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Chemical Compound Review

deoxyguanosine     2-amino-9-[4-hydroxy-5...

Synonyms: ACMC-1C8JT, AG-D-37261, D8415_SIGMA, NSC-22837, SureCN10068103, ...
 
 
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Disease relevance of deoxyguanosine

 

High impact information on deoxyguanosine

 

Chemical compound and disease context of deoxyguanosine

 

Biological context of deoxyguanosine

  • The promoter region of the chicken adult beta-globin gene contains a sequence of 16 deoxyguanosine residues located at a nucleosome boundary in tissues where the gene is inactive [15].
  • The studies also indicated that H2O2 formed hydroxyl radical (.OH) intracellularly, which appeared to be the most likely free radical responsible for DNA damage: .OH was detected in cells exposed to H2O2; the DNA base, deoxyguanosine, was hydroxylated in cells exposed to H2O2; and intracellular iron was essential for induction of DNA strand breaks [16].
  • At saturation, anti-diol-epoxide had covalently modified 1.5% of the total deoxyguanosine residues in naked DNA, and this was reduced to 29 and 15% of this level in saturating the available anti-diol-epoxide-binding sites in chromosomes or chromatin, respectively [17].
  • We show that cytostatic 2'-deoxyguanosine concentrations cause G1-phase arrest in PNP-inhibited T lymphoblasts, regardless of their hypoxanthine guanine phosphoribosyltransferase status [11].
  • The effects on leukemia cells were mediated by the cellular phosphorylation of deoxyguanosine and the accumulation of dGTP, an inhibitor of ribonucleotide diphosphate reductase [18].
 

Anatomical context of deoxyguanosine

  • Inhibition of suppressor T-cell development following deoxyguanosine administration [19].
  • Recent transplantation studies suggest that thymic epithelium, derived by organ culturing fetal mouse thymus in the presence of deoxyguanosine, survives in an allogeneic host environment despite the continued expression of MHC donor antigens, but fails to induce allotolerance [20].
  • It also interfered with the differentiation of fetal liver cells or fetal thymocytes within deoxyguanosine-treated thymic lobes, but did not affect thymocyte development in intact cultured fetal thymic lobes [21].
  • Cultured leukemic T and null lymphocytes are highly sensitive to growth inhibition by thymidine, as well as the other deoxynucleosides, deoxyguanosine and deoxyadenosine [22].
  • The latter infectants had PNP activities eight times the level of 0.74 mumol/hr per mg of protein observed in normal skin fibroblasts, enabling rapid metabolism of exogenous deoxyguanosine, the cytotoxic metabolite that accumulates in the plasma of PNP-deficient patients [23].
 

Associations of deoxyguanosine with other chemical compounds

 

Gene context of deoxyguanosine

 

Analytical, diagnostic and therapeutic context of deoxyguanosine

References

  1. Deoxyguanosine toxicity in a mouse T lymphoma: relationship to purine nucleoside phosphorylase-associated immune dysfunction. Gudas, L.J., Ullman, B., Cohen, A., Martin, D.W. Cell (1978) [Pubmed]
  2. Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA. Tomasz, M., Lipman, R., Chowdary, D., Pawlak, J., Verdine, G.L., Nakanishi, K. Science (1987) [Pubmed]
  3. A unique deoxyguanosine triphosphatase is responsible for the optA1 phenotype of Escherichia coli. Beauchamp, B.B., Richardson, C.C. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  4. Inhibition of the replication of hepatitis B virus by the carbocyclic analogue of 2'-deoxyguanosine. Price, P.M., Banerjee, R., Acs, G. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  5. Selective toxicity of deoxyguanosine and arabinosyl guanine for T-leukemic cells. Cohen, A., Lee, J.W., Gelfand, E.W. Blood (1983) [Pubmed]
  6. Deoxyguanosine toxicity on lymphoid cells as a cause for immunosuppression in purine nucleoside phosphorylase deficiency. Chan, T.S. Cell (1978) [Pubmed]
  7. Positive selection of CD4+ T cells mediated by MHC class II-bearing stromal cell in the thymic cortex. Bill, J., Palmer, E. Nature (1989) [Pubmed]
  8. Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and at adjacent residues. Kuchino, Y., Mori, F., Kasai, H., Inoue, H., Iwai, S., Miura, K., Ohtsuka, E., Nishimura, S. Nature (1987) [Pubmed]
  9. Identity of cells that imprint H-2-restricted T-cell specificity in the thymus. Lo, D., Sprent, J. Nature (1986) [Pubmed]
  10. Inhibition of purine nucleoside phosphorylase by 8-aminoguanosine: selective toxicity for T lymphoblasts. Kazmers, I.S., Mitchell, B.S., Dadonna, P.E., Wotring, L.L., Townsend, L.B., Kelley, W.N. Science (1981) [Pubmed]
  11. Deoxyadenosine triphosphate as a mediator of deoxyguanosine toxicity in cultured T lymphoblasts. Mann, G.J., Fox, R.M. J. Clin. Invest. (1986) [Pubmed]
  12. Deoxyribonucleoside triphosphate accumulation by leukemic cells. Mitchell, B.S., Edwards, N.L., Koller, C.A. Blood (1983) [Pubmed]
  13. 2,6-Diaminopurinedeoxyriboside as a prodrug of deoxyguanosine in L1210 cells. Weckbecker, G., Cory, J.G. Cancer Res. (1987) [Pubmed]
  14. Inhibition of hepatitis B virus DNA polymerase by enantiomers of penciclovir triphosphate and metabolic basis for selective inhibition of HBV replication by penciclovir. Shaw, T., Mok, S.S., Locarnini, S.A. Hepatology (1996) [Pubmed]
  15. An erythrocyte-specific protein that binds to the poly(dG) region of the chicken beta-globin gene promoter. Lewis, C.D., Clark, S.P., Felsenfeld, G., Gould, H. Genes Dev. (1988) [Pubmed]
  16. Oxidant-induced DNA damage of target cells. Schraufstätter, I., Hyslop, P.A., Jackson, J.H., Cochrane, C.G. J. Clin. Invest. (1988) [Pubmed]
  17. Human fibroblast chromatin states as effectors of the DNA-binding characteristics of benzo[a]pyrene anti-7,8-dihydrodiol 9,10-epoxide and two nonalkylating DNA-binding molecules. Warner, M.R., Iannaccone, P., Fahl, W.E. J. Natl. Cancer Inst. (1986) [Pubmed]
  18. Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes. Kicska, G.A., Long, L., Hörig, H., Fairchild, C., Tyler, P.C., Furneaux, R.H., Schramm, V.L., Kaufman, H.L. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  19. Inhibition of suppressor T-cell development following deoxyguanosine administration. Dosch, H.M., Mansour, A., Cohen, A., Shore, A., Gelfand, E.W. Nature (1980) [Pubmed]
  20. Thymic epithelium and the induction of transplantation tolerance in nude mice. Jordan, R.K., Robinson, J.H., Hopkinson, N.A., House, K.C., Bentley, A.L. Nature (1985) [Pubmed]
  21. Involvement of E-cadherin in thymus organogenesis and thymocyte maturation. Müller, K.M., Luedecker, C.J., Udey, M.C., Farr, A.G. Immunity (1997) [Pubmed]
  22. Ecto-adenosine triphosphatase deficiency in cultured human T and null leukemic lymphocytes. A biochemical basis for thymidine sensitivity. Fox, R.M., Piddington, S.K., Tripp, E.H., Tattersall, M.H. J. Clin. Invest. (1981) [Pubmed]
  23. Design of vectors for efficient expression of human purine nucleoside phosphorylase in skin fibroblasts from enzyme-deficient humans. Osborne, W.R., Miller, A.D. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  24. 2'-deoxyguanosine toxicity for B and mature T lymphoid cell lines is mediated by guanine ribonucleotide accumulation. Sidi, Y., Mitchell, B.S. J. Clin. Invest. (1984) [Pubmed]
  25. Purinogenic immunodeficiency diseases: clinical features and molecular mechanisms. Mitchell, B.S., Kelley, W.N. Ann. Intern. Med. (1980) [Pubmed]
  26. Deoxycytidine kinase and deoxyguanosine kinase of Lactobacillus acidophilus R-26 are colinear products of a single gene. Ma, N., Ikeda, S., Guo, S., Fieno, A., Park, I., Grimme, S., Ikeda, T., Ives, D.H. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  27. Importance of specific purine amino and hydroxyl groups for efficient cleavage by a hammerhead ribozyme. Fu, D.J., McLaughlin, L.W. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  28. Extensive oxidative DNA damage in hepatocytes of transgenic mice with chronic active hepatitis destined to develop hepatocellular carcinoma. Hagen, T.M., Huang, S., Curnutte, J., Fowler, P., Martinez, V., Wehr, C.M., Ames, B.N., Chisari, F.V. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
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  30. T cell developmental defects in 'viable motheaten' mice deficient in SHP-1 protein-tyrosine phosphatase. Developmental defects are corrected in vitro in the presence of normal hematopoietic-origin stromal cells and in vivo by exogenous IL-7. Christianson, S.W., Greiner, D.L., Deluca, D., Leif, J., Phillips, N.E., Hayes, S.M., Hayashi, S., Joliat, M.J., Lyons, B.L., Shultz, L.D. J. Autoimmun. (2002) [Pubmed]
  31. Genetic changes and expression of the mannose 6-phosphate/insulin-like growth factor II receptor gene in human hepatitis B virus-associated hepatocellular carcinoma. Yang, E.B., Qin, L.L., Zhao, Y.N., Zhang, K., Chow, P. Int. J. Mol. Med. (2003) [Pubmed]
  32. Effect of oxidative stress on DNA damage and beta-amyloid precursor proteins in lymphoblastoid cell lines from a Nigerian population. Lahiri, D.K., Xu, Y., Klaunig, J., Baiyewu, O., Ogunniyi, A., Hall, K., Hendrie, H., Sahota, A. Ann. N. Y. Acad. Sci. (1999) [Pubmed]
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  34. A single stem cell can recolonize an embryonic thymus, producing phenotypically distinct T-cell populations. Kingston, R., Jenkinson, E.J., Owen, J.J. Nature (1985) [Pubmed]
  35. Transcription of granzyme A and B genes is differentially regulated during lymphoid ontogeny. Ebnet, K., Levelt, C.N., Tran, T.T., Eichmann, K., Simon, M.M. J. Exp. Med. (1995) [Pubmed]
  36. Benzo[alpha]pyrene diol epoxide I binds to DNA at replication forks. Paules, R.S., Cordeiro-Stone, M., Mass, M.J., Poirier, M.C., Yuspa, S.H., Kaufman, D.G. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  37. Induction of the Z conformation in poly(dG-dC).poly(dG-dC) by binding of N-2-acetylaminofluorene to guanine residues. Santella, R.M., Grunberger, D., Weinstein, I.B., Rich, A. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  38. O6-alkyldeoxyguanosine detection by 32P-postlabeling and nucleotide chromatographic analysis. Wilson, V.L., Basu, A.K., Essigmann, J.M., Smith, R.A., Harris, C.C. Cancer Res. (1988) [Pubmed]
 
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