A new look at lipid-membrane structure in relation to drug research

Pharmaceutical Research

Volumn 15, Issue 10, 1998, Pages 1507-1519

  Mouritsen, Ole G ^a   Jørgensen, Kent ^b  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Lipid bilayer; Lipid protein interaction; Molecular organization; Permeability; Phase transitions

Indexed keywords

LIPOSOME; MEMBRANE RECEPTOR;

CELL MEMBRANE PERMEABILITY; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG PENETRATION; DRUG RESEARCH; DRUG TARGETING; LIPID BILAYER; MEMBRANE BINDING; MEMBRANE STRUCTURE; MICROENCAPSULATION; PRIORITY JOURNAL; PROTEIN ASSEMBLY; PROTEIN LIPID INTERACTION; SHORT SURVEY;

ANIMALS; CELL MEMBRANE; DRUG CARRIERS; HUMANS; LIPID BILAYERS; LIPOSOMES; MEMBRANE LIPIDS; MEMBRANE PROTEINS; PERMEABILITY;

EID: 0031695897     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1011986613392     Document Type: Short Survey

References (131)

1. S. Singer and G. L. Nicolson. The fluid mosaic model of cell membranes. Science 172:720-730 (1972).
2. M. Bloom, E. Evans, and O. G. Mouritsen. Physical properties of the fluid lipid-bilayer component of cell membranes. Quart. Rev. Biophys. 24:293-397.
3. O. G. Mouritsen and O. S. Andersen (eds.) In Search of a New Biomembrane Model. Biol. Skr. Dun. Vid. Selsk. 49:1-224 (1998).
4. R. Lipowsky and E. Sackmann (eds.) Structure and Dynamics of Membranes. Handhook of Biological Physics. Vol. 1A&B. Elsevier, Amsterdam, 1995, pp. 1-1020.
5. O. G. Mouritsen and K. J̈rgensen. Dynamical order and disorder in lipid bilayers. Chem. Phys. Lipids 73:3-25 (1994).
6. O. G. Mouritsen and P. K. J. Kinnunen. Role of lipid organization and dynamics for membrane functionality. In K. M. Merz and B. Roux (eds.) Biological Membranes. From Computation to Experiment, Birkhäuser, Boston, 1996, pp. 463-502.
7. D. P. Tieleman, S. J. Marrink, and H. J. C. Berendsen. A computer's perspective of membranes: molecular dynamics studies of lipid bilayer systems. Biochim. Biophys. Acta 1331:235-270 (1997).
8. S. H. White. Hydrophobicity scales and hydrophobicity plots in the prediction of membrane protein structure. In S. H. White (ed.) Membrane Protein Structure: Experimental Approaches, Oxford University Press, New York, 1994, pp. 97-124.
9. W. C. Wimley and S. H. White. Experimentally determined hydrophobicity scale for proteins at membrane interfaces. Nature Struct. Biol. 3:842-848 (1996).
10. M. T. Hyvönen, T. T. Rantala, and M. Ala-Korpela. Structure and dynamics properties of diunsaturated 1-palmitoyl-2-linoleoylsn-glycero-3-phosphatidylcholine lipid bilayer from molecular dynamics simulation. Biophys. J. 73:2907-2923 (1997).
11. T. X. Xiang and B. D. Anderson. The relationship between permeant size and permeability in lipid bilayer membranes. J. Memb. Biol. 140:111-122 (1994).
12. H. K. Alper and T. R. Stouch. Orientation and diffusion of a drug analogue in biomembranes: molecular dynamics simulations. J. Phys. Chem. 99:5724-5731 (1995).
13. L. O. Bergelson, K. Gawrisch, J. A. Ferretti, and R. Blumenthal. (Eds.) Special Issue on Domain Organization in Biological Membranes. Mol. Memb. Biol. 12:1-162 (1995).
14. O. G. Mouritsen and K. Jørgensen. Small-scale lipid-membrane structure: simulation versus experiment. Curr. Opin. Struct. Biol. 7:518-527 (1997).
15. O. G. Mouritsen. Self-assembly and organization of lipid-protein membranes. Curr. Opin. Colloid Int. Sci. 3:78-87 (1998).
16. A. Kusumi and S. Yashushi. Cell surface organization by the membrane skeleton. Curr. Opin. Biol. 8:566-574 (1996).
17. M. Edidin. Lipid microdomains in cell surface membranes. Curr. Opin. Struct. Biol. 7:528-532 (1997).
18. S. Pedersen, K. Jørgensen, T. Bækmark, and O. G. Mouritsen. Indirect evidence for lipid-domain formation in the transition region of phospholipid bilayers by two-probe fluorescence energy transfer. Biophys. J. 71:554-560 (1996).
19. J. Y. A. Lehtonen, J. M. Holopainen, and P. J. K. Kinnunen. Evidence for the formation of microdomains in liquid crystalline large unilamellar vesicles caused by hydrophobic mismatch of the constituent phospholipids. Biophys. J. 70:1753-1760 (1996).
20. B. Piknová, D. Marsh, and T. H. Thompson. Flourescence-quenching study of percolation and compartmentalization in two-phase lipid hilayers. Biophys. J. 71:892-897 (1996).
21. V. Schram, H. N. Lin, and T. E. Thompson. Topology of gel-phase domains and lipid mixing properties in phase separated two-component phosphatidylcholine bilayers. Biophys. J. 71: 1811-1822 (1996).
22. C. Gliss, H. Clausen-Schaumann, R. Günther, S. Odenbach, O. Randl, and T. M. Bayerl. Direct detection of domains in phospholipid hilayers by grazing incidence diffraction of neutrons and atomic force microscopy. Biophys. J. 74:2443-2450 (1998).
23. L. Kildemark, T. Bjørnholm, and O. G. Mouritsen. Direct visualization of critical fluctuations in lipid monolayers. (preprint, 1998).
24. O. G. Mouritsen, K. J̈rgensen, and T. Hønger. Permeability of lipid bilayers near the phase transition. In: Permeability and Stability of Lipid Bilayers (E. A. Disalvo and S. A. Simon, eds.). CRC Press, Boca Raton, Florida, 1995, pp. 137-160.
25. T. Hønger, K. Mortensen, J. H. Ipsen, J. Lemmich, R. Bauer, and O. G. Mouritsen. Anomalous swelling of multilamellar lipid hilayers in the transition region by renormalization of curvature elasticity. Phys. Rev. Lett. 72:3911-3914 (1994).
26. E. Sackmann. Membrane bending energy concept of vesicle-and cell-shapes and shape transitions. FEBS Lett. 346:3-16 (1994).
27. G. Cevc. Transfersomes, liposomes and other lipid suspensions on the skin: permeation enhancement, vesicle penetration, and transdermal drug delivery. Crit. Rev. Ther. Drug Carr. Syst. 13:257-388 (1996).
28. P. K. J. Kinnunen, A. Kõiv, J. Y. A. Lehtonen, M. Rytsmaa, and P. Mustonen. Lipid dynamics and peripheral interactions of proteins with membrane surfaces. Chem. Phys. Lipids 73:181-207 (1994).
29. A. R. G. Dibble, A. K. Hinderleiter, J. J. Sando, and R. L. Biltonen. Lipid lateral heterogeneity in phosphatidylcholine/ phosphatidylserine/diacylglycerol vesicles and its influence on protein kinase C activation. Biophys. J. 71:1877-1890 (1996).
30. L. Yang and M. Glaser. Formation of membrane domains during the activation of protein kinase C. Biochemistry 35:13966-13974 (1996).
31. A. K. Hinderleiter, A. R. G. Dibble, R. L. Biltonen, and J. J. Sando. Activation of protein kinase C by coexisting diacylglycerol/enriched and diacylglycerol-poor lipid domains. Biochemistry 36:6141-6148 (1997).
32. M. Glaser, S. Wanaski, C. A. Buser, V. Boguslavsky, W. Rashidzada, A. Morris, M. Rebecchi, S. F. Scarlata, L. W. Runnels, G. D. Prestwich, J. Chen, A. Aderem, J. Ahn, and S. McLaughlin. Myristoylated alanine-rich C kinase substrate (MARCKS) produces reversible inhibition of phospholipase C by sequestering phosphatidylinositol 4,5-bisphosphate in lateral domains. J. Biol. Chem. 271:26187-26193 (1996).
33. 2 activity and dynamic lipid bilayer microheterogeneity. Biochemistry 35:9003-9006 (1996).
34. 2 activity and physical properties of lipid-bilayer substrates. Methods Enzymol. 286:168-190 (1997).
35. 2 as a mechanosensor. Biophys. J. 68:1888-1894 (1995).
36. G. Basanez, J.-L. Nieva, F. Goñ, and A. Alonso. Origin of the lag period in the phospholipase C cleavage of phospholipids in membranes. Concomitant vesicle aggregation and enzyme activation. Biochemistry 35:15183-15187 (1996).
37. K. Jærgensen, J. H. Ipsen, O. G. Mouritsen, and M. J. Zuckermann. The effect of anaesthetics on the dynamic heterogeneity of lipid membranes. Chem. Phys. Lipids 65:205-216 (1993).
38. E. C. C. Melo, I. M. Lourtie, M. B. Sankaram, T. E. Thompson, and W. L. C. Vaz. The effect of domain connection and disconnection on the yields of in-plane bimolecular reactions in membranes. Biophys. J. 63:1506-1512 (1992).
39. R. M. Epand. The properties and biological roles of non-lamellar forming lipids. Chem. Phys. Lipids 81:101-264 (1996).
40. D. Marsh. Intrinsic curvature in normal and inverted lipid structures and in membranes. Biophys. J. 70:2248-2255 (1996).
41. P. K. J. Kinnunen. On the molecular-level mechanics of peripheral protein-membrane interactions induced by lipids forming inverted non-lamellar phases. Chem. Phys. Lipids 81:151-166 (1996).
42. J. S. Lundbaek, A. M. Maer, and O. S. Andersen. Lipid bilayer elactrostatic energy, curvature stress, and assembly of gramicidin channels. Biochemistry 36:5695-5701 (1997).
43. M. F. Brown. Influence of nonlamellar-forming lipids on rhodopsin. Curr. Topics in Membranes 44:285-356 (1997).
44. II propensity. In Handbook of nonmedical applications of liposomes. Vol. I., D. D. Lasic and Y. Barenholz, eds. CRC Press, Boca Raton, FL, 1996, pp. 153-171.
45. T. Gil, J. H. Ipsen, O. G. Mouritsen, M. C. Sabra, M. M. Sperotto, and M. J. Zuckermann. Theoretical analysis of protein organization in lipid membranes. Biochim. Biophys. Acta. Reviews on Biomembranes (in press, 1998).
46. O. G. Mouritsen and M. Bloom. Mattress model of lipid-protein interactions in membranes. Biophys. J. 46:141-153 (1984).
47. P. A. Kralchevsky, V. N. Paunov, and N. D. Denkov. Stresses in lipid membranes and interactions between inclusions. J. Chem. Soc. Faraday Trans. 91:3415-3432 (1995).
48. R. S. Cantor. Lateral pressures in cell membranes: a mechanism for modulation of protein function. J. Phys. Chem. B 101:1723-1726 (1997).
49. F. Dumas, M. M. Sperotto, C. Lebrun, J.-F. Tocanne, and O. G. Mouritsen. Molecular sorting of lipids by bacteriorhodopsin in DLPC/DSPC lipid bilayers. Biophys. J. 73:1940-1953 (1997).
50. D. Marsh. Lipid-protein interactions in membranes. FEBS Lett. 268:371-375 (1990).
51. L. I. Horváth, H. R. Arias, H. O. Hankovszky, K. Hideg, F. J. Barrantes, and D. Marsh. Association of spin-labeled local anesthetics at the hydrophobic surface of acetylcholine receptor in native membranes from Torpedo marmotata. Biochemistry 29:8707-8713 (1990).
52. C. Ho, M. B. Kelly, and C. D. Stubbs. The effects of phospholipid unsaturation and alcohol perturbation at the protein/lipid interface probed using fluorophore lifetime heterogeneity. Biochim. Biophys. Acta 1193:307-315 (1994).
53. N. P. Franks and W. R. Lieb. Where do general anaesthetics act? Nature 274:339-342 (1978).
54. B. Piknová, D. Marsh, and T. E. Thompson. Flourescence quenching and ESR study of percolation in a two-phase lipid bilayer containing bacteriorhodopsin. Biophys. J. 72:2660-2668 (1997).
55. V. Schram and T. E. Thompson. Influence of the intrinsic membrane protein bacteriorhodopsin on the gel phase domain topology in two-component phase-separated bilayers. Biophys. J. 72:2217-2225 (1997).
56. T. Gil, M. C. Sabra, J. H. Ipsen, and O. G. Mouritsen. Wetting and capillary condensation as means of protein organization in membranes. Biophys. J. 73:1728-1741 (1997).
57. M. C. Sabra and A. Watts. A general model for 2D-array formation of membrane proteins. Biophys. J. (1997) (submitted).
58. D. Papahadjopoulos, K. Jacobsen, S. Nir, and T. Isac. Phase transitions in phospholipid vesicles. Fluorescence polarization and permeability measurements concerning the effects of temperature and cholesterol. Biochim. Biophys. Acta 311:330-348 (1973).
59. L. Cruzeiro-Hansson and O. G. Mouritsen. Passive ion permeability of lipid membranes modelled via lipid-domain interfacial area. Biochim. Biophys. Acta 944:63-72 (1988).
60. J. Liu, E. Y. Rosenberg, and H. Nikaido. Fluidity of the lipid domain of cell wall from Mycobacterium chelonae. Proc. Natl. Acad. Sci. USA 92:11254-11258 (1995).
61. J. Thewalt, N. Kitson, C. Araujo, A. Mackay, and M. Bloom. Models of stratum corneum intercellular membranes: the spingo-lipid headgroup is a determinant of phase behavior in mixed lipid dispersions. Biochem. Biphys. Res. Commun. 188:1247-1252 (1992).
62. N. Kitson, J. Thewalt, M. Lafleur, and M. Bloom. A model membrane approach to the epidermal permeability barrier. Biochemistry 33:6707-6715 (1994).
63. J. E. Harrison, P. W. Groundwater, K. R. Brain, and J. Hadgraft. Azone induced fluidity in human stratum corneum. A fourier transform infrared spectroscopy investigation using the perdeuterated analogue. J. Contr. Rel. 41:283-290 (1996).
64. V. H. L. Lee. Protease inhibitors and penetration enhancers to modify peptide absorption. J. Contr. Rel. 13:69-97 (1990).
65. J. Risbo, K. Jørgensen, M. M. Sperotto, and O. G. Mouritsen. Phase behavior and permeability properties of phospholipid bilayers containing a short-chain phospholipid permeability enhancer. Biochim. Biophys. Acta 1329:85-96 (1997).
66. K. Jørgensen, M. M. Sperotto, O. G. Mouritsen, J. H. Ipsen, and M. J. Zuckermann. Phase equilibria and local structure in binary lipid bilayers. Biochim. Biophys. Acta. 1152:135-145 (1993).
67. O. G. Mouritsen and K. Jørgensen. Micro-, nano-. and meso-scale heterogeneity of lipid bilayers and its influence on macroscopic membrane properties. Mol. Memb. Biol. 12:15-20 (1995).
68. M. C. Sabra, K. Jørgensen, and O. G. Mouritsen. Lindane suppresses the lipid-bilayer permeability in the main transition region. Biochim. Biophys. Acta 1282:85-92 (1996).
69. M. C. Sabra, K. Jørgensen, and O. G. Mouritsen. Calorimetric and theoretical studies of the effects of lindane on lipid bilayers of different acyl-chain length. Biochim. Biophys. Acta 1233:89-104 (1995).
70. M. C. Antunes-Madeira and V. M. C. Madeira. Partitioning of lindane in synthetic and native membranes. Biochim. Biophys. Acta 820:165-172 (1985).
71. G. S. Clerc and T. E. Thompson. Permeability of dimyristoyl phosphatidylcholine/dipalmitoyl phosphatidylcholine bilayer membranes with coexisting gel and liquid-crystalline phases. Biophys. J. 68:2333-2341 (1995).
72. E. Freire and R. L. Biltonen. Estimation of molecular averages and equilibrium fluctuations in lipid bilayer systems from excess heat capacity function. Biochim. Biophys. Acta 514:54-68 (1978).
73. J. S. Andersen, K. Jørgensen, and O. G. Mouritsen. Permeability of lipid bilayer mixtures using fluorescence quenching methods. submitted to Biophys. J. (1998).
74. K. Jørgensen and O. G. Mouritsen. Phase separation dynamics and lateral organization of two-component lipid membranes. Biophys. J. 69:942-954 (1995).
75. K. Jørgensen, A. Klinger, M. Braiman, and R. L. Biltonen. Slow nonequilibrium dynamical rearrangement of the lateral structure of a lipid membrane. J. Chem. Phys. 100:2766-2769 (1996).
76. U. Seifert. Curvature-induced lateral phase separation in two-component vesicles. Phys. Rev. Lett. 70:1335-1338 (1993).
77. J. N. Weinstein, R. L. Magin, M. B. Yatvin, and D. S. Zaharko. Liposomes and local hyperthermia: selective delivery of methotrexate to heated tumors. Science 204:188-191 (1979).
78. J. B. Bassett, J. R. Tacker, R. U. Anderson, and D. Bostwick. Treatment of experimental bladder cancer with hyperthermia and phase transtition liposomes containing methotrexate. J. Urology 139:634-636 (1987).
79. A. Sharma and U. S. Sharma. Liposomes in drug delivery: progress and limitations. Int. J. Pharm. 154:123-140 (1997).
80. J. H. Ipsen, K. Jørgensen, and O. G. Mouritsen. Density fluctuations in saturated phospholipid bilayers increase as the acyl-chain length decreases. Biophys. J. 58:1099-1107 (1990).
81. J. Y. Lai, D. D. Chow, and K.J. Hwang. Effect of lipid composition on insulin-mediated fusion of small unilamellar liposomes: a kinetic study. J. Pharm. Sci. 77:432-437 (1988).
82. L. V. Chernomordik and J. Zimmerberg. Bending membranes to the task: structural intermediates in bilayer fusion. Curr. Opin. Struc. Biol. 5:541-547 (1995).
83. G. Cevc, J. M. Seddon, R. Hartung, and W. Eggert. Phosphatidylcholine-fatty acid membranes. I. Effects of protonation, salt concentration, temperature and chain-length on the colloidal and phase properties of mixed vesicles, bilayers and nonlamellar structures. Biochim. Biophys. Acta 940:219-240 (1988).
84. S. Zellmer, G. Cevc, and P. Risse. Temperature-and pH-controlled fusion between complex lipid membranes. Examples with the diacylphosphatidylcholme/fatty acid mixed liposomes. Biochim. Biophys. Acta 1196:101-113 (1994).
85. G. Cevc. Agent targeting by means of the chemically or physically directed, fusogenic liposomes. J. Lip. Res. 6:643-663 (1996).
86. J. Senior. Fate and behaviour of liposomes in vivo: a review of controlling factors. Crit. Rev. Ther. Drug Curr. Syst. 3:123-193 (1987).
87. J. H. Ipsen, O. G. Mouritsen, and M. J. Zuckermann. Theory of thermal anomalies in the specific heat of lipid bilayers containing cholesterol. Biophys. J. 56:661-667 (1989).
88. J. H. Ipsen, O. G. Mouritsen, and M. Bloom. Relationship between lipid membrane area, hydrophobic thickness, and acyl-chain orientational order. The effects of cholesterol. Biophys. J. 57:405-412 (1990).
89. O. Zelphati and F. C. S. Szoka Jr. Liposomes as a carrier for intracellular delivery of antisense oligonucleotides: a real or magic bullet? J. Cont. Release 41:99-119 (1996).
90. R. I. Mahato, A. Rolland, and R. Tomlinson. Cationic lipid-based gene delivery systems: pharmaceutical perspectives. Pharm. Res. 14:853-859 (1997).
91. D. D. Lasic and N. S. Templeton. Liposomes in gene therapy. Adv. Drug Deliv. Rev. 20:221-266 (1996).
92. J. O. Rädler, I. Koltover, T. Salditt, and C. R. Safinya. Structure of DNA-cationic liposome complexes: DNA intercalation in multilamellar membranes in distinct interhelical packing regimes. Science 275:811-814 (1997).
93. I. van der Woude, H. W. Visser, M. B. A. ter Beest, A. Wagenaar. M. H. J. Ruiters, J. B. F. N. Engberts, and D. Hoekstra. Parameters influencing the introduction of plasmid DNA into cells by the use of synthetic amphiphiles as a carrier system. Biochim. Biophys. Acta 1240:34-40 (1995).
94. D. Harries, S. May, W. M. Gelbart, and A. Ben-Shaul. Structure, stability and thermodynamics of lamellar DNA-lipid complexes. Biophys. J. (preprint, 1998).
95. A. K. Hinderliter, J. Huang, and G. W. Feigenson. Detection of phase separation in fluid phosphatidylserine/phosphatidylcholine mixtures. Biophys. J. 67:1906-1911 (1994).
96. J. Lemmich, T. Hønger, K. Mortensen, J. H. Ipsen, R. Bauer, and O. G. Mouritsen. Solutes in small amounts provide for lipid-bilayer softness: cholesterol, short-chain lipids, and bola lipids. Eur. Biophys. J.: Biophysics Letters 25:61-65 (1996).
97. G. Cevc, A. Schätzlein, and G. Blume. Transdermal drug carriers: basic properties, optimization and transfer efficiency in the case of epicutaneously applied peptides. J. Contr. Rel. 36:3-16 (1995).
98. D. E. Vance and J. Vance. (Eds.) Biochemistry of lipids, lipoproteins and membranes. Elsevier, Amsterdam, (1991).
99. 2 activity toward phosphatidylcholine vesicle by lysolecithin and palmitic acid: studies with fluorescent probes of membrane structure. Biochemistry 34:7796-7806 (1995).
100. D. D. Lasic and F. Martin. (Eds.) Stealth liposomes. CRC Press, Boca Raton, Florida. (1995).
101. A. Chonn and P. R. Cullis. Recent advances in liposomal drug-delivery systems. Curr. Opin. Biotechnol. 6:698-708 (1995).
102. K. Hristova and D. Needham. The influence of polymer-grafted lipids on the physical properties of lipid bilayers: a theoretical study. J. Colloid Interface Sci. 168:302-314 (1994).
103. K. Hristova, A. Kenworthy, and T. J. McIntosh. Effect of bilayer composition on the phase behaviour of liposomal suspensions containing poly(ethylene glycol)-lipids. Macromolecules 28: 7693-7699 (1995).
104. A. K. Kenworthy, S. A. Simon, and T. J. McIntosh. Structure and phase behavior of lipid suspensions containing phospholipids with covalently attached poly(ethylene glycol). Biophys. J. 68:1903-1920 (1995).
105. T. R. Baekmark, S. Pedersen, K. Jørgensen, and O. G. Mouritsen. The effects of ethylene oxide containing lipopolymers and tri-block copolymers on lipid bilayers of dipalmitoylphosphatidylcholine. Biophys. J. 73:1479-1491 (1997).
106. A. K. Kenworthy, K. Hristova, D. Needham, and T. J. McIntosh. Range and magnitude of the steric pressure between bilayers containing phospholipids with covalently attached poly(ethylene glycol). Biophys. J. 68:1921-1936 (1995).
107. A. Chonn, S. C. Semple, and P. R. Cullis. Association of blood proteins with large unilamellar liposomes in vivo. Relation to circulation lifetimes. J. Biol. Chem. 267:18759-18765 (1992).
108. G. Blume and G. Cevc. Molecular mechanism of the lipid vesicle longevity in vivo. Biochim. Biophys. Acta 1146:157-168 (1993).
109. D. D. Lasic and D. Needham. The "Stealth" liposome: a prototypical biomaterial. Chem. Rev. 95:2601-2628 (1995).
110. 2 activity towards lipopolymer containing liposomes. Biochim. Biophys. Acta 1373:27-36 (1998).
111. 2. FASEB J. 8:916-924 (1994).
112. 2 and regulation of interfacial activation: hopping versus scooting. Biochim. Biophys. Acta 1002:127-156 (1989).
113. L. P. Zanello, E. Aztiria, S. Antollini, and F. J. Barrantes. Nicotinic acetylcholine receptor channels are influenced by the physical state of their membrane environment. Biophys. J. 70:2155-2164 (1996).
114. J. S. Lundbaek and O. S. Andersen. Lysophospholipids modulate channel function by altering the mechanical properties of lipid bilayers. J. Gen. Physiol. 104:645-673 (1994).
115. J. S. Lundbaek, P. Birn, J. Girshman, A. J. Hansen, and O. S. Andersen. Membrane stiffness and channel function. Biochemistry 35:3825-2830 (1996).
116. I. Bosch, K. Dunussi-Joannopoulos, R.-L. Wu, S. T. Furlong, and J. Croop. Phosphatidylcholine and phosphatidylethanolamine behave as substrates of the human MDR1 P-glycoprotein. Biochemistry 36:5685-5694 (1997).
117. M. E. Taub, B. A. Moss, B. Steffansen, and S. Frokjaer. Influence of oligopeptide transporter binding affinity upon uptake and transport of d-Asp(OBzl)-Ala and Asp(OBzl)-Sar in filter-grown Caco-2 monolayers. Int. J. Pharm. 156:219-228 (1997).
118. H. J. Little. How has molecular pharmacology contributed to our understanding of the mechanism(s) of general anesthesia. Pharmacol. Ther. 69:37-58 (1996).
119. D. Goren, A. Gabizon, and Y. Barenholz. The influence of physical characteristics of liposomes containing doxorubicin on their pharmacological behavior. Biochim. Biophys. Acta 1029:285-294 (1990).
120. A. Gawron, K. Wojtowicz, L. E. Misiak, and W. I. Gruszecki. Effects of incorporation of lutein and 8-mehoxypsoralen into erythrocyte and liposomal membranes. Pharm. Sci. 2:89-91 (1996).
121. J. G. Bovill. Mechanisms of actions of anaesthetic drugs. Curr. Opin. Anaesthesiol. 10:261-266 (1997).
122. R. C. Aloia, C. C. Curtain, and L. M. Gordon. (Eds.) Advances in membrane fluidity. Drug and anesthetic effects on membrane structure and function. Vol. 5, Wiley-Liss, Inc. New York. (1991).
123. E. Lasonder and W. D. Weringa. An NMR and DSC study of the interaction of phospholipid vesicles with some anti-inflammatory agents. J. Colloid Int. Sci. 139:469-478 (1990).
124. S-J Bae, S. Kitamura, L. G. Herbette, and J. M. Sturtevant. The effects of calcium channel blocking drugs on the thermotropic behavior of dimyristoylphosphatidylcholine. Chem. Phys. Lipids 51:1-7 (1989).
125. R. S. Cantor. The lateral pressure profile in membranes: a physical mechanism of general anesthesia. Biochemistry 36:2339-2344 (1997).
126. J. A. Barry and K. Gawrisch. Direct NMR evidence for ethanol binding to the lipid-water interface of phospholipid bilayers. Biochemistry 33:8082-8088 (1994).
127. C. Trandum, P. Westh, K. Jørgensen, and O. G. Mouritsen. Effects of ethanol on unilamellar liposomes containing cholesterol, sphingomyelin and ganglioside: a titration calorimetry study. submitted to Biophys. J. (1998).
128. 10F NMR study. Biophys. J. 72:1676-1682 (1997).
129. C. North and D. S. Cafiso. Contrasting membrane localization and behavior of halogenated cyclobutanes that follow or violate the Meyer-Overton hypothesis of general anesthetic potency. Biophys. J. 72:1754-1761 (1997).
130. D. B. Mountcastle, R. L. Biltonen, and M. J. Halsey. Effects of anesthetics and pressure on the thermotropic behavior of multilamellar dipalmitoylphosphatidylcholine liposomes. Proc. Natl. Acad. Sci. USA 75:4906-4910 (1979).
131. F. Rinaldi, M. Lin, M. J. Shapiro, and M. Petersheim. δ-opiate DPDPE in magnetically oriented phospholipid micelles: binding and arrangement of aromatic pharmacophores. Biophys. J. 73:3337-3348 (1997).