Selective Inhibition of Phosphatidylinositol Phospholipase C by Cytotoxic Ether Lipid Analogues

Cancer Research

Volumn 52, Issue 10, 1992, Pages 2835-2840

  Modest, E J ^b   Seewald, M J ^a   Gratas, C ^a   Melder, D ^a   Riebow, J ^a  

^a MAYO CLINIC   (United States)

^b BOSTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 O ALKYLGLYCERO 3 PHOSPHORYLCHOLINE; EDELFOSINE; LIPID; PHOSPHATIDYLINOSITOL; PHOSPHOLIPASE C; PHOSPHOLIPASE D; TRIPHOSPHOINOSITIDE;

ANIMAL CELL; ARTICLE; CELL LINE; CONTROLLED STUDY; CYTOSOL; CYTOTOXICITY; DRUG EFFECT; ENZYME ACTIVITY; ENZYME INHIBITION; FIBROBLAST; GROWTH INHIBITION; MOUSE; NONHUMAN; OVARY ADENOCARCINOMA; PRIORITY JOURNAL;

3T3 CELLS; ADENOCARCINOMA; ANIMAL; CELL DIVISION; CHOLINE; COMPARATIVE STUDY; FEMALE; MICE; OVARIAN NEOPLASMS; PHOSPHOLIPASE D; PHOSPHOLIPASES; PHOSPHOLIPID ETHERS; PHOSPHORIC DIESTER HYDROLASES; SIGNAL TRANSDUCTION; SUPPORT, U.S. GOV'T, P.H.S.; TRITIUM; TUMOR CELLS, CULTURED;

EID: 0026742177     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (59)

1. Berdel, W. E., and Munder, P. G. Antineoplastic actions of ether lipids related to platelet-activating factor. In: F. Snyder (ed.), Platelet-activating Factor and Related Lipid Mediators, pp. 449-468. New York: Plenum Publishing Corp., 1987.
2. Modest, E. J., Noseda, A., Daniel, L. W., and Piantadosi, C. Membrane-targeted ether lipid analogs with antineoplastic activity. Cancer Chemother. Pharmacol., 24 (Suppl. 2): 359,1989.
3. Honma, Y., Kasukabe, T., Hozumi, M., Tsushima, S., and Nomura, H. Cytotoxicity and metabolism of alkyl phospholipid analogues in neoplastic cells. Cancer Res., 46:5803-5809,1980.
4. Berdel, W. E., Bausert, W. R., Weltzien, H. U., Modolell, M. L., Widmann, K. H., and Munder, P. The influence of alkyl-phospholipids and phospholipid-activated macrophages on the development of metastasis of 3-Lewis-lung carcinoma. Eur. J. Cancer, 16:1199-1204,1980.
5. Andressen, R., Modolell, M., Weltzien, H. U., Eibl, H., Common, H. H., Lohr, G. W., and Munder, P. G. Selective destruction of human leukemic cells by alkyl-phospholipids. Cancer Res., 38:3894-3899,1978.
6. Seewald, M. J., Olsen, R. A., Sehgal, I., Melder, D. C., Modest, E. J., and Powis, G. Inhibition of growth factor-dependent inositol phosphate Ca2 signalling by antitumor ether lipid analogues. Cancer Res., 50:4458-4463, 1990.
7. Tucker, R. W., Chang, D. T., and Meade-Cobun, K. Effects of platelet-derived growth factor and fibroblast growth factor on free intracellular calcium and mitogenesis. J. Cell. Biochem., 61:203-212,1989.
8. Cantley, L. C., Auger, K. R., Carpenter, C., Duckworth, B., Graziani, A., Kapeller, R., and Soltoff, S. Oncogenes and signal transduction. Cell, 64: 281-302,1991.
9. Martin, T. F. J. Receptor regulation of phosphoinositidase C. Pharmacol. Ther., 40:329-345,1991.
10. Heikkila, R., Trepel, J. B., Cultitta, F., Neckers, L. M., and Sausville, E. A. Bombesin-related peptides induce calcium mobilization in a subset of human small cell lung cancer cell lines. J. Biol. Chem., 262:16456-16460,1987.
11. Kriz, R., Lin, L-L., Sultzman, L., Ellis, C., Heldin, C-H., Pawson, T., and Knopf, J. Phospholipase C isozymes: structural and functional similarities. In: 1990 Proto-Oncogenes in Cell Development, Ciba Foundation Symposium, pp. 112-127. Chichester, United Kingdom: John Wiley and Sons, Inc., 1990.
12. Rhee, S. G., Suh, P-G., Ryu, S-H., and Lee, S. Y. Studies of inositol phospholipid-specific phospholipase C. Science (Washington DC), 244:546-550, 1989.
13. Haas, N., McDanel, H., Godwin, A., Humphrey, P., Bigner, S., and Wong, A. Specific expression of phospholipase C-³ in human glial tumors. Proc. Am. Assoc. Cancer Res., 32:17, 1991.
14. Arteaga, C. L., Johnson, M., Coffey, R. J., and Todderud, G. Tyrosine phosphorylated phospholipase C (PLC) gamma 1 is coexpressed with EGF receptors (R) or erbBi-2 in malignant but not benign human breast epithelial cells. Proc. Am. Assoc. Cancer Res., 32:46,1991.
15. Rhee, S. G., Kim, H., Suh, P-G., and Choi, W. C. Multiple forms of phosphoinositide-specific phospholipase C and different modes of activation. Biochem. Soc. Trans., 19:337-341,1991.
16. Dennis, E. A., Rhee, S. G., Billah, M. M., and Hannun, Y. A. Role of phospholipases in generating lipid second messengers in signal transduction. FASEB J., 5:2068-2077,1991.
17. Wakelam, M. J. O., Cook, S. J., Currie, S., Palmer, S., and Plevin, R. Receptor regulation of intracellular phospholipases. Biochem. Soc. Trans., 79:321-324,1991.
18. Insel, P. A., Weiss, B. A., Slivka, S. R., Howard, M. J., Waite, J. J., and Godson, C. A. Regulation of phospholipase A2 by receptors in MDCK-D1 cells. Biochem. Soc. Trans., 19:329-333,1991.
19. Noseda, A., Berens, M. E., Piantodosi, C., and Modest, E. J. Neoplastic cell inhibition with new ether lipid analogs. Lipids, 22:878-883,1987.
20. Marasco, C. J., Jr., Piantadosi, C., Ishaq, K. S., Meyer, K. L., Morris-Natschke, S., Small, G. W., and Daniel, L. W. Synthesis and biological activity of novel quaternary ammonium derivatives of alkylglycerols as potent inhibitors of protein kinase C. J. Med. Chem., 33:985-991,1990.
21. Wahl, M. I., Daniel, T. O., and Carpenter, G. Antiphosphotyrosine recovery of phospholipase C activity after EGF treatment of A-431 cells. Science (Washington DC), 241:968-970,1988.
22. Bligh, E., and Dyer, W. A rapid method for total lipid extraction and purification. Can. J. Biochem. Physiol., 37:911-917, 1959.
23. Cook, S. J., and Wakelam, M. J. O. Analyses of the water soluble products of phosphatidylcholine breakdown by ion-exchange chromatography. Biochem. J., 263:581-587, 1989.
24. Kiss, Z., and Anderson, W. B. Phorbol ester stimulates the hydrolysis of phosphatidyl ethanolamine in leukemic HL-60, NIH 3T3 and baby hamster kidney cells. J. Biol. Chem., 264:1483-1487,1989.
25. Wallen, C. A., Fujiwara, K., and Modest, E. J. Cell kill and cytostasis by an ether lipid. Proc. Am. Assoc. Cancer Res., 31:409,1990.
26. Powis, G., and Kozikowski, A. Growth factor and oncogene signalling pathways as targets of rational anticancer drug development. Clin. Biochem., 24:385-397,1991.
27. Bleasdale, J. E., Bundy, G. L., Bunting, S., Fitzpatrick, F. A., Huff, R. M., Sun, F. F., and Pike, J. E. Inhibition of phospholipase C-dependent processes by U-73,122. In: B. Samuelsson, P. Y-K. Wong, and F. F. Sun (eds.), Advances in Prostaglandin, Thromboxane and Leukotriene Research, pp. 590-593. New York: Raven Press. 1989.
28. Smith, M. R., Liu, Y-L., Kim, H., Rhee, S. G., and Kung, H. F. Inhibition of serum-and raf-stimulated DNA synthesis by antibodies to phospholipase C. Science (Washington DC), 247:1074-1077,1990.
29. Muller-Decker, K., Doppler, C., Amtmann, E., and Sauer, G. Interruption of growth signal transduction by an antiviral and antitumoral xanthate compound. Exp. Cell Res., 177:295-302, 1988.
30. Amtmann, E., and Sauer, G. Selective killing of tumor cells by xanthates. Cancer Lett., 35:237-244,1987.
31. Prentki, M., Deeney, J. T., Matschinsky, F. M., and Jospeh, S. K. Neomycin: a specific drug to study the inositol-phospholipid signalling system? FEBS Lett., 197:285-288,1986.
32. van Blitterswjjk, W. J., Hilkmann, H., and Storme, G. A. Accumulation of an alkyl-phospholipid in tumor cell membranes affects membrane fluidity and tumor cell invasion. Lipids, 22:820-823,1987.
33. Martin, T. W. Receptor regulation of phosphoinositidase C. Biochim. Biophys. Acta, 962:282-296,1991.
34. Meisenhelder, J., Suh, P-G., Rhee, S. G., and Hunter, T. Phospholipase C-7 is a substrate for the PDGF and EGF receptor protein-tyrosine kinoses in vivo and in vitro. Cell, 57: 1109-1122,1989.
35. Wahl, M. I., Oleshaw, N. E., Nishibe, B., Rhee, S. G., Pledger, W. J., and Carpenter, G. Platelet-derived growth factor induces rapid and sustained tyrosine phosphorylation of phospholipase C-7 in quiescence BALB/c 3T3 cells. Mol. CeU. Biol., 9:2934-2943,1989.
36. Bigay, J., Deterre, P., Pfister, C., and Chabre, M. Fluoride complexes of aluminium or beryllium act on G-proteins as reversibly bound analogues of the gamma phosphate of GTP. EMBO J., 6:2907-2915,1987.
37. Taylor, S. J., Chae, H. Z., Rhee, S. G., and Exton, J. H. Activation of the 01 isozyme of phospholipase C by a subunits of the Gq class of G proteins. Nature (Lond.), 350:516-518,1991.
38. Goldschmidt-Clermont, P. J., Kim, J. W., Machesky, L. M., Rhee, S. G., and Pollard, T. D. Regulation of phospholipase C-gammal by profilin and tyrosine phosphorylation. Science (Washington DC), 251:1231-1233,1991.
39. Carter, H. R., Wallace, M. A., and Fain, J. N. Purification and characterization of PLC-²m, a muscarinic cholinergic regulated phospholipase C from rabbit brain membrane. Biochim. Biophys. Acta, 1054:119-128, 1990.
40. Mqerus, P. W., Ross, T. S., Cunningham, T. W., Caldwell, K. K., Jefferson, A. B., and Bansal, V. S. Recent insights in phosphatidylinositol signaling. Cell, 63:459-465, 1990.
41. Perrella, F. W., Piantadosi, C., Marasco, C. J., and Modest, E. J. Inhibition of phospholipase C and cell growth by ether lipid analogues of phosphatidylinositol. Proc. Am. Assoc. Cancer Res., 31:409, 1990.
42. Berridge, M. J. Rapid accumulation of inositol trisphosphate reveals that agonists hydrolyse polyphosphoinositides instead of phosphatidylinositol. Biochem. J., 212:849-858,1983.
43. Michell, R. H., Kirk, C. J., Jones, L. M., Dawnes, C. P., and Creba, J. A. The stimulation of inositol metabolism that accompanies calcium mobilization in stimulated cells: defined characteristics and unanswered questions. Philos. Trans. R. Soc. Lond. B., 296:123-137,1981.
44. Hoffman, D. R., Hoffman, L. H., and Snyder, F. Cytotoxicity and metabolism of alkyl phospholipid analogues in neoplastic cells. Cancer Res., 46: 5803-5809,1986.
45. Wilcox, R. W., Wykle, R. L., Schmitt, J. D., and Daniel, L. W. The degradation of platelet-activating factor and related lipids: susceptibility to phospholipases C and D. Lipids, 22:800-807,1987.
46. Wykle, R. L., and Schremmer, J. M. Alkylphospholipase D pathway in the metabolism of ether-linked lipids in brain microsomes. J. Biol. Chem., 249: 1742-1746,1974.
47. Billah, M. M., and Anthe, J. C. The regulation and cellular functions of phosphatidylcholine hydrolysis. Biochem. J., 269:281-291,1990.
48. Larrodera, P., Cornet, M. E., Diaz-Meco, M. T., Lopez-Barahona, M., Diaz-Laviada, I., Guddal, P. H., Johansen, T., and Moscat, J. Phospholipase C-mediated hydrolysis of phosphatidylcholine is an important step in PDGF-stimulated DNA synthesis. Cell, 61:1113-1120,1990.
49. Storme, G. A., Berdel, W. E., van Blitterswijk, W. J., Bruyneel, E. A., De Bruyne, G. K., and Mareel, M. M. Anti-invasive effect of racemic 1-O-octadecyl-2-O-methylglycero-3-phosphocholineon M04 mouse fibrosarcoma cells in vitro. Cancer Res., 45:351-357,1985.
50. Noseda, A., Godwin, P.L., and Modest, E. J. Effects of antineoplastic ether lipids on model and biological membranes. Biochim. Biophys. Acta, 945: 92-100,1988.
51. Daniel, L. W., Small, G. W., and Strum, J. C. Characterization of cells sensitive and resistant to ET-18-OCH3. Proc. Am. Assoc. Cancer Res., 31: 412,1990.
52. Bazill, G. W., and Dexter, T. M. Role of endocytosis in the action of ether lipids on WEHI-3B, HL60, and FDCP-mix A4 cells. Cancer Res., 50:7505-7512,1990.
53. Chabot, M. C., Wykle, R. L., Modest, E. J., and Daniel, L. W. Correlation of ether lipid content of human leukemia cell lines and their susceptibility to 1-O-octadecyl-2-O-methyl-nic-glycero-3-phosphocholine. Cancer Res., 49: 4441-4445,1989.
54. Diomede, L., Bizzi, A., Magistrelli, A., Modest, E. J., Salmona, M., and Noseda, A. Role of cell cholesterol in modulating antineoplastic ether lipid uptake, membrane effects and cytotoxicity. Int J. Cancer, 46: 341-346, 1990.
55. Smith, M. R., Ryu, S. H., Suh, P. G., Rhee, S. G., and Kung, H. F. S-phase induction and transformation of quiescent NIH 3T3 cells by microiqjection of phospholipase C. Proc. Natl. Acad. Sci. USA, 86:3659-3663,1989.
56. Rath, H. M., Doyle, G. A. R., and Silbert, D. F. Hamster fibroblasts defective in thrombin-induced mitogenesis. J. Biol. Chem., 264:13387-13390,1989.
57. Margolis, B., Zilberstein, A., Franks, C., Felder, S., Kremer, S., Ullrich, A., Rhee, S. G., Skorecki, K., and Schlessinger, J. Effect of phospholipase C-7 overexpression on PDGF-induced second messengers and mitogenesis. Science (Washington DC), 248:607-616,1990.
58. Cuadrado, A., and Molloy, C. J. Overexpression of phospholipase C-7 in NIH 3T3 fibroblasts results in increased phosphatidylinositol hydrolysis in response to platelet-derived growth factor and basic fibroblast growth factor. Mol. Cell. Biol., 10:6069-6072,1990.
59. Helfman, D. M., Barnes, K. C., Kinkade, J. M., Vogler, W. R., Shoji, M. M., and Kuo, J. F. Phospholipid-sensitive Ca2+-dependent protein phosphorylation system in various types of leukemic cells from human patients and in human leukemic cell lines HL60 and K562, and its inhibition by alkyl-phospholipid. Cancer Res., 43:2955-2961, 1983.