Local partition coefficients govern solute permeability of cholesterol-containing membranes

Biophysical Journal

Volumn 105, Issue 12, 2013, Pages 2760-2770

  Zocher, Florian ^a   Van Der Spoel, David ^b,c   Pohl, Peter ^a   Hub, Jochen S ^d  

^a JOHANNES KEPLER UNIVERSITY LINZ   (Austria)

^b UPPSALA UNIVERSITY   (Sweden)

^c SCIENCE FOR LIFE LABORATORY   (Sweden)

^d UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL;

ARTICLE; CELL MEMBRANE PERMEABILITY; CHEMISTRY; DIFFUSION; LIPID BILAYER; METABOLISM; MOLECULAR DYNAMICS;

CELL MEMBRANE PERMEABILITY; CHOLESTEROL; FACILITATED DIFFUSION; LIPID BILAYERS; MOLECULAR DYNAMICS SIMULATION;

EID: 84890648633     PISSN: 00063495     EISSN: 15420086     Source Type: Journal    
DOI: 10.1016/j.bpj.2013.11.003     Document Type: Article

References (62)

1. D.W. Deamer, and J. Bramhall Permeability of lipid bilayers to water and ionic solutes Chem. Phys. Lipids 40 1986 167 188
2. S. Paula, and A.G. Volkov D.W. Deamer Permeation of protons, potassium ions, and small polar molecules through phospholipid bilayers as a function of membrane thickness Biophys. J. 70 1996 339 348
3. J.C. Mathai, and A. Missner P. Pohl No facilitator required for membrane transport of hydrogen sulfide Proc. Natl. Acad. Sci. USA 106 2009 16633 16638
4. A. Missner, and P. Kügler P. Pohl Carbon dioxide transport through membranes J. Biol. Chem. 283 2008 25340 25347
5. J. Gutknecht, and D.C. Tosteson Diffusion of weak acids across lipid bilayer membranes: effects of chemical reactions in the unstirred layers Science 182 1973 1258 1261
6. S.M. Saparov, and K. Liu P. Pohl Fast and selective ammonia transport by aquaporin-8 J. Biol. Chem. 282 2007 5296 5301
7. E.E. Pohl, and A.V. Krylov P. Pohl Changes of the membrane potential profile induced by verapamil and propranolol Biochim. Biophys. Acta 1373 1998 170 178
8. S.M. Saparov, Y.N. Antonenko, and P. Pohl A new model of weak acid permeation through membranes revisited: does Overton still rule? Biophys. J. 90 2006 L86 L88
9. A. Seelig The role of size and charge for blood-brain barrier permeation of drugs and fatty acids J. Mol. Neurosci. 33 2007 32 41
10. K. Sugano, and M. Kansy F. Senner Coexistence of passive and carrier-mediated processes in drug transport Nat. Rev. Drug Discov. 9 2010 597 614
11. A. Missner, and P. Pohl 110 years of the Meyer-Overton rule: predicting membrane permeability of gases and other small compounds ChemPhysChem 10 2009 1405 1414
12. W.R. Lieb, and W.D. Stein Non-Stokesian nature of transverse diffusion within human red cell membranes J. Membr. Biol. 92 1986 111 119
13. T.X. Xiang, and B.D. Anderson The relationship between permeant size and permeability in lipid bilayer membranes J. Membr. Biol. 140 1994 111 122
14. M. Luxnat, and H.J. Galla Partition of chlorpromazine into lipid bilayer membranes: the effect of membrane structure and composition Biochim. Biophys. Acta 856 1986 274 282
15. R.S. Cantor Bilayer partition coefficients of alkanols: predicted effects of varying lipid composition J. Phys. Chem. B 105 2001 7550 7553
16. S.J. Marrink, and H.J.C. Berendsen Permeation process of small molecules across lipid-membranes studied by molecular-dynamics simulations J. Phys. Chem. 100 1996 16729 16738
17. C.L. Wennberg, D. van der Spoel, and J.S. Hub Large influence of cholesterol on solute partitioning into lipid membranes J. Am. Chem. Soc. 134 2012 5351 5361
18. J.F. Nagle, and J.C. Mathai S. Tristram-Nagle Theory of passive permeability through lipid bilayers J. Gen. Physiol. 131 2008 77 85
19. S.J. Marrink, and H.J.C. Berendsen Simulation of water transport through a lipid membrane J. Phys. Chem. 98 1994 4155 4168
20. J.C. Mathai, and S. Tristram-Nagle M.L. Zeidel Structural determinants of water permeability through the lipid membrane J. Gen. Physiol. 131 2008 69 76
21. M. Montal, and P. Mueller Formation of bimolecular membranes from lipid monolayers and a study of their electrical properties Proc. Natl. Acad. Sci. USA 69 1972 3561 3566
22. J.S. Hub, and F.K. Winkler B.L. de Groot Potentials of mean force and permeabilities for carbon dioxide, ammonia, and water flux across a Rhesus protein channel and lipid membranes J. Am. Chem. Soc. 132 2010 13251 13263
23. J.P. Ulmschneider, and M.B. Ulmschneider United atom lipid parameters for combination with the optimized potentials for liquid simulations all-atom force field J. Chem. Theory Comput. 5 2009 1803 1813
24. W.L. Jorgensen, and J. Chandrasekhar M.L. Klein Comparison of simple potential functions for simulating liquid water J. Chem. Phys. 79 1983 926 935
25. D. van der Spoel, and E. Lindahl H.J.C. Berendsen GROMACS: fast, flexible, and free J. Comput. Chem. 26 2005 1701 1718
26. B. Hess, and C. Kutzner E. Lindahl GROMACS 4: algorithms for highly efficient, load-balanced, and scalable molecular simulation J. Chem. Theory Comput. 4 2008 435 447
27. O. Berger, O. Edholm, and F. Jähnig Molecular dynamics simulations of a fluid bilayer of dipalmitoylphosphatidylcholine at full hydration, constant pressure, and constant temperature Biophys. J. 72 1997 2002 2013
28. M. Höltje, and T. Förster H.D. Höltje Molecular dynamics simulations of stratum corneum lipid models: fatty acids and cholesterol Biochim. Biophys. Acta 1511 2001 156 167
29. W.L. Jorgensen, D.S. Maxwell, and J. Tirado-Rives Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids J. Am. Chem. Soc. 118 1996 11225 11236
30. G.A. Kaminski, and R.A. Friesner W.L. Jorgensen Evaluation and reparameterization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides J. Phys. Chem. B 105 2001 6474 6487
31. D. Shivakumar, and J. Williams W. Sherman Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the OPLS force field J. Chem. Theory Comput. 6 2010 1509 1519
32. 2, CO, NO, and Xe inside myoglobin Biophys. J. 91 2006 1844 1857
33. A.D. Becke Density-functional exchange-energy approximation with correct asymptotic behavior Phys. Rev. A 38 1988 3098 3100
34. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B Condens. Matter 37 1988 785 789
35. A.D. Becke Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98 1993 5648 5652
36. R.A. Kendall, J. Dunning, and R.J. Harrison Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions J. Chem. Phys. 96 1992 6796 6806
37. D.E. Woon, and J. Dunning Benchmark calculations with correlated molecular wave functions. I. Multireference configuration interaction calculations for the second row diatomic hydrides J. Chem. Phys. 99 1993 1914 1929
38. M.J. Frisch, and G.W. Trucks J.A. Pople Gaussian 03, Rev. C.02 2004 Gaussian Wallingford, CT
39. U.C. Singh, and P.A. Kollman An approach to computing electrostatic charges for molecules J. Comput. Chem. 5 1984 129 145
40. B. Besler, K. Merz, and P. Kollman Atomic charges derived from semiempirical methods J. Comput. Chem. 11 1990 431 439
41. G. Bussi, D. Donadio, and M. Parrinello Canonical sampling through velocity rescaling J. Chem. Phys. 126 2007 014101
42. H.J.C. Berendsen, and J.P.M. Postma J.R. Haak Molecular dynamics with coupling to an external bath J. Chem. Phys. 81 1984 3684 3690
43. S. Miyamoto, and P. Kollman SETTLE: an analytical version of the SHAKE and RATTLE algorithm for rigid water models J. Comput. Chem. 13 1992 952 962
44. B. Hess P-LINCS: a parallel linear constraint solver for molecular simulation J. Chem. Theory Comput. 4 2007 116 122
45. T. Darden, D. York, and L. Pedersen Particle mesh Ewald: an N-log(N) method for Ewald sums in large systems J. Chem. Phys. 98 1993 10089 10092
46. U. Essmann, and L. Perera L. Pedersen A smooth particle mesh Ewald method J. Chem. Phys. 103 1995 8577 8593
47. M. Parrinello, and A. Rahman Polymorphic transitions in single crystals: a new molecular dynamics method J. Appl. Phys. 52 1981 7182 7190
48. S. Kumar, and J. Rosenberg P. Kollman The weighted histogram analysis method for free-energy calculations on biomolecules. I. The method J. Comput. Chem. 13 1992 1011 1021
49. J.S. Hub, B.L. de Groot, and D. van der Spoel G-WHAM-A-free weighted histogram analysis implementation including robust error and autocorrelation estimates J. Chem. Theory Comput. 6 2010 3713 3720
50. B. Hess Determining the shear viscosity of model liquids from molecular dynamics simulations J. Chem. Phys. 116 2002 209 217
51. Y.N. Antonenko, P. Pohl, and G.A. Denisov Permeation of ammonia across bilayer lipid membranes studied by ammonium ion selective microelectrodes Biophys. J. 72 1997 2187 2195
52. + Biochim. Biophys. Acta 255 1972 321 330
53. M.B. Lande, J.M. Donovan, and M.L. Zeidel The relationship between membrane fluidity and permeabilities to water, solutes, ammonia, and protons J. Gen. Physiol. 106 1995 67 84
54. M. Jurak Thermodynamic aspects of cholesterol effect on properties of phospholipid monolayers: Langmuir and Langmuir-Blodgett monolayer study J. Phys. Chem. B 117 2013 3496 3502
55. A. Horner, and F. Goetz P. Pohl Mechanism for targeting the A-kinase anchoring protein AKAP18δ to the membrane J. Biol. Chem. 287 2012 42495 42501
56. G. Lindblom, L.B.A. Johansson, and G. Arvidson Effect of cholesterol in membranes. Pulsed nuclear magnetic resonance measurements of lipid lateral diffusion Biochemistry 20 1981 2204 2207
57. N. Kahya, and P. Schwille How phospholipid-cholesterol interactions modulate lipid lateral diffusion, as revealed by fluorescence correlation spectroscopy J. Fluoresc. 16 2006 671 678
58. M.H. Abraham, and H.S. Chadha R.C. Mitchell Hydrogen bonding: an analysis of water-octanol and water-alkane partitioning and the Δlog P parameter of Seiler J. Pharm. Sci. 83 1994 1085 1100
59. T. Róg, and M. Pasenkiewicz-Gierula M. Karttunen Ordering effects of cholesterol and its analogues Biochim. Biophys. Acta 1788 2009 97 121
60. 2 permeability of cell membranes is regulated by membrane cholesterol and protein gas channels FASEB J. 26 2012 5182 5191
61. 2 transport through urothelium J. Biol. Chem. 287 2012 11011 11017
62. D. Fulton, J.P. Gratton, and W.C. Sessa Post-translational control of endothelial nitric oxide synthase: why isn't calcium/calmodulin enough? J. Pharmacol. Exp. Ther. 299 2001 818 824