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Interaction of 7-Nitrobenz-2-oxa-1,3-diazol-4-yl-Labeled Fatty Amines with 1-Palmitoyl, 2-Oleoyl-sn-glycero-3-phosphocholine Bilayers: A Molecular Dynamics Study

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Centro de Química de Coimbra, Universidade de Coimbra, Largo D. Dinis, Rua Larga, 3004-535 Coimbra, Portugal
Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, Largo D. Dinis, Rua Larga, 3004-535 Coimbra, Portugal
Faculdade de Farmácia, Universidade de Coimbra, Pólo das Ciências da Saúde, Azinhaga de Santa Comba, 3000-548 Coimbra, Portugal
Telephone: +351 239488485. Fax: +351 239827126. E-mail: [email protected]
Cite this: J. Phys. Chem. B 2011, 115, 33, 10109–10119
Publication Date (Web):July 12, 2011
https://doi.org/10.1021/jp203532c
Copyright © 2011 American Chemical Society
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Abstract

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A complete homologous series of fluorescent 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD)-labeled fatty amines of varying alkyl chain length, NBD-Cn, inserted in 1-palmitoyl, 2-oleoyl-sn-glycero-3-phosphocholine (POPC) bilayers, was studied using atomistic molecular dynamics (MD) simulations. For all amphiphiles, the NBD fluorophore locates near the glycerol backbone/carbonyl region of POPC and establishes stable hydrogen bonding with POPC ester oxygen atoms. Small differences observed in the transverse location of the fluorophore correlate with other calculated parameters and with small discrepancies recently measured in the photophysical properties of the molecules. The longer-chained NBD-Cn amphiphiles show significant mass density near the bilayer midplane, and the chains of these derivatives interdigitate to some extent the opposite bilayer leaflet. This phenomenon leads to a slower lateral diffusion for the longer-chained derivatives (n > 12). Effects of these amphiphiles on the structure and dynamics of the host lipid were found to be relatively mild, in comparison with acyl-chain-labeled NBD probes. The molecular details obtained by this work allow the rationalization of the nonmonotonic behavior, recently obtained experimentally, for the photophysical parameters of the amphiphiles and the kinetic and thermodynamic parameters for their interaction with the POPC membranes.

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Time variation of area/lipid for all systems; correlation between short axis to bilayer normal angle and transverse position of fluorophore; POPC order parameter profiles. This material is available free of charge via the Internet at http://pubs.acs.org.

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Cited By

This article is cited by 24 publications.

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  2. João R. Robalo, J. P. Prates Ramalho, and Luís M. S. Loura . NBD-Labeled Cholesterol Analogues in Phospholipid Bilayers: Insights from Molecular Dynamics. The Journal of Physical Chemistry B 2013, 117 (44) , 13731-13742. https://doi.org/10.1021/jp406135a
  3. Alexander Kyrychenko and Alexey S. Ladokhin . Molecular Dynamics Simulations of Depth Distribution of Spin-Labeled Phospholipids within Lipid Bilayer. The Journal of Physical Chemistry B 2013, 117 (19) , 5875-5885. https://doi.org/10.1021/jp4026706
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  5. David Poger and Alan E. Mark . Lipid Bilayers: The Effect of Force Field on Ordering and Dynamics. Journal of Chemical Theory and Computation 2012, 8 (11) , 4807-4817. https://doi.org/10.1021/ct300675z
  6. Hugo A. L. Filipe, Maria João Moreno, Luís M. S. Loura. The Secret Lives of Fluorescent Membrane Probes as Revealed by Molecular Dynamics Simulations. Molecules 2020, 25 (15) , 3424. https://doi.org/10.3390/molecules25153424
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  9. Moirangthem Kiran Singh, Him Shweta, Sobhan Sen. New Family of Fluorescent Probes for Characterizing Depth-Dependent Static and Dynamic Properties of Lipid/Water Interfaces. 2020,,, 161-187. https://doi.org/10.1007/978-1-0716-0631-5_10
  10. Patrícia A.T. Martins, Neuza Domingues, Cristiana Pires, Ana Maria Alves, Tiago Palmeira, Jaime Samelo, Renato Cardoso, Adrian Velazquez-Campoy, Maria João Moreno. Molecular crowding effects on the distribution of amphiphiles in biological media. Colloids and Surfaces B: Biointerfaces 2019, 180 , 319-325. https://doi.org/10.1016/j.colsurfb.2019.04.065
  11. Hugo A. L. Filipe, Šárka Pokorná, Martin Hof, Mariana Amaro, Luís M. S. Loura. Orientation of nitro-group governs the fluorescence lifetime of nitrobenzoxadiazole (NBD)-labeled lipids in lipid bilayers. Physical Chemistry Chemical Physics 2019, 21 (4) , 1682-1688. https://doi.org/10.1039/C8CP06064A
  12. Filipe M. Coreta-Gomes, Winchil L. C. Vaz, Maria J. Moreno. Effect of Acyl Chain Length on the Rate of Phospholipid Flip-Flop and Intermembrane Transfer. The Journal of Membrane Biology 2018, 251 (3) , 431-442. https://doi.org/10.1007/s00232-017-0009-4
  13. Yevgen Posokhov, Alexander Kyrychenko. Location of fluorescent probes (2′-hydroxy derivatives of 2,5-diaryl-1,3-oxazole) in lipid membrane studied by fluorescence spectroscopy and molecular dynamics simulation. Biophysical Chemistry 2018, 235 , 9-18. https://doi.org/10.1016/j.bpc.2018.01.005
  14. Roland Faller. Molecular modeling of lipid probes and their influence on the membrane. Biochimica et Biophysica Acta (BBA) - Biomembranes 2016, 1858 (10) , 2353-2361. https://doi.org/10.1016/j.bbamem.2016.02.014
  15. Mariusz Kepczynski, Tomasz Róg. Functionalized lipids and surfactants for specific applications. Biochimica et Biophysica Acta (BBA) - Biomembranes 2016, 1858 (10) , 2362-2379. https://doi.org/10.1016/j.bbamem.2016.02.038
  16. Mariana Amaro, Hugo A. L. Filipe, J. P. Prates Ramalho, Martin Hof, Luís M. S. Loura. Fluorescence of nitrobenzoxadiazole (NBD)-labeled lipids in model membranes is connected not to lipid mobility but to probe location. Physical Chemistry Chemical Physics 2016, 18 (10) , 7042-7054. https://doi.org/10.1039/C5CP05238F
  17. Moirangthem Kiran Singh, Him Shweta, Mohammad Firoz Khan, Sobhan Sen. New insight into probe-location dependent polarity and hydration at lipid/water interfaces: comparison between gel- and fluid-phases of lipid bilayers. Physical Chemistry Chemical Physics 2016, 18 (35) , 24185-24197. https://doi.org/10.1039/C6CP01201A
  18. Athanassios Karkabounas, Dimitra G. Georgiadou, Panagiotis Argitis, Vassilios Psycharis, George Nakos, Agni M. Kosmas, Marilena E. Lekka. Immobilization of Lipid Substrates: Application on Phospholipase A2 Determination. Lipids 2015, 50 (12) , 1259-1271. https://doi.org/10.1007/s11745-015-4076-y
  19. Alexander Kyrychenko, Mykola V. Rodnin, Alexey S. Ladokhin. Calibration of Distribution Analysis of the Depth of Membrane Penetration Using Simulations and Depth-Dependent Fluorescence Quenching. The Journal of Membrane Biology 2015, 248 (3) , 583-594. https://doi.org/10.1007/s00232-014-9709-1
  20. Hugo A. L. Filipe, Lennon S. Santos, J. P. Prates Ramalho, Maria João Moreno, Luís M. S. Loura. Behaviour of NBD-head group labelled phosphatidylethanolamines in POPC bilayers: a molecular dynamics study. Physical Chemistry Chemical Physics 2015, 17 (31) , 20066-20079. https://doi.org/10.1039/C5CP01596K
  21. João R. Robalo, J. P. Prates Ramalho, Daniel Huster, Luís M. S. Loura. Influence of the sterol aliphatic side chain on membrane properties: a molecular dynamics study. Physical Chemistry Chemical Physics 2015, 17 (35) , 22736-22748. https://doi.org/10.1039/C5CP03097H
  22. Hugo A. L. Filipe, David Bowman, Tiago Palmeira, Renato M. S. Cardoso, Luís M. S. Loura, Maria João Moreno. Interaction of NBD-labelled fatty amines with liquid-ordered membranes: a combined molecular dynamics simulation and fluorescence spectroscopy study. Physical Chemistry Chemical Physics 2015, 17 (41) , 27534-27547. https://doi.org/10.1039/C5CP04191K
  23. Luís M.S. Loura, António M.T. Martins do Canto, Jorge Martins. Sensing hydration and behavior of pyrene in POPC and POPC/cholesterol bilayers: A molecular dynamics study. Biochimica et Biophysica Acta (BBA) - Biomembranes 2013, 1828 (3) , 1094-1101. https://doi.org/10.1016/j.bbamem.2012.12.014
  24. Luís Loura. Lateral Distribution of NBD-PC Fluorescent Lipid Analogs in Membranes Probed by Molecular Dynamics-Assisted Analysis of Förster Resonance Energy Transfer (FRET) and Fluorescence Quenching. International Journal of Molecular Sciences 2012, 13 (12) , 14545-14564. https://doi.org/10.3390/ijms131114545

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