On the Phosphorylation of 2-chlorodeoxy-adenosine (CdA) and Its Correlation with Clinical Response in Leukemia Treatment

Leukemia and Lymphoma

Volumn 21, Issue 42067, 1996, Pages 225-231

  Arnér, Elias S J ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

2 Chlorodeoxyadenosine; Deoxycytidine kinase; Deoxyguanosine kinase; Leukemia; Review; Therapy

Indexed keywords

CLADRIBINE; DEOXYCYTIDINE KINASE; NUCLEOSIDE ANALOG;

B CELL LEUKEMIA; BIOCHEMISTRY; CLINICAL TRIAL; DRUG METABOLISM; DRUG RESISTANCE; ENZYME DEFICIENCY; HAIRY CELL LEUKEMIA; HUMAN; HUMAN CELL; INTRAVENOUS DRUG ADMINISTRATION; LEUKEMIA; LYMPHOID CELL; LYMPHOMA; META ANALYSIS; ORAL DRUG ADMINISTRATION; PHOSPHORYLATION; PRIORITY JOURNAL; REVIEW;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; CLADRIBINE; HUMANS; LEUKEMIA; PHOSPHORYLATION;

EID: 0029936431     PISSN: 10428194     EISSN: 10292403     Source Type: Journal    
DOI: 10.3109/10428199209067604     Document Type: Article

References (64)

1. Giblett E. R., Anderson J. E., Cohen F., Pollara B., Meuwissen H. J. Adenosine-deaminase deficiency in two patients with severely impaired cellular immunity. Lancet 1972; 2: 1067 – 1069
2. Inborn Errors of Specific Immunity, B. Poelara, R. J. Pickering, H. J. Meuwissen, I. J. Porter. Academic Press, New York 1979
3. Combined Immunodeficiency Disease and Adenosine Deaminase Deficiency, H. J. Meuwissen, R. J. Pickering, B. Pollara, I. H. Porter. Academic Press, New York 1975
4. Carson D. A., Kaye J., Matsumoto S., Seegmiller J. E., Thompson L. Biochemical basis for the enhanced toxicity of deoxyribonucleosides toward malignant human T cell lines. Proc. Natl. Acad. Sci. USA 1979; 76: 2430 – 2433
5. Donofrio J., Coleman M. S., Hutton J. J., Daoud A., Lampkin B., Dyminski J. Overproduction of adenine deoxynucleosides and deoxynucleotides in adenosine deaminase deficiency with severe combined immunodeficiency disease. J. Clin. Invest 1978; 62: 884 – 887
6. Cohen A., Hirschhorn R., Horowitz S. D., Rubinstein A., Polmar S. H., Hong R., Wartin D. W. J. Deoxyadenosine triphosphate as a potentially toxic metabolite in adenosine deaminase deficiency. Proc. Natl. Acad. USA 1978; 75: 472
7. Beutler E., Carson D. A. 2-Chlorodeoxyadenosine: hairy cell leukemia takes a surprising turn. Blood Cells 1993; 19: 559 – 68
8. Carrera C. J., Saven A., Piro L. D. Purine metabolism of lymphocytes. Targets for chemotherapy drug development. Hematology Oncology Clinics of North America 1994; 8: 357 – 81
9. Foon K. A., Rai K. R., Gale R. P. Chronic lymphocytic leukemia: new insights into biology and therapy. Annals of Internal Medicine 1990; 113: 525 – 39
10. Jaiyesimi I. A., Kantarjian H. M., Estey E. H. Advances in therapy for hairy cell leukemia. A review. Cancer 1993; 72: 5 – 16
11. Saven A., Piro L. D. 2-Chlorodeoxyadenosine in the treatment of hairy cell leukemia. Cancer Investigation 1993; 11: 559 – 64
12. Bennett L. L. J., Chang C.-H., Allan P. W., Adamson D. J., Rose L. M., Brockman R. W., Secrist J. A., III, Shortnacy A., Montgomery J. A. Metabolism and metabolic effects of halopurine nucleosides in tumor cells in culture. Nucleosides & Nucleotides 1985; 4: 107 – 116
13. Simon L. N., Bauer R. J., Tolman R. L., Robins R. K. Calf adenosine deaminase. Substrate specificity. Biochemistry 1970; 9: 573
14. Carson D. A., Wasson D. B., Kaye J., Ullman B., Martin D. W. J., Robins R. K., Montgomery J. A. Deoxycytidine kinase-mediated toxicity of deoxyadenosine analogs toward malignant human lymphoblasts in vitro and toward murine L1210 leukemia in vivo. Proc Natl Acad Sci USA 1980; 77: 6865 – 9
15. Christensen L. F., Broom A. D., Robins M. J., Bloch A. Synthesis and biological activity of selected 2,6-disubstituted-(2-deoxy-α– and -β–D-erythro-pentofuranosyl)purines. J Med Chem 1972; 15: 735 – 739
16. Carson D. A., Wasson D. B., Lakow E., Kamatani N. Possible metabolic basis for the different immunodeficient states associated with genetic deficiencies of adenosine deaminase and purine nucleoside phosphorylase. Proceedings of the National Academy of Sciences of the United States of America 1982; 79: 3848 – 52
17. Carson D. A., Wasson D. B., Taetle R., Yu A. Specific toxicity of 2-chlorodeoxyadenosine toward resting and proliferating human lymphocytes. Blood 1983; 62: 737 – 43
18. Carson D. A., Wasson D. B., Beutler E. Antileukemic and immunosuppressive activity of 2-chloro-2'-deoxyadenosine. Proceedings of the National Academy of Sciences of the United States of America 1984; 81: 2232 – 6
19. Piro L. D., Carrera C. J., Beutler E., Carson D. A. 2-Chlorodeoxyadenosine: an effective new agent for the treatment of chronic lymphocytic leukemia. Blood 1988; 72: 1069 – 73
20. Piro L. D., Carrera C. J., Carson D. A., Beutler E. Lasting remissions in hairy-cell leukemia induced by a single infusion of 2-chlorodeoxyadenosine. New England Journal of Medicine 1990; 322: 1117 – 21
21. Liliemark J., Juliusson G. On the pharmacokinetics of 2-chloro-2'-deoxyadenosine in humans. Cancer Research 1991; 51: 5570 – 2
22. Carson D. A., Wasson D. B., Esparza L. M., Carrera C. J., Kipps T. J., Cottam H. B. Oral antilymphocyte activity and induction of apoptosis by 2-chloro-2'-arabino-fluoro-2'-deoxyadenosine. Proceedings of the National Academy of Sciences of the United States of America 1992; 89: 2970 – 4
23. Juliusson G., Johnson S. A. N., Christiansen I., Kimby E., Björkholm M., Läan G., Liliemark J. Oral 2-chlorodeoxyadenosine (CdA) as Primary treatment for symptomatic chronic lymphocytic leukemia (CLL). Blood 1993; 82: A141
24. Juliusson G., Liliemark J. Complete remission of B-cell chronic lymphocytic leukaemia after oral cladribine. Lancet 1993; 341: 54
25. Liliemark J., Albertioni F., Hassan M., Juliusson G. On the bioavailability of oral and subcutaneous 2-chloro-2-deoxyadenosine in humans: alternative routes of administration [see comments]. Journal of Clinical Oncology 1992; 10: 1514 – 8
26. Albertioni F., Juliusson G., Liliemark J. On the bioavailability of 2-chloro-2'-deoxyadenosine (CdA). The influence of food and omeprazole. European Journal of Clinical Pharmacology 1993; 44: 579 – 82
27. Datta N. S., Shewach D. S., Hurley M. C., Mitchell B. S., Fox I. H. Human T-lymphoblast deoxycytidine kinase: Purification and properties. Biochem 1989; 28: 114 – 123
28. Bohman C., Eriksson S. Deoxycytidine kinase from human leukemic spleen: preparation and characteristics of homogeneous enzyme. Biochemistry 1988; 27: 4258 – 65
29. Kim M.-Y., Ikeda S., Ives D. H. Affinity purification of human deoxycytidine kinase: avoidance of structural and kinetic artifacts arising from limited proteolysis. Biochem. Biophys. Res. Commun 1988; 156: 92 – 98
30. Kim M.-Y., Ives D. H. Human deoxycytidine kinase: kinetic mechanism and end product regulation. Biochemistry 1989; 28: 9043 – 9047
31. Chottiner E. G., Shewach D. S., Datta N. S., Ashcraft E., Gribbin D., Ginsburg D., Fox I. H., Mitchell B. S. Cloning and expression of human deoxycytidine kinase cDNA. Proc. Natl. Acad. Sci. U.S.A 1991; 88: 1531 – 5
32. Karlsson A., Johansson M., Eriksson S. Cloning and expression of mouse deoxycytidine kinase; Pure recombinant mouse and human enzymes show differences in substrate specificity. J. Biol. Chem 1994; 269: 24374 – 24318
33. Reichelova V., Juliusson G., Spasokoukotskaja T., Eriksson S., Liliemark J. Interspecies diferences in the kinetic properties of deoxycytidine kinase elucidate the poor utility of a phase I pharmacologically directed dose-escalation concept for 2-chloro-2'-deoxyadenosine. Cancer Chemother Pharmacol. 1995, in press
34. Johansson M., Karlsson A. Differences in kinetic properties of pure recombinant human and mouse deoxycytidine kinase. Biochem Pharmacol. 1995, in press
35. Habteyesus A., Nordenskjöld A., Bohman C., Eriksson S. Deoxynucleoside phosphorylating enzymes in monkey and human tissues show great similarities, while mouse deoxycytidine kinase has a different substrate specificity. Biochem Pharmacol 1991; 42: 1829 – 36
36. Balzarini J., Pauwels R., Baba M., Herdewijn P., de Clercq E., Broder S., Johns D. G. The in vitro and in vivo anti-retrovirus activity, and intracellular metabolism of 3'-azido-2',3'-dideoxythymidine and 2',3'-dideoxycytidine are highly dependent on the cell species. Biochem. Pharmacol 1988; 1988: 897 – 903
37. Ullman B., Coons T., Rockwell S., McCartan K. Genetic analysis of 2',3'-dideoxycytidine incorporation into cultured human T lymphoblasts. J. Biol. Chem 1988; 263: 12391 – 6
38. Amér E. S. J., Eriksson S. Mammalian deoxyribonucleoside kinases. Pharm. Ther 1994, in press
39. Datta N. S., Shewach D. S., Mitchell B. S., Fox I. H. Kinetic properties and inhibition of human T lymphoblast deoxycytidine kinase. J. Biol. Chem 1989; 264: 9359 – 9364
40. Kierdaszuk B., Eriksson S. Selective inactivation of the deoxyadenosine phosphorylating activity of pure human deoxycytidine kinase: stabilization of different forms of the enzyme by substrates and biological detergents. Biochemistry 1990; 29: 4109 – 14
41. Eriksson S., Kierdaszuk B., Munch-Petersen B., öberg B., Johansson N. G. Comparison of the substrate specificities of human thymidine kinase 1 and 2 and deoxycytidine kinase toward antiviral and cytostatic nucleoside analogs. Biochem. Biophys. Res. Commun 1991; 176: 586 – 592
42. White J. C., Capizzi R. L. A critical role for uridine nucleotides in the regulation of deoxycytidine kinase and the concentration dependence of 1-b-D-arabinofuranosylcytosine phoshporylation in human leukemia cells. Cancer Res 1991; 51: 2559 – 2565
43. Shewach D. S., Reynolds K. K., Hertel L. Nucleotide specificity of human deoxycytidine kinase. Mol. Pharmacol 1992; 42: 518 – 524
44. Amér E. S. J., Spasokoukotskaja T., Eriksson S. Selective Assays for Thymidine kinase 1 and 2 and Deoxycytidine Kinase and Their Activities in Extracts from Human Cells and Tissues. Biochem. Biophys. Res. Comm 1992; 188: 712 – 718
45. Wang L., Karlsson A., Amér E. S. J., Eriksson S. Substrate specificity of mitochondrial 2'-deoxyguanosine kinase: Efficient phosphorylation of 2-chlorodeoxyadenosine (CdA). J. Biol. Chem 1993; 268: 22847 – 228852
46. Avery T. L., Rehg J. E., Lumm W. C., Harwood F. C., Santana V. M., Blakley R. L. Biochemical pharmacology of 2-chlorodeoxyadenosine in malignant human hematopoietic cell lines and therapeutic effects of 2-bromodeoxyadenosine in drug combinations in mice. Cancer Res 1989; 49: 4972 – 4978
47. Kawasaki H., Carrera C. J., Piro L. D., Saven A., Kipps T. J., Carson D. A. Relationship of deoxycytidine kinase and cytoplasmic 5'-nucleotidase to the chemotherapeutic efficacy of 2-chlorodeoxyadenosine. Blood 1993; 81: 597 – 601
48. Kawasaki H., Carrera C. J., Carson D. A. Quantitative immunoassay of human deoxycytidine kinase in malignant cells. Analyt. Biochem 1992; 207: 193 – 196
49. Amér E. S. J., Spasokoukotskaja T., Juliusson G., Liliemark J., Eriksson S. Phosphorylation of 2-chlorodeoxyadenosine (CdA) in extracts of peripheral blood mononuclear cells of leukaemia patients. Br. J. Haematol 1994; 87: 715 – 718
50. Spasokoukotskaja T., Amér E. S. J., Brosjö O., Gunvén P., Juliusson G., Liliemark J., Eriksson S. Expression of Deoxycytidine Kinase and the Phosphorylation of 2-Chloro-deoxyadenosine in Human Normal and Malignant Cells and Tissues. Eur. J. Cancer 1995; 31A: 202 – 208
51. Plunkett W., Saunders P. P. Metabolism and action of purine nucleoside analogs. Pharmacol Ther 1991; 49: 239 – 68
52. Robertson L. E., Chubb S., Meyn R. E., Story M., Ford R., Hittelman W. M., Plunkett W. Induction of apoptotic cell death in chronic lymphocytic leukemia by 2-chloro-2'-deoxyadenosine and 9-beta-D-arabinosyl-2-fluoroadenine. Blood 1993; 81: 143
53. Seto S., Carrera C. J., Kubota M., Wasson D. B., Carson D. A. Mechanism of deoxyadenosine and 2-chlorodeoxyadenosine toxicity to nondividing human lymphocytes. Journal of Clinical Investigation 1985; 75: 377 – 83
54. Carrera C. J., Piro L. D., Saven A., Beutler E., Terai C., Carson D. A. 2-Chlorodeoxyadenosine chemotherapy triggers programmed cell death in normal and malignant lymphocytes. Advances in Experimental Medicine & Biology. 1991
55. Hentosh P., Koob R., Blakley R. L. Incorporation of 2-halogeno-2'-deoxyadenosine 5-triphosphates into DNA during replication by human polymerases alpha and beta. Journal of Biological Chemistry 1990; 265: 4033 – 40
56. Chunduru S. K., Appleman J. R., Blakley R. L. Activity of human DNA polymerases alpha and beta with 2-chloro-2'-deoxyadenosine 5'-triphosphate as a substrate and quantitative effects of incorporation on chain extension. Arch. Biochem. Biophys 1993; 302: 19
57. Seto S., Carrera C. J., Wasson D. B., Carson D. A. Inhibition of DNA repair by deoxyadenosine in resting human lymphocytes. Journal of Immunology 1986; 136: 2839 – 43
58. Griffig J., Koob R., Blakley R. L. Mechanisms of inhibition of DNA synthesis by 2-chlorodeoxyadenosine in human lymphoblastic cells. Cancer Research 1989; 49: 6923
59. Hirota Y., Yoshioka A., Tanaka S., Watanabe K., Otani T., Minowada J., Matsuda A., Ueda T., Wataya Y. Imbalance of deoxyribonucleoside triphosphates, DNA double-strand breaks, and cell death caused by 2-chlorodeoxyadenosine in mouse FM3A cells. Cancer Research 1989; 49: 915 – 9
60. Fox R. M. Changes in deoxynucleoside triphosphate pools induced by inhibitors and modulators of ribonucleotide reductase. Pharmacol. Ther 1985; 30: 31 – 42
61. Meuth M. The molecular basis of mutations induced by deoxyribonucleoside triphosphate pool imbalances in mammalian cells. Exp. Cell. Res 1989; 181: 305 – 316
62. Meuth M. The genetic consequences of nucleotide precursor pool imbalance in mammalian cells. Mutat. Res 1984; 126: 107 – 12
63. Kunz B. A. Mutagenesis and deoxyribonucleotide poo imbalance. Mut. Res 1988; 200: 133 – 147
64. Arnér E. S., Flygar M., Bohman C., Wallström B., Eriksson S. Deoxycytidine kinase is constitutively expressed in human lymphocytes: consequences for compartmentation effects, unscheduled DNA synthesis, and viral replication in resting cells. Exp. Cell Res 1988; 178: 335 – 42