Synthesis and biological evaluation of Nα-(4-amino-4-deoxy-10-methylpteroyl)-DL-4,4-difluoroornithine

Journal of Medicinal Chemistry

Volumn 39, Issue 13, 1996, Pages 2536-2540

  Tsukamoto, Takashi ^a   Haile, William H ^b   McGuire, John J ^b   Coward, James K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NALPHA (4 AMINO 4 DEOXY 10 METHYLPTEROYL) 4,4 DIFLUOROORNITHINE; ORNITHINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER GROWTH; CELL GROWTH; CELL MEMBRANE TRANSPORT; CYTOTOXICITY; DRUG SYNTHESIS; FLUORINATION; FOLATE METABOLISM; GROWTH INHIBITION; INHIBITION KINETICS; NONHUMAN;

BIOLOGICAL TRANSPORT; CELL DIVISION; ENZYME INHIBITORS; FOLIC ACID ANTAGONISTS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORNITHINE; PEPTIDE SYNTHASES; TETRAHYDROFOLATE DEHYDROGENASE; TUMOR CELLS, CULTURED;

EID: 0029934297     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960046w     Document Type: Review

References (27)

1. Shane, B. Folylpolyglutamate synthesis and role in the regulation of one-carbon metabolism. Vitam. Horm. 1989, 45, 263-335.
2. McGuire, J. J.; Coward, J. K. In Folates and Pterins; Blakley, R. L., Benkovic, S. J., Eds.; Wiley: New York, 1984; Vol. 1, pp 135-190.
3. Matherly, L. H.; Seither, R. L.; Goldman, I. D. Metabolism of the diaminoantifolates: Biosynthesis and pharmacology of the 7-hydroxyl and polyglutamyl metabolites of methotrexate and related antifolates. Pharmacol. Ther. 1987, 35, 27-56.
4. Cichowicz, D. J.; Cook, J. D.; George, S.; Shane, B. In Proceedings of the Second Workshop on Folyl and Antifolylpolyglutamates; Goldman, I. D., Ed.; Praeger: New York, 1985; pp 7-13.
5. George, S.; Cichowicz, D. J.; Shane, B. Mammalian folylpoly-γ-glutamate synthetase. 3. Specificity for folate analogues. Biochemistry 1987, 26, 522-529.
6. Rosowsky, A.; Freisheim, J. H.; Moran, R. G.; Solan, V. C.; Bader, H.; Wright, J. E.; Radike-Smith, M. Methotrexate analogues. 26. Inhibition of dihydrofolate reductase and folylpolyglutamate synthetase activity and in vitro tumor cell growth by methotrexate and aminopterin analogues containing a basic amino acid side chain. J. Med. Chem. 1986, 29, 655-660.
7. McGuire, J. J.; Hsieh, P.; Franco, C. T.; Piper, J. R. Folylpolyglutamate synthetase inhibition and cytotoxic effects of methotrexate analogs containing 2,ω-diaminoalkanoic acids. Biochem. Pharmacol. 1986, 35, 2607-2613.
8. McGuire, J. J.; Bolanowska, W. E.; Piper, J. R. Structural specificity of inhibition of human folylpolyglutamate synthetase by ornithine-containing folate analogs. Biochem. Pharmacol. 1988, 37, 3931-3939.
9. Patil, S. A.; Shane, B.; Freisheim, J. H.; Singh, S. K.; Hynes, J. B. Inhibition of mammalian folylpolyglutamate synthetase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin bearing a terminal L-ornithine. J. Med. Chem 1989, 32, 1559-1565.
10. Hynes, J. B.; Singh, S. K.; Fetzer, O.; Shane, B. Inhibition of hog liver folylpolyglutamate synthetase by 5-substituted 5,8-dideaza analogues of folic acid bearing a terminal L-ornithine residue. J. Med. Chem. 1992, 35, 4078-4085.
11. Shirota, F. N.; Nagasawa, H. T.; Elberling, J. A. Potential inhibitors of collagen biosynthesis. 5,5-Difluoro-DL-lysine and 5,5-dimethyl-DL-lysine and their activation by lysyl-tRNA ligase. J. Med. Chem. 1977, 20, 1623-1627.
12. Hudlicky, M. Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes. Org. React. 1988, 35, 513-637.
13. Heath, H.; Lawson, A.; Remington, C. 2-Mercaptoglyoxalines. Part I. The synthesis of ergothioneine. J. Chem. Soc. 1951, 2215-2217.
14. Furuta, T.; Katayama, M.; Shibasaki, H.; Kasuya, Y. Synthesis of selectively multi-labelled histidines with stable isotopes and chiral synthesis of L-histidine from L-aspartic acid. J. Chem. Soc., Perkin Trans. I 1992, 1643-1648.
15. Tsukamoto, T.; Coward, J. K. Facile Synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-containing peptides: Regiospecific addition of nucleophiles to N-Cbz-di-tert-butyl-DL-4,4-difluoroglutamate. J. Org. Chem. 1996, 61, 2497-2500.
16. 1,β-diamino-α,α-difluoroketones, new dipeptide isoteres. Tetrahedron Lett. 1988, 29, 3687-3690.
17. Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. One-pot transformation of azido-group to N-(tert-Butoxycarbonyl)amino group. Tetrahedron Lett. 1989, 30, 837-838.
18. Piper, J. R.; 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. 1977, 42, 208-211.
19. Piper, J. R; McCaleb, G. S.; Montgomery, J. A.; Schmid, F. A.; Sirotnak, F. M. Syntheses and evaluation as antifolates of MTX analogues derived from 2, ω-diaminoalkanoic acids. J. Med. Chem. 1985, 28, 1016-1025.
20. Piper, J. R.; Montgonery, J. A. Syntheses of α- and γ-substituted amides, peptides, and esters of methotrexate and their evaluation as inhibitors of folate metabolism. J. Med. Chem. 1982, 25, 182-187.
21. Nimec, Z.; Galivan, J. Regulatory aspects of the glutamylation of methotrexate in cultured hepatoma cells. Arch. Biochem. Biophys. 1983, 226, 671-680.
22. Foley, G. F.; Lazarus, H.; Farber, S.; Uzman, B. G.; Boone, B. A.; McCarthy, R. E. Continuous culture of lymphoblasts from peripheral blood of a child with acute leukemia. Cancer 1965, 18, 522-529.
23. McCloskey, D. E.; McGuire, J. J.; Russell, C. A.; Rowan, B. G.; Bertino, J. R.; Pizzorno, G.; Mini, E. Decreased folylpolyglutamate synthetase activity as a mechanism of methotrexate resistance in CCRF-CEM human leukemia sublines. J. Biol. Chem. 1991, 266, 6181-6187.
24. McGuire, J. J.; Bergoltz, V. V.; Heitzman, K. J.; Haile, W. H.; Russell, C. A.; Bolanowska, W. E.; Kotake, Y.; Haneda, T.; Nomura, H. Novel 6,5-fused-ring heterocyclic antifolates: Biochemical and biological characterization. Cancer Res. 1994, 54, 2673-2679.
25. McGuire, J. J.; Hsieh, P.; Coward, J. K.; Bertino, J. R. In vitro methotrexate polyglutamate synthesis by rat liver folylpolyglutamate synthetase and inhibition by bromosulfophthalein. Adv. Exp. Med. Biol. 1983, 163, 199-214.
26. Bolanowska, W. E.; Russell, C. A.; McGuire, J. J. Activation of mammalian folylpolyglutamate synthetase by sodium bicarbonate. Arch. Biochem. Biophys. 1990, 281, 198-203.
27. McGuire, J. J.; Russell, C. A.; Bolanowska, W. E.; Freitag, C. M.; Jones, C. S.; Kalman, T. I. Biochemical and growth inhibition studies of methotrexate and aminopterin analogues containing a tetrazole ring in place of the γ-carboxyl group. Cancer Res. 1990, 50, 1726-1731.