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Chemical Compound Review

Pyrazofurin     (3E)-3-(amino-hydroxy- methylidene)-5-[(2R...

Synonyms:
 
 
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Disease relevance of Pyrazomycin

 

High impact information on Pyrazomycin

 

Chemical compound and disease context of Pyrazomycin

 

Biological context of Pyrazomycin

  • These data indicate that gene amplification is the major factor contributing to the enzyme overproduction in the pyrazofurin-resistant cells [14].
  • Phosphorylation of unprotected 4 with POCl3 and subsequent debenzylation of the intermediate 17 gave pyrazofurin 5'-phosphate (18), which provided the first chemical synthesis of 18 [15].
  • 5-Amino-3-beta-D-ribofuranosylpyrazolo[3,4-e][1,3]oxazin-7-o ne has been synthesized via cyclization of the appropriately protected pyrazofurin derivatives and subsequent transformations of the heterocyclic moiety [16].
  • The enrichment of carbons 3, 4, and 5 of pyrazofurin from [2-13C]acetate by S. candidus confirms earlier findings that acetate is converted to glutamate by the combined action of the Krebs cycle and malic enzyme [Elstner, E. F., Suhadolnik, R. J., & Allerhand, A. (1973) J. Biol. Chem. 248, 5385] [4].
  • Cytidine, which can be deaminated to uridine, will substitute for uridine to maintain normal cell growth in the presence of growth-inhibitory concentrations of pyrazofurin (5 microM) [17].
 

Anatomical context of Pyrazomycin

  • Pyrazofurin (PYF), a C-riboside, inhibited the replication of cultured Novikoff rat hepatoma cells, HeLa cells, and mouse L-cells at concentrations as low as 0.1 to 10 muM, but Novikoff cells were more sensitive than the cells of the other two cell lines [9].
  • Instead, these findings indicate that the primary mechanism for exogenous Urd reversal of pyrazofurin inhibition of DNA synthesis involves the reversal of pyrazofurin inhibition of UMP synthase, thus restoring orotic acid incorporation into lymphocyte DNA through the pyrimidine de novo pathway [18].
 

Associations of Pyrazomycin with other chemical compounds

 

Gene context of Pyrazomycin

 

Analytical, diagnostic and therapeutic context of Pyrazomycin

  • Amplification of the UMP synthase gene and enzyme overproduction in pyrazofurin-resistant rat hepatoma cells. Molecular cloning of a cDNA for UMP synthase [14].
  • A number of nucleoside and nucleotide derivatives of 4-hydroxy-3-beta-D-ribofuranosylpyrazole-5-carboxamide (pyrazofurin, 1) were prepared and tested for their antiviral and cytostatic activity in cell culture [15].
  • Twenty-five patients with inoperable carcinoma and lymphoma were given pyrazofurin (pf) by iv bolus at a dose level ranging from 100 to 300 mg/m2 of estimated body surface area [27].

References

  1. Rat hepatomas: chemotherapy with lycurim and pyrazofurin. Lui, M.S., Jackson, R.C., Harkrader, R.J., Weber, G. J. Natl. Cancer Inst. (1982) [Pubmed]
  2. Synergistic effect of purine derivatives on the toxicity of pyrazofurin and 6-azauridine towards cultured mammalian cells. Gupta, R.S., Moffat, M.R. J. Cell. Physiol. (1982) [Pubmed]
  3. Inhibitory effects of antiviral compounds on respiratory syncytial virus replication in vitro. Kawana, F., Shigeta, S., Hosoya, M., Suzuki, H., De Clercq, E. Antimicrob. Agents Chemother. (1987) [Pubmed]
  4. Glutamate as the common precursor for the aglycon of the naturally occurring C-nucleoside antibiotics. Suhadolnik, R.J., Reichenbach, N.L. Biochemistry (1981) [Pubmed]
  5. Sequential combination of pyrazofurin and 5-azacytidine in patients with acute myelocytic leukemia and carcinoma. Chahinian, A.P., Ohnuma, T., Greenfield, D.S., Holland, J.F. Oncology (1981) [Pubmed]
  6. Role of uridine triphosphate in the phosphorylation of 1-beta-D-arabinofuranosylcytosine by Ehrlich ascites tumor cells. White, J.C., Hines, L.H. Cancer Res. (1987) [Pubmed]
  7. Kinetics of N-(phosphonacetyl)-L-aspartate and pyrazofurin depletion of pyrimidine ribonucleotide and deoxyribonucleotide pools and their relationship to nucleic acid synthesis in intact and permeabilized cells. Moyer, J.D., Smith, P.A., Levy, E.J., Handschumacher, R.E. Cancer Res. (1982) [Pubmed]
  8. Phase and cell cycle specificity of pyrazofurin action. Olah, E., Lui, M.S., Tzeng, D.Y., Weber, G. Cancer Res. (1980) [Pubmed]
  9. Inhibition of de novo pyrimidine nucleotide and DNA synthesis and growth of cultured Novikoff rat hepatoma cells and other cell lines by pyrazofurin (NSC 143095). Plagemann, P.G., Behrens, M. Cancer Res. (1976) [Pubmed]
  10. Increased levels of UMP synthase protein and mRNA in pyrazofurin-resistant rat hepatoma cells. Suttle, D.P. J. Biol. Chem. (1983) [Pubmed]
  11. Potentiation of antimetabolite action by dibromodulcitol in cell culture. Oláh, E., Kremmer, T., Boldizsár, M. Adv. Enzyme Regul. (1985) [Pubmed]
  12. Inhibition of hepatitis A virus replication in vitro by antiviral compounds. Crance, J.M., Biziagos, E., Passagot, J., van Cuyck-Gandré, H., Deloince, R. J. Med. Virol. (1990) [Pubmed]
  13. Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. Wyde, P.R., Gilbert, B.E., Ambrose, M.W. Antiviral Res. (1989) [Pubmed]
  14. Amplification of the UMP synthase gene and enzyme overproduction in pyrazofurin-resistant rat hepatoma cells. Molecular cloning of a cDNA for UMP synthase. Kanalas, J.J., Suttle, D.P. J. Biol. Chem. (1984) [Pubmed]
  15. Synthesis and biological activity of certain nucleoside and nucleotide derivatives of pyrazofurin. Petrie, C.R., Revankar, G.R., Dalley, N.K., George, R.D., McKernan, P.A., Hamill, R.L., Robins, R.K. J. Med. Chem. (1986) [Pubmed]
  16. Synthetic approaches to the guanosine and xanthosine analogues 5-amino-3-beta-D-ribofuranosylpyrazolo[3,4-e][1,3]oxazin-7-one and 3-beta-D-ribofuranosylpyrazolo[3,4-e][1,3]oxazine-5,7-dione and studies of their antitumor potential. Zou, R.M., Beylin, V.G., Groziak, M.P., Wotring, L.L., Townsend, L.B. J. Med. Chem. (1991) [Pubmed]
  17. Uridine and cytidine metabolism following inhibition of de novo pyrimidine synthesis by pyrazofurin. Cadman, E., Benz, C. Biochim. Biophys. Acta (1980) [Pubmed]
  18. Alteration in de novo pyrimidine biosynthesis during uridine reversal of pyrazofurin-inhibited DNA synthesis. Ringer, D.P., Howell, B.A., Etheredge, J.L. J. Biochem. Toxicol. (1991) [Pubmed]
  19. Coordinate overproduction of orotate phosphoribosyltransferase and orotidine-5'-phosphate decarboxylase in hamster cells resistant to pyrazofurin and 6-azauridine. Suttle, D.P., Stark, G.R. J. Biol. Chem. (1979) [Pubmed]
  20. Synthesis and antiviral activity of 5'-deoxypyrazofurin. Chen, X., Schneller, S.W., Ikeda, S., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E. J. Med. Chem. (1993) [Pubmed]
  21. Ultrasensitive assay for ribonucleoside triphosphates in 50-1000 cells. Application to studies with pyrazofurin and mycophenolic acid. Moyer, J.D., Henderson, J.F. Biochem. Pharmacol. (1983) [Pubmed]
  22. Recent advances in the design of anticancer chemotherapy. Weber, G. Oncology (1980) [Pubmed]
  23. Broad-spectrum antiviral and cytocidal activity of cyclopentenylcytosine, a carbocyclic nucleoside targeted at CTP synthetase. De Clercq, E., Murase, J., Marquez, V.E. Biochem. Pharmacol. (1991) [Pubmed]
  24. Cytidine deaminase levels in cultured mammalian cell lines measured by the growth tests and enzyme assays. Ishii, K., Sakamoto, H., Furuyama, J., Hanaoka, M. Cell Struct. Funct. (1984) [Pubmed]
  25. Characterization of pyrazofurin-resistant HeLa cells with amplification of UMP synthase gene. Kanalas, J.J., Hutton, J.J., Suttle, D.P. Somat. Cell Mol. Genet. (1985) [Pubmed]
  26. Pyrazofurin-resistant hepatoma cells deficient in adenosine kinase. Suttle, D.P., Harkrader, R.J., Jackson, R.C. European journal of cancer. (1981) [Pubmed]
  27. Initial clinical study with pyrazofurin. Ohnuma, T., Holland, J.F. Cancer treatment reports. (1977) [Pubmed]
 
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