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Chemical Compound Review

Formycin     (2R,3R,4S,5R)-2-(5-amino- 2,4,7,8...

Synonyms: formycin A, CHEMBL471524, SureCN980049, SureCN4196088, CHEBI:42452, ...
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Disease relevance of Formycin


High impact information on Formycin

  • Uninfected macrophages also convert formycin B into the same products, but the levels are markedly lower than those seen in infected macrophages [6].
  • Na(+)-dependent formycin B transport activity in intestinal epithelium decreases from jejunum to ileum and is absent in descending colon [7].
  • From the metabolic profile, we conclude that formycin B is first converted to the 5'-monophosphate by the nucleoside phosphotransferase found in Leishmania and is subsequently converted to cytotoxic adenosine nucleotide analogs of formycin A that become incorporated into RNA [8].
  • The nucleoside triphosphates (NTPs) with an amino group at the 6 position and hydrogen at the 8 position, and formycin 5'-triphosphate (FTP) were hydrolyzed by myosin very slowly in the presence of Mg2+ and rapidly in the presence of EDTA and K+ [9].
  • In cell hybrids formed between FomR X FomS cells and FomR X Toyr cells, the formycin-resistant phenotype of both of the FomR mutants behaved codominantly [10].

Chemical compound and disease context of Formycin


Biological context of Formycin

  • Formycin B inhibited growth of L5178Y mouse leukemia cells in concentrations of less than twice the concentration that inhibits cell proliferation at 50% by cytostasis; at higher concentrations (more than twice the 50% concentration mentioned), the cells were killed [15].
  • In contrast, [3H]adenosine phosphorylation was insensitive to formycin A except at very high concentrations [16].
  • Deletion of amino acids 128-135, corresponding to DGSELTLD, produced an enzyme with a 20-fold decrease in Vmax but with smaller changes in substrate saturation kinetics, activation by MgATP, inhibition by inorganic phosphate, and inhibition by the tight-binding inhibitor, formycin 5-phosphate [17].
  • Study of the nucleotide binding site of the yeast Schizosaccharomyces pombe plasma membrane H+-ATPase using formycin triphosphate-terbium complex [18].
  • Biochemical genetic analysis of formycin B action in Leishmania donovani [2].

Anatomical context of Formycin


Associations of Formycin with other chemical compounds


Gene context of Formycin


Analytical, diagnostic and therapeutic context of Formycin

  • The purification involves DEAE-Sephadex chromatography followed by affinity chromatography on a column of Sepharose/formycin B [29].
  • Several 3-beta-D-ribofuranosyl-1,2,4-triazolo[3,4-f]-1,2,4-triazines related to formycin were prepared and tested for their antitumor activity in cell culture [30].
  • The advantages of using HPLC to examine the interconnecting activities of a multienzyme complex in subcellular fractions are discussed, including the increased sensitivity obtained by using formycin analogs in the assay procedures.(ABSTRACT TRUNCATED AT 400 WORDS)[31]
  • The levels of formycin B in serum after the final oral administration of 26 mg/kg/day were 1.4 micrograms/ml at 1 hr and 0.3 microgram/ml at 2 hr [32].
  • This early inhibitory effect of formycin A upon insulin release coincided, in perforated patch whole-cell recordings, with an initial transient increase of ATP-sensitive K+ channel activity [33].


  1. Crystallization and preliminary X-ray study of AMP nucleosidase. Giranda, V.L., Berman, H.M., Schramm, V.L. J. Biol. Chem. (1986) [Pubmed]
  2. Biochemical genetic analysis of formycin B action in Leishmania donovani. Robinson, N., Kaur, K., Emmett, K., Iovannisci, D.M., Ullman, B. J. Biol. Chem. (1984) [Pubmed]
  3. Antileishmanial activity of human red blood cells containing formycin A. Berman, J.D., Gallalee, J.V. J. Infect. Dis. (1985) [Pubmed]
  4. Difluoromethylornithine and formycin B in toxoplasmosis. Hofflin, J.M., Guptill, D.R., Araujo, F.G., Remington, J.S. J. Infect. Dis. (1985) [Pubmed]
  5. Inhibition of Rous sarcoma virus production by formycin. Sarih, L., Agoutin, B., Lecoq, O., Weill, D., Jullien, P., Heyman, T. Virology (1985) [Pubmed]
  6. Metabolism of formycin B by Leishmania amastigotes in vitro. Comparative metabolism in infected and uninfected human macrophages. Berman, J.D., Rainey, P., Santi, D.V. J. Exp. Med. (1983) [Pubmed]
  7. Sodium-dependent nucleoside transport in rabbit intestinal epithelium. Roden, M., Paterson, A.R., Turnheim, K. Gastroenterology (1991) [Pubmed]
  8. Metabolism and mechanism of action of formycin B in Leishmania. Rainey, P., Santi, D.V. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  9. Interaction between actomyosin and 8-substituted ATP analogs. Takenaka, H., Ikehara, M., Tonomura, Y. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  10. Formycin B-resistant mutants of Chinese hamster ovary cells: novel genetic and biochemical phenotype affecting adenosine kinase. Mehta, K.D., Gupta, R.S. Mol. Cell. Biol. (1983) [Pubmed]
  11. Crystal structure of the ternary complex of E. coli purine nucleoside phosphorylase with formycin B, a structural analogue of the substrate inosine, and phosphate (Sulphate) at 2.1 A resolution. Koellner, G., Luić, M., Shugar, D., Saenger, W., Bzowska, A. J. Mol. Biol. (1998) [Pubmed]
  12. Interpretation of fluorescence decays using a power-like model. Włodarczyk, J., Kierdaszuk, B. Biophys. J. (2003) [Pubmed]
  13. A new approach to interpretation of heterogeneity of fluorescence decay: effect of induced tautomeric shift and enzyme-->ligand fluorescence resonance energy transfer. Wlodarczyk, J., Kierdaszuk, B. Biophys. Chem. (2006) [Pubmed]
  14. Effects of a new adenosine deaminase inhibitor, isocoformycin, on toxicity, antitumor activity and tissue distribution of formycin A and 9-beta-D-arabinofuranosyladenine. Hidaka, T., Katayama, K., Yamashita, K., Yamashita, T., Watanabe, K., Shimazaki, M., Ohno, M., Takeuchi, T., Umezawa, H. J. Antibiot. (1980) [Pubmed]
  15. Influence of formycin B on polyadenosine diphosphoribose synthesis in vitro and in vivo. Müller, W.E., Rohde, H.J., Steffen, R., Maidhof, A., Lachmann, M., Zahn, R.K., Umezawa, H. Cancer Res. (1975) [Pubmed]
  16. Immunochemical and catalytic characteristics of adenosine kinase from Leishmania donovani. Bhaumik, D., Datta, A.K. J. Biol. Chem. (1989) [Pubmed]
  17. Mutagenic analysis of AMP nucleosidase from Escherichia coli. Deletion of a region similar to AMP deaminase and peptide characterization by mass spectrometry. Kvalnes-Krick, K., Labdon, J.E., Ma, X., Nieves, E., Schramm, V.L. J. Biol. Chem. (1993) [Pubmed]
  18. Study of the nucleotide binding site of the yeast Schizosaccharomyces pombe plasma membrane H+-ATPase using formycin triphosphate-terbium complex. Ronjat, M., Lacapere, J.J., Dufour, J.P., Dupont, Y. J. Biol. Chem. (1987) [Pubmed]
  19. Sodium-dependent nucleoside transport in mouse intestinal epithelial cells. Two transport systems with differing substrate specificities. Vijayalakshmi, D., Belt, J.A. J. Biol. Chem. (1988) [Pubmed]
  20. Characterization of purine nucleoside phosphorylase from human granulocytes and its metabolism of deoxyribonucleosides. Wiginton, D.A., Coleman, M.S., Hutton, J.J. J. Biol. Chem. (1980) [Pubmed]
  21. 2',5'-Oligoadenylates and related 2',5'-oligonucleotide analogues. 2. Effect on cellular proliferation, protein synthesis, and endoribonuclease activity. Hughes, B.G., Robins, R.K. Biochemistry (1983) [Pubmed]
  22. Dual effect of formycin A upon the hydrolysis of phosphoinositides in perifused pancreatic islets. Ulusoy, S., Sener, A., Malaisse, W.J. Cell. Signal. (1995) [Pubmed]
  23. The role of serine-123 in the activity and specificity of ribonuclease. Reactivation of ribonuclease 1-118 by the synthetic COOH-terminal tetradecapeptide, ribonuclease 111-124, and its O-methylserine and alanine analogs. Hodges, R.S., Merrifield, R.B. J. Biol. Chem. (1975) [Pubmed]
  24. The catalytic site of AMP nucleosidase. Substrate specificity and pH effects with AMP and formycin 5'-PO4. DeWolf, W.E., Fullin, F.A., Schramm, V.L. J. Biol. Chem. (1979) [Pubmed]
  25. Carbon-13 magnetic resonance spectra of C-nucleosides. 3. la-c Tautomerism in formycin and formycin B and certain pyrazolo[4,3-d]pyrimidines. Chenon, M.T., Panzica, R.P., Smith, J.C., Pugmire, R.J., Grant, D.M., Townsend, L.B. J. Am. Chem. Soc. (1976) [Pubmed]
  26. Characterization of a mutant Leishmania donovani deficient in adenosine kinase activity. Iovannisci, D.M., Ullman, B. Mol. Biochem. Parasitol. (1984) [Pubmed]
  27. Formycin B, purine nucleoside phosphorylase and lymphocyte function. Osborne, W.R., Sullivan, J.L., Scott, C.R. Immunol. Commun. (1980) [Pubmed]
  28. Formycin anhydronucleosides. Conformation of formycin and conformational specificity of adenosine deaminase. Zemlicks, J. J. Am. Chem. Soc. (1975) [Pubmed]
  29. Purification and characterization of human erythrocyte purine nucleoside phosphorylase and its subunits. Zannis, V., Doyle, D., Martin, D.W. J. Biol. Chem. (1978) [Pubmed]
  30. Synthesis and antitumor activity of certain 3-beta-D-ribofuranosyl-1,2,4-triazolo[3,4-f]-1,2,4-triazines related to formycin prepared via ring closure of a 1,2,4-triazine precursor. Ramasamy, K., Ugarkar, B.G., McKernan, P.A., Robins, R.K., Revankar, G.R. J. Med. Chem. (1986) [Pubmed]
  31. Intermediary purine-metabolizing enzymes from the cytosol of Dictyostelium discoideum monitored by high-performance liquid chromatography. Jahngen, E.G., Rossomando, E.F. Anal. Biochem. (1984) [Pubmed]
  32. Leishmania donovani: oral efficacy and toxicity of formycin B in the infected hamster. Berman, J.D., Keenan, C.M., Lamb, S.R., Hanson, W.L., Waits, V.B. Exp. Parasitol. (1983) [Pubmed]
  33. Dynamics of the cationic, bioelectrical and secretory responses to formycin A in pancreatic islet cells. Lebrun, P., Renström, E., Antoine, M.H., Bokvist, K., Holmquist, M., Rorsman, P., Malaisse, W.J. Pflugers Arch. (1996) [Pubmed]
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