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Chemical Compound Review

deoxyadenosine     5-(6-aminopurin-9-yl)-2...

Synonyms: dAdo, AGN-PC-00G0D1, CHEMBL416340, NSC-83258, NSC-91774, ...
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Disease relevance of deoxyadenosine


Psychiatry related information on deoxyadenosine


High impact information on deoxyadenosine

  • The ADA substrates, adenosine and deoxyadenosine, are increased in ADA-deficient mice [8].
  • The activity of S-adenosylhomocysteine hydrolase, which is inactivated by deoxyadenosine, increased to normal in red cells and nucleated marrow cells [9].
  • Each BcPh diol epoxide isomer exhibits a remarkable preference for covalent binding to DNA over hydrolysis, each yields a unique distribution of products with the nucleosides of DNA and each reacts extensively with deoxyadenosine residues in DNA [10].
  • This enzyme, although constitutively expressed in most tissues, is expressed at high level in immature T cells, and study of the pathophysiology of the disorder indicates that increased deoxyadenosine or altered methylation capacity have toxic effects on T-cell maturation [11].
  • The metabolic basis of the immunodeficiency is likely related to the sensitivity of lymphocytes to the accumulation of the ADA substrates adenosine and 2'-deoxyadenosine [12].

Chemical compound and disease context of deoxyadenosine


Biological context of deoxyadenosine


Anatomical context of deoxyadenosine


Associations of deoxyadenosine with other chemical compounds


Gene context of deoxyadenosine


Analytical, diagnostic and therapeutic context of deoxyadenosine


  1. Deoxyadenosine metabolism and cytotoxicity in cultured mouse T lymphoma cells: a model for immunodeficiency disease. Ullman, B., Gudas, L.J., Cohen, A., Martin, D.W. Cell (1978) [Pubmed]
  2. Deoxyadenosine triphosphate as a mediator of deoxyguanosine toxicity in cultured T lymphoblasts. Mann, G.J., Fox, R.M. J. Clin. Invest. (1986) [Pubmed]
  3. T lymphocyte ontogeny in adenosine deaminase-deficient severe combined immune deficiency after treatment with polyethylene glycol-modified adenosine deaminase. Weinberg, K., Hershfield, M.S., Bastian, J., Kohn, D., Sender, L., Parkman, R., Lenarsky, C. J. Clin. Invest. (1993) [Pubmed]
  4. 2'-Deoxycoformycin-induced hemolysis in the mouse. Spremulli, E., Crabtree, G.W., Dexter, D.L., Diamond, I., Calabresi, P. J. Natl. Cancer Inst. (1982) [Pubmed]
  5. Deoxycytidine kinase-mediated toxicity of deoxyadenosine analogs toward malignant human lymphoblasts in vitro and toward murine L1210 leukemia in vivo. Carson, D.A., Wasson, D.B., Kaye, J., Ullman, B., Martin, D.W., Robins, R.K., Montgomery, J.A. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  6. Adduct formation identification between phenyl glycidyl ether and 2'-deoxyadenosine and thymidine by chromatography, mass spectrometry and nuclear magnetic resonance spectroscopy. Van den Eeckhout, E., De Bruyn, A., Pepermans, H., Esmans, E.L., Vryens, I., Claereboudt, J., Claeys, M., Sinsheimer, J.E. J. Chromatogr. (1990) [Pubmed]
  7. The treatment of hairy-cell leukaemia with 2'-deoxycoformycin. Johnston, J.B., Glazer, R.I., Pugh, L., Israels, L.G. Br. J. Haematol. (1986) [Pubmed]
  8. Adenosine-deaminase-deficient mice die perinatally and exhibit liver-cell degeneration, atelectasis and small intestinal cell death. Migchielsen, A.A., Breuer, M.L., van Roon, M.A., te Riele, H., Zurcher, C., Ossendorp, F., Toutain, S., Hershfield, M.S., Berns, A., Valerio, D. Nat. Genet. (1995) [Pubmed]
  9. Treatment of adenosine deaminase deficiency with polyethylene glycol-modified adenosine deaminase. Hershfield, M.S., Buckley, R.H., Greenberg, M.L., Melton, A.L., Schiff, R., Hatem, C., Kurtzberg, J., Markert, M.L., Kobayashi, R.H., Kobayashi, A.L. N. Engl. J. Med. (1987) [Pubmed]
  10. Optically active benzo[c]phenanthrene diol epoxides bind extensively to adenine in DNA. Dipple, A., Pigott, M.A., Agarwal, S.K., Yagi, H., Sayer, J.M., Jerina, D.M. Nature (1987) [Pubmed]
  11. Expression of human adenosine deaminase in murine haematopoietic progenitor cells following retroviral transfer. Belmont, J.W., Henkel-Tigges, J., Chang, S.M., Wager-Smith, K., Kellems, R.E., Dick, J.E., Magli, M.C., Phillips, R.A., Bernstein, A., Caskey, C.T. Nature (1986) [Pubmed]
  12. Adenosine deaminase deficiency: metabolic basis of immune deficiency and pulmonary inflammation. Blackburn, M.R., Kellems, R.E. Adv. Immunol. (2005) [Pubmed]
  13. Enhanced cytotoxicity and inhibition of DNA damage repair in irradiated murine L5178Y lymphoblasts and human chronic lymphocytic leukemia cells treated with 2'-deoxycoformycin and deoxyadenosine in vitro. Begleiter, A., Pugh, L., Israels, L.G., Johnston, J.B. Cancer Res. (1988) [Pubmed]
  14. Effects of nucleoside transport inhibitors on the salvage and toxicity of adenosine and deoxyadenosine in L1210 and P388 mouse leukemia cells. Plagemann, P.G., Wohlhueter, R.M. Cancer Res. (1985) [Pubmed]
  15. 5-Hexyl-2'-deoxyuridine blocks the cytotoxic effects of 5-fluorodeoxyuridine or deoxyadenosine in leukemia L1210 cells in culture. Cory, J.G., Halley, M.C., Jeney, A., Lapis, K. Cancer Res. (1990) [Pubmed]
  16. Leukemia L1210 cell lines resistant to ribonucleotide reductase inhibitors. Cory, J.G., Carter, G.L. Cancer Res. (1988) [Pubmed]
  17. Restimulation of cell cycle progression by hypoxic tumour cells with deoxynucleosides requires ppm oxygen tension. Löffler, M. Exp. Cell Res. (1987) [Pubmed]
  18. Mechanism of deoxyadenosine and 2-chlorodeoxyadenosine toxicity to nondividing human lymphocytes. Seto, S., Carrera, C.J., Kubota, M., Wasson, D.B., Carson, D.A. J. Clin. Invest. (1985) [Pubmed]
  19. Effects of N-hydroxy-N'-aminoguanidine isoquinoline in combination with other inhibitors of ribonucleotide reductase on L1210 cells. Weckbecker, G., Weckbecker, A., Lien, E.J., Cory, J.G. J. Natl. Cancer Inst. (1988) [Pubmed]
  20. Illegitimate recombination induced by benzo[a]pyrene diol epoxide in Escherichia coli. Kokontis, J.M., Vaughan, J., Harvey, R.G., Weiss, S.B. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  21. The benzene metabolite p-benzoquinone forms adducts with DNA bases that are excised by a repair activity from human cells that differs from an ethenoadenine glycosylase. Chenna, A., Hang, B., Rydberg, B., Kim, E., Pongracz, K., Bodell, W.J., Singer, B. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  22. Recognition and transport of adenine derivatives with synthetic receptors. Benzing, T., Tjivikua, T., Wolfe, J., Rebek, J. Science (1988) [Pubmed]
  23. Overproduction of adenine deoxynucleosides and deoxynucletides in adenosine deaminase deficiency with severe combined immunodeficiency disease. Donofrio, J., Coleman, M.S., Hutton, J.J., Daoud, A., Lampkin, B., Dyminski, J. J. Clin. Invest. (1978) [Pubmed]
  24. Plasma deoxyadenosine, adenosine, and erythrocyte deoxyATP are elevated at birth in an adenosine deaminase-deficient child. Hirschhorn, R., Roegner, V., Rubinstein, A., Papageorgiou, P. J. Clin. Invest. (1980) [Pubmed]
  25. Adenosine kinase initiates the major route of ribavirin activation in a cultured human cell line. Willis, R.C., Carson, D.A., Seegmiller, J.E. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  26. Purine excretion by mouse peritoneal macrophages lacking adenosine deaminase activity. Chan, T.S. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  27. Metabolic consequences of adenosine deaminase deficiency in mice are associated with defects in alveogenesis, pulmonary inflammation, and airway obstruction. Blackburn, M.R., Volmer, J.B., Thrasher, J.L., Zhong, H., Crosby, J.R., Lee, J.J., Kellems, R.E. J. Exp. Med. (2000) [Pubmed]
  28. Adenosine kinase inhibition promotes survival of fetal adenosine deaminase-deficient thymocytes by blocking dATP accumulation. Van De Wiele, C.J., Vaughn, J.G., Blackburn, M.R., Ledent, C.A., Jacobson, M., Jiang, H., Thompson, L.F. J. Clin. Invest. (2002) [Pubmed]
  29. Possible metabolic basis for the different immunodeficient states associated with genetic deficiencies of adenosine deaminase and purine nucleoside phosphorylase. Carson, D.A., Wasson, D.B., Lakow, E., Kamatani, N. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  30. Purinogenic immunodeficiency diseases: selective toxicity of deoxyribonucleosides for T cells. Mitchell, B.S., Mejias, E., Daddona, P.E., Kelley, W.N. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  31. Nucleotide pool imbalance and adenosine deaminase deficiency induce alterations of N-region insertions during V(D)J recombination. Gangi-Peterson, L., Sorscher, D.H., Reynolds, J.W., Kepler, T.B., Mitchell, B.S. J. Clin. Invest. (1999) [Pubmed]
  32. Resistance of an adenosine kinase-deficient human lymphoblastoid cell line to effects of deoxyadenosine on growth, S-adenosylhomocysteine hydrolase inactivation, and dATP accumulation. Hershfield, M.S., Kredich, N.M. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  33. 2'Deoxycoformycin and deoxyadenosine affect IL 2 production and IL 2 receptor expression of human T cells. Ruers, T.J., Buurman, W.A., van der Linden, C.J. J. Immunol. (1987) [Pubmed]
  34. S-adenosylmethionine increases erythrocyte ATP in vitro by a route independent of adenosine kinase. Montero, C., Smolenski, R.T., Duley, J.A., Simmonds, H.A. Biochem. Pharmacol. (1990) [Pubmed]
  35. Antileukemic and immunosuppressive activity of 2-chloro-2'-deoxyadenosine. Carson, D.A., Wasson, D.B., Beutler, E. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  36. G1-phase arrest of cultured human leukemic T-cells induced by deoxyadenosine. Fox, R.M., Kefford, R.F., Tripp, E.H., Taylor, I.W. Cancer Res. (1981) [Pubmed]
  37. Evidence that binding of 7,12-dimethylbenz(a)anthracene to DNA in mouse embryo cell cultures results in extensive substitution of both adenine and guanine residues. Dipple, A., Pigott, M., Moschel, R.C., Costantino, N. Cancer Res. (1983) [Pubmed]
  38. Human placental deoxyadenosine and deoxyguanosine phosphorylating activity. Hurley, M.C., Palella, T.D., Fox, I.H. J. Biol. Chem. (1983) [Pubmed]
  39. Retention of configuration in the action of human plasma 3'-exonuclease on oligo(deoxynucleoside phosphorothioate). A new method for assignment of absolute configuration at phosphorus in isotopomeric deoxyadenosine 5'-O-[(18)O]phosphorothioate. Koziołkiewicz, M., Owczarek, A., Wójcik, M., Domański, K., Guga, P., Stec, W.J. J. Am. Chem. Soc. (2002) [Pubmed]
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