Hexadecylphosphocholine inhibits phosphatidylcholine biosynthesis and the proliferation of HepG2 cells

European Journal of Biochemistry

Volumn 269, Issue 18, 2002, Pages 4649-4655

  Jiménez López, José M ^a   Carrasco, María P ^a   Segovia, Josefa L ^a   Marco, Carmen ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

Alkylphosphocholines; CTP:phosphocholine cytidylyltransferase; Human hepatoblastoma cells; Phosphatidylcholine metabolism; Proliferation

Indexed keywords

CHOLINEPHOSPHOTRANSFERASE; CYTIDINE TRIPHOSPHATE; MILTEFOSINE; PHOSPHATIDYLCHOLINE;

ARTICLE; BIOACCUMULATION; BIOSYNTHESIS; CANCER CHEMOTHERAPY; CELL MEMBRANE; CELL PROLIFERATION; CHOLINE UPTAKE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOSOL; DRUG ACTIVITY; DRUG EFFECT; DRUG INHIBITION; HEP 2 CELL; HEPATOMA CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPID LIVER LEVEL; LIPID METABOLISM; PRECURSOR; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; CELL DIVISION; CHOLINE; HUMANS; PHOSPHATIDYLCHOLINES; PHOSPHORYLCHOLINE; TUMOR CELLS, CULTURED;

EID: 0036381777     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1033.2002.03169.x     Document Type: Article

References (34)

1. Berkovic, D. (1998) Cytotoxic etherphospholipid analogues. Gen. Pharmacol. 31, 511-517.
2. Clive, S., Gardiner, J. & Leonard, R.C. (1999) Miltefosine as a topical treatment for cutaneous metastases in breast carcinoma. Cancer Chemother. Pharmacol. 44, S29-S30.
3. Kaufmann-Kolle, P., Berger, M.R., Unger, C. & Eibl, H. (1996) Systemic administration of alkylphosphocholines. Erucylphosphocholine and liposomal hexadecylphosphocholine. In Platelet-Activating Factor and Related Lipid Mediators 2 (Nigam, S., Kunkel, G. & Prescott, S.M., eds), pp. 165-168. Plenum Press, New York.
4. Zeisig, R., Arndt, D., Stahn, R. & Fichtner, I. (1998) Physical properties and pharmacological activity in vitro and in vivo of optimised liposomes prepared from a new cancerostatic alkylphospholipid. Biochim. Biophys. Acta 1414, 238-248.
5. Eue, I. (2001) Growth inhibition of human mammary carcinoma by liposomal hexadecylphosphocholine: Participation of activated macrophages in the antitumor mechanism. Int. J. Cancer 92, 426-433.
6. Wieder, T., Reutter, W., Orfanos, C.E. & Geilen, C.C. (1999) Mechanisms of action of phospholipid analogs as anticancer compounds. Prog. Lipid Res. 38, 249-259.
7. Arthur, G. & Bittman, R. (1998) The inhibition of cell signaling pathways by antitumor ether lipids. Biochim. Biophys. Acta 1390, 85-102.
8. Berkovic, D., Goeckenjan, M., Luders, S., Hiddemann, W. & Fleer, E.A. (1996) Hexadecylphosphocholine inhibits phosphatidylinositol and phosphatidylcholine phospholipase C in human leukemia cells. J. Exp. Ther. Oncol. 1, 302-311.
9. Berkovic, D., Luders, S., Goeckenjan, M., Hiddemann, W. & Fleer, E.A. (1997) Differential regulation of phospholipase A2 in human leukemia cells by the etherphospholipid analogue hexadecylphosphocholine. Biochem. Pharmacol. 53, 1725-1733.
10. Dittrich, N., Haftendorn, R. & Ulbrich-Hofmann, R. (1998) Hexadecylphosphocholine and 2-modified 1,3-diacylglycerols as effectors of phospholipase D. Biochim. Biophys. Acta 1391, 265-272.
11. Lucas, L., Hernandez-Alcoceba, R., Penalva, V. & Lacal, J.C. (2001) Modulation of phospholipase D by hexadecylphosphorylcholine: a putative novel mechanism for its antitumoral activity. Oncogene 20, 1110-1117.
12. 2+ concentration in a normal and a breast cancer cell line. Anticancer Res. 14, 1549-1556.
13. Wieder, T., Haase, A., Geilen, C.C. & Orfanos, C.E. (1995) The effect of two synthetic phospholipids on cell proliferation and phosphatidylcholine biosynthesis in Madin-Darby canine kidney cells. Lipids 30, 389-393.
14. Wieder, T., Orfanos, C.E. & Geilen, C.C. (1998) Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J. Biol. Chem. 273, 11025-11031.
15. Boggs, K.P., Rock, C.O. & Jackowski, S. (1998) The antiproliferative effect of hexadecylphosphocholine toward HL60 cells is prevented by exogenous lysophosphatidylcholine. Biochim. Biophys. Acta 1389, 1-12.
16. Posse de Chaves, E., Vance, D.E., Campenot, R.B. & Vance, J.E. (1995) Alkylphosphocholines inhibit choline uptake and phosphatidylcholine biosynthesis in rat symphatetic neurons and impair axonal extension. Biochem. J. 312, 411-417.
17. Carrasco, M.P., Sánchez-Amate, M.C., Marco, C. & Segovia, J.L. (1996) Evidence of differential effects produced by ethanol on specific phospholipid biosynthesis pathways in rat hepatocytes. Br. J. Pharmacol. 119, 233-238.
18. Jiménez-López, J.M., Carrasco, M.P., Segovia, J.L. & Marco, C. (2002) Resistance of HepG2 cells against the adverse effects of ethanol related to neutral lipid and phospholipid metabolism. Biochem. Pharmacol. 63, 1485-1490.
19. Carmichael, J., DeGraff, W.G., Gazdar, A.F., Minna, J.D. & Mitchell, J.B. (1987) Evaluation of a tetrazolium-based semi-automated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 47, 936-942.
20. Bligh, E.G. & Dyer, W.J. (1959) A rapid method for total lipid extraction and purification. Can. J. Biochem. Physiol. 37, 911-917.
21. Bradford, M.M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
22. Pelech, S.L., Power, E & Vance, D.E. (1983) Activities of the phosphatidylcholine biosynthetic enzymes in rat liver during development. Can. J. Biochem. Cell. Biol. 61, 1147-1152.
23. Weinhold, P.A & Feldman, D.A. (1992) Choline-phosphate cytidylyltransferase. Methods Enzymol. 209, 248-258.
24. Cornell, R.B. (1992) Cholinephosphotransferase from mammalian sources. Methods Enzymol. 209, 267-272.
25. Weinhold, P.A., Charles, L., Rounsifer, M.E. & Feldman, D.A. (1991) Control of phosphatidylcholine synthesis in Hep G2 cells. Effect of fatty acids on the activity and immunoreactive content of choline phosphate cytidylyltransferase. J. Biol. Chem. 266, 6093-6100.
26. Holy, A., Otova, B., Budesinsky, M., Emerson, D. & Wiles, M.E. (2001) O-Phosphonatomethylcholine, its analogues, alkyl esters, and their biological activity. J. Med. Chem. 44, 4462-4467.
27. Wieder, T., Geilen, C.C & Reutter, W. (1993) Antagonism of phorbol-ester-stimulated phosphatidylcholine biosynthesis by the phospholipid analogue hexadecylphosphocholine. Biochem. J. 291, 561-567.
28. Geilen, C.C., Wieder, T., Haase, A., Reutter, W., Morré, D.M. & Morré, D.J. (1994) Uptake, subcellular distribution and metabolism of the phospholipid analogue hexadecylphosphocholine in MDCK cells. Biochim. Biophys. Acta 1211, 14-22.
29. Fleer, E.A.M., Berkovic, D., Grunwald, U. & Hiddemann, W. (1996) Induction of resistance to hexadecylphosphocholine in the highly sensitive human epidermoid tumour cell line KB. Eur. J. Cancer 32A, 506-511.
30. Ries, U.J., Fleer, E.A., Breiser, A., Unger, C., Stekar, J., Fenneberg, K. & Eibl, H. (1993) In vitro and in vivo antitumoral activity of alkylphosphonates. Eur. J. Cancer 29A, 96-101.
31. Geilen, C.C., Wieder, T. & Reutter, W. (1992) Hexadecylphosphocholine inhibits translocation of CTP: choline-phosphate cytidylyltransferase in Madin-Darby canine kidney cells. J. Biol. Chem. 267, 6719-6724.
32. Berkovic, D., Grunwald, U., Menzel, W., Unger, C., Hiddemann, W. & Fleer, E.A.M. (1995) Effects of hexadecylphosphocholine on membrane phospholipid metabolism in human tumour cells. Eur. J. Cancer 31, 2080-2081.
33. Vance, D.E. (1990) Phosphatidylcholine metabolism: masochistic enzymology, metabolic regulation, and lipoprotein assembly. Biochem. Cell Biol. 68, 1151-1165.
34. Van Hellemond, J.J., Slot, W.J., Geelen, M.J.H., Van Golde, M.G. & Vermenlen, P.S. (1994) Ultrastructural localization of CTP: phosphoethanolamine cytidylyltransferase in rat liver. J. Biol. Chem. 269, 15415-15418.