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Chemical Compound Review

Cytosine deoxyribonucleoside     4-amino-1-[4-hydroxy-5...

Synonyms: AGN-PC-0053CY, SureCN6676882, ACMC-209rv6, D3897_SIGMA, SureCN10238960, ...
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Disease relevance of deoxycytidine


Psychiatry related information on deoxycytidine


High impact information on deoxycytidine


Chemical compound and disease context of deoxycytidine


Biological context of deoxycytidine


Anatomical context of deoxycytidine

  • Human T-cells (CCRF-HSB2) did not incorporate tritiated thymidine ([3H]TDR)--1.0-5.0 muCi/ml--into the nuclei, they readily incorporated tritiated deoxycytidine (E13H]CDR) [20].
  • BACKGROUND: Gemcitabine, a pyrimidine analogue of deoxycytidine, is an anticancer nucleoside drug that requires functional plasma membrane nucleoside transporter proteins to reach its intracellular targets and cause cytotoxicity [21].
  • Furthermore, a new deoxycytidine deaminase species with a characteristic electrophoretic mobility that is different from that of the host cell enzyme is found in cell extracts prepared from a human cell line infected with herpesvirus [2].
  • The reduced expression of deoxycytidine and deoxyadenosine kinases in B lymphoblasts may account for the lower accumulation of deoxypurine nucleotides in B cells as compared with T cells [22].
  • We examined, in vitro, the effect of high, but clinically achievable and nontoxic, concentrations of 2'-deoxycytidine (dCyd) (greater than or equal to 100 mumol/L) on high-dose AZT mediated growth inhibition and intracellular biochemical perturbations in normal bone marrow progenitor cells [23].

Associations of deoxycytidine with other chemical compounds


Gene context of deoxycytidine


Analytical, diagnostic and therapeutic context of deoxycytidine


  1. Reversal of deamination-related cytotoxicity of 5-methyl-2'-deoxycytidine by tetrahydrouridine in human leukemia cells. Jekunen, A., Vilpo, J.A. J. Natl. Cancer Inst. (1984) [Pubmed]
  2. Induction of deoxycytidine deaminase activity in mammalian cell lines by infection with herpes simplex virus type 1. Chan, T.S. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  3. Cloning and screening with nanogram amounts of immunopurified mRNAs: cDNA cloning and chromosomal mapping of cystathionine beta-synthase and the beta subunit of propionyl-CoA carboxylase. Kraus, J.P., Williamson, C.L., Firgaira, F.A., Yang-Feng, T.L., Münke, M., Francke, U., Rosenberg, L.E. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  4. Deoxynucleoside [1-thio]triphosphates prevent proofreading during in vitro DNA synthesis. Kunkel, T.A., Eckstein, F., Mildvan, A.S., Koplitz, R.M., Loeb, L.A. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  5. 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]
  6. Nucleoside and oxypurine homeostasis in adult rabbit cerebrospinal fluid and plasma. Eells, J.T., Spector, R., Huntoon, S. J. Neurochem. (1984) [Pubmed]
  7. A targeting sequence directs DNA methyltransferase to sites of DNA replication in mammalian nuclei. Leonhardt, H., Page, A.W., Weier, H.U., Bestor, T.H. Cell (1992) [Pubmed]
  8. Methylation of deoxycytidine incorporated by excision-repair synthesis of DNA. Kastan, M.B., Gowans, B.J., Lieberman, M.W. Cell (1982) [Pubmed]
  9. Induction of sister chromatid exchanges by BUdR is largely independent of the BUdR content of DNA. Davidson, R.L., Kaufman, E.R., Dougherty, C.P., Ouellette, A.M., DiFolco, C.M., Latt, S.A. Nature (1980) [Pubmed]
  10. Hydralazine-pyrimidine interactions may explain hydralazine-induced lupus erythematosus. Dubroff, L.M., Reid, R.J. Science (1980) [Pubmed]
  11. Activity of thymidine kinase and of polymerase alpha as well as activity and gene expression of deoxycytidine deaminase in leukemic blasts are correlated with clinical response in the setting of granulocyte-macrophage colony-stimulating factor-based priming before and during TAD-9 induction therapy in acute myeloid leukemia. Jahns-Streubel, G., Reuter, C., Auf der Landwehr, U., Unterhalt, M., Schleyer, E., Wörmann, B., Büchner, T., Hiddemann, W. Blood (1997) [Pubmed]
  12. Transport and metabolism of deoxycytidine and 1-beta-D-arabinofuranosylcytosine into cultured Novikoff rat hepatoma cells, relationship to phosphorylation, and regulation of triphosphate synthesis. Plagemann, P.G., Marz, R., Wohlhueter, R.M. Cancer Res. (1978) [Pubmed]
  13. Inhibition of a yeast LTR retrotransposon by human APOBEC3 cytidine deaminases. Dutko, J.A., Schäfer, A., Kenny, A.E., Cullen, B.R., Curcio, M.J. Curr. Biol. (2005) [Pubmed]
  14. Deoxyadenosine/deoxycytidine kinase from Bacillus subtilis. Purification, characterization, and physiological function. Møllgaard, H. J. Biol. Chem. (1980) [Pubmed]
  15. Potent toxicity of 2-chlorodeoxyadenosine toward human monocytes in vitro and in vivo. A novel approach to immunosuppressive therapy. Carrera, C.J., Terai, C., Lotz, M., Curd, J.G., Piro, L.D., Beutler, E., Carson, D.A. J. Clin. Invest. (1990) [Pubmed]
  16. A transforming growth factor beta 1 receptor type II mutation in ulcerative colitis-associated neoplasms. Souza, R.F., Lei, J., Yin, J., Appel, R., Zou, T.T., Zhou, X., Wang, S., Rhyu, M.G., Cymes, K., Chan, O., Park, W.S., Krasna, M.J., Greenwald, B.D., Cottrell, J., Abraham, J.M., Simms, L., Leggett, B., Young, J., Harpaz, N., Meltzer, S.J. Gastroenterology (1997) [Pubmed]
  17. "Trans-differentiation" from epidermal to mesenchymal/myogenic phenotype is associated with a drastic change in cell-cell and cell-matrix adhesion molecules. Boukamp, P., Fusenig, N.E. J. Cell Biol. (1993) [Pubmed]
  18. Activation induced deaminase: the importance of being specific. Smith, H.C., Bottaro, A., Sowden, M.P., Wedekind, J.E. Trends Genet. (2004) [Pubmed]
  19. Cloning and expression of human deoxycytidine kinase cDNA. Chottiner, E.G., Shewach, D.S., Datta, N.S., Ashcraft, E., Gribbin, D., Ginsburg, D., Fox, I.H., Mitchell, B.S. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  20. Dependency of sister chromatid exchange in T- and B-cells on the incorporation of deoxyribonucleosides into chromosomal DNA. Shiraishi, Y., Weinfeld, H., Minowada, J., Sandberg, A.A. J. Natl. Cancer Inst. (1976) [Pubmed]
  21. Gemcitabine transport in xenopus oocytes expressing recombinant plasma membrane mammalian nucleoside transporters. Mackey, J.R., Yao, S.Y., Smith, K.M., Karpinski, E., Baldwin, S.A., Cass, C.E., Young, J.D. J. Natl. Cancer Inst. (1999) [Pubmed]
  22. Nucleoside kinases in T and B lymphoblasts distinguished by autoradiography. Osborne, W.R. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  23. 2'-Deoxycytidine protects normal human bone marrow progenitor cells in vitro against the cytotoxicity of 3'-azido-3'-deoxythymidine with preservation of antiretroviral activity. Bhalla, K., Birkhofer, M., Li, G.R., Grant, S., MacLaughlin, W., Cole, J., Graham, G., Volsky, D.J. Blood (1989) [Pubmed]
  24. Bromodeoxyuridine mutagenesis in mammalian cells is stimulated by thymidine and suppressed by deoxycytidine. Davidson, R.L., Kaufman, E.R. Nature (1978) [Pubmed]
  25. Strand-biased defect in C/G transversions in hypermutating immunoglobulin genes in Rev1-deficient mice. Jansen, J.G., Langerak, P., Tsaalbi-Shtylik, A., van den Berk, P., Jacobs, H., de Wind, N. J. Exp. Med. (2006) [Pubmed]
  26. Deoxyribonucleoside kinases: two enzyme families catalyze the same reaction. Sandrini, M.P., Piskur, J. Trends Biochem. Sci. (2005) [Pubmed]
  27. Mechanism of synergistic cell killing when methotrexate precedes cytosine arabinoside: study of L1210 and human leukemic cells. Cadman, E., Eiferman, F. J. Clin. Invest. (1979) [Pubmed]
  28. Cellular penetration and antisense activity by a phenoxazine-substituted heptanucleotide. Flanagan, W.M., Wagner, R.W., Grant, D., Lin, K.Y., Matteucci, M.D. Nat. Biotechnol. (1999) [Pubmed]
  29. Yeast ribonucleotide reductase has a heterodimeric iron-radical-containing subunit. Chabes, A., Domkin, V., Larsson, G., Liu, A., Graslund, A., Wijmenga, S., Thelander, L. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  30. Characterization of human UMP/CMP kinase and its phosphorylation of D- and L-form deoxycytidine analogue monophosphates. Liou, J.Y., Dutschman, G.E., Lam, W., Jiang, Z., Cheng, Y.C. Cancer Res. (2002) [Pubmed]
  31. Increased frequency of aberrations in the p53/MDM2/p14(ARF) pathway in neuroblastoma cell lines established at relapse. Carr, J., Bell, E., Pearson, A.D., Kees, U.R., Beris, H., Lunec, J., Tweddle, D.A. Cancer Res. (2006) [Pubmed]
  32. Silencing of the hypoxia-inducible cell death protein BNIP3 in pancreatic cancer. Okami, J., Simeone, D.M., Logsdon, C.D. Cancer Res. (2004) [Pubmed]
  33. The Anti-HIV-1 Editing Enzyme APOBEC3G Binds HIV-1 RNA and Messenger RNAs That Shuttle between Polysomes and Stress Granules. Kozak, S.L., Marin, M., Rose, K.M., Bystrom, C., Kabat, D. J. Biol. Chem. (2006) [Pubmed]
  34. The persistence of maternal inheritance in Chlamydomonas despite hypomethylation of chloroplast DNA induced by inhibitors. Feng, T.Y., Chiang, K.S. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  35. Identification by UV resonance Raman spectroscopy of an imino tautomer of 5-hydroxy-2'-deoxycytidine, a powerful base analog transition mutagen with a much higher unfavored tautomer frequency than that of the natural residue 2'-deoxycytidine. Suen, W., Spiro, T.G., Sowers, L.C., Fresco, J.R. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  36. Evaluation of the antitumor activity of gemcitabine (2',2'-difluoro-2'-deoxycytidine). Hertel, L.W., Boder, G.B., Kroin, J.S., Rinzel, S.M., Poore, G.A., Todd, G.C., Grindey, G.B. Cancer Res. (1990) [Pubmed]
  37. Identification of novel target genes by an epigenetic reactivation screen of renal cancer. Ibanez de Caceres, I., Dulaimi, E., Hoffman, A.M., Al-Saleem, T., Uzzo, R.G., Cairns, P. Cancer Res. (2006) [Pubmed]
  38. High-resolution magnetic resonance imaging of the efficacy of the cytosine analogue 1-[2-C-cyano-2-deoxy-beta-D-arabino-pentofuranosyl]-N(4)-palmitoyl cytosine (CS-682) in a liver-metastasis athymic nude mouse model. Wu, M., Mazurchuk, R., Chaudhary, N.D., Spernyak, J., Veith, J., Pera, P., Greco, W., Hoffman, R.M., Kobayashi, T., Bernacki, R.J. Cancer Res. (2003) [Pubmed]
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