Abstract
The interactions of methanol with lipid bilayers were studied by means of molecular dynamics (MD) simulations. Our MD simulations focus on the effect of ∼11.3 mol% methanol on two fully hydrated dipalmitoylphosphatidylcholine (DPPC) and palmitoyloleoylphosphatidylcholine (POPC) lipid bilayers both in the fluid phase and under equilibrium conditions at 323 and 298 K, respectively. The effects of methanol on bilayers structural characteristics were investigated. In both systems the simulations show that the presence of relatively high concentration of methanol leads to a significant increase in the area per lipid. The increase in the area per lipid is accompanied by a corresponding decrease of the bilayer thickness such that the volume occupied per lipid does not change significantly in the presence of methanol. Other properties such as ordering of phospholipid tails and lateral diffusion of the lipids are also affected significantly by the presence of methanol. Consistent with other previously reported MD simulation studies of bilayers in the presence of methanol (albeit at a significantly smaller concentration of 1 mol%) our study shows very few hydrogen bonding formation between lipids and methanol.
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REFERENCES
Bandyopadhyay, S., M. Tarek, and M. L. Klein. Computer simulation studies of amphiphilic interfaces. Curr. Opin. Coll. Int. Sci. 3:242–246, 1998.
Bemporad, D., J. W. Essex, and C. Luttmann. Permeation of small molecules through a lipid bilayer: a computer simulation study. J. Phys. Chem. B. 108:4875–4884, 2004.
Berendsen, H. J. C., J. P. M. Postma, W. F. van Gunsteren, and J. Hermans. Interaction Models for Water in Relation to Protein Hydration, In B. Pullman, editor, Intermolecular Forces, Reidel, Dordrecht, 331–342, 1981.
Berendsen, H. J. C., J. P. M. Postma, W. F. van Gunsteren, A. DiNola, and J. R. Haak. Molecular dynamics coupling to an external bath. J. Chem. Phys. 81:3684–3690, 1984.
Berneche, S., M. Nina, and B. Roux. Molecular dynamics simulation of melittin in a dimyristoylphosphatidylcholine bilayer membrane. Biophys. J. 75:1603–1618, 1998.
Berger, O., O. Edholm, and F. Jahnig. Molecular dynamics simulations of a fluid bilayer of dipalmitoylphosphatidylcholine at full hydration, constant pressure and constant temperature. Biophys. J. 72:2002–2013, 1997.
Borin, I. A., and M. S. Skaf. Molecular association between water and dimethylsulfoxide in solution: A molecular dynamics simulation study. J. of Chem. Phys. 110:6412–6420, 1999.
Devireddy, R. V., B. Fahrig, R. A. Godke, and S. P. Leibo. Subzero water transport characteristics of boar spermatozoa confirm observed optimal cooling rates. Mol. Reprod. Dev. 67:446–457, 2004.
Devireddy, R. V. Predicted permeability parameters of human ovarian tissue cells to various cryoprotectants and water. Mol. Reprod. Dev. 70:333–343, 2005.
Dicky, A. N., and R. Faller. Investigating interactions of biomembranes and alcohols: A multiscale approach. J. Polym. Sci. B 43:1025–1032, 2005.
Essman, U., L. Perera, M. L. Berkowitz, H. L. T. Darden, and L. G. Pedersen. A smooth particle mesh Ewald method. J. Chem. Phys. 103:8577–8593, 1995.
Feller, S. E., Z. Yuhong, and R. W. Pastor. Computer simulation of liquid/liquid interfaces. II. Surface tension-area dependence of a bilayer and monolayer. J. Chem. Phys. 103:10267–10276, 1995.
Feller, S. E., C. A. Brown, D. T. Nizza, and K. Gawrisch. Nuclear overhauser enhancement spectrotroscopy cross-relaxation rates and ethanol distribution across membranes. Biophys. J. 82:1396–1404, 2002.
He, Y., and R. V. Devireddy. An inverse approach to determine solute and solvent permeability parameters in artificial tissues. Ann. Biomed. Eng. 33:709–718, 2005.
Hess, B., H. Bekker, H. J. C. Berendsen, and J. G. E. M. Fraaije. LINCS: A linear constraint solver for molecular simulations. J. Comp. Chem. 18:1463–1472, 1997.
Hoff, B., E. Strandberg, A. S. Ulrich, D. P. Tieleman, and C. Posten. 2h-NMR study and molecular dynamics simulation of the location, alignment and mobility of pyrene in popc bilayers. Biophys. J. 88:1818–1827, 2005.
Lee, B. W., R. Faller, A. K. Sum, I. Vattulainen, M. Patra, and M. Karttunen. Structural effects of small molecules on phospholipids bilayers investigated by molecular simulations. Fluid Phase Equi. 225:63–68, 2004.
Lindahl, E., B. Hess, and D. van der Spoel. A package for molecular simulation and trajectory analysis. J. Mol. Mod. 7:306–317, 2001.
del Luzardo, M. C., F. Amalfa, A. M. Nunez, S. Diaz, A. C. deBiondi Lopez, and E. A. Disalvo. Effect of trehalose and sucrose on the hydration and dipole potential of lipid bilayers. 78:2452–2458, 2000.
Ly, H. V., D. E. Block, and M. L. Longo. Interfacial tension effect of ethanol on lipid bilayer rigidity, stability, and area/molecule: A micropipet aspiration approach. Langmuir 18:8988–8995, 2002.
Marrink, S. J., and H. J. C. Berendsen. Simulation of water transport through a lipid-membrane. J. Phys. Chem. 98:4155–4168, 1994.
Marrink, S. J., E. Lindahl, O. Edholm, and A. E. Mark. Simulation of the spontaneous aggregation of phospholipids into bilayers. J. Am. Chem. Soc. 123:8638–8639, 2001.
Martyna, G. J., M. E. Tuckerman, D. J. Tobias, and M. L. Klein. Explicit reversible integrators for extended systems dynamics. Mol. Phys. 87:1117–1157, 1996.
Merz, K. M., Jr., and B. Roux. Biological Membranes: A Molecular Perspective from Computation and Experiment. Birkhauser, Boston, 1996.
Mou, J., J. Yang, C. Huang, and Z. Shao. Alcohol induces interdigitated domains in unilamellar phosphatidylcholine bilayers. Biochemistrty. 33:9981–9985, 1994.
Nagle, J. F., and S. Tristram-Nagle. Structure of lipid bilayers. Biochim. Biophys. Acta. 1469:159–195, 2000.
Paci, E., and M. Marchi. Membrane crossing by a polar molecule: A molecular dynamics simulation. Mol. Simul. 14:1–10, 1994.
Pasenkiewicz-Gierula, M., T. Rog, J. Grochowski, P. Serda, R. Czarnecki, R. Librowski, and S. Lochyski. Effects of a carane derivative local anesthetic on a phospholipids bilayer studied by molecular dynamics simulation. Biophys. J. 85:1248–1258, 2003.
Patra, M., M. Karttunen, M. T. Hyvonen, E. Falck, P. Lindqvist, and I. Vattulainen. Molecular dynamics simulations of lipid bilayers: Major artifacts due to electrostatic intercations. Biophys. J. 84:3636–3645, 2003.
Patra, M., E. Salonen, E. Terama, I. Vattulainen, R. Faller, B. W. Lee, J. Holopainen, and M. Karttunen. Under the influence of alcohol: The effect of ethanol and methanol on lipid bilayers. arXiv.org:cond-mat/0408122 (2004).
Pereira, C. S., R. D. Lins, I. Chandrasekhar, L. C. G. Freitas, and P. H. Hunenberger. Interaction of the disaccharide trehalose with a phospholipids bilayer: A molecular dynamics simulation study. Biophys. J. 86:2273–2285, 2004.
Pickholz, M., L. Saiz, and M. L. Klein. Concentration effects of volatile anesthetics on the properties of model membranes: A coarse-grain approach. Biophys. J. 88:1524–1534, 2005.
Pinisetty, D., C. Huang, Q. Dong, T. Tiersch, and R. V. Devireddy. Subzero water permeability parameters and optimal freezing rates for sperm cells of the southern platyfish, Xiphophorus maculatus. Cryobiology 50:250–263, 2005.
Polge, C., A. U. Smith, and A. S. Parks. Revival of spermatozoa after vitrification and dehydration at low temperatures. Nature 164:666–676, 1949.
Repakova, J., P. Capkova, J. M. Holopainen, and I. Vattulainen. Distribution, orientation and dynamics of DPH probes in DPPC bilayer. J. Phys. Chem. B 108:13438–13448, 2004.
Rog, T., and M. Pasenkiewicz-Gierula. Cholesterol effects on the phosphatidylcholine bilayer non-polar region: A molecular simulation study. Biophys. J. 81:2190–2202, 2001.
Saiz, L., and M. L. Klein. Structural properties of a highly polyunsaturated lipid bilayer from molecular dynamics simulations. Biophys. J. 81:204–216, 2001.
Schlichter, J., J. Friedrich, L. Herenyi, and J. Fidy. Trehalose effect on low temperature protein dynamics: Fluctuation and relaxation phenomena. Biophys. J. 80:2011–2017, 2001.
Smondyrev, A. M., and M. L. Berkowitz. Molecular dynamics simulation of DPPC bilayer in DMSO. Biophys. J. 76:2472–2478, 1999.
Song Guallar, Y. V., and N. A. Baker. Molecular dynamics simulations of saliculate effects on the micro-and mesoscopic properties of dipalmitoylphosphatidylcholine bilayers. Biochemistry 44:13425–13438, 2005.
Sum, A. K., R. Faller, and J. J. de Pablo. Molecular simulation study of phospholipid bilayers and insights of the interactions with disaccharides. Biophys. J. 85:2830–2844, 2003.
Sum, A. K., and J. J. de Pablo. Molecular simulation study on the influence of dimethylsulfoxide on the structure of phospholipid bilayers. Biophys. J. 85:3636–3645, 2003.
Tieleman, D. P., and H. J. C. Berendsen. Molecular dynamics simulations of a fully hydrated dipalmitoylphosphatidycholine bilayer with different macroscopic boundary conditions and parameters. J. Chem. Phys. 105:4871–4880, 1996.
Tieleman, D. P., S. J. Marrink, and H. J. C. Berendsen. A computer perspective of membranes: molecular dynamics studies of lipid bilayer systems. Biochim. Biophys. Acta. 1331:235–270, 1997.
Thirumala, S., and R. V. Devireddy. A simplified to determine the optimal rate of freezing biological systems. ASME J. Biomech. Eng. 127:295–300, 2005.
Villarreal, M. A., S. B. Diaz, E. Anibal Disalvo, and G. G. Montich. Molecular dynamics simulation study of the interaction of trehalose with lipid membranes. Langmuir 20:7844–7851, 2004.
ACKNOWLEDGMENTS
This work was supported in part by grants from the Louisiana Board of Regents to DM {LEQSF 2003-06–RD–A–13} and to RD {LEQSF 2002-05–RD–A–03}. We would also like to thank Dr. M. Patra for numerous helpful suggestions and consistent expert advice
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Pinisetty, D., Moldovan, D. & Devireddy, R. The Effect of Methanol on Lipid Bilayers: An Atomistic Investigation. Ann Biomed Eng 34, 1442–1451 (2006). https://doi.org/10.1007/s10439-006-9148-y
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DOI: https://doi.org/10.1007/s10439-006-9148-y