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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

deoxyadenosine     (2R,3S,5R)-5-(6-aminopurin-9- yl)-2...

Synonyms: Adenylriboside, SureCN19877, CCRIS 1782, AG-J-04266, CHEBI:17256, ...
 
 
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Disease relevance of deoxyadenosine

  • 5'-Iodotubercidin in nanomolar concentrations completely and dose-dependently inhibited formation of dATP and also protected against toxicity of submillimolar concentrations of dAdo in sympathetic neurons [1].
  • In the present study we examined whether dAdo/dCF, can enhance the antitumor activity of CLB and 4-HC in chronic lymphocytic leukemia (CLL) cells in vitro [2].
 

High impact information on deoxyadenosine

  • Because the orientations of the intercalated hydrocarbon are known from NMR solution structures of duplex oligonucleotides containing these dA adducts, a detailed analysis of the relationship between the position of intercalation and trapping of Top2 is possible [3].
  • Of the deoxyribonucleosides, dGuo was the most potent cell growth inhibitor; however, the potency of added dAdo was probably attenuated by the presence of adenosine deaminase in the tissue culture growth medium [4].
  • We investigated the mechanism of cell growth inhibition caused by the deoxyribonucleosides thymidine (dThd), deoxyguanosine (dGuo), deoxyadenosine (dAdo), and deoxycytidine (dCyd) [4].
  • This differs from our previous observation that intercalating dA adducts derived from benzo[c]phenanthrene (BcPh) DEs inhibit WRN activity in a strand- and stereospecific manner [5].
  • In support of such a mechanism we show that 2-deoxyadenosine (dAdo) induces apoptosis in chick embryonic sympathetic neurons supported in culture by NGF, excess K+, phorbol 12,13-dibutyrate, or forskolin [1].
 

Biological context of deoxyadenosine

  • Supportive evidence for a central role of dATP was gained by inhibition of kinases necessary for phosphorylation of dAdo [1].
  • In addition, a minor dGuo adduct derived from the bay-region syn-diol-epoxide of 7-MBA was detected as well as a minor dAdo adduct from this diol-epoxide [6].
  • We have observed that deoxyadenosine (dAdo) plus dCF (dAdo/dCF) inhibit the repair of x-irradiation-induced and bleomycin-induced DNA damage in vitro, and that this results in either synergistic or additive cytotoxicity, respectively [2].
 

Anatomical context of deoxyadenosine

  • Although some of these actions of dAdo were remarkably similar to those reported for human lymphoid cells, several were uniquely different [1].
  • Incubation with dCF (10(-5)M) and dAdo (10(-4)M) for 18 hours, inhibited protein and RNA synthesis in unstimulated lymphocytes and impaired the ability of the cells to respond to PHA stimulation or to give rise to T-cell colonies in methyl-cellulose [7].
 

Associations of deoxyadenosine with other chemical compounds

 

Gene context of deoxyadenosine

  • When carried out under oxygen-enriched atmosphere, the reaction of HNE with dAdo yielded 1,N6-ethenodeoxyadenosine (1,N6-EdAdo) and 7-(1',2'-dihydroxyheptyl)-1,N6-EdA in 0.03% and 0.48% yield [9].

References

  1. Deoxynucleoside induces neuronal apoptosis independent of neurotrophic factors. Wakade, A.R., Przywara, D.A., Palmer, K.C., Kulkarni, J.S., Wakade, T.D. J. Biol. Chem. (1995) [Pubmed]
  2. Combination therapy with nucleoside analogs and alkylating agents. Johnston, J.B., Verburg, L., Shore, T., Williams, M., Israels, L.G., Begleiter, A. Leukemia (1994) [Pubmed]
  3. Position-specific trapping of topoisomerase II by benzo[a]pyrene diol epoxide adducts: implications for interactions with intercalating anticancer agents. Khan, Q.A., Kohlhagen, G., Marshall, R., Austin, C.A., Kalena, G.P., Kroth, H., Sayer, J.M., Jerina, D.M., Pommier, Y. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  4. Effects of deoxynucleosides on cultured human leukemia cell growth and deoxynucleotide pools. Ross, D.D., Akman, S.A., Schrecker, A.W., Bachur, N.R. Cancer Res. (1981) [Pubmed]
  5. Inhibition of Werner syndrome helicase activity by benzo[a]pyrene diol epoxide adducts can be overcome by replication protein A. Choudhary, S., Doherty, K.M., Handy, C.J., Sayer, J.M., Yagi, H., Jerina, D.M., Brosh, R.M. J. Biol. Chem. (2006) [Pubmed]
  6. Analysis of 7-methylbenz[a]anthracene-DNA adducts formed in SENCAR mouse epidermis by 32P-postlabeling. Baer-Dubowska, W., Vulimiri, S.V., Harvey, R.G., Cortez, C., DiGiovanni, J. Carcinogenesis (1997) [Pubmed]
  7. Inability of poly-ADP-ribosylation inhibitors to protect peripheral blood lymphocytes from the toxic effects of ADA inhibition. Ganeshaguru, K., Piga, A., Latini, L., Hoffbrand, A.V. Adv. Exp. Med. Biol. (1989) [Pubmed]
  8. A nucleoside-sensitive organic cation transporter in opossum kidney cells. Chen, R., Pan, B.F., Sakurai, M., Nelson, J.A. Am. J. Physiol. (1999) [Pubmed]
  9. Formation of etheno adducts in reactions of enals via autoxidation. Chen, H.J., Chung, F.L. Chem. Res. Toxicol. (1994) [Pubmed]
 
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