Cell membranes and apoptosis: Role of cardiolipin, phosphatidylcholine, and anticancer lipid analogues

Biochemistry and Cell Biology

Volumn 82, Issue 1, 2004, Pages 18-26

  Wright, Marcia M ^a   Howe, Alicia G ^a   Zaremberg, Vanina ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

Apoptosis; Cardiolipin; Edelfosine; Farnesol; Phosphatidylcholine

Indexed keywords

CELL MEMBRANES; METABOLISM; PHOSPHOLIPIDS;

APOPTOSIS; CARDIOLIPIN; MITOCHONDRIA SURFACE;

BIOCHEMISTRY;

ANTINEOPLASTIC AGENT; CARDIOLIPIN; CYTOCHROME C; EDELFOSINE; FARNESOL; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; PROTEIN BID;

ACYLATION; APOPTOSIS; CELL GROWTH; CELL MEMBRANE; CELL ORGANELLE; ENZYME ACTIVATION; HUMAN; LIPID METABOLISM; LIPOGENESIS; MEDIATOR; MITOCHONDRION; NONHUMAN; PHENOTYPE; PHOSPHOLIPID SYNTHESIS; PROTEIN LOCALIZATION; PROTEIN SECRETION; PROTEIN TRANSPORT; SHORT SURVEY; SIGNAL TRANSDUCTION;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARDIOLIPINS; CELL MEMBRANE; CYTIDINE DIPHOSPHATE CHOLINE; MITOCHONDRIA; PHOSPHATIDYLCHOLINES; PHOSPHOLIPID ETHERS; SIGNAL TRANSDUCTION;

EID: 2342530364     PISSN: 08298211     EISSN: None     Source Type: Journal    
DOI: 10.1139/o03-092     Document Type: Short Survey

References (83)

1. Andreesen, R., Modolell, M., Weltzien, H.U., Eibl, H., Common, H.H., Lohr, G.W., and Munder, P.G. 1978. Selective destruction of human leukemic cells by alkyl-lysophospholipids. Cancer Res. 38: 3894-3899.
2. Andreesen, R., Modolell, M., and Munder, P.G. 1979. Selective sensitivity of chronic myelogenous leukemia cell populations to alkyl-lysophospholipids. Blood, 54: 519-523.
3. Anthony, M.L., Zhao, M., and Brindle, K.M. 1999. Inhibition of phosphatidylcholine biosynthesis following induction of apoptosis in HL-60 cells. J. Biol. Chem. 274: 19 686 - 19 692.
4. Ardail, D., Privat, J., Egret-Charlier, M., Levrat, C., Lerme, F., and Louisot, P. 1990. Mitochondrial contact sites. J. Biol. Chem. 265: 18 797 - 18 802.
5. Aroca, J.D., Sanchez-Pinera, P., Corbalan-Garcia, S., Conesa-Zamora, P., de Godos, A., and Gomez-Fernandez, J.C. 2001. Correlation between the effect of the anti-neoplastic ether lipid 1-O-octadecyl-2-O-methyl-glycero-3- phosphocholine on the membrane and the activity of protein kinase C alpha. Eur. J. Biochem. 268: 6369-6378.
6. Arthur, G., and Bittman, R. 1998. The inhibition of cell signaling pathways by antitumor ether lipids. Biochim. Biophys. Acta, 1390: 85-102.
7. Baburina, I., and Jackowski, S. 1998. Apoptosis triggered by 1-O-octadecyl-2-O-methyl-rac-glycero-3 phosphocholine is prevented by increased expression of CTP:phosphocholine cytidylyltransferase. J. Biol. Chem. 273: 2169-2173.
8. Berdel, W.E., Bausert, W.R., Weltzien, H.U., Modolell, M.L., Widmann, K.H., and Munder, P.G. 1980. The influence of alkyllysophospholipids and lysophospholipid-activated macrophages on the development of metastasis of 3-Lewis lung carcinoma. Eur. J. Cancer, 16: 1199-1204.
9. Boggs, K.P., Rock, C.O., and Jackowski, S. 1995a. Lysophosphatidylcholine and 1-O-octadecyl-2-O-methyl rac-glycero-3-phosphocholine inhibit the CDP-choline pathway of phosphatidylcholine synthesis at the CTP:phosphocholine cytidylyltransferase step. J. Biol. Chem. 270: 7757-7764.
10. Boggs, K.P., Rock, C.O., and Jackowski, S. 1995b. Lysophosphatidylcholine attenuates the cytotoxic effects of the antineoplastic phospholipid 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine. J. Biol. Chem. 270: 11 612 - 11 618.
11. Cornell, R.B., and Northwood, I.C. 2000. Regulation of CTP:phosphocholine cytidylyltransferase by amphitropism and relocalization. Trends Biochem. Sci. 25: 441-447.
12. Cui, Z., and Houweling, M. 2002. Phosphatidylcholine and cell death. Biochim. Biophys. Acta, 1585: 87-96.
13. Cui, Z., Houweling, M., Chen, M.H., Record, M., Chap, H., Vance, D.E., and Terce, F. 1996. A genetic defect in phosphatidylcholine biosynthesis triggers apoptosis in Chinese hamster ovary cells. J. Biol. Chem. 271: 14 668 - 14 671.
14. Cuvillier, O., Mayhew, E., Janoff, A.S., and Spiegel, S. 1999. Liposomal ET-18-OCH(3) induces cytochrome c-mediated apoptosis independently of CD95 (APO-1/Fas) signaling. Blood, 94: 3593-3592.
15. Dolder, M., Wendt, S., and Walliman, T.-F. 2001. Mitochondrial creatine kinase in contact sites: interaction with porin and adenine nucleotide translocase, role in permeability transition and sensitivity to oxidative damage. Biol. Signals Recept. 10: 93-111.
16. Esposti, M.D. 2002. Sequence and functional similarities between pro-apoptotic Bid and plant lipid transfer proteins. Biochim. Biophys. Acta, 1553: 331-340.
17. Esposti, M.D. 2003. The mitochondrial battlefield and membrane lipids during cell death signalling. Ital. J. Biochem. 52: 43-50.
18. Esposti, M.D., Cristea, I.M., Gaskell, S.J., Nakao, Y., and Dive, C. 2003. Proapoptotic Bid binds to monolysocardiolipin, a new molecular connection between mitochondrial membranes and cell death. Cell Death Differ. 10: 1300-1309.
19. Gajate, C., and Mollinedo, F. 2001. The antitumor ether lipid ET-18-OCH(3) induces apoptosis through translocation and capping of Fas/CD95 into membrane rafts in human leukemic cells. Blood, 98: 3860-3863.
20. 2-terminal kinase activation and c-Jun in the induction of apoptosis by the ether phospholipid 1-O-octadecyl-2-O-methyl-rac- glycero-3-phosphocholine. Mol. Pharmacol. 53: 602-612.
21. Gajate, C., Fonteriz, R.I., Cabaner, C., Alvarez-Noves, G., Alvarez-Rodriguez, Y., Modolell, M., and Mollinedo, F. 2000. Intracellular triggering of Fas, independently of FasL, as a new mechanism of antitumor ether lipid-induced apoptosis. Int. J. Cancer, 85: 674-682.
22. Garcia Fernandez, M., Troiano, L., Moretti, L., Nasi, M., Pinti, M., Salvioli, S., Dobrucki, J., and Cossarizza, A. 2002. Early changes in intramitochondrial cardiolipin distribution during apoptosis. Cell Growth Differ. 13: 449-455.
23. Geilen, C.C., Haase, A., Wieder, T., Arndt, D., Zeisig, R., and Reutter, W. 1994. Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis. J. Lipid Res. 35: 625-632.
24. Ghosh, A., Akech, J., Mukherjee, S., and Das, S.K. 2002. Differential expression of cholinephosphotransferase in normal and cancerous human mammary epithelial cells. Biochem. Biophys. Res. Comm. 297: 1043-1048.
25. Grieb, P., and Rejdak, R. 2002. Pharmacodynamics of citicoline relevant to the treatment of glaucoma. J. Neurosci. Res. 67: 143-148.
26. Gutcher, I., Webb, P.R., and Anderson, N.G. 2003. The isoform-specific regulation of apoptosis by protein kinase C. Cell. Mol. Life Sci. 60: 1061-1070.
27. Hatch, G.M. 1998. Cardiolipin: biosynthesis, remodeling, and trafficking in the heart and mammalian cells. Int. J. Mol. Med. 1: 33-41.
28. He, L., Perkins, G.A., Poblenz, A.T., Harris, J.B., Hung, M., Ellisman, M.H., and Fox, D.A. 2003. Bcl-xL overexpression blocks bax-mediated mitochondrial contact site formation and apoptosis in rod photoreceptors of lead-exposed mice. Proc. Natl. Acad. Sci. U.S.A. 100: 1022-1027.
29. Hoffman, D.R., Hoffman, L.H., and Snyder, F. 1986. Cytotoxicity and metabolism of alkyl phospholipid analogues in neoplastic cells. Cancer Res. 46: 5803-5809.
30. Hofman, B., Stockl, A., Schlame, M., Beyer, K., and Klingenberg, M. 1994. The reconstituted ADP/ATP carrier activity has an absolute requirement for cardiolipin as shown in cysteine mutants. J. Biol. Chem. 269: 1940-1944.
31. Jendrossek, V., Muller, I., Eibl, H., and Belka, C. 2003. Intracellular mediators of erucylphosphocholine-induced apoptosis. Oncogene, 22: 2621-2631.
32. Johnson, J.E., Xie, M., Singh, L.M., Edge, R., and Cornell, R.B. 2003. Both acidic and basic amino acids in an amphitropic enzyme, CTP:phosphocholine cytidylyltransferase, dictate its selectivity for anionic membranes. J. Biol. Chem. 278: 514-522.
33. Kawasaki, K., Kuge, O., Chang, S.C., Heacock, P.N., Rho, M., Suzuki, K., Nishijima, M., and Dowhan, W. 1999. Isolation of a chinese hamster ovary (CHO) cDNA encoding phosphatidylglycerophosphate (PGP) synthase, expression of which corrects the mitochondrial abnormalities of a PGP synthase-defective mutant of CHO-K1 cells. J. Biol. Chem. 274: 1828-1834.
34. Kawasaki, K., Kuge, O., Yamakawa, Y., and Nishijima, M. 2001. Purification of phosphatidylglycerophosphate synthase from Chinese hamster ovary cells. Biochem. J. 354: 9-15.
35. Kiss, Z., Crilly, K.S., and Anderson, W.H. 1998. Phorbol ester stimulation of phosphatidylcholine synthesis requires expression of both protein kinase C-α and phospholipase. Biochim. Biophys. Acta, 1392: 109-118.
36. Kuwana, T., Mackey, M.R., Perkins, G., Ellisman, M.H., Latterich, M., Schneiter, R., Green, D.R., and Newmeyer, D.D. 2002. Bid, Bax, and lipids cooperate to form supramolecular openings in the outer mitochondrial membrane. Cell, 111: 331-342.
37. Lagace, T.A., Miller, J.R., and Ridgway, N.D. 2002. Caspase precessing and nuclear export of CTP:phosphocholine cytidylyltransferase alpha during farnesol-induced apoptosis. Mol. Cell Biol. 22: 4851-4862.
38. Lutter, M., Fang, M., Luo, X., Nishijima, M., Xie, X., and Wang, X. 2000. Cardiolipin provides specificity for targeting of tBid to mitochondria. Nat. Cell Biol. 2: 754-761.
39. Lutter, M., Perkins, G.A., and Wang, X. 2001. The pro-apoptotic Bcl-2 family member tBid localizes to mitochondrial contact sites. BMC Cell Biol. 2: 22.
40. Lykidis, A., Jackson, P., and Jackowski, S. 2001. Lipid activation of CTP: phosphocholine cytidylyltransferase alpha: characterization and identification of a second activation domain. Biochemistry, 40: 494-503.
41. Ma, B.J., Taylor, W.A., Dolinsky, V.W., and Hatch, G.M. 1999. Acylation of monolysocardiolipin in rat heart. J. Lipid Res. 40: 1837-1845.
42. Machida, K., Hayashi, Y., and Osada, H. 2002. A novel adenine nucleotide translocase inhibitor, MT-21, induces cytochrome c release by a mitochondrial permeability transition-independent mechanism. J. Biol. Chem. 277: 31 243 - 31 248.
43. McMaster, C.R. 2001. Lipid metabolism and vesicle trafficking: more than just greasing the transport machinery. Biochem. Cell Biol. 79: 681-692.
44. McMillin, J.B., and Dowhan, W. 2002. Cardiolipin and apoptosis. Biochim. Biophys. Acta, 1585: 97-107.
45. Melnykovych, G., Haug, J.S., and Goldner, C.M. 1992. Growth inhibition of leukemia cell line CEM-C1 by farnesol: effects of phosphatidylcholine and diacylglycerol. Biochem. Biophys. Res. Commun. 186: 543-548.
46. Mimeault, M. 2002. New advances on structural and biological functions of ceramide in apoptotic/necrotic cell death and cancer. FEBS Lett. 530: 9-16.
47. Miquel, K., Pradines, A., Terce, F., Selmi, S., and Favre, G. 1998. Competitive inhibition of choline phosphotransferase by geranylgeraniol and farnesol inhibits phosphatidylcholine synthesis and induces apoptosis in human lung adenocarcinoma A549 cells. J. Biol. Chem. 273: 26 179 - 26 186.
48. Mollinedo, F., Fernandez-Luna, J.L., Gajate, C., Martin-Martin, B., Benito, A., Martinez-Dalmau, R., and Modolell, M. 1997. Selective induction of apoptosis in cancer cells by the ether lipid ET-18-OCH3 (Edelfosine): molecular structure requirements, cellular uptake, and protection by Bcl-2 and Bcl-X(L). Cancer Res. 57: 1320-1328.
49. Mozzi, R., Buratta, S., and Goracci, G. 2003. Metabolism and functions of phosphatidylserine in mammalian brain. Neurochem. Res. 28: 195-214.
50. Munder, P.G., and Westphal, O. 1990. Antitumoral and other biomedical activities of synthetic ether lysophospholipids. Chem. Immunol. 49: 206-235.
51. Newmeyer, D.D., and Ferguson-Miller, S. 2003. Mitochondria: releasing power for life and unleashing the machineries of death. Cell, 112: 481-490.
52. Ohtsuka, T., Nishijima, M., and Akamatsu, Y. 1993a. A somatic cell mutant defective in phosphatidylglycerophosphate synthase, with impaired phosphatidylglycerol and cardiolipin biosynthesis. J. Biol. Chem. 268: 22 908 - 22 913.
53. Ohtsuka, T., Nishijima, M., Suzuki, K., and Akamatsu, Y. 1993b. Mitochondrial dysfunction of a cultured Chinese hamster ovary cell mutant deficient in cardiolipin. J. Biol. Chem. 268: 22 914 - 22 919.
54. Ostrander, D.B., Sparagna, G.C., Amoscato, A.A., McMillin, J.B., and Dowhan, W. 2001. Decreased cardiolipin synthesis corresponds with cytochrome c release in palmitate-induced cardiomyocyte apoptosis. J. Biol. Chem. 276: 38 061 - 38 067.
55. Ott, M., Robertson, J.D., Gogvadze, V., Zhivotovsky, B., and Orrenius, S. 2002. Cytochrome c release from mitochondria proceeds by a two-step process. Proc. Natl. Acad. Sci. U.S.A. 99: 1259-1263.
56. Parone, P.A., James, D., and Martinou, J.C. 2002. Mitochondria: regulating the inevitable. Biochimie, 8: 105-111.
57. Petrosillo, G., Ruggiero, F.M., Pistolese, M., and Paradies, G. 2001. Reactive oxygen species generated from the mitochondrial electron transport chain induce cytochrome c dissociation from beef-heart submitochondrial particles via cardiolipin peroxidation. Possible role in the apoptosis. FEBS Lett. 509: 435-438.
58. Petrosillo, G., Ruggiero, F.M., Di Venosa, N., and Paradies, G. 2003. Decreased complex in activity in mitochondria isolated from rat heart subjected to ischemia and reperfusion: role of reactive oxygen species and cardiolipin. FASEB J. 17: 714-716.
59. Pike, L.J. 2003. Lipid rafts: bringing order to chaos. J. Lipid Res. 44: 655-667.
60. Pushkareva, M.Y., Wannberg, S.L., Janoff, A.S., and Mayhew, E. 2000. Increased cell-surface receptor expression on U-937 cells induced by 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine. Cancer Immunol. Immunother. 48: 569-578.
61. Raetz, C.R. 1986. Molecular genetics of membrane phospholipid synthesis. Annu. Rev. Genet. 20: 253-295.
62. Ravichandran, K.S. 2003. "Recruitment signals" from apoptotic cells: invitation to a quiet meal. Cell, 113: 817-820.
63. Ruiter, G.A., Zerp, S.F., Bartelink, H., van Blitterswijk, W.J., and Verheij, M. 1999. Alkyl-lysophospholipids activate the SAPK/JNK pathway and enhance radiation-induced apoptosis. Cancer Res. 59: 2457-2463.
64. Ruiter, G.A., Zerp, S.F., Bartelink, H., Van Blitterswijk, W.J., and Verheij, M. 2003. Anti-cancer alkyl-lysophospholipids inhibit the phosphatidylinositol 3-kinase-Akt/PKB survival pathway. Anticancer Drugs, 14: 167-173.
65. Runge, M.H., Andreesen, R., Pfleiderer, A., and Munder, P.G. 1980. Destruction of human solid tumors by alkyl lysophospholipids. J. Natl. Cancer Inst. 64: 1301-1306.
66. Schlame, M., Rua, D., and Greenberg, M.L. 2000. The biosynthesis and functional role of cardiolipin. Prog. Lipid Res. 39: 257-288.
67. Schneiter, R., Brugger, B., Sandhoff, R., Zellnig, G., Leber, A., Lampl, M., Athenstaedt, K., Hrastnik, C., Eder, S., Daum, G., Paltauf, F., Wieland, F.T., and Kohlwein, S.D. 1999. Electrospray ionization tandem mass spectrometry (ESI-MS/MS) analysis of the lipid molecular species composition of yeast subcellular membranes reveals acyl chain-based sorting/remodeling of distinct molecular species en route to the plasma membrane. J. Cell Biol. 146: 741-754.
68. Shafer, S.H., and Williams, C.L. 2003. Non-small and small cell lung carcinoma cell lines exhibit cell type-specific sensitivity to edelfosine-induced cell death and different cell line-specific responses to edelfosine treatment. Int. J. Oncol. 23: 389-400.
69. Sproull, S.A., Morash, S.C., Byers, D.M., Palmer, B.C., St., and Cook, H.W. 1995. Phorbol ester stimulation of phosphatidylcholine synthesis in four cultured neural cell lines: correlations with expression of protein kinase C isoforms. Neurochem. Res. 20: 1397-1407.
70. Stahlhut, M., Sandvig, K., and van Deurs, B. 2000. Caveolae: uniform structures with multiple functions in signaling, cell growth, and cancer. Exp. Cell Res. 261: 111-118.
71. Taylor, W.A., and Hatch, G.M. 2003. Purification and characterization of monolysocardiolipin acyltransferase from pig liver mitochondria. J. Biol. Chem. 278: 12 716 - 12 721.
72. Toker, A. 2002. Phosphoinositides and signal transduction. Cell. Mol. Life Sci. 59: 761-779.
73. Tuominen, E.K., Wallace, C.J., and Kinnunen, P.K. 2002. Phospholipid-cytochrome c interaction: evidence for the extended lipid anchorage. J. Biol. Chem. 277: 8822-8826.
74. van Blitterswijk, W.J., van der Luit, A.H., Veldman, R.J., Verheij, M., and Borst, J. 2003. Ceramide: second messenger or modulator of membrane structure and dynamics? Biochem. J. 369: 199-211.
75. van der Luit, A.H., Budde, M., Ruurs, P., Verheij, M., and van Blitterswijk, W.J. 2002. Alkyl-lysophospholipid accumulates in lipid rafts and induces apoptosis via raft-dependent endocytosis and inhibition of phosphatidylcholine synthesis. J. Biol. Chem. 277: 39 541 - 39 547.
76. van der Luit, A.H., Budde, M., Verheij, M., and van Blitterswijk, W.J. 2003. Different modes of internalization of apoptotic alkyllysophospholipid and cell-rescuing lysophosphatidylcholine. Biochem. J. 374: 747-753.
77. Vogler, W.R., Olson, A.C., Okamoto, S., Shoji, M., Raynor, R.L., Kuo, J.F., Berdel, W.E., Eibl, H., Hajdu, J., and Nomura, H. 1991. Comparison of selective cytotoxicity of alkyl lysophospholipids. Lipids, 26: 1418-1423.
78. Wieder, T., Orfanos, C.E., and Geilen, C.C. 1998. Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J. Biol. Chem. 273: 11 025 - 11 031.
79. 31P MRS. Magn. Reson. Med. 40: 411-420.
80. Wright, M.M., Henneberry, A.L., Lagace, T.A., Ridgway, N.D., and McMaster, C.R. 2001. Uncoupling farnesol induced apoptosis from its inhibition of phosphatidylcholine synthesis. J. Biol. Chem. 276: 25 254 - 25 261.
81. Zamzami, N., Marchetti, P., Castedo, M., Hirsch, T., Susin, S.A., Masse, B., and Kroemer, G. 1996. Inhibitors of permeability transition interfere with the disruption of the mitochondrial transmembrane potential during apoptosis. FEBS Lett. 384: 53-57.
82. Zaremberg, V., and McMaster, C.R. 2002. Differential partitioning of lipids metabolized by separate yeast glycerol-3-phosphate acyltransferases reveals that phospholipase D generation of phosphatidic acid mediates sensitivity to choline-containing lysolipids and drugs. J. Biol. Chem. 277: 39 035 - 39 044.
83. Zinser, E., Sperka-Gottlieb, C.D., Fasch, E.V., Kohlwein, S.D., Paltauf, F., and Daum, G. 1991. Phospholipid synthesis and lipid composition of subcellular membranes in the unicellular eukaryote Saccharomyces cerevisiae. J. Bacteriol. 173: 2026-2034.