Synthesis and antitumor properties of a plasmalogen methyl ether analogue

Tetrahedron

Volumn 57, Issue 20, 2001, Pages 4277-4282

  Bittman, Robert ^a   Qin, Donghui ^a   Wong, De An ^b   Tigyi, Gabor ^b   Samadder, Pranati ^c   Arthur, Gilbert ^c  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^c UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Antitumor compounds; Lipids; Phospholipids

Indexed keywords

1 O (1' OCTADECENYL) 2 O METHYL GLYCERO 3 O PHOSPHOCHOLINE; 4 HYDROXYMETHYL 2,2 DIMETHYL 1,3 DIOXOLANE; EDELFOSINE; G PROTEIN COUPLED RECEPTOR; GLYCEROL DERIVATIVE; GROWTH FACTOR RECEPTOR; PLASMALOGEN; PLASMALOGEN O METHYL ETHER DERIVATIVE; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; BREAST EPITHELIUM; CANCER CELL; CANCER GROWTH; CANCER INHIBITION; CELL PROLIFERATION; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PRIORITY JOURNAL;

EID: 0035858683     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00371-4     Document Type: Article

References (27)

1. Klenk E., Debuch H. Holman R.T., Lundberg W.O., Malkin T. Prog. Chem. Fats and Other Lipids. 1963;1-29 Pergamon, New York.
2. Horrocks L.A., Sharma M. Hawthorne J.N., Ansell G.B. Phospholipids. Vol. 4:1982;50-93 Elsevier, Amsterdam.
3. Some of the distinctive functions of plasmalogens in membranes include: (a) facilitation of membrane fusion: Glaser P.E., Gross R.W. Biochemistry. 33:1994;5805-5812.
4. 2 activated by agonists: Farooqui A.A., Rapoport S.I., Horrocks L.A. Neurochem. Res. 22:1997;523-527.
5. (c) storage depot for arachidonic acid (at the sn-2 position): Ford D.A., Gross R.W. Proc. Natl. Acad. Sci. USA. 86:1989;3479-3483.
6. 2+ exchange: Ford D.A., Hale C.C. FEBS Lett. 394:1996;99-102.
7. Paltauf F. Chem. Phys. Lipids. 74:1994;101-139.
8. Bräutigam C., Engelmann B., Reiss D., Reinhardt U., Thiery J., Richter W.O., Brosche T. Atherosclerosis. 119:1996;77-88.
9. Hofer G., Lichtenberg D., Kostner G.M., Hermetter A. Clin. Biochem. 29:1996;445-450.
10. Jira W., Spiteller G. Chem. Phys. Lipids. 79:1996;95-100.
11. For reviews of antitumor ether lipids, see: (a) Bittman R., Arthur G. Janoff A.S. Liposomes: Rational Design. 1998;125-144 Marcel Dekker, New York.
12. Lohmeyer M., Bittman R. Drugs Fut. 19:1994;1021-1037.
13. Arthur G., Bittman R. Biochim. Biophys. Acta. 1390:1998;85-102.
14. Houlihan W.J., Lohmeyer M., Workman M., Cheon S.H. Med. Res. Rev. 15:1995;157-223.
15. For a recent review about PAF, see: Montrucchio G., Alloatti G., Camussi G. Physiol. Rev. 80:2000;1669-1699.
16. For structures of previous analogues of 2, see: Refs. 4a and 4d.
17. After this manuscript was first submitted, a paper appeared on the synthesis and activity of rac-4 in pancreatic tumor cells: Shin J., Qualls M.M., Boomer J.A., Robarge J., Thompson D.H. J. Am. Chem. Soc. 123:2001;508-509.
18. Qin D., Byun H.-S., Bittman R. J. Am. Chem. Soc. 121:1999;662-668.
19. Moyano A., Charbonnier F., Greene A.E. J. Org. Chem. 52:1987;2919-2922.
20. Gajate C., Santos-Beneit A., Modolell M., Mollinedo F. Mol. Pharmacol. 53:1998;606-612.
21. Chai Y.C., Binion D.G., Chisolm G.M. Am. J. Physiol. Heart Circ. Physiol. 279:2000;H1830-H1838.
22. Goetzl E.J., Lee H., Dolezalova H., Kalli K.R., Conover C.A., Hu Y.L., Azuma T., Stossel T.P., Karliner J.S., Jaffe R.B. Ann. N. Y. Acad. Sci. 905:2000;177-187.
23. Fischer D.J., Liliom K., Guo Z., Nusser N., Virag T., Murakami-Murofushi K., Kobayashi S., Erickson J.R., Sun G., Miller D.D., Tigyi G. Mol. Pharmacol. 54:1998;979-988.
24. Spiteller G. Free Radical Biol. Med. 21:1996;1003-1009.
25. It was recently demonstrated that mitogenesis in rat hepatoma cells in response to lysophosphatidic acid (LPA, 1-acyl-2-hydroxy-sn-glycero-3-phosphate), a phospholipid structurally similar to 4, is independent of Edg receptor activation: Hooks S.B., Santos W.L., Im D.-S., Heise C.E., Macdonald T.L., Lynch K.R. J. Biol. Chem. 276:2001;4611-4621.
26. Byun H.-S., Kumar E.R., Bittman R. J. Org. Chem. 59:1994;2630-2633.
27. Samadder P., Byun H.-S., Bittman R., Arthur G. Anticancer Res. 18:1998;465-470.