Glycosylated antitumor ether lipids are more effective against oncogene-transformed fibroblasts than alkyllysophospholipids

Anticancer Research

Volumn 18, Issue 1 A, 1998, Pages 465-470

  Samadder, Pranati ^a   Byun, Hoe Sup ^b   Bittman, Robert ^b   Arthur, Gilbert ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

^b CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Alkyllysophospholipids; Fibroblasts; Glycosylated ether linked diglycerides; Oncogenes

Indexed keywords

ALKYLLYSOPHOSPHOLIPID; ETHER LIPID; PHOSPHORYLCHOLINE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL PROLIFERATION; CELL TRANSFORMATION; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; FIBROBLAST; FIBROSARCOMA; MOUSE; NONHUMAN; ONCOGENE; PRIORITY JOURNAL;

3T3 CELLS; ANIMALS; ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL TRANSFORMATION, NEOPLASTIC; GLYCOLIPIDS; GLYCOSYLATION; LYSOPHOSPHOLIPIDS; MICE; ONCOGENES; PHOSPHATIDYLCHOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0031899953     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. Munder PG and Westphal O: Antitumoral and other biomedical activities of synthetic ether lysophospholipids in 1939-1987: fifty years progress in allergy (Waksman B.H. ed) Karger, Basel pp 206-235, 1990.
2. Principe P and Braquet P: Advances in ether phospholipid treatment of cancer. Crit Rev Oncol Hematol 18: 155-178, 1995.
3. Houlihan WJ, Lohmeyer M, Workman P and Cheon SH: Phospholipid antitumor agents. Med Res Rev 15: 157-223, 1995.
4. Lohmeyer M and Bittman R: Antitumor ether lipids and alkylphosphocholines. Drugs Future 19: 1021-1037, 1994.
5. Haase R, Wieder T, Geilen CC and Reutter W: The phospholipid analogue hexadecylphosphocholine inhibits phosphatidylcholine biosynthesis in Madin-Darby canine kidney cells. FEBS Lett 288: 129-132, 1991.
6. Boggs KP, Rock CO and Jackowski S: Lysophosphatidylcholine attenuates the cytotoxic effects of the antineoplastic phospholipid 1-O-octadecyl-2-O-methyl-rac-glycerophosphocholine. J. Biol. Chem. 270: 11612-11618, 1995.
7. Beggren MI, Gallegos A, Dressler LA, Modest EJ and Powis G: Inhibition of the signalling enzyme phosphatidylinositol-3-kinase by antitumor ether lipid analogues. Cancer Res 53: 4297-4302, 1993.
8. Zhou X, Lu X, Richard C, Xiong W, Litchfield DW, Bittman R and 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: 937-944, 1996.
9. 2+ 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- lysophospholipid. Cancer Res 43: 2955-2961, 1983.
10. Arthur G and Bittman R: The inhibition of cell signaling pathways by antitumor ether lipids. Biochim. Biophys. Acta (in press), 1997.
11. Huffman DR, Thomas VL and Snyder F: Inhibition of cellular transport systems by alkylphospholipid analogs in human leukemia cells. Biochim. Biophys Acta 1127: 74-80, 1992.
12. Diomede L, Piovani B, Re F, Principe P, Colotta F, Modest EJ and Salmona M: The induction of apoptosis is a common feature of the cytotoxic action of ether-linked glycerophospholipids in human leukemic cells. Int J Cancer 57: 645-649 1994.
13. 3 (edelfosine): molecular structure requirements, cellular uptake and protection by Bcl-2 and Bcl-XL. Cancer Res. 57: 1320-1328, 1997.
14. Lu X, Rengan K, Bittman R and Arthur G: The α and β anomers of 1-O-hexadecyl-2-O-methyl-3-S-thioglucosyl-sn-glycerol inhibit the proliferation of epithelial cancer cell lines. Oncology Rep 1: 933-936, 1994.
15. Erukulla RK, Zhou X, Samadder P, Arthur G and Bittman R: Synthesis and evaluation of the antiproliferative effects of 1-O-hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-sn- glycerol and 1-O-hexadecyl-2-O-methyl-3-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-sn- glycerol on epithelial cancer cell growth. J Med Chem 39: 1545-1548, 1996.
16. 3. Lipids 22: 84-890, 1987.
17. Andressen R, Modolell M, Weltzien HU, Eibl H, Common, HH, Lohr GW and Munder PG: Selective destruction of human leukemic cells by alkyl-lysophospholipids. Cancer Res 38: 3894-3899, 1978.
18. Glasser L, Somberg LR and Vogler WR: Purging murine leukemic marrow with alkyl- lysophospholipids. Blood 64: 1288-1291, 1984.
19. Andreesen R, Modolell M and Munder PG: Selective sensitivity of chronic myelogenous leukemia cell populations to alkyllysophospholipids. Blood 54: 519-523, 1979.
20. Storch J and Munder PG: Increased membrane permeability for an antitumoral alkyl lysophospholipid in sensitive tumor cells. Lipids 22: 813-819, 1987.
21. Powis G, Seewald MJ, Gratas C, Elder D, Riebow J and Modest EJ: Selective inhibition of phosphatidylinositol phospholipase C by cytotoxic ether lipid analogues. Cancer Res 52: 2835-2840, 1992.
22. Junghahn I, Bergmann J, Langen P, Thun I, Vollgraf C and Brachwitz H: Effect of ALP analogs on inositol trisphosphate formation on H184 mammary epithelial cells before and after transfection with verbB oncogene. Anticancer Res 15: 449-454, 1995.
23. Powis G: Signalling pathways as targets for anticancer drug development. Pharmac Ther 62: 57-95, 1994.
24. Givol I, Givol D, Rulong S, Resan J, Tsarfaly I and Hughes SH: Overexpression of human p21waf1/cip1 arrests the growth of chicken fibroblasts transformed by individual oncogenes. Oncogene 11: 2609-2618, 1995.
25. Slamon DJ, Clark GM, Wong SG, Levin WJ, Ullrich A and McGuire WL: Human breast cancer correlation of relapse and survival with amplification of the HER-2/neu oncogene. Science 235: 177-182, 1987.
26. Egan SE, Wright JA, Jarolim L, Yanagihara K, Bassin RH and Greenberg AH: Transformation by oncogene encoding protein kinases induces the metastatic phenotype. Science 238: 202-205, 1987.
27. Marshall CJ: Specificity of receptor tyrosine kinase signaling: transients versus sustained extracellular regulated kinase activation. Cell 80: 179-185, 1995.
28. Bittman R, Byun H-S, Reddy KC, Samadder P and Arthur G: Enantioselective synthesis and antiproliferative properties of an analog of ilmofosine, 2'-(trimethylammonio)ethyl 3-(hexadecyloxy)-2-(methoxymethyl)propanephosphate, on epithelial cancer cell growth. J Med Chem 40: 1391-1395, 1997.
29. Guivisdalsky PN, Bittman R, Smith Z, Blank ML, Snyder F, Howard S and Salari H: Synthesis and antineoplastic properties of ether-linked thioglycolipids. J. Med. Chem 33: 2614-2621, 1990.
30. Bittman R, Byun H-S, Mercier B and Salari H: Isosteric phosphonate analogs of ET-16-OMe. Synthesis and biological evaluation of the enantiomers of 2'-(trimethylammonio)ethyl 4-(hexadecyloxy)-3-methoxybutanephosphonate and 2'-(trimethylammonio)ethyl 4-(hexadecylthio)-3-methoxybutanephosphonate. J Med Chem 37: 425-430, 1994.
31. Chen M, Li D, Krebs EG and Cooper JA: The casein kinase II β subunit binds to mos and inhibits mos activity. Mol Cell Biol 17: 1904-1912, 1997.
32. Wu X, Noh SJ, Zhou G, Dixon JE and Guan K-L: Selective activation of MEK1 but not MEK 2 by A-Raf from epidermal growth factor stimulated Hela cells. J Biol Chem 271: 3265-3271, 1996.
33. Huleihel M, Goldsborough M, Cleveland J, Gunnel M, Bonner T and Rapp UR: Characterization of murine A-raf, a new oncogene related to v-raf oncogene. Mol Cell Biol 6: 2655-2622, 1986.
34. Beck TW, Huleihel M, Gunnel M, Bonner T and Rapp UR: The complete coding sequence of the human A-raf-1 oncogene and transforming activity of a human A-raf carrying retrovirus. Nucleic Acid Res 15: 595-609, 1987.
35. Rogan AM, Hamilton TC, Young RC, Klecker RW Jr and Ozols RF: Reversal of adriamycin resistance by verapamil in human ovarian cancer. Science 224: 994-996, 1984.
36. Green JA, Vistica DT, Young RC, Hamilton TC, Rogan AM and Ozols RF: Potentiation of mephalan cytotoxicity in human ovarian cancer cell lines by glutathione depletion. Cancer Res 44: 5427-5431, 1984.