The cytotoxic effect of the vitamin B12 inhibitor cyanocobalamin [c-lactam], and a review of other vitamin B12 antagonists

Leukemia and Lymphoma

Volumn 31, Issue 1-2, 1998, Pages 21-37

  Matthews, J H ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

Enzyme inhibitors; Folic acid; HL 60 cells; Homocysteine; Methionine; Methionine synthase; Methylmalonyl CoA; Vitamin B12

Indexed keywords

CYANOCOBALAMIN; DEOXYURIDINE; HOMOCYSTEINE; HYDROXOCOBALAMIN; METHIONINE; METHYL GROUP; SERINE;

AMINO ACID METABOLISM; ARTICLE; CANCER CELL CULTURE; CELL STRAIN HL 60; CYTOTOXICITY; DNA SYNTHESIS; GROWTH RATE; HUMAN; HUMAN CELL; LEUKEMIA CELL; MEGALOBLASTIC ANEMIA; PRIORITY JOURNAL;

EID: 0031706423     PISSN: 10428194     EISSN: None     Source Type: Journal    
DOI: 10.3109/10428199809057582     Document Type: Article

References (56)

1. Smith, E. L., Parker, L. F. J. and Gant, D. E. (1956). Antimetabolites from Vitamin B12. Biochemical Journal, 52, 14P.
2. Chanarin, I. (1990). The Megaloblastic Anaemias, 3rd edn., (Blackwell, Oxford).
3. Herbert, V. and Zalusky, R. (1962). Interrelations of Vitamin B12 and folic acid metabolism: folic acid clearance studies. Journal of Clinical Investigation, 41, 1263-1276.
4. Chanarin, I., Deacon, R., Lumb, M., Muir, M. and Perry, J. (1985). Cobalamin-folate interrelations: a critical review. Blood, 66, 479-489.
5. D'Angelo, A and Selhub, J. (1997). Homocysteine and thrombotic disease. Blood, 90, 1-11.
6. Stabler, S. P., Brass, E. P., Marcell, P. D., and Allen, R. H. (1991). Inhibition of cobalamin-dependent enzymes by cobalamin analogues in rats. Journal of Clinical Investigation, 87, 1422-1430.
7. Matthews, J. H. (1997). Cyanocobalamin [c-lactam[ inhibits vitamin B12 and causes cytotoxicity in HL60 cells: methionine protects cells completely. Blood, 89, 4600-4607.
8. Judde, J. G. and Frost, P. (1988). Patterns of methionine auxotrophy in normal and neoplastic cells: the methionine independence of lymphocyte mitogenesis and low frequency of the methionine-dependent phenotype in human tumors. Cancer Research, 48, 6775-6779.
9. Halpern, B. C., Clark, B. R., Hardy, D. N., Halpern, R. M. and Smith, R. A. (1974). The effect of replacement of methionine by homocystine on survival of malignant and normal adult mammalian cells in culture. Proceedings of the National Academy of Sciences of the USA, 71, 1133-1136.
10. Liteplo, R. G., Hipwell, S. E., Rosenblatt, D. S., Sillaots, S. and Lue-Shing, H. (1991). Changes in cobalamin metabolism are associated with the altered methionine auxotrophy of highly growth autonomous human melanoma cells. Journal of Cellular Physiology, 149, 332-338.
11. Djurhuus, R., Svardal, A. M., Ueland, P. M., Male, R. and Lillehaug, J. R. (1988). Growth support and toxicity of homocysteine and its effects on methionine metabolism in nontransformed and chemically transformed C3H/1OT1/2 cells. Carcinogenesis. 9, 9-16,
12. McCully, K. S. (1976). Homocysteine thiolactone metabolism in malignant cells. Cancer Research, 36, 3198-3202.
13. Mellman, I., Willard, H. F., Youngdahl-Turner, P. and Rosenberg. L. E. (1979). Cobalamin coenzyme synthesis in normal and mutant human fibroblasts. Evidence for a processing enzyme activity deficient in cb1C cells. Journal of Biological Chemistry, 254, 11847-11853.
14. Kamely, D., Littlefield, J. W. and Erbe, R. W. (1973). Regulation of 5-methyltetrahydrofolate: homocysteine methyltransferase activity by methionine. vitamin B12, and folate in cultured baby hamster kidney cells. Proceedings of the National Academy of Sciences of the USA, 70, 2585-2589.
15. Bonnett, R., Cannon, J. R., Clark, V. M. et al. (1957). Chemistry of the vitamin B 12 group. V. The structure of the chromophoric grouping. Journal of the Chemistry Society, 1158-1168.
16. Binder, M., Kolhouse, J. F., Van Home, K. C. and Allen, R. H. (1982). High-pressure liquid chromatography of cobalamins and cobalamin analogs. Analytical Biochemistry, 125, 253-258.
17. Nixon, P. F. and Bertino, J. F. (1971). Enzymatic preparations of radiolabeled (+)-L-5-methyltetrahydrofolate and (+)-L-5-formyltetrahydrofolate. Analytical Biochemistry, 43, 162-172.
18. Matthews, J. H. and Wickramasinghe, S. N. (1986). A method for performing deoxyuridine suppression tests on microtitre plates. Clinical & Laboratory Haematology, 8, 61.
19. Willard, H. F., Ambani, L. M., Hart, A. C., Mahoney, M. J. and Rosenberg, L. E. (1976). Rapid prenatal and postnatal detection of inborn errors of propionate, methylmalonate, and cobalamin metabolism: a sensitive assay using cultured cells. Human Genetics. 34, 277-283.
20. Matthews, J. H., Armitage, J. and Wickramasinghe, S. N. (1989). Thymidylate synthesis and utilization via the de novo pathway in normal and megaloblastic human bone marrow cells. European Journal of Haematology, 42, 396-404.
21. Drennan, C. L., Huang. S., Drummond, J. T., Matthews, R. G. and Lidwig. M. L. (1994). How a protein binds B12: A 3.0 A X-ray structure of B12-binding domains of methionine synthase. Science, 266, 1669-1674.
22. Stubbe, J. (1994). Binding site revealed of nature' s most beautiful cofactor. Science. 266, 1663-1664.
23. Metz, J. (1992). Cobalamin deficiency and the pathogenesis of nervous system disease. Annual Review of Nutrition, 12, 59-79.
24. Weir, D. G., Keating, S., Molloy, A., et al. (1988). Methylation deficiency causes vitamin B12-associated neuropathy in the pig. Journal of Neurochemistry, 51, 1949-1952.
25. Young, P. B., Kennedy, S., Molloy, A. M., Scott, J. M., Weir, D. G. and Kennedy, D. G. (1995). Effect of N2O treatment/ vitamin B12 deficiency in pigs on tissue concentrations of odd-numbered, branched-chain fatty acids. International Journal for Vitamin & Nutrition Research, 65, 255-260.
26. McLean, G. R., Quadros, E. V., Rothenberg, S. P., Morgan, A. C., Schrader, J. W. and Ziltener. H. J. (1997). Antibodies to transcobalamin II block in vitro proliferation of leukemic cells. Blood. 89, 235-242.
27. Koppenhagen, V. B., Wagner, F. and Pfiffner, J. J. (1973). alpha-(5,6-dimethylbenzimidazolyl)rhodibamide and rhodibinamide, the rhodium analogues of vitamin B12 and cobinamide. Journal of Biological Chemistry, 248, 7999-8002.
28. Carmel, R. and Koppenhagen, V. B. (1977). The effect of rhodium and copper analogs of cobalamin on human cells in vitro. Archives of Biochemistry & Biophysics, 184, 135-140.
29. Bieganowski, R. and Friedrich, W. (1979). Preparation and some properties of ferribalamin, the Fe(III) analogue of vitamin B12. FEBS Letters. 97, 325-326.
30. Koppenhagen, V. B., Elsenhans, B. and Wagner, F. (1974). Methylrhodibalamin and 5′-deoxyadenosyIrhodibalamin, the rhodium analogues of methylcobalamin and cobalamin coenzyme. Journal of Biological Chemistry, 249, 6532-6540.
31. McLean, G. R., Pathare, P. M., Wilbur, D. S., et al. (1997). Cobalamin analogues modulate the growth of leukemia cells in vitro. Cancer Research, 57, 4015-4022.
32. Myasishcheva, N. V., Quadros, E. V., Matthews, D. M. and Linnell, J. C. (1979). Interference by methylcobalamin analogues with synthesis of cobalamin coenzymes in human lymphocytes in vitro. Biochimica et Biophysica Acta, 588, 81-88.
33. Siddons, R. C., Spence, J. A. and Dayan, A. D. (1975). Experimental vitamin B12 deficiency in the baboon. Advances in Neurology, 10, 239-252.
34. Siddons. R. C. (1975). Changes in folate metabolism in baboons Papio cynocephalus treated with 2-methyl-2-aminopropanol-B12. British Journal of Haematology, 29, 263-271.
35. 12 antagonism by monocarboxylic acids and anilides of cyanocobalamin. Nature, 247. 308-309.
36. Kondo. H., Osborne, M. L., Kolhouse, J. F., et al. (1981). Nitrous oxide has multiple deleterious effects on cobalamin metabolism and causes decreases in activities of both mammalian cobalamin-dependent enzymes in rats. Journal of Clinical Investigation, 67, 1270-1283.
37. 12- deficient subjects? JAMA, 255, 1605-1606.
38. Chanarin, I. (1982). The effects of nitrous oxide on cobalamins, folates, and on related events. Critical Reviews in Toxicology, 10, 179-213.
39. Skacel, P. O., Hewlett, A. M., Lewis, J. D., Lumb, M., Nunn, J. F. and Chanarin, I. (1983). Studies on the haemopoietic toxicity of nitrous oxide in man. British Journal of Haematology, 53, 189-200.
40. Kano, Y., Sakamoto, S., Sakuraya, K., et al. (1983). Effects of nitrous oxide on human cell lines. Cancer Research, 43, 1493-1496.
41. Kroes, A. C., Lindemans, J., Hagenbeek, A. and Abels, J. (1984). Nitrous oxide reduces growth of experimental rat leukemia. Leukemia Research, 8, 441-448.
42. Abels, J., Kroes, A. C., Ermens, A. A., et al (1990). Antileukemic potential of methyl-cobalamin inactivation by nitrous oxide. American Journal of Hematology, 34, 128-131.
43. Kroes, A. C., Lindemans, J., Schoester, M. and Abels, J. (1986). Enhanced therapeutic effect of methotrexate in experimental rat leukemia after inactivation of cobalamin (vitamin B12) by nitrous oxide. Cancer Chemotherapy & Pharmacology, 17. 114-120.
44. Kroes, A. C., Ermens. A. A., Lindemans, J. and Abels, J. (1986). Effects of 5-fluorouracil treatment of rat leukemia with concomitant inactivation of cobalamin. Anticancer Research, 6, 737-742.
45. Kroes, A. C., Lindemans, J. and Abels, J. (1984). Synergistic growth inhibiting effect of nitrous oxide and cycloleucine in experimental rat leukaemia. British Journal of Cancer, 50, 793-800.
46. Abels, J., Kroes, A. C. M., Ermens, A. A. M., et al. (1990). Anti-leukemic potential of methyl-cobalamin inactivation by nitrous oxide. American Journal of Hematology, 34, 128-131.
47. Ermens, A. A., Schoester, M., Spijkers, L. J., Lindemans, J. and Abels, J. (1989). Toxicity of methotrexate in rats preexposed to nitrous oxide. Cancer Research, 49, 6337-6341.
48. Ermens, A. A., Vink, N., Schoester, M., van Lorn, K., Lindemans, J. and Abels, J. (1989). Nitrous oxide selectively reduces the proliferation of the malignant cells in experimental rat leukemia. Cancer Letters, 45, 123-128.
49. Ikeda, K., Aosaki, T., Furukawa, Y., et al. (1989). Antileukemic effect of nitrous oxide in a patient with chronic myelogenous leukemia. American Journal of Hematology. 30, 114.
50. Ermens, A. A., Kroes, A. C., Schoester, M., van Lorn, K., Lindemans, J. and Abels, J. (1988). Effect of cobalamin inactivation on folate metabolism of leukemic cells. Leukemia Research, 12, 905-910.
51. Ermens, A. A., Schoester, M., Lindemans, J. and Abels, J. (1991). Effect of nitrous oxide and methotrexate on folate coenzyme pools of blast cells from leukemia patients. Leukemia Research, 15, 165-171.
52. Lurab, M., Deacon, R., Perry, J., et al. (1980). The effect of nitrous oxide inactivation of vitamin B12 on rat hepatic folate. Implications for the methylfolate-trap hypothesis. Biochemical Journal. 186, 933-936.
53. Lumb, M., Chanarin, I., Perry, J. and Deacon, R. (1985). Turnover of the methyl moiety of 5-methyltetrahydropteroylglutamic acid in the cobalamin-inactivated rat. Blood. 66, 1171-1175.
54. Lumb, M., Deacon. R., Perry, J. and Chanarin, I. (1989). Oxidation of 5-methyltetrahydrofolate in cobalamin-inactivated rats. Biochemical Journal. 258, 907-910.
55. Christensen, B., Guttormsen, A. B., Schneede, J., et al. (1994). Preoperative methionine loading enhances restoration of the cobalamin-dependent enzyme methionine synthase after nitrous oxide anesthesia. Anesthesiology, 80, 1046-1056.
56. Christensen, B., Refsum, H., Garras, A. and Ueland, P. M. (1992). Homocysteine remethylation during nitrous oxide exposure of cells cultured in media containing various concentrations of folates. Journal of Pharmacology & Experimental Therapeutics. 261, 1096-1105.