Inhibition of phosphatidylcholine synthesis is not the primary pathway in hexadecylphosphocholine-induced apoptosis

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1636, Issue 2-3, 2004, Pages 99-107

  Van Der Sanden, Michiel H M ^a   Houweling, Martin ^a   Duijsings, Daniël ^a   Vaandrager, Arie B ^a   Van Golde, Lambert M G ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

alkyl lysophospholipid analog; ALP; Anticancer drug; CT; CTP:phosphocholine cytidylyltransferase; DAG; diacylglycerol; HePC; hexadecylphosphocholine; Phosphatidylethanolamine; Phosphatidylserine; Phospholipid synthesis

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; CELL PROTEIN; CERAMIDE; CYCLOHEXIMIDE; DIACYLGLYCEROL; LYSOPHOSPHATIDYLETHANOLAMINE; MILTEFOSINE; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLSERINE; PROTEIN DERIVATIVE; SPHINGOMYELIN; UNCLASSIFIED DRUG;

ANALYTIC METHOD; APOPTOSIS; COMPARATIVE STUDY; DRUG SYNTHESIS; GENETIC DISORDER; IMMUNOBLOTTING; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; REVIEW; SCINTILLATION COUNTING; X RAY FILM;

ANIMALS; APOPTOSIS; CHO CELLS; CRICETINAE; PHOSPHATIDYLCHOLINES; PHOSPHORYLCHOLINE;

EID: 2942674883     PISSN: 13881981     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbalip.2003.08.008     Document Type: Review

References (43)

1. Ruiter G.A., Verheij M., Zerp S.F., van Blitterswijk W.J. Alkyl-lysophospholipids as anticancer agents and enhancers of radiation-induced apoptosis. Int. J. Radiat. Oncol. Biol. Phys. 49:2001;415-419
2. Cui Z., Houweling M. Phosphatidylcholine and cell death. Biochim. Biophys. Acta. 1585:2002;87-96
3. Boggs K., Rock C.O., Jackowski S. The antiproliferative effect of hexadecylphosphocholine toward HL60 cells is prevented by exogenous lysophosphatidylcholine. Biochim. Biophys. Acta. 1389:1998;1-12
4. Baburina L., Jackowski S. 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. 273:1998;2169-2173
5. Van der Luit A.H., Budde M., Buurs P., Verheij M., van Blitterswijk W.J. Alkyl-lysophospholipid accumulates in lipid rafts and induces apoptosis via raft-dependent endocytosis and inhibition of phosphatidylcholine synthesis. J. Biol. Chem. 277:2002;39541-39547
6. Geilen C.C., Haase A., Wieder T., Arndt D., Zeisig R., Reutter W. Phospholipid analogues: side chain- and polar head group-dependent effects on phosphatidylcholine biosynthesis. J. Lipid Res. 35:1994;625-632
7. Holmes-McNary M.Q., Loy R., Mar M.H., Albright C.D., Zeisel S.H. Apoptosis is induced by choline deficiency in fetal brain and in PC12 cells. Brain Res. Dev. Brain Res. 18:1997;9-16
8. Cui Z., Houweling M., Chen M.H., Record M., Chap H., Vance D.E., Terce F. A genetic defect in phosphatidylcholine biosynthesis triggers apoptosis in Chinese hamster ovary cells. J. Biol. Chem. 271:1996;14668-14671
9. Esko J.D., Wermuth M.M., Raetz C.R. Thermolabile CDP-choline synthetase in an animal cell mutant defective in lecithin formation. J. Biol. Chem. 256:1981;7388-7393
10. van der Sanden M.H.M., Houweling M., van Golde L.M.G., Vaandrager A.B. Inhibition of phosphatidylcholine synthesis induces expression of the endoplasmic reticulum stress and apoptosis-related protein CCAAT/enhancer- binding protein-homologous protein (CHOP/GADD153). Biochem. J. 369:2003;643-650
11. Esko J.D., Nishijima M., Raetz C.R. Animal cells dependent on exogenous phosphatidylcholine for membrane biogenesis. Proc. Natl. Acad. Sci. U. S. A. 79:1982;1698-1702
12. Houweling M., Cui Z., Vance D.E. Expression of phosphatidylethanolamine N-methyltransferase-2 cannot compensate for an impaired CDP-choline pathway in mutant Chinese hamster ovary cells. J. Biol. Chem. 270:1995;16277-16282
13. Lykidis A., Baburina L., Jackowski S. Distribution of CTP:phosphocholine cytidylyltransferase (CCT) isoforms. Identification of a new CCTbeta splice variant. J. Biol. Chem. 274:1999;26992-27001
14. Bligh E.G., Dyer W.J. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37:1959;911-917
15. Preiss J., Loomis C.R., Bishop W.R., Stein R., Niedel J.E., Bell R.M. Quantitative measurement of sn-1, 2-diacylglycerols present in platelets, hepatocytes, and ras and sis-transformed normal rat kidney cells. J. Biol. Chem. 261:1986;8597-8600
16. Rouser G., Siakotos A.N., Fleischer S. Quantitative analysis of phospholipids by thin-layer chromatography and phosphorus analysis of spots. Lipids. 1:1966;85-86
17. Sweitzer T.D., Kent C. Expression of wild-type and mutant rat liver CTP: phosphocholine cytidylyltransferase in a cytidylyltransferase-deficient Chinese hamster ovary cell line. Arch. Biochem. Biophys. 311:1994;107-116
18. Flores I., Jones D.R., Merida I. Changes in the balance between mitogenic and antimitogenic lipid second messengers during proliferation, cell arrest, and apoptosis in T-lymphocytes. FASEB J. 14:2000;1873-1875
19. Martin S.J., Reutelingsperger C.P.M., McGahon A.J., Rader A.J., van Schie R.C.A.A., LaFace D.M., Green D.R. Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl. J. Exp. Med. 182:1995;1545-1556
20. Verhoven B., Schlegel R.A., Williamson P. Mechanisms of phosphatidylserine exposure, a phagocyte recognition signal, on apoptotic T lymphocytes. J. Exp. Med. 182:1995;1597-1601
21. Waite K.A., Vance D.E. Why expression of phosphatidylethanolamine N-methyltransferase does not rescue Chinese hamster ovary cells that have an impaired CDP-choline pathway. J. Biol. Chem. 275:2000;21197-21202
22. Wieder T., Zhang Z., Geilen C.C., Orfanos C.E., Giuliano A.E., Cabot M.C. The antitumor phospholipid analog, hexadecylphosphocholine, activates cellular phospholipase D. Cancer Lett. 100:1996;71-79
23. Lucas L., Hernandez-Alcoceba R., Penalva V., Lacal J.C. Modulation of phospholipase D by hexadecylphosphorylcholine: a putative novel mechanism for its antitumoral activity. Oncogene. 20:2001;1110-1117
24. Vaandrager A.B., Houweling M. Effect of ceramides on phospholipid biosynthesis and its implication for apoptosis. Quinn P., Kagan V. Phospholipid Metabolism in Apoptosis. Subcell. Biochem. vol. 36:2002;207-227 Kluwer Academic/Plenum publishers, New York
25. Allan D. Lipid metabolic changes caused by short-chain ceramides and the connection with apoptosis. Biochem. J. 345:2000;603-610
26. Wieder T., Orfanos C.E., Geilen C.C. Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J. Biol. Chem. 273:1998;11025-11031
27. Tepper A.D., Ruurs P., Wiedmer T., Sims P.J., Borst J., van Blitterswijk W.J. Sphingomyelin hydrolysis to ceramide during the execution phase of apoptosis results from phospholipid scrambling and alters cell-surface morphology. J. Cell Biol. 150:2000;155-164
28. Gajate C., Santos-Beneit A., Modolell M., Mollinedo F. Involvement of c-Jun NH2-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. 53:1998;602-612
29. Ruiter G.A., Zerp S.F., Bartelink H., van Blitterswijk W.J., Verheij M. Alkyl-lysophospholipids activate the SAPK/JNK pathway and enhance radiation-induced apoptosis. Cancer Res. 59:1999;2457-2463
30. Gajate C., Fonteriz R.I., Cabaner C., Alvarez-Noves G., Alvarez-Rodriguez Y., Modolell M., Mollinedo F. Intracellular triggering of Fas, independently of FasL, as a new mechanism of antitumor ether lipid-induced apoptosis. Int. J. Cancer. 85:2000;674-682
31. Zhou X., Lu X., Richard C., Xiong W., Litchfield D.W., Bittman R., Arthur G. 1-O-octadecyl-2-O-methyl-glycerophosphocholine inhibits the transduction of growth signals via the MAPK cascade in cultured MCF-7 cells. J. Clin. Invest. 98:1996;937-944
32. Powis G., Seewald M.J., Gratas C., Melder D., Riebow J., Modest E.J. Selective inhibition of phosphatidylinositol phospholipase C by cytotoxic ether lipid analogues. Cancer Res. 52:1992;2835-2840
33. Uberall F., Oberhuber H., Maly K., Zaknun J., Demuth L., Grunicke H.H. Hexadecylphosphocholine inhibits inositol phosphate formation and protein kinase C activity. Cancer Res. 51:1991;807-812
34. Ghafourifar P., Klein S.D., Schucht O., Pruschy M., Rocha S., Richter C. Ceramide-induced cytochrome c release from isolated mitochondria. Importance of mitochondrial redox state. J. Biol. Chem. 274:1991;6080-6084
35. Kagedal K., Zhao M., Svenssson I., Brink U.T. Sphingosine-induced apoptosis is dependent on lysosomal proteases. Biochem. J. 359:2001;335-343
36. Yuan X.M., Li W., Dalen H., Lotem J., Kama R., Sachs L., Brink U.T. Lysosomal destabilization in p53-induced apoptosis. Proc. Natl. Acad. Sci. U. S. A. 99:2002;6286-6291
37. van Blitterswijk W.J., van der Luit A.H., Veldman R.J., Verheij M., Borst J. Ceramide: second messenger or modulator of membrane structure and dynamics? Biochem. J. 369:2003;199-211
38. Bladergroen B.A., Bussiere M., Klein W., Geelen M.J.H., van Golde L.M.G., Houweling M. Inhibition of phosphatidylcholine and phosphatidylethanol-amine biosynthesis in rat-2 fibroblasts by cell-permeable ceramides. Eur. J. Biochem. 264:1999;152-160
39. Ramos B., Salido G.M., Campo M.L., Claro E. Inhibition of phosphatidyl-choline synthesis precedes apoptosis induced by C2-ceramide: protection by exogenous phosphatidylcholine. NeuroReport. 11:2000;3103-3108
40. Voziyan P.A., Goldner C.M., Melnykovych G. Farnesol inhibits phosphatidylcholine biosynthesis in cultured cells by decreasing cholinephosphotransferase activity. Biochem. J. 295:1993;757-762
41. Miquel K., Pradines A., Terce F., Selmi S., Favre G. Competitive inhibition of choline phosphotransferase by geranylgeraniol and farnesol inhibits phosphatidylcholine synthesis and induces apoptosis in human lung adenocarcinoma A549 cells. J. Biol. Chem. 273:1998;26179-26186
42. Anthony M.L., Zhao M., Brindle K.M. Inhibition of phosphatidylcholine biosynthesis following induction of apoptosis in HL-60 cells. J. Biol. Chem. 274:1999;19686-19692
43. Wright M.M., Henneberry A.L., Lagace T.A., Ridgway N.D., McMaster C.R. Uncoupling farnesol induced apoptosis from its inhibition of phosphatidylcholine synthesis. J. Biol. Chem. 2001;25254-25261