Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/113183
DC Field | Value | Language |
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dc.contributor.author | Filipe, Hugo A. L. | - |
dc.contributor.author | Loura, Luís M. S. | - |
dc.contributor.author | Moreno, Maria João | - |
dc.date.accessioned | 2024-02-08T10:26:47Z | - |
dc.date.available | 2024-02-08T10:26:47Z | - |
dc.date.issued | 2023-05-25 | - |
dc.identifier.issn | 2077-0375 | pt |
dc.identifier.uri | https://hdl.handle.net/10316/113183 | - |
dc.description.abstract | Permeation through biomembranes is ubiquitous for drugs to reach their active sites. Asymmetry of the cell plasma membrane (PM) has been described as having an important role in this process. Here we describe the interaction of a homologous series of 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD)-labeled amphiphiles (NBD-Cn, n = 4 to 16) with lipid bilayers of different compositions (1-palmitoyl, 2-oleoyl-sn-glycero-3-phosphocholine (POPC):cholesterol (1:1) and palmitoylated sphingomyelin (SpM):cholesterol (6:4)), including an asymmetric bilayer. Both unrestrained and umbrella sampling (US) simulations (at varying distances to the bilayer center) were carried out. The free energy profile of NBD-Cn at different depths in the membrane was obtained from the US simulations. The behavior of the amphiphiles during the permeation process was described regarding their orientation, chain elongation, and H-bonding to lipid and water molecules. Permeability coefficients were also calculated for the different amphiphiles of the series, using the inhomogeneous solubility-diffusion model (ISDM). Quantitative agreement with values obtained from kinetic modeling of the permeation process could not be obtained. However, for the longer, and more hydrophobic amphiphiles, the variation trend along the homologous series was qualitatively better matched by the ISDM when the equilibrium location of each amphiphile was taken as reference (ΔG = 0), compared to the usual choice of bulk water. | pt |
dc.language.iso | eng | pt |
dc.publisher | MDPI | pt |
dc.relation | UIDB/00313/2020 | pt |
dc.relation | UIDP/00313/2020 | pt |
dc.relation | CENTRO-04-3559-FSE-000162 | pt |
dc.rights | openAccess | pt |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | pt |
dc.subject | amphiphilic molecules | pt |
dc.subject | asymmetric lipid bilayers | pt |
dc.subject | lipid membranes | pt |
dc.subject | molecular dynamics simulations | pt |
dc.subject | nitrobenzoxadiazole | pt |
dc.subject | permeation | pt |
dc.subject | potential of mean force | pt |
dc.subject | umbrella sampling | pt |
dc.title | Permeation of a Homologous Series of NBD-Labeled Fatty Amines through Lipid Bilayers: A Molecular Dynamics Study | pt |
dc.type | article | - |
degois.publication.firstPage | 551 | pt |
degois.publication.issue | 6 | pt |
degois.publication.title | Membranes | pt |
dc.peerreviewed | yes | pt |
dc.identifier.doi | 10.3390/membranes13060551 | pt |
degois.publication.volume | 13 | pt |
dc.date.embargo | 2023-05-25 | * |
uc.date.periodoEmbargo | 0 | pt |
item.fulltext | Com Texto completo | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.languageiso639-1 | en | - |
item.openairetype | article | - |
item.cerifentitytype | Publications | - |
item.grantfulltext | open | - |
crisitem.project.grantno | Coimbra Chemistry Center | - |
crisitem.project.grantno | Coimbra Chemistry Center | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0001-6935-4307 | - |
crisitem.author.orcid | 0000-0002-1051-2312 | - |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais FFUC- Artigos em Revistas Internacionais I&D CQC - Artigos em Revistas Internacionais I&D CNC - Artigos em Revistas Internacionais |
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Permeation-of-a-Homologous-Series-of-NBDLabeled-Fatty-Amines-through-Lipid-Bilayers-A-Molecular-Dynamics-StudyMembranes.pdf | 3.24 MB | Adobe PDF | View/Open |
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