiminebenzimidazole |
| spellingShingle | Alberto Aragón-Muriel Yamil Liscano David Morales-Morales Dorian Polo-Cerón Jose Oñate-Garzón A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes Membranes model membranes molecular dynamics calorimetry Schiff base imine benzimidazole |
| title | A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes |
| title_full | A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes |
| title_fullStr | A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes |
| title_full_unstemmed | A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes |
| title_short | A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes |
| title_sort | study of the interaction of a new benzimidazole schiff base with synthetic and simulated membrane models of bacterial and mammalian membranes |
| topic | model membranes molecular dynamics calorimetry Schiff base imine benzimidazole |
| url | https://www.mdpi.com/2077-0375/11/6/449 |
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