1-;-D-Arabinofuranosylcytosine-diphosphate-choline Is Formed by the Reversal of Cholinephosphotransferase and not via Cytidylyltransferase

Cancer Research

Volumn 52, Issue 14, 1992, Pages 3886-3891

  Kucera, Gregory L ^a   Capizzi, Robert L ^a,b  

^a WAKE FOREST BAPTIST HEALTH   (United States)

^b US Bioscience   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINE PHOSPHATE CYTIDYLYLTRANSFERASE; CHOLINEPHOSPHOTRANSFERASE; CYTARABINE;

ACUTE GRANULOCYTIC LEUKEMIA; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CANCER CHEMOTHERAPY; CATALYSIS; CYTOLYSIS; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME SYNTHESIS; MOUSE; NONHUMAN; PHOSPHOLIPID SYNTHESIS; PRIORITY JOURNAL;

ANIMAL; CHOLINE-PHOSPHATE CYTIDYLYLTRANSFERASE; CYTARABINE; CYTIDINE DIPHOSPHATE CHOLINE; DIACYLGLYCEROL CHOLINEPHOSPHOTRANSFERASE; LEUKEMIA L5178; NUCLEOTIDYLTRANSFERASES; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.; VIDARABINE PHOSPHATE;

EID: 0026638006     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

1. Furth, J. J., and Cohen, S. S. Inhibition of mammalian DNA polymerase by the 5′triphoshate of l-β-a-arabinofuranosylcytosine and 5′triphosphate of 1-β-D-arabinofuranosyladenine. Cancer Res., 28: 2061-2067, 1968.
2. Kufe, D. W., Major, P. P., Egan, E. M., and Beardsley, G. P. Correlation of cytotoxicity with incorporation of ara-C into DNA. J. Biol. Chem., 255: 8997-9000, 1980.
3. Kufe, D., Major, P., Egan, E., and Beardsley, P. Incorporation of ara-C into L1210 DNA as a correlate of cytotoxicity. J. Biol. Chem., 235: 3235-3239, 1981.
4. Lauzon, G. J., Paran, J. H., and Paterson, A. R. P. Formation of 1-β-D-arabinofuranosylcytosine diphosphate choline in cultured human leukemic RPMI 6410 cells. Cancer Res., 38: 1723-1729, 1978.
5. Lauzon, G. J., Paterson, A. R. P., and Belch, A. W. Formation of 1-β-D-arabinofuranosylcytosine diphosphate choline in neoplastic and normal cells. Cancer Res., 38: 1730-1733, 1978.
6. Yang, J-L., Cheng, E. H., Capizzi, R. L., Cheng, Y-C., and Kute, T. Effect of uracil arabinoside on metabolism and cytotoxicity of cytosine arabinoside in L5178Y murine leukemia. J. Clin. Invest., 75: 141-146, 1985.
7. Yang, J-L., White, J. C., and Capizzi, R. L. Modulation of the cellular pharmacokinetics of ara-CTP in patient leukemic blasts by dipyridamole. Cancer Chemother. Pharmacol., 29: 236-240, 1992.
8. Capizzi, R. L., Poole, M., Cooper, M. R., Richards, F., II, Stuart, J. J., Jackson, D. V., Jr., White, D. R., Spurr, C. L., Hopkins, J. O., Muss, H. B., Rudnick, S. A., Wells, R., Gabriel, D., and Ross, D. Treatment of poor risk acute leukemia with sequential high dose ara-C and asparaginase. Blood, 63: 694-700, 1984.
9. Capizzi, R. L., Yang, J-L., Cheng, E., Bjornson, D., Sahasrabudhe, D., Tan, R-S., and Cheng, Y-C. Alteration of the pharmacokinetics of high dose ara-C by its metabolite, high araU, in patients with acute leukemia. J. Clin. Oncol., 1: 763-771, 1983.
10. Capizzi, R. L., Oliver, L., Friedman, H., Davis, R., Mayer, R., Schiffer, C., Lunghofer, B., Royer, G., and Van Echo, D. A. Variations in ara-C plasma concentrations at steady-state (Cp.) during remission induction and intensification therapy of AML. A population pharmacokinetics study by CALGB. Proc. Am. Soc. Clin Oncol., 7: 57, 1988.
11. Amadori, S., Petti, M. C., Mastrovincenzo, C., Testa, M. G., Antonelli, A., and Mandelli, F. Blast cell kinetics and prognosis in acute nonlymphocytic leukemia. Leuk. Res., 4: 239-244, 1980.
12. Raza, A., Maheshwari, Y., and Preisler, H. D. Differences in cell cycle characteristics among patients with acute nonlymphocytic leukemia. Blood, 69: 1647-1653, 1987.
13. Kennedy, E. P., and Weiss, S. B. Cytidine diphosphate choline: a new intermediate in lecithin biosynthesis. J. Am. Chem. Soc., 77: 250-251, 1955.
14. Pelech, S. L., and Vance, D. E. Regulation of phosphatidylcholine biosynthesis. Biochim. Biophys. Acta, 779: 217-251, 1984.
15. Sundler, R., and Akesson, B. Regulation of phospholipid biosynthesis in isolated rat hepatocytes. Effect of different substrates. J. Biol. Chem., 250: 3359-3367, 1975.
16. Sugino, Y. Deoxycytidine diphosphate choline, a new deoxyribosidic compound. J. Am. Chem. Soc., 79: 5074-5075, 1957.
17. Bjomstad, P., and Bremer, J. In vivo studies on pathways for the biosynthesis of lecithin in the rat. J. Lipid Res., 7: 38-45, 1966.
18. Kanoh, H., and Ohno, K. Utilization of endogenous phospholipids by the backreaction of CDP-choline (-ethanolamine): 1,2-diglyceride choline (ethanolamine)phosphotransferase in rat liver microsomes. Biochim. Biophys. Acta, 306: 203-217, 1973.
19. Goracci, G., Horrocks, L. A., and Porcellati, G. Reversibility of ethanolamine and choline phosphotransferases (EC 2.7.8.1 and EC 2.7.8.2) in rat brain microsomes with labelled alkylacylglycerols. FEBS Lett., 80: 41-44, 1977.
20. Kanoh, H., and Ohno, K. Studies on 1,2-diglycerides formed from endogenous lecithins by the back-reaction of rat liver microsomal CDP-choline: 1,2-diacylglycerolcholinephosphotransferase. Biochim. Biophys. Acta, 326: 17-25, 1973.
21. Kanoh, H., and Ohno, K. Substrate-selectivity of rat liver microsomal 1,2-diacylglycerol:CDP-choline(ethanolamine)choline (ethanolamine)phosphotransferase in utilizing endogenous substrates. Biochim. Biophys. Acta, 380: 199-207, 1975.
22. Sundler, R., Akesson, B., and Nilsson, A. Sources of diacylglycerols for phospholipid synthesis in rat liver. Biochim. Biophys. Acta, 557: 248-254, 1974.
23. Goracci, G., Francescangeli, E., Horrocks, L. A., and Porcellati, G. The reverse reaction of cholinephosphotransferase in rat brain microsomes. Bio chim. Biophys. Acta, 664: 373-379, 1981.
24. Strum, J. C., Emilsson, A., Wykle, R. L., and Daniel, L. W. Conversion of l-O-alkyl-2-acetyl-5/f-glycero-3-phosphocholine to l-0-alk-1′-enyl-2-snglycero-3-phosphoethanolamine. J. Biol. Chem., 267: 1576-1583, 1992.
25. Capizzi, R. L., Papirmeister, B., Mullins, J. M., and Cheng, E. The detection of chemical mutagens using the L5178Y/asn” murine leukemia in vitro and in a host-mediated assay. Cancer Res., 34: 3073-3082, 1974.
26. Kanoh, H. Biosynthesis of lecithins and phosphatidylethanolamines from various radioactive 1,2-diglycerides in rat liver microsomes. Biochim. Biophys. Acta, 218: 249-258, 1970.
27. Weinhold, P. A., Rounsifer, M. E., and Feldman, D. A. The purification and characterization of CTP:phosphorylcholine cytidylyltransferase from rat liver. J. Biol. Chem., 261: 5104-5110, 1986.
28. Vance, D. E., Pelech, S. D., and Choy, P. C. CTP:phosphocholine cytidylyltransferase from rat liver. Methods Enzymol., 71: 576-581, 1991.
29. Khym, J. An analytical system for rapid separation of tissue nucleotides at low pressures on conventional anion exchangers. Clin. Chem., 21: 1245-1252, 1975.
30. Spriggs, D., Robbins, G., Ohno, Y., and Kufe, D. Detection of l-β-D-arabinofuranosylcytosine incorporation into DNA in vivo. Cancer Res., 47: 6532-6536, 1987.
31. Preisler, H., Davis, R. B., Kirshner, J., Dupre, E., Richards, P., III, Hoag-land, H. C., Kopel, S., Levy, R. N., Carey, R., Schulman, P., et al. Comparison of three remission induction regimens and two postinduction strategies for the treatment of acute nonlymphocytic leukemia: a Cancer and Leukemia Group B study. Blood, 69: 1441-1449, 1987.
32. Momparler, R. L. A model for the chemotherapy of acute leukemia with l-β-D-arabinofuranosylcytosine. Cancer Res., 34: 1775-1777, 1974.
33. Rudnick, S. A., Cadman, E. C., Capizzi, R. L., Skeel, R. T., Bertino, J. R., and McIntosh, S. High dose cytosine arabinoside (HDARAC) in refractory acute leukemia. Cancer (Phila.), 44: 1189-1193, 1979.
34. Capizzi, R. L., Yang, J-L., Rathmell, J. P., White, J. C., Cheng, E., Cheng, Y-C., and Kute, T. Dose-related pharmacologic effects of high dose ara-C and its self-potentiation. Semin. Oncol., 12 (Suppl. 3); 65-75, 1985.
35. Herzig, R. H., Wolff, S. N., and Lazarus, H. M. High dose cytosine arabinoside therapy for refractory leukemia. Blood, 62: 361-369, 1983.
36. Early, A. P., Preisler, H. D., and Slocum, H. A pilot study of high dose 1-β-D-arabinofuranosylcytosine for acute leukemia and refractory lymphoma: clinical response and pharmacology. Cancer Res., 42: 1587-1594, 1982.
37. Rathmell, J., Capizzi, R., Craig, J., Waite, M., and Daniel, L. Membrane phospholipids as a possible target for ara-C in human leukemia. Proc. Am. Soc. Clin. Oncol., 5: 47, 1986.
38. Kucera, G. L., and Capizzi, R. L. Ara-C-induced leukemia cell lysis may be due to alterations in phospholipid metabolism. Proc. Am. Assoc. Cancer Res., 12;416, 1991.
39. White, J. C., and Capizzi, R. L. A critical role for uridine nucleotides in the regulation of deoxycytidine kinase and the concentration dependence of 1-β-D-arabinofuranosylcytosine phosphorylation in human leukemia cells. Cancer Res., 51: 2559-2565, 1991.
40. De Korte, D., Haverkort, W. A., Roos, D., and van Gennip, A. H. Anion-exchange high performance liquid chromatography method for the quantitation of nucleotides in human blood cells. Clin. Chem. Acta, 148: 185-196, 1985.
41. Jackson, R. C., Lui, M. S., Boritzki, T. J., Morris, H. P., and Weber, G. Purine and pyrimidine nucleotide patterns of normal, differentiating, and regenerating liver and of hepatomas in rats. Cancer Res., 40: 1286-1291, 1980.
42. Vance, D. E. Phosphatidylcholine metabolism: masochistic enzymology, metabolic regulation, and lipoprotein assembly. Biochem. Cell Biol., 68: 1151-1165, 1990.
43. Veech, R. L., Lawson, J. W., Cornell, N. W., and Krebs, H. A. Cytosolic phosphorylation potential. J. Biol. Chem., 254: 6538-6547, 1979.
44. Pontoni, G., Manna, C., Salluzzo, A., del Paino, L., Galletti, P., De Rosa, M., and Zappia, V. Studies on enzyme-substrate interactions of cholinephosphotransferase from rat liver. Biochim. Biophys. Acta, 836: 222-232, 1985.