5-Amino-4-imidazolecarboxamide riboside potentiates both transport of reduced folates and antifolates by the human reduced folate carrier and their subsequent metabolism

Cancer Research

Volumn 66, Issue 7, 2006, Pages 3836-3844

  McGuire, John J ^a   Haile, William H ^a   Yeh, Chen Chen ^a  

^a ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [5 [[(1,2 DIHYDRO 3 METHYL 1 OXOBENZO[F]QUINAZOLIN 9 YL)METHYL]AMINO] 1 OXO 2 ISOINDOLINYL]GLUTARIC ACID; 5 AMINO 4 IMIDAZOLECARBOXAMIDE RIBOSIDE; AMINOPTERIN; FOLIC ACID; FOLIC ACID ANTAGONIST; METHOTREXATE; RALTITREXED; REDUCED FOLATE CARRIER;

ACUTE DISEASE; ARTICLE; DRUG INHIBITION; DRUG POTENTIATION; DRUG STRUCTURE; DRUG TRANSPORT; FOLATE METABOLISM; FOLIC ACID DEFICIENCY; GROWTH INHIBITION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROTEIN SYNTHESIS; T CELL LEUKEMIA;

AMINOIMIDAZOLE CARBOXAMIDE; BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; CHILD; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SYNERGISM; FOLIC ACID ANTAGONISTS; HUMANS; KINETICS; LEUKEMIA, LYMPHOCYTIC, ACUTE, L1; LEUKEMIA, T-CELL; MEMBRANE TRANSPORT PROTEINS; METHOTREXATE; PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE; POLYGLUTAMIC ACID; RIBONUCLEOTIDES; SUBCELLULAR FRACTIONS; TEMPERATURE; THYMIDYLATE SYNTHASE; TRITIUM;

EID: 33645730358     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-05-3226     Document Type: Article

References (51)

1. Shane B. Folylpolyglutamate synthesis and role in the regulation of one-carbon metabolism. Vitam Horm 1989;45:263-335.
2. Matherly LH, Goldman DI. Membrane transport of folates. Vitam Horm 2003;66:403-56.
3. Sirotnak FM, Tolner B. Carrier-mediated membrane transport of folates in mammalian cells. Annu Rev Nutr 1999;19:91-122.
4. Whetstine JR, Flatley RM, Matherly LH. The human reduced folate carrier gene is ubiquitously and differentially expressed in normal human tissues: identification of seven noncoding exons and characterization of a novel promoter. Biochem J 2002;367:629-40.
5. Weitman SD, Lark RH, Coney LR, et al. Distribution of the folate receptor GP38 in normal and malignant cell lines and tissues. Cancer Res 1992;52:3396-401.
6. Jansen G, Westerhof GR, Jarmuszewski MJ. Methotrexate transport in variant human CCRF-CEM leukemia cells with elevated levels of the reduced folate carrier. Selective defect on carrier-mediated transport of physiological concentrations of reduced folates. J Biol Chem 1990;265:18272-7.
7. Gong M, Cowan KH, Gudas J, Moscow JA. Isolation and characterization of genomic sequences involved in the regulation of the human reduced folate carrier gene (RFCl). Gene 1999;233:21-31.
8. Whetstine JR, Witt TL, Matherly LH. The human reduced folate carrier gene is regulated by the AP2 and spl transcription factor families and a functional 61-base pair polymorphism. J Biol Chem 2002;277:43873-80.
9. McGuire JJ. Anticancer antifolates: Current status and future directions. Curr Pharm Des 2003;9:2593-613.
10. Banerjee D, Mayer-Kuckuk P, Capiaux G, Budak-Alpdogan T, Gorlick R, Bertino JR. Novel aspects of resistance to drugs targeted to dihydrofolate reductase and thymidylate synthase. Biochim Biophys Acta 2002;1587:164-73.
11. McGuire JJ. Antifolate polyglutamylation in preclinical and clinical antifolate resistance. In: Jackman AL, editor. Antifolate drugs: basic research and clinical practice. Totowa (NJ): Humana Press; 1999. p. 339-63.
12. Whitehead VM, Vuchich MJ, Cooley LD, et al. Accumulation of methotrexate polyglutamates, ploidy and trisomies of both chromosomes 4 and 10 in lymphoblasts from children with B-progenitor cell acute lymphoblastic leukemia: a pediatric oncology group study. Leuk Lymphoma 1998;31:507-19.
13. Synold TW, Relling MV, Boyett JM, et al. Blast cell methotrexate- polyglutamate accumulation in vivo differs by lineage, ploidy, and methotrexate dose in acute lymphoblastic leukemia. J Clin Invest 1994;94:1996-2001.
14. Bochner BR, Ames BN. ZTP (5-amino 4-imidazole carboxamide riboside 5′-triphosphate): a proposed alarmone for 10-formyl-tetrahydrofolate deficiency. Cell 1982;29:929-37.
15. Foley GF, Lazarus H, Farber S, Uzman BG, Boone BA, McCarthy RE. Continuous culture of lymphoblasts from peripheral blood of a child with acute leukemia. Cancer 1965;18:522-9.
16. Tomsho JW. Folylpoly-γ-glutamate synthetase: kinetics of multiple glutamate ligations. Ann Arbor: University of Michigan; 2005.
17. McCloskey DE, McGuire JJ, Russell CA, et al. Decreased folylpolyglutamate synthetase activity as a mechanism of methotrexate resistance in CCRF-CEM human leukemia sublines. J Biol Chem 1991;266:6181-7.
18. McGuire JJ, Haile WH, Coward JK. Interaction of erythro- and threo-γ-fluoromethotrexate with human leukemia cell dihydrofolate reductase. Biochem Pharmacol 1989;38:4321-5.
19. McGuire JJ, Graber M, Licato N, et al. Biochemical and growth inhibitory effects of the erythro and threo isomers of γ-fluoromethotrexate, a methotrexate analogue defective in polyglutamylation. Cancer Res 1989;49:4517-25.
20. Rosowsky A, Lazarus H, Yuan GC, et al. Effects of methotrexate esters and other lipophilic antifolates on methotrexate-resistant human leukemic lymphoblasts. Biochem Pharmacol 1980;29:648-52.
21. Henderson GB, Zevely EM. Use of nonphysiological buffer systems in the analysis of methotrexate transport in L1210 cells. Biochem Int 1983;6:507-15.
22. McGuire JJ, Russell CA, Balinska M. Human cytosolic and mitochondrial folylpolyglutamate synthetase are electrophoretically distinct. Expression in antifolate-sensitive and -resistant human cell lines. J Biol Chem 2000;275:13012-6.
23. Balinska M, Galivan J, Coward JK. Efflux of methotrexate and its polyglutamate derivatives from hepatic cells in vitro. Cancer Res 1981;41:2751-6.
24. Henderson GB, Tsuji JM, Kumar HP. Characterization of the individual transport routes that mediate the influx and efflux of methotrexate in CCRF-CEM human lymphoblastic cells. Cancer Res 1986;46:1633-8.
25. Suresh MR, Huennekens FM. Transport of 6-hydroxymethylpterin by L1210 mouse leukemia cells. Biochem Int 1982;4:533-41.
26. Belt JA, Marina NM, Phelps DA, Crawford CR. Nucleoside transport in normal and neoplastic cells. Adv Enzyme Regul 1993;33:235-52.
27. Titus SA, Moran RG. Retrovirally mediated complementation of the glyB phenotype. Cloning of a human gene encoding the carrier for entry of folates into mitochondria. J Biol Chem 2000;275:36811-7.
28. Home DW, Holloway RS, Said HM. Uptake of 5-formyltetrahydrofolate in isolated rat liver mitochondria is carrier-mediated. J Nutr 1992;122:2204-9.
29. Barrueco JR, Sirotnak FM. Evidence for the facilitated transport of methotrexate polyglutamates into lysosomes derived from S180 cells. Basic properties and specificity for polyglutamate chain length. J Biol Chem 1991;266:11732-7.
30. Jackson RC, Fry DW, Boritzki TJ, et al. Biochemical pharmacology of the lipophilic antifolate, trimetrexate. Adv Enzyme Regul 1984;22:187-206.
31. White JC, Goldman ID. Mechanism of action of methotrexate. IV. Free intracellular methotrexate required to suppress dihydrofolate reduction to tetrahydrofolate by Ehrlich ascites tumor cells in vitro. Mol Pharmacol 1976;12:711-9.
32. McGuire JJ, Canestrari JG, Nagel GS. Characterization of the effect of AG337, a novel lipophilic thymidylate synthase inhibitor, on human head and neck and human leukemia cell lines. Int J Oncol 1999;15:1245-50.
33. Kamen BA, Capdevila A. Receptor-mediated folate accumulation is regulated by the cellular folate content. Proc Natl Acad Sci U S A 1986;83:5983-7.
34. Jansen G, Schornagel J, Westerhof GR, Rijksen G, Newell DR, Jackman A. Multiple membrane transport systems for the uptake of folate-based thymidylate synthase inhibitors. Cancer Res 1990;50:7544-8.
35. Wong SC, Zhang L, Witt TL, Proefke SA, Bhushan A, Matherly LH. Impaired membrane transport in methotrexate-resistant CCRF-CEM cells involves early translation termination and increased turnover of a mutant reduced folate carrier. J Biol Chem 1999;274:10388-94.
36. Mini E, Moroson BA, Franco CT, Bertino JR. Cytotoxic effects of folate antagonists against methotrexate-resistant human leukemic lymphoblast CCRF-CEM cell lines. Cancer Res 1985;45:325-30.
37. Jansen G, Westerhof GR, Kathmann I, Rademaker BC, Rijksen G, Schornagel JH. Identification of a membrane-associated folate-binding protein in human leukemic CCRF-CEM cells with transport-related methotrexate resistance. Cancer Res 1989;49:2455-9.
38. Fry DW, Yalowich JC, Goldman ID. Augmentation of the intracellular levels of polyglutamyl derivatives of methotrexate by vincristine and probenecid in Ehrlich ascites tumor cells. Cancer Res 1982;42:2532-6.
39. McGuire JJ, Russell CA. Folylpolyglutamate synthetase expression in antifolate-sensitive and -resistant human cell lines. Oncol Res 1998;10:193-200.
40. Ha T, Baggott JE. 5-Aminoimidazole-4-carboxamide ribotide (AlCAR) and its metabolites: Metabolic and cytotoxic effects and accumulation during methotrexate treatment. J Nutr Biochem 1994;5:522-8.
41. Kamen BA, Caston JD. Properties of a folate binding protein (FBP) isolated from porcine kidney. Biochem Pharmacol 1986;35:2323-9.
42. Moran RG, Mulkins M, Heidelberger C. Role of thymidylate synthetase in development of methotrexate cytotoxicity. Proc Natl Acad Sci U S A 1979;76:5924-8.
43. Bhushan A, Wroblewski D, Xuan YZ, Tritton TR, Hacker MP. Correlation of altered tyrosine phosphorylation with methotrexate resistance in a cisplatin-resistant subline of L1210 cells. Biochem Pharmacol 1996;51:477-82.
44. Nabokina SM, Ma TY, Said HM. Mechanism and regulation of folate uptake by human pancreatic epithelial MIA PaCa-2 cells. Am J Physiol Cell Physiol 2004;287:C142-8.
45. Hardie DG, Scott JW, Pan DA, Hudson ER. Management of cellular energy by the AMP-activated protein kinase system. FEBS Lett 2003;546:113-20.
46. Hawley SA, Boudeau J, Reid JL, et al. Complexes between the LKB1 tumor suppressor, STRAD α/β and MO25 α/β are upstream kinases in the AMP-activated protein kinase cascade. J Biol Chem 2003;2:28.1-16.
47. Spicer J, Ashworth A. LKBI kinase: master and commander of metabolism and polarity. Curr Biol 2004;14:R383-5.
48. Kirn YI. Folate and carcinogenesis: evidence, mechanisms, and implications. J Nutr Biochem 1999;10:66-88.
49. Pui CH, Evans WE. Acute lymphoblastic leukemia. N Engl J Med 1998;339:605-15.
50. Relling MV, Fairclough D, Ayers D, et al. Patient characteristics associated with high-risk methotrexate concentrations and toxicity. J Clin Oncol 1994;12:1667-72.
51. Dixon R, Gourzis J, McDermott D, Fujitaki J, Dewland P, Gruber H. AICA-riboside: safety, tolerance, and pharmacokinetics of a novel adenosine-regulating agent. J Clin Pharmacol 1991;31:342-7.