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Chemical Compound Review

CHEMBL117470     4-amino-1-[4-hydroxy-5...

Synonyms: SureCN1651086, SureCN6674896, LS-1031, NSC-127716, NSC-127717, ...
 
 
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Disease relevance of Dacogen

 

High impact information on Dacogen

  • In vivo application of the chromatin-modifying agents 5-azadeoxycytidine and phenylbutyrate as well as local damage by cardiotoxin injections caused a small increase in dystrophin-positive fibers without abolishing the appearance of "silent" nuclei [6].
  • Furthermore, treatment of PWS cells with the DNA methyltransferase inhibitor 5-azadeoxycytidine (5-aza-dC) induced demethylation of the SNURF-SNRPN CpG island and restoration of gene expression on the maternal allele [7].
  • Three of four TK- epimutants could be reactivated at very high frequency (8-73%) to the TK+ AZT-sensitive phenotype by 24 hr of exposure to the demethylating agent 5-azadeoxycytidine (5-azadC), implying that drug-induced DNA hypermethylation, rather than classical mutation, was involved in the original gene-silencing event in these three clones [8].
  • Cell cycle-specific reactivation of an inactive X-chromosome locus by 5-azadeoxycytidine [9].
  • We recently showed that transcriptional reactivation of FMR1 full mutations can be achieved by inducing DNA demethylation with 5-azadeoxycytidine (5-azadC) [10].
 

Chemical compound and disease context of Dacogen

 

Biological context of Dacogen

 

Anatomical context of Dacogen

 

Associations of Dacogen with other chemical compounds

 

Gene context of Dacogen

References

  1. Inactivation of the tumor suppressor PTEN/MMAC1 in advanced human prostate cancer through loss of expression. Whang, Y.E., Wu, X., Suzuki, H., Reiter, R.E., Tran, C., Vessella, R.L., Said, J.W., Isaacs, W.B., Sawyers, C.L. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  2. Retroviral expression in embryonic stem cells and hematopoietic stem cells. Cherry, S.R., Biniszkiewicz, D., van Parijs, L., Baltimore, D., Jaenisch, R. Mol. Cell. Biol. (2000) [Pubmed]
  3. Differential hypermethylation of SOCS genes in ovarian and breast carcinomas. Sutherland, K.D., Lindeman, G.J., Choong, D.Y., Wittlin, S., Brentzell, L., Phillips, W., Campbell, I.G., Visvader, J.E. Oncogene (2004) [Pubmed]
  4. 5-azacytidine and 5-azadeoxycytidine inhibit human immunodeficiency virus type 1 replication in vitro. Bouchard, J., Walker, M.C., Leclerc, J.M., Lapointe, N., Beaulieu, R., Thibodeau, L. Antimicrob. Agents Chemother. (1990) [Pubmed]
  5. 5-Aza-2'-deoxycytidine (NSC 127716) in non-seminomatous testicular cancer. Phase II from the EORTC Early Clinical Trials Cooperative Group and Genito-Urinary Group. Clavel, M., Monfardini, S., Fosså, S., Smyth, J., Renard, J., Kaye, S.B. Ann. Oncol. (1992) [Pubmed]
  6. The vast majority of bone-marrow-derived cells integrated into mdx muscle fibers are silent despite long-term engraftment. Wernig, G., Janzen, V., Schäfer, R., Zweyer, M., Knauf, U., Hoegemeier, O., Mundegar, R.R., Garbe, S., Stier, S., Franz, T., Wernig, M., Wernig, A. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  7. Parent-of-origin specific histone acetylation and reactivation of a key imprinted gene locus in Prader-Willi syndrome. Saitoh, S., Wada, T. Am. J. Hum. Genet. (2000) [Pubmed]
  8. Epigenetic mechanisms of drug resistance: drug-induced DNA hypermethylation and drug resistance. Nyce, J., Leonard, S., Canupp, D., Schulz, S., Wong, S. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  9. Cell cycle-specific reactivation of an inactive X-chromosome locus by 5-azadeoxycytidine. Jones, P.A., Taylor, S.M., Mohandas, T., Shapiro, L.J. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  10. Synergistic effect of histone hyperacetylation and DNA demethylation in the reactivation of the FMR1 gene. Chiurazzi, P., Pomponi, M.G., Pietrobono, R., Bakker, C.E., Neri, G., Oostra, B.A. Hum. Mol. Genet. (1999) [Pubmed]
  11. In vitro reactivation of the FMR1 gene involved in fragile X syndrome. Chiurazzi, P., Pomponi, M.G., Willemsen, R., Oostra, B.A., Neri, G. Hum. Mol. Genet. (1998) [Pubmed]
  12. Epigenetic regulation of the MGMT and hMSH6 DNA repair genes in cells resistant to methylating agents. Bearzatto, A., Szadkowski, M., Macpherson, P., Jiricny, J., Karran, P. Cancer Res. (2000) [Pubmed]
  13. Expression of antisense to DNA methyltransferase mRNA induces DNA demethylation and inhibits tumorigenesis. MacLeod, A.R., Szyf, M. J. Biol. Chem. (1995) [Pubmed]
  14. 5-Azadeoxycytidine-induced chromatin remodeling of the inactive X-linked HPRT gene promoter occurs prior to transcription factor binding and gene reactivation. Litt, M.D., Hansen, R.S., Hornstra, I.K., Gartler, S.M., Yang, T.P. J. Biol. Chem. (1997) [Pubmed]
  15. Kinetochore formation in experimentally undercondensed chromosomes. Haaf, T., Schmid, M. Hum. Genet. (1990) [Pubmed]
  16. Asymmetric methylation in the hypermethylated CpG promoter region of the human L1 retrotransposon. Woodcock, D.M., Lawler, C.B., Linsenmeyer, M.E., Doherty, J.P., Warren, W.D. J. Biol. Chem. (1997) [Pubmed]
  17. Complex relationships between 5-aza-dC induced DNA demethylation and chromosome compaction at mitosis. Flagiello, D., Bernardino-Sgherri, J., Dutrillaux, B. Chromosoma (2002) [Pubmed]
  18. Differential effects of 5-azacytidine and 5-azadeoxycytidine on cytotoxicity, DNA-strand breaking and repair of X-ray-induced DNA damage in HeLa cells. Snyder, R.D., Lachmann, P.J. Mutat. Res. (1989) [Pubmed]
  19. DNA demethylation and pericentromeric rearrangements of chromosome 1. Ji, W., Hernandez, R., Zhang, X.Y., Qu, G.Z., Frady, A., Varela, M., Ehrlich, M. Mutat. Res. (1997) [Pubmed]
  20. Possible involvement of DNA methylation in 5-azacytidine-induced neuronal cell apoptosis. Nakayama, H., Kajikawa, S., Shinozuka, J., Su, W.P., Doi, K. Histol. Histopathol. (1999) [Pubmed]
  21. Methyl-CpG binding domain protein 2 represses transcription from hypermethylated pi-class glutathione S-transferase gene promoters in hepatocellular carcinoma cells. Bakker, J., Lin, X., Nelson, W.G. J. Biol. Chem. (2002) [Pubmed]
  22. Studies on hypomethylation of liver DNA during early stages of chemical carcinogenesis in rat liver. Rao, P.M., Antony, A., Rajalakshmi, S., Sarma, D.S. Carcinogenesis (1989) [Pubmed]
  23. Evolutionary conservation of fragile sites induced by 5-azacytidine and 5-azadeoxycytidine in man, gorilla, and chimpanzee. Schmid, M., Ott, G., Haaf, T., Scheres, J.M. Hum. Genet. (1985) [Pubmed]
  24. Effect of 5-aza-2'-deoxycytidine (Dacogen) on covalent histone modifications of chromatin associated with the epsilon-, gamma-, and beta-globin promoters in Papio anubis. Lavelle, D., Vaitkus, K., Hankewych, M., Singh, M., DeSimone, J. Exp. Hematol. (2006) [Pubmed]
  25. Selection of drug-resistant transduced cells with cytosine nucleoside analogs using the human cytidine deaminase gene. Beauséjour, C.M., Eliopoulos, N., Momparler, L., Le, N.L., Momparler, R.L. Cancer Gene Ther. (2001) [Pubmed]
  26. Regulation of the intestinal mucin MUC2 gene expression in vivo: evidence for the role of promoter methylation. Gratchev, A., Siedow, A., Bumke-Vogt, C., Hummel, M., Foss, H.D., Hanski, M.L., Kobalz, U., Mann, B., Lammert, H., Mansmann, U., Stein, H., Riecken, E.O., Hanski, C. Cancer Lett. (2001) [Pubmed]
  27. Trans-regulated silencing and reactivation of TP53 tumor suppressor gene in malignant transformation and its reversion. Yang, L., Sasaki, M.S. Jpn. J. Cancer Res. (2000) [Pubmed]
  28. DNA methylation alters chromatin structure and regulates Thy-1 expression in EL-4 T cells. Sneller, M.C., Gunter, K.C. J. Immunol. (1987) [Pubmed]
  29. Regulated expression of tumor-specific and MHC class I antigens in an ultraviolet radiation-induced murine skin cancer. Ananthaswamy, H.N. J. Invest. Dermatol. (1988) [Pubmed]
  30. Inhibition of condensation in the late-replicating X chromosome induced by 5-azadeoxycytidine in human lymphocyte cultures. Haaf, T., Ott, G., Schmid, M. Hum. Genet. (1988) [Pubmed]
 
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