Interaction of salicylate and a terpenoid plant extract with model membranes: Reconciling experiments and simulations

Biophysical Journal

Volumn 99, Issue 12, 2010, Pages 3887-3894

  Khandelia, Himanshu ^a   Witzke, Sarah ^a   Mouritsen, Ole G ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

TETRA;

EID: 78650180773     PISSN: 00063495     EISSN: 15420086     Source Type: Journal    
DOI: 10.1016/j.bpj.2010.11.009     Document Type: Article

References (51)

1. Vane, J. R. 1971. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat. New Biol. 231:232-235.
2. Balasubramanian, S. V., R. M. Straubinger, and M. E. Morris. 1997. Salicylic acid induces changes in the physical properties of model and native kidney membranes. J. Pharm. Sci. 86:199-204.
3. Tomisato, W., K. Tanaka,., T. Mizushima. 2004. Membrane permeabilization by non-steroidal anti-inflammatory drugs. Biochem. Biophys. Res. Commun. 323:1032-1039.
4. Jung, T. T. K., C. K. Rhee,., D. C. Choi. 1993. Ototoxicity of salicylate, nonsteroidal antiinflammatory drugs, and quinine. Otolaryngol. Clin. North Am. 26:791-810.
5. Lichtenberger, L. M., Z. M. Wang,., J. C. Barreto. 1995. Non-steroidal anti-inflammatory drugs (NSAIDs) associate with zwitterionic phospholipids: insight into the mechanism and reversal of NSAID-induced gastrointestinal injury. Nat. Med. 1:154-158.
6. Søgaard, R., T. M. Werge,., J. A. Lundbaek. 2006. GABAA receptor function is regulated by lipid bilayer elasticity. Biochemistry. 45:13118-13129.
7. Lichtenberger, L. M., Y. Zhou,., R. M. Raphael. 2006. NSAID injury to the gastrointestinal tract: evidence that NSAIDs interact with phospholipids to weaken the hydrophobic surface barrier and induce the formation of unstable pores in membranes. J. Pharm. Pharmacol. 58:1421-1428.
8. Zhou, Y., and R. M. Raphael. 2005. Effect of salicylate on the elasticity, bending stiffness, and strength of SOPC membranes. Biophys. J. 89: 1789-1801.
9. Zhi, M., J. T. Ratnanather,., W. E. Brownell. 2007. Hypotonic swelling of salicylate-treated cochlear outer hair cells. Hear. Res. 228:95-104.
10. Greeson, J. N., and R. M. Raphael. 2009. Amphipath-induced nanoscale changes in outer hair cell plasma membrane curvature. Biophys. J. 96:510-520.
11. Fox, C. B., R. A. Horton, and J. M. Harris. 2006. Detection of drugmembrane interactions in individual phospholipid vesicles by confocal Raman microscopy. Anal. Chem. 78:4918-4924.
12. Kyrikou, I., S. K. Hadjikakou,., T. Mavromoustakos. 2004. Effects of non-steroid anti-inflammatory drugs in membrane bilayers. Chem. Phys. Lipids. 132:157-169.
13. Song, Y., V. Guallar, and N. A. Baker. 2005. Molecular dynamics simulations of salicylate effects on the micro- and mesoscopic properties of a dipalmitoylphosphatidylcholine bilayer. Biochemistry. 44: 13425-13438.
14. Böckmann, R. A., A. Hac,., H. Grubmüller. 2003. Effect of sodium chloride on a lipid bilayer. Biophys. J. 85:1647-1655.
15. Petrache, H. I., S. Tristram-Nagle,., V. A. Parsegian. 2006. Swelling of phospholipids by monovalent salt. J. Lipid Res. 47:302-309.
16. + counterions and NaCl. Biophys. J. 86:1601-1609.
17. Gurtovenko, A. A. 2005. Asymmetry of lipid bilayers induced by monovalent salt: atomistic molecular-dynamics study. J. Chem. Phys. 122:244902.
18. Gurtovenko, A. A., and I. Vattulainen. 2008. Effect of NaCl and KCl on phosphatidylcholine and phosphatidylethanolamine lipid membranes: insight from atomic-scale simulations for understanding salt-induced effects in the plasma membrane. J. Phys. Chem. B. 112:1953-1962.
19. +-lipid interactions and finite size effects. Biophys. J. 94: 3565-3576.
20. Zhao, W., T. Róg,., M. Karttunen. 2007. Atomic-scale structure and electrostatics of anionic palmitoyloleoylphosphatidylglycerol lipid bilayers with Na+ counterions. Biophys. J. 92:1114-1124.
21. Crowell, P. L., and M. N. Gould. 1994. Chemoprevention and therapy of cancer by d-limonene. Crit. Rev. Oncog. 5:1-22.
22. Marostica, M. R., and G. M. Pastore. 2009. Limonene and its oxyfunctionalized compounds: biotransformation by microorganisms and their role as functional bioactive compounds. Food Sci. Biotechnol. 18:833-841.
23. Berger, O., O. Edholm, and F. Jähnig. 1997. Molecular dynamics simulations of a fluid bilayer of dipalmitoylphosphatidylcholine at full hydration, constant pressure, and constant temperature. Biophys. J. 72:2002-2013.
24. Berendsen, H. J. C., J. P. M. Postma,., J. Hermans. 1981. Interaction models for water in relation to protein hydration. In Intermolecular Forces (Jerusalem Symposia). B. Pullman, editor. Springer, New York. 331-342.
25. Witzke, S., L. Duelund,., H. Khandelia. 2010. Inclusion of terpenoid plant extracts in lipid bilayers investigated by molecular dynamics simulations. J. Phys. Chem. B., 2010 Nov 11. [Epub ahead of print].
26. Frisch, M. J., G. W. Trucks,., C. T. Wallingford. 2004. Gaussian 03, Rev. D.01. University of Groningen, Groningen, The Netherlands.
27. Siwko, M. E., S. J. Marrink,., A. E. Mark. 2007. Does isoprene protect plant membranes from thermal shock? A molecular dynamics study. Biochim. Biophys. Acta. Biomembr. 1768:198-206.
28. Hess, B., C. Kutzner,., E. Lindahl. 2008. GROMACS 4: algorithms for highly efficient, load-balanced, and scalable molecular simulation. J. Chem. Theory Comput. 4:435-447.
29. Berendsen, H. J. C., D. van der Spoel, and R. van Drunen. 1995. GROMACS: a message-passing parallel molecular dynamics implementation. Comput. Phys. Commun. 91:43-56.
30. Lindahl, E., B. Hess, and D. van der Spoel. 2001. GROMACS 3.0: a package for molecular simulation and trajectory analysis. J. Mol. Model. 7:306-317.
31. Van Der Spoel, D., E. Lindahl,., H. J. Berendsen. 2005. GROMACS: fast, flexible, and free. J. Comput. Chem. 26:1701-1718.
32. Leach, A. R. 2001. Molecular Modeling: Principles and Applications. Pearson Prentice Hall, Harlow, England.
33. Hess, B., H. Bekker,., J. G. E. M. Fraaije. 1997. LINCS: a linear constraint solver for molecular simulations. J. Comput. Chem. 18:1463-1472.
34. Hess, B. 2008. P-LINCS: a parallel linear constraint solver for molecular simulation. J. Chem. Theory Comput. 4:116-122.
35. Miyamoto, S., and P. A. Kollman. 1992. SETTLE: an analytical version of the SHAKE and RATTLE algorithm for rigid water models. J. Comput. Chem. 13:952-962.
36. Darden, T., D. York, and L. Pedersen. 1993. Particle mesh Ewald: an N·log(N) method for Ewald sums in large systems. J. Chem. Phys. 98:10089-10092.
37. Essmann, U., L. Perera,., L. G. Pedersen. 1995. A smooth particle mesh Ewald method. J. Chem. Phys. 103:8577-8593.
38. Berendsen, H. J. C., J. P. M. Postma,., J. R. Haak. 1984. Molecular dynamics with coupling to an external bath. J. Chem. Phys. 81:3684-3690.
39. Humphrey, W., A. Dalke, and K. Schulten. 1996. VMD: visual molecular dynamics. J. Mol. Graph. 14:33-38, 27-28.
40. + counterions. Biophys. J. 82:1818-1827.
41. Douliez, J. P., A. Léonard, and E. J. Dufourc. 1995. Restatement of order parameters in biomembranes: calculation of C-C bond order parameters from C-D quadrupolar splittings. Biophys. J. 68:1727-1739.
42. Petrache, H. I., S.W. Dodd, and M. F. Brown. 2000. Area per lipid and acyl length distributions in fluid phosphatidylcholines determined by 2H NMR spectroscopy. Biophys. J. 79:3172-3192.
43. Rosso, L., and I. R. Gould. 2008. Structure and dynamics of phospholipid bilayers using recently developed general all-atom force fields. J. Comput. Chem. 29:24-37.
44. Poger, D., and A. E. Mark. 2010. On the validation of molecular dynamics simulations of saturated and cis-monounsaturated phosphatidylcholine lipid bilayers: a comparison with experiment. J. Chem. Theory Comput. 6:325-336.
45. Damodaran, K. V., and K. M. Merz, Jr. 1994. A comparison of DMPCand DLPE-based lipid bilayers. Biophys. J. 66:1076-1087.
46. Abramson, S. B., B. Cherksey,., G. Weissmann. 1990. Nonsteroidal antiinflammatory drugs exert differential effects on neutrophil function and plasma membrane viscosity. Studies in human neutrophils and liposomes. Inflammation. 14:11-30.
47. Pandit, S. A., D. Bostick, and M. L. Berkowitz. 2003. Molecular dynamics simulation of a dipalmitoylphosphatidylcholine bilayer with NaCl. Biophys. J. 84:3743-3750.
48. Cordomí, A., O. Edholm, and J. J. Perez. 2009. Effect of force field parameters on sodium and potassium ion binding to dipalmitoyl phosphatidylcholine bilayers. J. Chem. Theory Comput. 5:2125-2134.
49. Khandelia, H., and O. G. Mouritsen. 2009. Lipid gymnastics: evidence of complete acyl chain reversal in oxidized phospholipids from molecular simulations. Biophys. J. 96:2734-2743.
50. Kandasamy, S. K., and R. G. Larson. 2006. Effect of salt on the interactions of antimicrobial peptides with zwitterionic lipid bilayers. Biochim. Biophys. Acta. 1758:1274-1284.
51. Kandasamy, S. K., and R. G. Larson. 2006. Molecular dynamics simulations of model trans-membrane peptides in lipid bilayers: a systematic investigation of hydrophobic mismatch. Biophys. J. 90:2326-2343.