A lysophosphatidic acid analogue is revealed as a potent inhibitor of phosphatidylcholine synthesis, inducing apoptosis

Biochemical Journal

Volumn 368, Issue 2, 2002, Pages 447-459

  Gueguen, Geneviéve ^a   Granci, Virginie ^a   Rogalle, Pierre ^a   Briand Mésange, Fabienne ^a   Wilson, Michéle ^b   Klaébé, Alain ^b   Tercé, François ^a   Chap, Hugues ^a   Salles, Jean Pierre ^a   Simon, Marie Françoise ^a   Gaits, Frédérique ^a,c  

^a CHU PURPAN   (France)

^b Université Paul Sabatier   (France)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Ceramide; Cholinephosphotransferase; Stress activated protein kinase

Indexed keywords

BIOASSAY; BIOSYNTHESIS; CELLS; ENZYMES; METABOLISM; STEREOCHEMISTRY;

APOPTOSIS;

PHOSPHOLIPIDS;

ANTINEOPLASTIC AGENT; CASPASE 3; CERAMIDE; CHOLINEPHOSPHOTRANSFERASE; LYSOPHOSPHATIDIC ACID; N PALMITOYLNORLEUCINOL 1 PHOSPHATE; PHOSPHATIDYLCHOLINE; STRESS ACTIVATED PROTEIN KINASE; SYNAPTOPHYSIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CONTROLLED STUDY; DEPHOSPHORYLATION; DRUG SCREENING; ENANTIOMER; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; FIBROBLAST; HUMAN; HUMAN CELL; METABOLISM; MITOGENESIS; PHOSPHOLIPID SYNTHESIS; PRIORITY JOURNAL; STEREOSPECIFICITY; THROMBOCYTE AGGREGATION;

APOPTOSIS; CELL DIVISION; CELLS, CULTURED; CERAMIDES; DIACYLGLYCEROL CHOLINEPHOSPHOTRANSFERASE; ENZYME INHIBITORS; FIBROBLASTS; FUMONISINS; HUMANS; LYSOPHOSPHATIDYLCHOLINES; LYSOPHOSPHOLIPIDS; MITOGEN-ACTIVATED PROTEIN KINASE 8; MITOGEN-ACTIVATED PROTEIN KINASE 9; MITOGEN-ACTIVATED PROTEIN KINASES; NORLEUCINE; NUCLEAR PROTEINS; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PHOSPHATIDYLCHOLINES; PHOSPHORIC ACID ESTERS; RECEPTORS, CELL SURFACE; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, LYSOPHOSPHATIDIC ACID; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION FACTORS;

EID: 18744398095     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20020273     Document Type: Article

References (52)

1. Moolenaar, W. H. Kranenburg, O., Postma, F. R. and Zondag, G. C. (1997) Lysophosphatidic acid: G-protein signalling and cellular responses. Curr. Opin. Cell Biol. 9, 168-173
2. Moolenaar, W. H. (2000) Development of our current understanding of bioactive lysophospholipids. Ann. N.Y. Acad. Sci. 905, 1-10
3. Fang, X., Gaudette, D., Furui, T., Mao, M., Estrella, V., Eder, A., Pustilnik, T., Sasagawa, T., Lapushin, R., Yu, S. et al. (2000) Lysophospholipid growth factors in the initiation, progression, metastases, and management of ovarian cancer. Ann. N.Y. Acad. Sci. 905, 188-208
4. van Corven, E. J., van Rijswijk, A., Jalink, K., van der Bend, R. L., van Blitterswijk, W. J. and Moolenaar, W. H. (1992) Mitogenic action of lysophosphatidic acid and phosphatidic acid on fibroblasts. Dependence on acyl-chain length and inhibition by suramin. Biochem. J. 261, 163-169
5. Jalink, K., Hordijk, P. L. and Moolenaar, W. H. (1994) Growth factor-like effects of lysophosphatidic acid, a novel lipid mediator. Biochim. Biophys. Acta 1198, 185-196
6. Tigyi, G., Dyer, D. L. and Miledi, R. (1994) Lysophosphatidic acid possesses dual action in cell proliferation. Proc. Natl. Acad. Sci. U.S.A. 91, 1908-1912
7. Imagawa, W., Bandyopadhyay, G. K. and Nandi, S. (1995) Analysis of the proliferative response to lysophosphatidic acid in primary cultures of mammary epithelium: Differences between normal and tumor cells. Exp. Cell Res. 216, 178-186
8. Piazza, G. A., Ritter, J. L. and Baracka, C. A. (1995) Lysophosphatidic acid induction of transforming growth factors alpha and beta: Modulation of proliferation and differentiation in cultured human keratinocytes and mouse skin. Exp. Cell Res. 216, 51-64
9. Gaits, F., Salles, J. P. and Chap, H. (1997) Dual effect of lysophosphatidic acid on proliferation of glomerular mesangial cells. Kidney Int. 51, 1022-1027
10. Holtsberg, F. W., Steiner, M. R., Bruce-Keller, A. J., Keller, J. N., Mattson, M. P., Moyers, J. C. and Steiner, S. M. (1998) Lysophosphatidic acid and apoptosis of nerve growth factor-differentiated PC12 cells. J. Neurosci. Res. 53, 685-696
11. Holtsberg, F. W., Steiner, M. R., Keller, J. N., Mark, R. J., Mattson, M. P. and Steiner, S. M. (1998) Lysophosphatidic acid induces necrosis and apoptosis in hippocampal neurons. J. Neurochem. 70 66-76
12. Hooks, S., Santos, W. L., Im, D.-S., Heise, C. E., Macdonald, T. L. and Lynch, K. R. (2000) Lysophosphatidic acid-induced mitogenesis is regulated by lipid phosphate phosphatases and is Edg-receptor independent. J. Biol. Chem. 276, 4611-4621
13. Bünemann, M., Liliom, K., Brandts, B. K., Pott, L., Tseng, J. L., Desiderio, D. M., Sun, G., Miller, D. and Tigyi, G. (1996) A novel membrane receptor with high affinity for lysosphingomyelin and sphingosine 1-phosphate in atrial myocytes. EMBO J. 15, 5527-5534
14. Gueguen, G., Gaige, B., Grevy, J. M., Rogalle, P., Bellan, J., Wilson, M., Klaebe, A., Pont, F., Simon, M. F. and Chap, H. (1999) Structure-activity analysis of the effects of lysophosphatidic acid on platelet aggregation. Biochemistry 38, 8440-8450
15. 2+ mobilization in human A431 cells: Structure-activity analysis. Biochem. J. 307, 609-616
16. Bittman, R., Swords, B., Liliom, K. and Tigyi, G. (1996) Inhibitors of lipid phosphatidate receptors: N-palmitoyl-serine and N-palmitoyl-tyrosine phosphoric acids. J. Lipid Res. 37, 391-398
17. Liliom, K., Bittman, R., Swords, B. and Tigyi, G. (1996) N-palmitoyl-serine and N-palmitoyl-tyrosine phosphoric acids are selective competitive antagonists of the lysophosphatidic acid receptors. Mol. Pharmacol. 50, 616-623
18. Hooks, S. B., Ragan, S. P., Hopper D. W., Honemann, C. W., Durieux, M. E., Macdonald, T. L. and Lynch, K. R. (1998) Characterization of a receptor subtype-selective lysophosphatidic acid mimetic. Mol. Pharmacol. 53, 188-194
19. Bligh, E. G. and Dyer, W. J. (1959) A rapid method of total lipid extraction and purification. Can. J. Biochem. Phys. 37, 911-917
20. Preiss, J., Loomis, C. R., Bishop, W. R., Stein, R., Niedel, J. E. and Bell, R. M. (1986) Quantitative measurement of sn-1,2-diacytglycerols present in platelets, hepatocytes, and ras- and sis-transformed normal rat kidney cells. J. Biol. Chem. 261, 8597-8600
21. Santos, W. L., Rossi, J. A., Boggs, S. D. and Macdonald, T. L. (2000) The molecular pharmacology of lysophosphatidate signaling. Ann. N.Y. Acad. Sci. 905, 232-241
22. Cryns, V. and Yuan, J. (1998) Proteases to die for Genes Dev. 12, 1551-1570
23. An, S. (2000) Molecular identification and characterization of G protein-coupled receptors for lysophosphatidic acid and sphingosine 1-phosphate. Ann. N.Y. Acad. Sci. 905, 25-33
24. Weiss, S. B., Smith, S. W. and Kennedy, E. P. (1958) The enzymatic formation of lecithin from cytidine diphosphate and D-1,2-diglyceride, J. Biol. Chem. 233, 53-64
25. Cui, Z., Houweling, M., Chen, M. H., Record, M., Chap, H., Vance, D. E. and Tercé, F. (1996) A genetic defect in phosphatidylcholine biosynthesis triggers apoptosis in Chinese hamster ovary cells. J. Biol. Chem. 271, 14668-14671
26. Miquel, K., Pradines, A., Tercé, F., Selmi, S. and Favre, G. (1998) Competitive inhibition of choline phosphotransferase by geraniol and farnesol inhibits phosphatidylcholine synthesis in human lung adenocarcinoma A459 cells. J. Biol. Chem. 273, 26179-26186
27. McKean, M. L., Smith, J. B. and Silver, M J. (1982) Formation of phosphatidylcholine from 1-acyl lysophosphatidylcholine by acyl-CoA: 1-Acyl-sn-glycero-3-phosphocholine acyltransferase. J. Biol. Chem. 268, 19334-19340
28. Boggs, K. P., Rock, C. O. and Jackowski, S. (1995) Lysophosphatidylcholine attenuates the cytotoxic effects of the antineoplastic phospholipid 1-O-octadecyl-2-0-methyl-rac-glycero-3-phosphocholine. J. Biol. Chem. 270, 11612-11618
29. Jasinska, R., Zhang, Q. X., Pilquil, C., Singh, I., Xu, J., Dewald, J., Dillon, D. A., Berthiaume, L. G., Carman, G. M., Waggoner, D. W. and Brindley, D. N. (1999) Lipid phosphate phosphohydrolase-1 degrades exogenous glycerolipid and sphingolipid phosphate esters. Biochem. J. 340, 677-686
30. Xu, J., Zhang, Q. X., Pilquil, C., Berthiaume, L. G., Waggoner, D. W. and Brindley, D. N. (2000) Lipid phosphate phosphatase-1 in the regulation of lysophosphatidate signaling. Ann. N.Y. Acad. Sci. 905, 81-90
31. Hemrika, W., Renirie, R., Dekker, H. L., Barnett, P. and Wever, R. (1997) From phosphatases to vanadium peroxidases: A similar architecture of the active site. Proc. Natl. Acad. Sci. U.S.A. 94, 2145-2149
32. Brindley, D. N. and Waggoner, D. W. (1998) Mammalian lipid phosphate phosphohydrolases. J. Biol. Chem. 273, 24281-24284
33. Dutton, M. F. (1996) Fumonisins, mycotoxins of increasing importance: Their nature and their effects Pharmacol. Ther. 70, 137-161
34. Xia, Z., Dickens, M., Raingeaud, J., Davis, R. J. and Greenberg, M. E. (1995) Opposing effects of ERK and JNK-p38 MAP kinases on apoptosis. Science 270, 1326-1331
35. Hopper, D. W., Ragan, S. P., Hooks, S. B., Lynch, K. R. and Macdonald, T. L. (1999) Structure-activity relationships of lysophosphatidic acid: Conformationally restricted backbone mimetics. J. Med. Chem. 42, 963-970
36. Brindley, D. N. and Waggoner, D. W. (1996) Phosphatidate phosphohydrolase and signal transduction. Chem. Phys. Lipids 80, 45-57
37. 2+ control lysophosphatidate signaling through EDG-2 receptors. J. Biol. Chem. 275, 27520-27530
38. Pilquil, C., Singh, I., Zhang, Q., Ling, Z., Buri, K., Stromberg, L. M., Dewald, J. and Brindley, D. N. (2001) Lipid phosphate phosphatase-1 dephosphorylates exogenous lysophosphatidate and thereby attenuates its effects on cell signalling. Prostaglandins 64, 83-92
39. Vance, D. E. (1989) Regulatory and functional aspects of phosphatidylcholine metabolism. In Phosphatidylcholine Metabolism (Vance, D. E., ed.), pp. 225-239, CRC Press, Boca Raton, FL
40. Voziyan, P. A., Golner, C. M. and Melnykovych, G. (1993) Farnesol inhibits phosphatidylcholine biosynthesis in cultured cells by decreasing cholinephosphotransferase activity. Biochem. J. 295, 757-762
41. 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, 11025-11031
42. Gomez-Munoz, A. (1998) Modulation of cell signalling by ceramides. Biochim. Biophys. Acta 1391, 92-109
43. Pearson, G., Robinson, F., Beers-Gibson, T., Xu, B., Karandikar, M., Berman, K. and Cobb, M. H. (2001) Mitogen-activaterd protein (map) kinase pathways: Regulation and physiological functions. Endocr. Rev. 22, 153-183
44. Pouyssegur, J. (2000) Signal transduction. An arresting start for MAPK. Science 290, 1515-1518
45. Xu, Y., Zhu, K., Hong, G., Wu, W., Baudhuin, L. M., Xiao, Y. and Damron, D. S. (2000) Sphingosylphosphorylcholine is a ligand for ovarian cancer G-protein-coupled receptor 1. Nat. Cell Biol. 2, 261-267
46. Matsuda, S., Morigushi, T., Koyasu, S. and Nuishida, E. (1998) T lymphocyte activation signals for interleukin-2 production involve activation of MKK6-p38 and MKK7-SAPK/JNK signaling pathway sensitive to cyclosporin A. J. Biol. Chem. 273, 12378-12382
47. Hsu, S. C., Gavrilin, M. A., Tsai, M.-H., Han, J. and Lai, M.-Z. (1999) p38 mitogen-activated protein kinase is involved in Fas ligand expression. J. Biol. Chem. 274, 25769-25776
48. Le-Niculescu, H., Bonfoco, E., Kasuya, Y., Claret, F. X., Green, D. R. and Karin, M. (1999) Withdrawal of survival factors results in activation of the JNK pathway in neuronal cells leading to Fas ligand induction and cell death. Mol. Cell. Biol. 19, 751-763
49. Unger, C. and Eibl, H. (1991) Hexadecylphosphocholine: Preclinical and the first clinical results of a new antitumor drug. Lipids 26, 1412-1417
50. Unger, C., Fleer, E. A. M, Kötting, J., Neumüller, W. and Eibl, H. (1992) Antitumoral activity of alkylphosphocholines and analogues in human leukemia cell lines. Progr. Exp. Tumor. Res. 34, 25-32
51. Kaufmann-Kolle, P., Drevs, J., Berger, M. R., Kötting, J., Marschner, N., Unger, C. and Eibl, H. (1994) Pharmacokinetic behavior and antineoplastic activity of liposomal hexadecylphosphocholine. Cancer Chemother. Pharmacol. 34, 393-398
52. Unger, C., Sindermann, H., Peukert, M., Hilgard, P., Engel, J. and Eibl, H. (1992) Hexadecylphosphocholine in the topical treatment of skin metastases in breast cancer patients. Progr. Exp. Tumor. Res. 34, 153-159