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Chemical Compound Review

Tubercidine     2-(5-amino-2,4,9- triazabicyclo[4.3.0]nona...

Synonyms: CHEMBL599189, AG-J-16394, SureCN1652797, NSC-56408, CHEBI:120263, ...
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Disease relevance of tubercidin


Psychiatry related information on tubercidin

  • In the preceding article (Ugarkar et al. J. Med. Chem. 2000, 43) we reported that analogues of tubercidin are potent adenosine kinase (AK) inhibitors with antiseizure activity in the rat maximum electroshock (MES) model [6].

High impact information on tubercidin


Chemical compound and disease context of tubercidin


Biological context of tubercidin

  • A tubercidin-resistant clonal derivative of FBD5, FBD5-TUB, has acquired the combined biochemical phenotype of each single mutant [14].
  • Initial rate kinetics of the transport of adenosine and 4-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (tubercidin) in cultured cells [15].
  • These observations suggested that glycolysis could be a target of tubercidin action and that RNAi silencing of glycolytic enzymes was gradual enough to allow the parasites to adapt to alternative sources of energy [16].
  • The binding of tubercidin 5' -PO4 is not affected by either Mg2+ or MgATP2-; however, in initial velocity experiments MgATP2- caused from greater than100- to 4,000-fold activation of substrate hydrolysis depending on the concentration of AMP [17].
  • Binding studies with tritiated tubercidin 5' -PO4 (4-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5' -monophosphate), a competitive inhibitor with respect to the substrate, AMP, indicate the presence of three independent, identical binding sites for the substrate analog [17].

Anatomical context of tubercidin


Associations of tubercidin with other chemical compounds


Gene context of tubercidin

  • From a mutagenized population of wildtype Leishmania donovani promastigotes, a clonal cell line, TUBA2, was isolated by virtue of its ability to survive and grow in 20 microM tubercidin (7-deazaadenosine) [26].
  • The influx of tubercidin into MOLT 4 cells was found to occur primarily by means of the NBMPR-sensitive nucleoside transport system [27].
  • Short (1-h) exposures to 1 microM tubercidin alone inhibited colony formation (a) of normal human hematopoietic progenitors (CFU-GEMM, BFU-E, CFU-GM) by 100%, and (b) of HL-60/C1 and CCRF-CEM cells by > 90% [1].
  • We conclude that 5 microm tubercidin kills trypanosomes by targeting glycolysis, especially by inhibition of phosphoglycerate kinase [16].
  • We subsequently found that silencing of hexokinase, a glycolytic enzyme, also yielded tubercidin-resistant parasites [16].

Analytical, diagnostic and therapeutic context of tubercidin


  1. A comparison of the abilities of nitrobenzylthioinosine, dilazep, and dipyridamole to protect human hematopoietic cells from 7-deazaadenosine (tubercidin). Cass, C.E., King, K.M., Montaño, J.T., Janowska-Wieczorek, A. Cancer Res. (1992) [Pubmed]
  2. Treatment of mouse neoplasms with high doses of tubercidin. Lynch, T.P., Jakobs, E.S., Paran, J.H., Paterson, A.R. Cancer Res. (1981) [Pubmed]
  3. Isolation of genes mediating resistance to inhibitors of nucleoside and ergosterol metabolism in Leishmania by overexpression/selection. Cotrim, P.C., Garrity, L.K., Beverley, S.M. J. Biol. Chem. (1999) [Pubmed]
  4. Selective irreversible inactivation of replicating mengovirus by nucleoside analogues: a new form of viral interference. Brdar, B., Reich, E. J. Virol. (1999) [Pubmed]
  5. Synthesis and antiviral activity of certain 4- and 4,5-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidines. Pudlo, J.S., Saxena, N.K., Nassiri, M.R., Turk, S.R., Drach, J.C., Townsend, L.B. J. Med. Chem. (1988) [Pubmed]
  6. Adenosine kinase inhibitors. 2. Synthesis, enzyme inhibition, and antiseizure activity of diaryltubercidin analogues. Ugarkar, B.G., Castellino, A.J., DaRe, J.M., Kopcho, J.J., Wiesner, J.B., Schanzer, J.M., Erion, M.D. J. Med. Chem. (2000) [Pubmed]
  7. Isolation of variants in phagocytosis of a macrophage-like continuous cell line. Muschel, R.J., Rosen, N., Bloom, B.R. J. Exp. Med. (1977) [Pubmed]
  8. S-adenosylhomocysteine hydrolase is localized at the front of chemotaxing cells, suggesting a role for transmethylation during migration. Shu, S., Mahadeo, D.C., Liu, X., Liu, W., Parent, C.A., Korn, E.D. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  9. Combination therapy of schistosomiasis by tubercidin and nitrobenzylthioinosine 5'-monophosphate. el Kouni, M.H., Diop, D., Cha, S. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  10. Adenosine and tubercidin binding and transport in Chinese hamster ovary and Novikoff rat hepatoma cells. Plagemann, P.G., Wohlhueter, R.M. J. Cell. Physiol. (1983) [Pubmed]
  11. Prevention of tubercidin host toxicity by nitrobenzylthioinosine 5'-monophosphate for the treatment of schistosomiasis. el Kouni, M.H., Diop, D., O'Shea, P., Carlisle, R., Sommadossi, J.P. Antimicrob. Agents Chemother. (1989) [Pubmed]
  12. Adenosine kinase inhibitors. 5. Synthesis, enzyme inhibition, and analgesic activity of diaryl-erythro-furanosyltubercidin analogues. Boyer, S.H., Ugarkar, B.G., Solbach, J., Kopcho, J., Matelich, M.C., Ollis, K., Gomez-Galeno, J.E., Mendonca, R., Tsuchiya, M., Nagahisa, A., Nakane, M., Wiesner, J.B., Erion, M.D. J. Med. Chem. (2005) [Pubmed]
  13. Antiviral activity of C-5 substituted tubercidin analogues. Bergstrom, D.E., Brattesani, A.J., Ogawa, M.K., Reddy, P.A., Schweickert, M.J., Balzarini, J., De Clercq, E. J. Med. Chem. (1984) [Pubmed]
  14. Genetic analysis of nucleoside transport in Leishmania donovani. Iovannisci, D.M., Kaur, K., Young, L., Ullman, B. Mol. Cell. Biol. (1984) [Pubmed]
  15. Initial rate kinetics of the transport of adenosine and 4-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (tubercidin) in cultured cells. Harley, E.R., Paterson, A.R., Cass, C.E. Cancer Res. (1982) [Pubmed]
  16. The adenosine analog tubercidin inhibits glycolysis in Trypanosoma brucei as revealed by an RNA interference library. Drew, M.E., Morris, J.C., Wang, Z., Wells, L., Sanchez, M., Landfear, S.M., Englund, P.T. J. Biol. Chem. (2003) [Pubmed]
  17. Comparison of initial velocity and binding data for allosteric adenosine monophosphate nucleosidase. Schramm, V.L. J. Biol. Chem. (1976) [Pubmed]
  18. Adenosine receptors and modulation of natural killer cell activity by purine nucleosides. Priebe, T., Platsoucas, C.D., Nelson, J.A. Cancer Res. (1990) [Pubmed]
  19. Identification of the glycogenic compound 5-iodotubercidin as a general protein kinase inhibitor. Massillon, D., Stalmans, W., van de Werve, G., Bollen, M. Biochem. J. (1994) [Pubmed]
  20. Effects of novel anti-viral adenosine analogues on the activity of S-adenosylhomocysteine hydrolase from human liver. Fabianowska-Majewska, K., Duley, J.A., Simmonds, H.A. Biochem. Pharmacol. (1994) [Pubmed]
  21. Molecular identification of the equilibrative NBMPR-sensitive (es) nucleoside transporter and demonstration of an equilibrative NBMPR-insensitive (ei) transport activity in human erythroleukemia (K562) cells. Boleti, H., Coe, I.R., Baldwin, S.A., Young, J.D., Cass, C.E. Neuropharmacology (1997) [Pubmed]
  22. Manipulation of toxicity and tissue distribution of tubercidin in mice by nitrobenzylthioinosine 5'-monophosphate. Kolassa, N., Jakobs, E.S., Buzzell, G.R., Paterson, A.R. Biochem. Pharmacol. (1982) [Pubmed]
  23. Resistance to 9-beta-D-arabinofuranosyladenine in cultured leukemia L 1210 cells. Cass, C.E., Selner, M., Phillips, J.R. Cancer Res. (1983) [Pubmed]
  24. Flow cytometric analysis of adenosine analogue lymphocytotoxicity. Kefford, R.F., Taylor, I.W., Fox, R.M. Cancer Res. (1983) [Pubmed]
  25. Synthesis, cytotoxicity, and antiviral activity of some acyclic analogues of the pyrrolo[2,3-d]pyrimidine nucleoside antibiotics tubercidin, toyocamycin, and sangivamycin. Gupta, P.K., Daunert, S., Nassiri, M.R., Wotring, L.L., Drach, J.C., Townsend, L.B. J. Med. Chem. (1989) [Pubmed]
  26. Characterization of a mutant Leishmania donovani deficient in adenosine kinase activity. Iovannisci, D.M., Ullman, B. Mol. Biochem. Parasitol. (1984) [Pubmed]
  27. Transport and metabolism of 9-beta-D-arabinofuranosylguanine in a human T-lymphoblastoid cell line: nitrobenzylthioinosine-sensitive and -insensitive influx. Prus, K.L., Averett, D.R., Zimmerman, T.P. Cancer Res. (1990) [Pubmed]
  28. Favored incorporation of tubercidin in poly(adenylic, 7-deazadenylic acids) and their function as messenger ribonucleic acids in protein synthesis. Seela, F., Tran, T.Q., Mentzel, H., Erdmann, V.A. Biochemistry (1981) [Pubmed]
  29. A mutant strain of Polysphondylium with defects in many genes. Francis, D., Shaffer, A. Dev. Genet. (1988) [Pubmed]
  30. Treatment of schistosomiasis mansoni and japonica in baboons with tubercidin given by direct intravenous injection. Jaffe, J.J., Doremus, H.M., Dunsford, H.A., Meymarian, E. Am. J. Trop. Med. Hyg. (1975) [Pubmed]
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