The physicochemical properties of cardiolipin bilayers and cardiolipin-containing lipid membranes

Biochimica et Biophysica Acta - Biomembranes

Volumn 1788, Issue 10, 2009, Pages 2069-2079

  Lewis, Ruthven N A H ^a   McElhaney, Ronald N ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Cardiolipin membrane; DSC; FTIR spectroscopy; Halotropic phase behavior; Inverted nonlamellar phase; Molecular dynamics simulation; NMR spectroscopy; Thermotropic phase behavior; X ray diffraction

Indexed keywords

CARDIOLIPIN; PHOSPHATIDYLCHOLINE;

BIOPHYSICS; CHEMICAL BINDING; CHEMICAL INTERACTION; CONFORMATIONAL TRANSITION; LIPID ANALYSIS; MEMBRANE STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR MODEL; NONHUMAN; PHOSPHOLIPID BILAYER; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION; TEMPERATURE SENSITIVITY;

ANIMALS; CARDIOLIPINS; CELL MEMBRANE; HUMANS; LIPID BILAYERS; PHOSPHOLIPIDS;

EID: 70349551416     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2009.03.014     Document Type: Review

References (76)

1. Daum G. Lipids of mitochondria. Biochim. Biophys. Acta 822 (1985) 1-42
2. Ratledge C., and Wilkinson S.G. Fatty acids, related and derived lipids. In: Ratledge C., and Wilkinson S.G. (Eds). Microbial Lipids Vol. 1 (1988), Academic Press, London 23-53
3. O'Leary W.M., and Wilkinson S.G. Gram-positive bacteria. In: Ratledge C., and Wilkinson S.G. (Eds). Microbial Lipids Vol. 1 (1988), Academic Press, London 117-201
4. Wilkinson S.G. Gram-negative bacteria. In: Ratledge C., and Wilkinson S.G. (Eds). Microbial Lipids Vol. 1 (1988), Academic Press, London 299-488
5. Hoch F.L. Cardiolipins and biomembrane function. Biochim. Biophys. Acta 1113 (1992) 71-133
6. Kagawa Y., Kandrach A., and Racker E. Partial resolution of the enzymes catalyzing oxidative phosphorylation. XXVI. Specificity of phospholipids required for energy transfer reactions. J. Biol. Chem. 248 (1973) 676-684
7. Dale M.P., and Robinson N.C. Synthesis of cardiolipin derivatives with protection of the free hydroxyl: its application to the study of cardiolipin stimulation of cytochrome c oxidase. Biochemistry 27 (1988) 8270-8275
8. Arnold S., and Kadenbach B. Cell respiration is controlled by ATP, an allosteric inhibitor of cytochrome c oxidase. Eur. J. Biochem. 249 (1997) 350-354
9. Lange C., Nett J.H., Trumpower B.L., and Hunte C. Specific roles of protein-phospholipid interactions, in the yeast cytochrome bc1 complex structure. EMBO J. 20 (2001) 6591-6600
10. McAuley K.E., Fyfe P.K., Ridge J.P., Isaacs N.W., Cogdell R.J., and Jones M.R. Structural details of an interaction between cardiolipin and an integral membrane protein. Proc. Natl. Acad. Sci. U. S. A. 96 (1999) 14706-14711
11. Serrano R., Banner B.J., and Racker E. Purification and properties of the proton-translocating adenosine triphosphatase complex of bovine heart mitochondria. J. Biol. Chem. 251 (1976) 2453-2461
12. Hoch F.L. Cardiolipins and mitochondrial proton-selective leakage. J. Bioenerg. Biomem. 30 (1998) 511-532
13. McAuley K.E., Fyfe P.K., Ridge J.P., Isaacs N.W., Cogdell R.J., and Jones M.R. Structural details of an interaction between cardiolipin and an integral membrane protein. Proc. Nat. Acad. Sci. U. S. A. 96 (1999) 14706-14711
14. Koch H.U., Haas R., and Fischer W. The role of lipoteichoic acid biosynthesis in membrane lipid metabolism of growing Staphylococcus aureus. Eur. J. Biochem. 138 (1984) 357-363
15. Short S.A., and White D.C. Metabolism of phosphatidylglycerol, lysylphosphatidyl-glycerol and cardiolipin of Staphylococcus aureus. J. Bacteriol. 108 (1971) 219-226
16. Kanemasa Y., Yioshioka T., and Hayashi H. Alteration of the phospholipid composition of Staphylococcus aureus cultures in medium containing NaCl. Biochim. Biophys. Acta 280 (1972) 444-450
17. Okabe A., Hirai Y., Hayashi H., and Kanemasa Y. Alteration in phospholipid composition of Staphylococcus aureus during formation of autoplast. Biochim. Biophys. Acta 617 (1980) 28-35
18. Tanaka T., and Strauss J.F. Stimulation of luteal mitochondrial cholesterol side-chain cleavage by cardiolipin. Endocrinology 110 (1982) 1592-1598
19. Tuckey R.C., and Cameron K.J. Catalytic properties of cytochrome P-450(SCC) purified from the human placenta - comparison to bovine cytochrome P-450(SCC). Biochim. Biophys. Acta 1163 (1993) 185-194
20. Kisselev P., Tuckey R.C., Woods S.T., Triantopoulos T., and Schwartz D. Enzymatic properties of vesicle-reconstituted human cytochrome P450SCC (CYP11A1) - differences in functioning of the mitochondrial electron-transfer chain using human and bovine adrenodoxin and activation by cardiolipin. Eur. J. Biochem. 260 (1999) 768-773
21. Wakeham M.C., Sessions R.B., Jones M.R., and Fyfe P.K. Is there a conserved interaction between cardiolipin and the Type II bacterial reaction center?. Biophys. J. 80 (2001) 1395-1405
22. Schlame M., Ren M., Xu Y., Greenberg M.L., and Haller I. Molecular symmetry in mitochondrial cardiolipins. Chem. Phys. Lipids 138 (2005) 38-49
23. Chicco A.J., and Sparagna G.C. Role of cardiolipin alterations in mitochondrial dysfunction and disease. Amer. J. Physiol. Cell Physiol. 292 (2007) C33-C43
24. Cevc G., and Marsh D. Non-bilayer phases. Phospholipid Bilayers Physical Principles and Models (1987), John Wiley and Sons, New York 407-425
25. Israelachvili J. Intermolecular and surface forces (1992), Academic Press, San Diego 366-394
26. Lewis R.N.A.H., and McElhaney R.N. Surface charge density markedly attenuates the nonlamellar phase-forming properties of lipid bilayer membranes. Biophys. J. 79 (2000) 1455-1464
27. Tarahovsky Y.S., Arsenault A.L., MacDonald R.C., McIntosh T.J., and Epand R.M. Electrostatic control of phospholipid polymorphism. Biophys. J. 79 (2000) 3193-3200
28. Allegrini P.R., Pluschke G., and Seelig J. Cardiolipin conformation and dynamics in bilayer membranes as seen by deuterium magnetic resonance. Biochemistry 23 (1984) 6452-6458
29. Powell G.L., and Jacobus J. The nonequivalence of the phosphorous atoms in cardiolipin. Biochemistry 13 (1974) 4024-4026
30. Hirschberg C.B., and Kennedy E.P. The mechanism of enzymic synthesis of cardiolipin in Escherichia coli. Proc. Natl. Acad. Sci. U. S. A. 69 (1972) 648-651
31. Hostetler K.Y., van Den Bosch H., and van Deenen L.L.M. Mechanism of cardiolipin biosynthesis in mitochondria. Biochim. Biophys. Acta 260 (1972) 507-513
32. Henderson T.O., Glonek T., and Myers T.C. Phosphorous-31 nuclear magnetic resonance spectroscopy of phospholipids. Biochemistry 13 (1974) 623-628
33. Kates M., Syz J.-Y., Gosser D., and Haines T.H. pH-Dissociation characteristics of cardiolipin and its 2′-deoxy analogue. Lipids 28 (1993) 877-882
34. Ramirez F., Ioannou P.V., Marecek F.F., Dodd G.H., and Golding B.T. Synthesis of phospholipids by means of cyclic enediol pyrophosphates. Optically active monovalent and divalent salts of diphosphatidylglycerol (cardiolipin). Tetrahedron 33 (1977) 599-608
35. Keana J.F.W., Shimizu M., and Jernstedt K.K. A short, flexible route to symmetrically and unsymmetrically substituted diphosphatidylglycerols (cardiolipins). J. Org. Chem 51 (1986) 2297-2299
36. Lin Z., Ahmad M.U., Ali S.M., and Ahmad I. An efficient and novel method for the synthesis of cardiolipin and its analogs. Lipids 39 (2004) 285-290
37. Krishna U.M., Ahmad M.U., Ali S.M., and Ahmad I. A short, concise route to diphosphatidylglycerol (cardiolipin) and its variants. Lipids 39 (2004) 595-600
38. Lin Z., Ahmad M.U., Ahmad U., Ali S.M., and Ahmad I. A new convenient method for the synthesis of cardiolipin. Tetrahedron Lett. 45 (2004) 6923-6925
39. Krishna U.M., Ahmad M.U., and Ahmad I. Phosphoramidite approach for the synthesis of cardiolipin. Tetrahedron Lett. 45 (2004) 2077-2079
40. Ali A.M., Ahmad M.U., Koslosky P., Kasireddy K., Krishna U.M., and Ahmad I. Synthesis of short and long chain cardiolipins. Tetrahedron 62 (2006) 6990-6997
41. Ahmad M.U., Krishna U.M., Ali S.M., Choudhury S., and Ahmad I. Synthesis of 1,3- and 1,2-diphosphatidylglycerol. Lipids 42 (2007) 291-296
42. Hegner D., Schummer U., and Schnepel G.H. The effect of calcium on temperature-induced phase changes in liquid-crystalline cardiolipin structure. Biochim. Biophys. Acta 307 (1973) 452-458
43. Overath P., and Träuble H. Phase transitions in cells, membranes, and lipids of Escherichia coli. Detection by fluorescent probes, light scattering and dilatometry. Biochemistry 12 (1973) 2625-2634
44. Pluschke G., and Overath P. Function of phospholipids in Escherichia coli: influence of changes in polar headgroup composition on the lipid phase transition and characterization of a mutant containing only saturated phospholipid acyl chains. J. Biol. Chem. 256 (1981) 3207-3212
45. Hubner W., Mantsch H.H., and Kates M. Intramolecular hydrogen-bonding in cardiolipin. Biochim. Biophys. Acta 1066 (1991) 166-174
46. Rainer S., Jain M.K., Ramirez F., Ioannou P.V., Marecek J.F., and Wagner R. Phase transition characteristics of diphosphatidylglycerol (cardiolipin) and stereoisomeric phosphatidyldiacylglycerol bilayers. mono-valent and divalent metal-ion effects. Biochim. Biophys. Acta 558 (1979) 187-198
47. Nagamachi E., Kariyama R., and Kanemasa Y. The effect of headgroup structure on phase transition of phospholipids membranes as determined by differential scanning calorimetry. Physiol. Chem. Phys. and Medical NMR 17 (1985) 255-260
48. Sankaram M.B., Powell G.L., and Marsh D. Effect of acyl chain composition on salt-induced lamellar to inverted hexagonal phase transitions in cardiolipin. Biochim. Biophys. Acta 980 (1989) 389-392
49. Lewis R.N.A.H., Zweytick D., Pabst G., Lohner K., and McElhaney R.N. Calorimetric, X-ray diffraction, and spectroscopic studies of the thermotropic phase behavior and organization of tetramyristoyl cardiolipin membranes. Biophys. J. 92 (2007) 3166-3177
50. Lewis R.N.A.H., and McElhaney R.N. Calorimetric and spectroscopic studies of the polymorphic phase behavior of a homologous series of n-saturated 1,2-diacyl phosphatidylethanolamines. Biophys. J. 64 (1993) 1081-1096
51. Zhang Y.P., Lewis R.N.A.H., and McElhaney R.N. Calorimetric and spectroscopic studies of the thermotropic phase behavior of the n-saturated 1,2-diacylphosphatidylglycerols. Biophys. J. 72 (1997) 779-793
52. Lewis R.N.A.H., and McElhaney R.N. Calorimetric and spectroscopic studies of the thermotropic phase behavior of lipid bilayer model membranes composed of a homologous series of linear saturated phosphatidylserines. Biophys. J. 79 (2000) 2043-2055
53. 31P-NMR relaxation studies of the activation of the coenzyme phosphate of glycogen phosphorylase. The role of motion of the bound phosphate. Biophys. J. 48 (1985) 1019-1026
54. Borle F., and Seelig J. Structure of Escherichia coli membranes - deuterium magnetic resonance studies of the phosphatidyl headgroup in intact cells and model membranes. Biochemistry 24 (1983) 5536-5544
55. Seelig J., and Seelig A. Lipid conformation in model membranes and biological membranes. Quart. Rev. Biophys. 13 (1980) 19-61
56. MacDonald P.M., and Seelig J. Calcium binding to cardiolipin-phosphatidylcholine bilayers as studied by deuterium nuclear magnetic resonance. Biochemistry, 26 (1987) 6292-6298
57. 2H-NMR. Biochemistry 33 (1994) 4896-4902
58. MacDonald P.M., and Seelig J. Calcium binding to mixed phosphatidylglycerol-phosphatidylcholine bilayers as studied by deuterium nuclear magnetic resonance. Biochemistry 26 (1987) 1231-1240
59. Scherer P.G., and Seelig J. Structure and dynamics of the phosphatidylcholine and phosphatidylethanolamine headgroup in L-M fibroblasts as studied by deuterium nuclear magnetic resonance. EMBO J. 6 (1987) 2915-2922
60. Seelig J., MacDonald P.M., and Scherer P.G. Phospholipid head groups as sensors of electric charge in membranes. Biochemistry 26 (1987) 7535-7541
61. Cullis P.R., Verkleij A.J., and Ververgaert P.H.J.T. Polymorphic phase behavior of cardiolipin as detected by 31P-NMR and freeze-fracture techniques - effects of calcium, dibucane and chlorpromazine. Biochim. Biophys. Acta 513 (1978) 11-20
62. Seddon J.M., Kaye R.D., and Marsh D. Induction of lamellar-inverted hexagonal phase-transition in cardiolipin by protons and monovalent cations. Biochim. Biophys. Acta 734 (1983) 347-352
63. Rand R.P., and Sengupta S. Cardiolipin forms hexagonal structures with divalent cations. Biochim. Biophys. Acta 225 (1972) 484-492
64. de Kruijff B., and Cullis P.R. Cytochrome-C specifically induces nonlamellar structures in cardiolipin-containing membranes. Biochim. Biophys. Acta 602 (1980) 477-490
65. Lewis R.N.A.H., Mannock D.A., and McElhaney R.N. Membrane lipid molecular structure and polymorphism. In: Epand R.M. (Ed). Lipid Polymorphism and Membrane Properties Vol. 44 (1997), Academic Press, San Diego, CA 25-102
66. 31P-NMR and X-ray diffraction. Biochemistry 24 (1985) 2902-2908
67. Dahlberg M. Polymorphic phase behavior of cardiolipin derivatives studied by coarse-grained molecular dynamics. J. Phys. Chem. B 111 (2007) 7194-7200
68. Nichols-Smith S., The S.-Y., and Kuhl T.L. Thermodynamic and mechanical properties of model mitochondrial membranes. Biochim. Biophys. Acta, 1663 (2004) 82-88
69. Domenech O., Sanz F., Montero M.T., and Hernandez-Borell J. Thermodynamic and structural study of the main phospholipids components comprising the mitochondrial inner membrane. Biochim. Biophys. Acta, 1758 (2006) 213-221
70. Etienne F., Roche Y., Piretti P., and Bernard S. Cardiolipin packing ability studied by grazing incidence X-ray diffraction. Chem. Phys. Lipids 152 (2008) 13-23
71. Chen Q.P., and Li Q.T. Effect of cardiolipin on proton permeability of phospholipid liposomes: the role of hydration at the lipid-water interface. Arch. Biochem. Biophys. 389 (2001) 201-206
72. Sennato S., Bordi F., Cametti C., Coluzza C., Desideri A., and Rufini S. Evidence of domain formation in cardiolipin-glycerophospholipid mixed monolayers. A thermodynamic and AFM study. J. Phys. Chem. 109 (2005) 15950-15957
73. Dahlberg M., and Maliniak A. Molecular dynamics simulations of cardiolipin bilayers. J. Phys. Chem. B 112 (2008) 11655-11663
74. Marrink S.J., de Vries A.H., and Mark A.E. Coarse grained model for semiquantitative lipid simulations. J. Phys. Chem. B 108 (2004) 750-760
75. 2H-NMR. Biochim. Biophys. Acta 737 (1983) 117-171
76. 2H nuclear magnetic resonance. Biophys. J. 56 (1989) 1037-1041