Comparison of the Cellular Pharmacoldnetics and Toxicity of 2',2'-Difluorodeoxycytidine and 1-β-D-Arabinofuranosylcytosine

Cancer Research

Volumn 48, Issue 14, 1988, Pages 4024-4031

  Heinemann, Volker ^a   Hertel, Larry W ^b   Grindey, Gerald B ^b   Plunkett, William ^a  

^a UNIVERSITY OF TEXAS   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYTARABINE; DEOXYCYTIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; CELL CULTURE; CHO CELL; CYTOTOXICITY; NONHUMAN;

ANIMAL; ARABINOFURANOSYLCYTOSINE TRIPHOSPHATE; CELL LINE; CELL SURVIVAL; CLONE CELLS; COMPARATIVE STUDY; CYTARABINE; DEOXYCYTIDINE; DEOXYCYTIDINE KINASE; DNA REPLICATION; DRUG EVALUATION, PRECLINICAL; KINETICS; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0023783698     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Grindey, G. B., Boder, G. B., Hertel, L. H., Kroin, Poore, G. A., Rinzel, S. M., and Todd, G. C. Antitumor activity of 2',2'-difluorodeoxycytidine (LY188011). Proc. Am. Assoc. Cancer Res., 27:296,1986.
2. Hertel, L. W., Kroin, J. S., and Tustin, J. M. A simple stereo controlled synthesis of 2-deoxy-2,2-difluoro-D-ribose (Abstract 332). 191st American Chemical Society National Meeting, 1986.
3. Kroin, J. S., Hertel, L. W., and Misner, J. W. A practical synthesis of 2'- deoxy-2', 2'-difluoro-D-ribofuranosyl nucleosides (Abstract 44). 191st American Chemical Society National Meeting, 1986.
4. Chubb, S., Heinemann, V., Novotny, L., Hertel, L. W., Nowak, B., Mineishi, S., Grindey, G. B., and Plunkett, W. Metabolism and action of 2',2'-difluorodeoxycytidine in human leukemic cells. Proc. Am. Assoc. Cancer Res., 28:324, 1987.
5. Keating, M. J., McCredie, K. B., Bodey, G. P., Smith, T. L., Gehan, E., and Freireich, E. J. Improved prospects for long term survival in adults with acute myelogeneous leukemia. JAMA, 248:2481-2486, 1982.
6. Kessel, D., and Hall, T. C. Transport and phosphorylation as factors in antitumor action of cytosine arabinoside. Science (Wash. DC), 156: 1240-1241,1967.
7. Furth, J. J., and Cohen, S. S. Inhibition of mammalian DNA polymerases by the 5'-triphosphate of 1-β-D-arabinofuranosylcytosine and the 5'-triphos-phate of 9-β-D-arabinofuranosyladenine. Cancer Res., 28:2061-2067,1968.
8. Momparler, R. L., and Fischer, G. A. A proposed mechanism of 1-β-D-arabinofuranosylcytosine as an inhibitor of growth of leukemic cells. Biochem. Pharmacol., 11:423-430,1968.
9. Plagemann, P. G., Marz, R., and Wohlhueter, R. M. Transport and metabolism of deoxycytidine, and 1-β-D-arabinofuranosylcytosine into cultured Novikoff rat hepatoma cells, relationship to phosphorylation, and regulation of triphosphate synthesis. Cancer Res., 38:978-989,1978.
10. Wiley, J. S., Jones, S. P., and Sawyer, W. H. Cytosine arabinoside transport by human leukemic cells. Eur. J. Cancer Clin. Oncol., 19:1067-1074,1983.
11. Wiley, J. S., Taupin, J., Jamieson, G. P., Snook, M., Sawyer, W. H., and Finch, L. R. Cytosine arabinoside transport and metabolism in acute leuke-mias and T cell lymphoblastic lymphoma. J. Clin. Invest., 75: 632–642, 1985.
12. White, J. C., Rathmell, J. P., and Capizzi, R. L. Membrane transport influences the rate of accumulation of cytosine arabinoside in human leukemic cells. J. Clin. Invest., 79:380-387, 1987.
13. Kufe, D. W., Spriggs, D., Egan, E. M., and Munroe, D. Relationships among ara-CTP pools, formation of (ara-C)DNA, and cytotoxicity of human leukemic cells. Blood, 64:54-58,1984.
14. Plunkett, W., Iacoboni, S., Estey, E., Liliemark, J. O., and Keating, M. J. Pharmacologically directed ara-C therapy for refractory leukemia. Semin. Oncol., 12 (Suppl. 3): 20-30,1985.
15. Rustum, Y. M., and Preisler, H. D. Correlation between leukemic cell retention of 1-β-D-arabinofuranosylcytosine 5'-triphosphate and response to therapy. Cancer Res., 39:42-49, 1979.
16. Dicioccio, R. A., and Srivastava, B. I. S. Kinetics of inhibition of deoxyribonucleotide polymerizing activities from normal and leukemic human cells by 9-β-D-arabinofuranosyladenine 5'-triphosphate and 1-β-D-arabinofurano-sylcytosine 5'triphosphate. Eur. J. Biochem., 79:411-418,1977.
17. Graham, F. L., and Whitmore, G. F. Studies in mouse L-cells on the incorporation of 1-β-D-arabinofuranosylcytosine into DNA and on inhibition of DNA polymerase by 1-β-D-arabinofuranosylcytosine 5'-triphosphate. Cancer Res., 30:2636-2644,1970.
18. Kufe, D. W., Major, P. P., Egan, E. R., and Beardsley, G. P. Correlation of cytotoxicity with incorporation of ara-C into DNA. J. Biol. Chem., 255: 8997-9000,1980.
19. Hiss, E. A., and Preston, R. J. The effect of cytosine arabinoside on the frequency of single strand breaks in the DNA of mammalian cells following irradiation or chemical treatment. Biochim. Biophys. Acta, 478:1-8, 1977.
20. Snyder, R. D., Carrier, W. L., and Regan, J. D. Application of 1-β-D-arabinofuranosylcytosine in the kinetic analysis and quantitation of DNA repair in human cells after ultraviolet irradiation. Biophys. J., 35:339-350, 1981.
21. Kufe, D. W., Weichselbaum, R., Egan, E. M., Dahlberg, W., and Fram, J. Lethal effects of 1-β-D-arabinofuranosyl cytosine incorporation into deoxyribonucleic acid during ultraviolet repair. Mol. Pharmacol., 25: 322–326, 1987.
22. Lauzon, G. L., Paran, J. H., and Paterson, A. P. Formation of 1-β-D-arabinofuranosylcytosine diphosphate choline in cultured human leukemic RPMI 6410 cells. Cancer Res., 38:1723-1729,1978.
23. Lauzon, G. L., 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.
24. Hawtrey, A. O., Scott-Burden, T., and Robertson, G. Inhibition of glycoprotein and glycolipid synthesis in hamster embryo cells by cytosine arabinoside and hydroxyurea. Nature (Lond.), 252:58-60,1974.
25. Chaung, R. Y., and Chaung, L. F. Inhibition of RNA polymerase as a possible anti-leukemic action of cytosine arabinoside. Nature (Lond.), 260:549-550, 1976.
26. Saunders, P. P., and Lai, M. M. Nucleoside kinase activities of Chinese hamster ovary cells. Biochim. Biophys. Acta, 761:135-141,1983.
27. Plunkett, W., Chubb, S., Alexander, L., and Montgomery, J. A. Comparison of the toxicity and metabolism of 9-β-D-arabinofuranosyl-2-fluoroadenine and 9-β-D-arabinofuranosyladenine in human lymphoblastoid cells. Cancer Res., 40:2349-2355,1980.
28. Hansch, C., and Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology, pp. 18–43. New York: John Wiley & Sons, 1979.
29. Chou, T. C., Arlin, Z., Clarkson, B. D., and Philips, F. S. Metabolism of 1-β-D-arabinofuranosylcytosine in human leukemic cells. Cancer Res., 37: 3561-3570,1977.
30. Hunting, D., Hordern, J., and Henderson, F. Quantitative analysis of purine and pyrimidine metabolism in Chinese hamster ovary cells. Can. J. Biochem., 59:838-847,1981.
31. Abe, I., Saito, S., Hori, K., Suzuki, M., and Sato, H. Role of dephosphorylation in accumulation of 1-β-D-arabinofuranosyl 5'-triphosphate in human lymphoblastic cell lines with reference to their drug sensitivity. Cancer Res., 45:6244-6249,1985.