A fluorine-labeled methotrexate as a probe for monitoring tumor antifolate pharmacokinetics: Synthesis, in vitro cytotoxicity, and pilot in vivo 19F magnetic resonance spectra

Molecular Cancer Therapeutics

Volumn 2, Issue 10, 2003, Pages 933-939

  Spees, William M ^a   Yang, Guangli ^a   Veach, Darren ^a   Rubio, Maria Belen ^a   Koutcher, Jason A ^a   Bornmann, William ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIMETABOLITE; DIHYDROFOLATE REDUCTASE; FLUORINE; METHOTREXATE; THYMIDINE;

ANIMAL; ARTICLE; CANCER TRANSPLANTATION; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; IC 50; METABOLISM; METHODOLOGY; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; SYNTHESIS; TIME; TUMOR CELL LINE;

ANIMALS; ANTIMETABOLITES, ANTINEOPLASTIC; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; FLUORINE RADIOISOTOPES; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; METHOTREXATE; MICE; MODELS, CHEMICAL; MODELS, MOLECULAR; NEOPLASM TRANSPLANTATION; PROTEIN CONFORMATION; TETRAHYDROFOLATE DEHYDROGENASE; THYMIDINE; TIME FACTORS;

EID: 2442700347     PISSN: 15357163     EISSN: 15388514     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Rudin, M., Beckmann, N., Porszasz, R., Reese, T., Bochelen, D., and Sauter, A. In vivo magnetic resonance methods in pharmaceutical research: current status and perspectives. NMR Biomed., 12: 69-97, 1999. (Pubitemid 29198241)
2. 13C labeled anticancer agent Temozolomide detected in vivo by selective crosspolarization transfer. Magn. Reson. Med., 34: 338-342, 1995.
3. He, Q., Bhujwalla, Z. M., Maxwell, R. J., Griffiths, J. R., and Glickson, J. D. Proton NMR observation of the antineoplastic agent iproplatin in vivo by selective multiple quantum coherence transfer (Sel-MQC). Magn. Reson. Med., 33: 414-416, 1995.
4. 31P MRS: pulse-and-acquire, decoupling, and polarization transfer. Magn. Reson. Med., 44: 180-184, 2000.
5. 19F-NMRS of 5-fluorouracil in pharmacokinetics and pharmacodynamic studies. NMR Biomed., 11: 380-387, 1998.
6. Henkin, J. and Washtien, W. L. Novel fluorinated antifolates. Enzyme inhibition and cytotoxicity studies on 2′- and 3′-fluoroaminopterin. J. Med. Chem., 26: 1193-1196, 1983. (Pubitemid 13037372)
7. Galivan, J., Inglese, J., McGuire, J. J., Nimec, Z., and Coward, J. K. γ-Fluoromethotrexate: synthesis and biological activity of a potent inhibitor of dihydrofolate reductase with greatly diminished ability to form poly-γ-glutamates. Proc. Natl. Acad. Sci. USA, 82: 2598-2602, 1985. (Pubitemid 15095796)
8. Piper, J. R. and Montgomery, J. A. Preparation of 6-(bromomethyl)-2,4- pteridinediamine hydrobromide and its use in improved syntheses of methotrexate and related compounds. J. Org. Chem., 42: 208-211, 1977. (Pubitemid 8105690)
9. Boyle, P. H. and Pfleiderer, W. Synthesis and reactivity of 2,4-diamino-6-(hydroxymethyl)-pteridins. Chem. Ber., 113: 1514-1523, 1980.
10. Li, R., Sirawaraporn, R., Sirawaraporn, P. C. W., Wooden, J., Athappilly, F., Turley, S., and Hol, W. G. J. Three-dimensional structure of M. tuberculosis dihydrofolate reductase reveals opportunities for the design of novel tuberculosis drugs. J. Mol. Biol., 295: 307-323, 2000. (Pubitemid 30045362)
11. Jackman, A. L., Taylor, G. A., Calvert, A. H., and Harrrap, K. R. Modulation of anti-metabolite effects: effects of thymidine on the efficacy of the quinazoline-based thymidylate synthetase inhibitor, CB3717. Biochem. Pharmacol., 33: 3269-3275, 1984. (Pubitemid 14023263)
12. O'Dwyer, P. J., King, S. A., Hoth, D. F., and Leyland-Jones B. Role of thymidine in biochemical modulation: a review. Cancer Res., 47: 3911-3919, 1987. (Pubitemid 17108445)
13. Lamontagne, P., Maion, G., and Page, M. Cytotoxicity testing using a soluble tetrazolium formazan derivative. Cell. Pharmacol., 1: 171-174, 1994.
14. Scudiero, D. A., Shoemaker, R. H., Paull, K. D., Monks, A., Tierney, S., Nofziger, T. H., Currens, M. J., Seniff, D., and Boyd, M. R. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res., 48: 4827-4833, 1988.
15. Roberts, D., Kidd, W., Pratt, C. B., Peck, C., and Grinnel, J. Serum levels of methotrexate by the ligand-binding assay after "high-dose" therapy for osteosarcoma. Cancer, 44: 881-890, 1979. (Pubitemid 10242218)
16. Ballon, D., Mahmood, U., Jakubowski, A., and Koutcher, J. A. Resolution enhanced NMR spectroscopy in biological systems via magnetic susceptibility matched sample immersion chambers. Magn. Reson. Med., 30: 754-758, 1993. (Pubitemid 23360813)
17. Becker, E. D., Ferretti, J. A., and Gambhir, P. N. Selection of optimum parameters for pulse Fourier transform nuclear magnetic resonance. Anal. Chem., 51: 1413-1420, 1979.
18. Naressi, A., Couturier, C., Devos, J. M., Janssen, M., Mangeat, C., de Beer, R., and Graveron-Demilly, D. Java-based graphical user interface for the MRUI quantitation package. Magn. Reson. Mater. Phys. Biol. Med., 12: 141-152, 2001. (Pubitemid 32510133)
19. Gorlick, R., Goker, E., Trippett, T., Waltham, M., Banerjee, D., and Bertino, J. R. Intrinsic and acquired resistance to methotrexate in acute leukemia. N. Engl. J. Med., 335: 1041-1048, 1996. (Pubitemid 26338736)
20. Gorlick, R., Goker, E., Trippett, T., Steinheas, P., Elisseyeff, Y., Mazumdar, M., Flintoff, W. F., and Bertino, J. R. Defective transport is a common mechanism of acquired methotrexate resistance in acute lymphocytic leukemia and is associated with decreased reduced folate carrier expression. Blood, 89: 1013-1018, 1997. (Pubitemid 27121295)