Enhancement of the Toxicity and DNA Incorporation of Arabinosyl-5-azacytosine and 1-β-D-Arabinofuranosylcytosine by Cyclopentenyl Cytosine

Cancer Research

Volumn 50, Issue 22, 1990, Pages 7279-7284

  Grem, Jean L ^a   Allegra, Carmen J ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4,5 DIHYDROXY 3 HYDROXYMETHYL 2 CYCLOPENTEN 1 YL)CYTOSINE; CYTARABINE; FAZARABINE;

ARTICLE; COLON CARCINOMA; DNA DAMAGE; DRUG CYTOTOXICITY; DRUG INTERACTION; HUMAN; HUMAN CELL; PRIORITY JOURNAL;

ANTIMETABOLITES, ANTINEOPLASTIC; AZACITIDINE; CELL SURVIVAL; COLORECTAL NEOPLASMS; CYTARABINE; CYTIDINE TRIPHOSPHATE; DEOXYCYTOSINE NUCLEOTIDES; DNA, NEOPLASM; HUMAN; IN VITRO; TUMOR CELLS, CULTURED;

EID: 0025258496     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Moyer, J. D., Malinowski, N. M., Treanor, S. P., and Marquez, V. E. Antitumor activity and biochemical effects of cyclopentenyl cytosine in mice. Cancer Res., 46: 3325–3329, 1986.
2. Marquez, V. E., Lim, M-I., Treanor, S. P., Plowman, J., Priest, M. A., Markovac, A., Khan, M. S., Kaskar, B., and Driscoll, J. S. Cyclopentenyl-cytosine. A carbocyclic nucleoside with antitumor and antiviral properties. J. Med. Chem., 31:1687–1694, 1988.
3. Kang, G. J., Cooney, D. A., Moyer, J. D., Kelley, J. A., Kim, H-Y., Marquez, V. E., and Johns, D. G. Cyclopentenylcytosine triphosphate. Formation and inhibition of CTP synthetase. J. Biol. Chem., 264: 713–718, 1989.
4. Glazer, R. I., Knode, M. C., Lim, M-I., and Marquez, V.E. Cyclopentenyl cytidine analogue. An inhibitor of cytidine triphosphate synthesis in human colon carcinoma cells. Biochem. Pharmacol., 34: 2535–2539, 1985.
5. Grem, J. L., Shoemaker, D. D., Hoth, D. F., King, S. A., Plowman, J., Zaharko, D., Grieshaber, C. K., Harrison, S. D., Jr., Cradock, J. C., and Leyland-Jones, B. Arabinosyl-5-azacytosine: a novel nucleoside entering clinical trials. Invest. New Drugs, 5: 315–328, 1987.
6. Chabner, B. A. Cytidine analogues. In: B. A. Chabner and J. C. Collins (eds.), Cancer Chemotherapy, pp. 154–179. Philadelphia: J. B. Lippincott, 1990.
7. Townsend, A. J., and Cheng, Y-C. Sequence-specific effects of ara-5-aza-CTP and ara-CTP on DNA synthesis by purified human DNA polymerases in vitro: visualization of chain elongation on a defined template. Mol. Pharmacol., 32: 330–339, 1987.
8. Townsend, A., Leclerc, J-M., Dutschman, G., Cooney, D., and Cheng, Y-C. Metabolism of l-β-D-arabinofuranosyl-5-azacytosine and incorporation into DNA of human T-lymphoblastic cells (Molt-4). Cancer Res., 45:3522–3528, 1985.
9. Dalai, M., Plowman, J., Breitman, T. R., Schuller, H. M., del Cam po, A. A., Vistica, T., Driscoll, J. S., Cooney, D. A., and Johns, D. G. Arabinofuranosyl-5-azacytosine: antitumor and cytotoxic properties. Cancer Res., 46: 831–838, 1986.
10. Ahluwalia, G. S., Cohen, M. B., Kang, G-J., Arnold, S. T., McMahon, J. B., Dalai, M., Wilson, Y. A., Cooney, D. A., Balzarini, J., and Johns, D. G. Arabinosyl-5-azacytosine: mechanisms of native and acquired resistance. Cancer Res., 46:4479–4485, 1986.
11. Brattain, M. G., Fine, W. D., Khaled, F. M., Thompson, J., and Brattain, D. E. Heterogeneity of malignant cells from a human colonic carcinoma. Cancer Res., 41:1751–1756, 1981.
12. Grem, J. L., and Fischer, P. H. Augmentation of 5-fluorouracil cytotoxicity in human colon cancer cells by dipyridamole. Cancer Res., 45: 2967–2972, 1985.
13. Webb, J. L. Enzymes and Metabolic Inhibitors, Vol. 1, pp. 487–512. New York: Academic Press, 1963.
14. Chou, T-C., and Talalay, P. Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors. Adv. Enzyme Regul., 22: 27–55, 1984.
15. Chou, J. and Chou, T-C. Dose-Effect Analysis with Microcomputers. Mill-town, NJ: Biosoft, 1985.
16. Plunkett, W., Hug, V., Keating, M. J., and Chubb, S. Quantitation of 1–0-d-arabinofuranosylcytosine 5’-triphosphate in the leukemic cells from bone marrow and peripheral blood of patients receiving 1 -β-D-arabinofuranosyl-cytosine therapy. Cancer Res., 40: 588–591, 1980.
17. Plunkett, W., Chubb, S., and Barlogie, B. Simultaneous determination of 1–0-D-arabinofuranosylcytosine 5’-triphosphate and 3-deazauridine 5’-triphos-phate in human leukemia cells by high-performance liquid chromatography. J. Chromatogr., 221:425–430, 1980.
18. Hunting, D., and Henderson, J. F. Methods for the determination of deox-yribonucleotide triphosphate concentrations. Methods Cancer Res., 20:245– 283, 1982.
19. Solter, A. W., and Handschumacher, R. E. A rapid quantitative determination of deoxyribonucleoside triphosphate based on the enzymatic synthesis of DNA. Biochim. Biophys. Acta, 174: 585–590, 1969.
20. Williams, M. V., and Cheng, Y-C. Human deoxyuridine triphosphate nu-cleotidohydrolase. J. Biol. Chem., 254: 2897–2901, 1979.
21. Kufe, D. W., Major, P. P., Egan, E. M., and Beardsley, G. D. Correlation of cytotoxicity with incorporation of ara-C into DNA. J. Biol. Chem., 255: 8997–9000, 1980.
22. Lonn, W., and Lonn, S. Interaction between 5-fluorouracil and DNA of human colon adenocarcinoma. Cancer Res., 44: 3414–3418, 1984.
23. Riva, C. M., Rustum, Y. M., and Preisler, H. D. Pharmacokinetics and cellular determinants of response to 1-β-arabinofuranosylcytosine. Semin. Oncol., 12(Suppl. 3): 1–8, 1985.
24. Vesely, J., and Piskala, A. Mechanism of action of 1-β-D-arabinofuranosyl-5-azacytosine and its effects in LI 210 mouse leukemia cells. Neoplasma, 33: 3–10, 1986.
25. Dion, R. L., Jayaram, H. N., Cooney, D. A., Ahluwalia, G. S., and Johns, D. G. Studies on the mode of action of l-β-D-arabinofuranosyl-5-azacytosine (NSC 281272). Proc. Am. Assoc. Cancer Res., 27: 297, 1986.
26. Campbell, J., and Rustum, Y. Synergistic interaction between 3-deazauridine and arabinosylcytosine in mice bearing LI210 leukemia. Proc. Am. Assoc. Cancer Res., 21: 277, 1980.
27. Lauzon, G. J., Yang, S. E., and Paterson, A. R. P. Cell cycle arrest as a basis of enhancement of 1-β-D-arabinofuranosylcytosine anabolism in human lym-phoblastoid RPMI 6410 cells cultured with deazauridine. Biochem. Pharmacol., 30: 1889–1894, 1981.
28. Mills-Yamamoto, C., Lauzon, G. J., and Paterson, A. R. P. Toxicity of combinations of arabinosylcytosine and 3-deazauridine toward neoplastic cells in culture. Biochem. Pharmacol., 27: 181–186, 1983.
29. Blaney, S., Hegedus, L., Balis, F., Heideman, R., McCully, C., Kelley, J., and Poplack, D. Pharmacokinetics and metabolism of cyclopentenyl cytosine in primates: evidence for deamination as the primary route of elimination. Proc. Am. Assoc. Cancer Res., 31:419, 1990.
30. Heideman, R. L., Gillespie, A., Ford, H., Reaman, G. H., Balis, F. M., Tan, C., Sato, J., Ettinger, L. J., Packer, R. J., and Poplack, D. G. Phase I trial and pharmacokinetic evaluation of fazarabine in children. Cancer Res., 49: 5213–5216, 1989.