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Chemical Compound Review

AC1L9H2L     (4R)-1-[(3R,4S,5R)-3,4- dihydroxy-5...

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Disease relevance of Zebularine


High impact information on Zebularine


Chemical compound and disease context of Zebularine


Biological context of Zebularine


Anatomical context of Zebularine

  • Combined treatment of HCC cell lines with Ras and Jak/Stat inhibitors as well as with the demethylating agent zebularine induced a strong apoptotic response [12].
  • Three human tumor cell lines were used in this study (MiaPaCa, DU145, and U251) and the methylation status of three genes frequently hypermethylated in tumor cells (RASSF1A, HIC-1, and 14-3-3sigma) was determined as a function of zebularine exposure [13].
  • To aid in the clinical evaluation of zebularine, a potential oral antitumor agent, we initiated studies on the metabolism of zebularine in liver cytosol from humans and other mammals [14].
  • In addition, zebularine preferentially depleted DNA methyltransferase 1 (DNMT1) and induced expression of cancer-related antigen genes in cancer cells relative to normal fibroblasts [15].

Associations of Zebularine with other chemical compounds


Gene context of Zebularine


Analytical, diagnostic and therapeutic context of Zebularine


  1. The novel DNA methylation inhibitor zebularine is effective against the development of murine T-cell lymphoma. Herranz, M., Martín-Caballero, J., Fraga, M.F., Ruiz-Cabello, J., Flores, J.M., Desco, M., Marquez, V., Esteller, M. Blood (2006) [Pubmed]
  2. Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues. Driscoll, J.S., Marquez, V.E., Plowman, J., Liu, P.S., Kelley, J.A., Barchi, J.J. J. Med. Chem. (1991) [Pubmed]
  3. Zebularine inhibits human acute myeloid leukemia cell growth in vitro in association with p15INK4B demethylation and reexpression. Scott, S.A., Lakshimikuttysamma, A., Sheridan, D.P., Sanche, S.E., Geyer, C.R., Decoteau, J.F. Exp. Hematol. (2007) [Pubmed]
  4. RNA editing produces glycine receptor alpha3(P185L), resulting in high agonist potency. Meier, J.C., Henneberger, C., Melnick, I., Racca, C., Harvey, R.J., Heinemann, U., Schmieden, V., Grantyn, R. Nat. Neurosci. (2005) [Pubmed]
  5. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. Cheng, J.C., Matsen, C.B., Gonzales, F.A., Ye, W., Greer, S., Marquez, V.E., Jones, P.A., Selker, E.U. J. Natl. Cancer Inst. (2003) [Pubmed]
  6. Antimitogenic and chemosensitizing effects of the methylation inhibitor zebularine in ovarian cancer. Balch, C., Yan, P., Craft, T., Young, S., Skalnik, D.G., Huang, T.H., Nephew, K.P. Mol. Cancer Ther. (2005) [Pubmed]
  7. Zebularine reactivates silenced E-cadherin but unlike 5-Azacytidine does not induce switching from latent to lytic Epstein-Barr virus infection in Burkitt's lymphoma Akata cells. Rao, S.P., Rechsteiner, M.P., Berger, C., Sigrist, J.A., Nadal, D., Bernasconi, M. Mol. Cancer (2007) [Pubmed]
  8. Microarray analysis of epigenetic silencing of gene expression in the KAS-6/1 multiple myeloma cell line. Pompeia, C., Hodge, D.R., Plass, C., Wu, Y.Z., Marquez, V.E., Kelley, J.A., Farrar, W.L. Cancer Res. (2004) [Pubmed]
  9. Epigenetic regulation of tumor endothelial cell anergy: silencing of intercellular adhesion molecule-1 by histone modifications. Hellebrekers, D.M., Castermans, K., Vir??, E., Dings, R.P., Hoebers, N.T., Mayo, K.H., Oude Egbrink, M.G., Molema, G., Fuks, F., van Engeland, M., Griffioen, A.W. Cancer Res. (2006) [Pubmed]
  10. Evidence that DNA (cytosine-5) methyltransferase regulates synaptic plasticity in the hippocampus. Levenson, J.M., Roth, T.L., Lubin, F.D., Miller, C.A., Huang, I.C., Desai, P., Malone, L.M., Sweatt, J.D. J. Biol. Chem. (2006) [Pubmed]
  11. Origin of tight binding of a near-perfect transition-state analogue by cytidine deaminase: implications for enzyme catalysis. Guo, H., Rao, N., Xu, Q., Guo, H. J. Am. Chem. Soc. (2005) [Pubmed]
  12. Ubiquitous activation of Ras and Jak/Stat pathways in human HCC. Calvisi, D.F., Ladu, S., Gorden, A., Farina, M., Conner, E.A., Lee, J.S., Factor, V.M., Thorgeirsson, S.S. Gastroenterology (2006) [Pubmed]
  13. Enhancement of in vitro and in vivo tumor cell radiosensitivity by the DNA methylation inhibitor zebularine. Dote, H., Cerna, D., Burgan, W.E., Carter, D.J., Cerra, M.A., Hollingshead, M.G., Camphausen, K., Tofilon, P.J. Clin. Cancer Res. (2005) [Pubmed]
  14. Zebularine metabolism by aldehyde oxidase in hepatic cytosol from humans, monkeys, dogs, rats, and mice: influence of sex and inhibitors. Klecker, R.W., Cysyk, R.L., Collins, J.M. Bioorg. Med. Chem. (2006) [Pubmed]
  15. Preferential response of cancer cells to zebularine. Cheng, J.C., Yoo, C.B., Weisenberger, D.J., Chuang, J., Wozniak, C., Liang, G., Marquez, V.E., Greer, S., Orntoft, T.F., Thykjaer, T., Jones, P.A. Cancer Cell (2004) [Pubmed]
  16. Zebularine: a candidate for epigenetic cancer therapy. Bradbury, J. Drug Discov. Today (2004) [Pubmed]
  17. Potent inhibitors for the deamination of cytosine arabinoside and 5-aza-2'-deoxycytidine by human cytidine deaminase. Laliberté, J., Marquez, V.E., Momparler, R.L. Cancer Chemother. Pharmacol. (1992) [Pubmed]
  18. Comparison of biological effects of non-nucleoside DNA methylation inhibitors versus 5-aza-2'-deoxycytidine. Chuang, J.C., Yoo, C.B., Kwan, J.M., Li, T.W., Liang, G., Yang, A.S., Jones, P.A. Mol. Cancer Ther. (2005) [Pubmed]
  19. Epigenetic silencing of the human nucleotide excision repair gene, hHR23B, in interleukin-6-responsive multiple myeloma KAS-6/1 cells. Peng, B., Hodge, D.R., Thomas, S.B., Cherry, J.M., Munroe, D.J., Pompeia, C., Xiao, W., Farrar, W.L. J. Biol. Chem. (2005) [Pubmed]
  20. Methylation of the ASC gene promoter is associated with aggressive prostate cancer. Collard, R.L., Harya, N.S., Monzon, F.A., Maier, C.E., O'Keefe, D.S. Prostate (2006) [Pubmed]
  21. Continuous zebularine treatment effectively sustains demethylation in human bladder cancer cells. Cheng, J.C., Weisenberger, D.J., Gonzales, F.A., Liang, G., Xu, G.L., Hu, Y.G., Marquez, V.E., Jones, P.A. Mol. Cell. Biol. (2004) [Pubmed]
  22. Interleukin 6 supports the maintenance of p53 tumor suppressor gene promoter methylation. Hodge, D.R., Peng, B., Cherry, J.C., Hurt, E.M., Fox, S.D., Kelley, J.A., Munroe, D.J., Farrar, W.L. Cancer Res. (2005) [Pubmed]
  23. The in vitro and in vivo effects of re-expressing methylated von Hippel-Lindau tumor suppressor gene in clear cell renal carcinoma with 5-aza-2'-deoxycytidine. Alleman, W.G., Tabios, R.L., Chandramouli, G.V., Aprelikova, O.N., Torres-Cabala, C., Mendoza, A., Rogers, C., Rodgers, C., Sopko, N.A., Linehan, W.M., Vasselli, J.R. Clin. Cancer Res. (2004) [Pubmed]
  24. p53 expression after treatment with zebularine is not due to demethylation. Brandes, J.C., Herman, J.G. Cancer Res. (2006) [Pubmed]
  25. Zebularine: a unique molecule for an epigenetically based strategy in cancer chemotherapy. Marquez, V.E., Kelley, J.A., Agbaria, R., Ben-Kasus, T., Cheng, J.C., Yoo, C.B., Jones, P.A. Ann. N. Y. Acad. Sci. (2005) [Pubmed]
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