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Chemical Compound Review

Tabloid     2-amino-3,7-dihydropurine-6- thione

Synonyms: Lanvis, Tioguanine, thioguanine, ThioguaninGSK, Thioguanin-GSK, ...
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Disease relevance of Tabloid


High impact information on Tabloid


Chemical compound and disease context of Tabloid


Biological context of Tabloid

  • In V-79 Chinese hamster cells we have been measuring DNA damage by alkaline elution, mutation induction as detected by 6-thioguanine resistance, and cytotoxicity as detected by colony formation for different physical and chemical agents [16].
  • Do radiation-induced thioguanine-resistant mutants of cultured mammalian cells arise by HGPRT gene mutation or X-chromosome rearrangement [17]?
  • This mutant cell line, designated CEM-T15, was derived from the human T cell line CEM after chemical mutagenesis with ethane methylsulfonate and subsequent culture in medium containing 6-thioguanine [18].
  • Experiments on cross-resistance and delayed cytotoxicity showed differences in the cytotoxicities of TG-Pt(II) and SeG-Pt(II): TG-Pt(II) exerted its activity through its hydrolysis product thioguanine, whereas SeG-Pt(II) compound was cytotoxic itself [19].
  • Suppression of tumorigenicity is relieved by selecting cells which have lost the t(X;11) chromosome by growth in medium containing 6-thioguanine (6-TG) [20].

Anatomical context of Tabloid


Associations of Tabloid with other chemical compounds


Gene context of Tabloid

  • ES cells homozygous for the Msh2 mutation displayed increased resistance to killing by the cytotoxic drug 6-thioguanine (6TG), indicating that the 6TG cytotoxic mechanism is mediated by Msh2 [29].
  • Selective radiosensitization of drug-resistant MutS homologue-2 (MSH2) mismatch repair-deficient cells by halogenated thymidine (dThd) analogues: Msh2 mediates dThd analogue DNA levels and the differential cytotoxicity and cell cycle effects of the dThd analogues and 6-thioguanine [30].
  • A role for the Mut L homologue-1 (MLH1) protein, a necessary component of DNA mismatch repair (MMR), in G2-M cell cycle checkpoint arrest after 6-thioguanine (6-TG) exposure was suggested previously [31].
  • Alternative immunosuppressive drugs, particularly 6-thioguanine, should be considered for AZA-intolerant patients with ITPase deficiency [32].
  • Human CYP2A6, which is known to activate NNK to a mutagen, was lipofected via a retroviral vector into the Chinese hamster ovary AS52 cell line, which contains the bacterial gpt gene and can be mutated to 6-thioguanine resistance [33].
  • The association of lower TPMT activity with thioguanine-related liver damage could provide a means of identifying at-risk patients [34].

Analytical, diagnostic and therapeutic context of Tabloid


  1. Acquisition of high metastatic capacity after in vitro fusion of a nonmetastatic tumor line with a bone marrow-derived macrophage. Larizza, L., Schirrmacher, V., Pflüger, E. J. Exp. Med. (1984) [Pubmed]
  2. Modified chemotherapy with carmustine, cytarabine, cyclophosphamide, and 6-thioguanine (BACT) and autologous bone marrow transplantation in 24 poor-risk patients with acute lymphoblastic leukemia. Pico, J.L., Hartmann, O., Maraninchi, D., Beaujean, F., Benhamou, E., Mascret, B., Novakovitch, G., Ghalie, R., Kalifa, C., Hayat, M. J. Natl. Cancer Inst. (1986) [Pubmed]
  3. Chemotherapeutic evaluation using clinical criteria in spontaneous, autochthonous murine breast tumors. Stolfi, R.L., Stolfi, L.M., Sawyer, R.C., Martin, D.S. J. Natl. Cancer Inst. (1988) [Pubmed]
  4. 6-thioguanine can cause serious liver injury in inflammatory bowel disease patients. Dubinsky, M.C., Vasiliauskas, E.A., Singh, H., Abreu, M.T., Papadakis, K.A., Tran, T., Martin, P., Vierling, J.M., Geller, S.A., Targan, S.R., Poordad, F.F. Gastroenterology (2003) [Pubmed]
  5. Oesophageal varices associated with busulphan-thioguanine combination therapy for chronic myeloid leukaemia. Key, N.S., Kelly, P.M., Emerson, P.M., Chapman, R.W., Allan, N.C., McGee, J.O. Lancet (1987) [Pubmed]
  6. Genomic rearrangements in a mouse cell line containing integrated SV40 DNA. Sager, R., Anisowicz, A., Howell, N. Cell (1981) [Pubmed]
  7. The relationship between transformation and somatic mutation in human and Chinese hamster cells. Spandidos, D.A., Siminovitch, L. Cell (1978) [Pubmed]
  8. Evidence for functional hemizygosity at the Emtr locus in CHO cells through segregation analysis. Gupta, R.S., Chan, D.Y., Siminovitch, L. Cell (1978) [Pubmed]
  9. Mutant chinese hamster cells with a thermosensitive hypoxanthine-guanine phosphoribosyltransferase. Fenwick, R.G., Caskey, C.T. Cell (1975) [Pubmed]
  10. Alterations of the hprt gene in human in vivo-derived 6-thioguanine-resistant T lymphocytes. Albertini, R.J., O'Neill, J.P., Nicklas, J.A., Heintz, N.H., Kelleher, P.C. Nature (1985) [Pubmed]
  11. Mercaptopurine therapy intolerance and heterozygosity at the thiopurine S-methyltransferase gene locus. Relling, M.V., Hancock, M.L., Rivera, G.K., Sandlund, J.T., Ribeiro, R.C., Krynetski, E.Y., Pui, C.H., Evans, W.E. J. Natl. Cancer Inst. (1999) [Pubmed]
  12. Studies of the locus for androgen receptor: localization on the human X chromosome and evidence for homology with the Tfm locus in the mouse. Migeon, B.R., Brown, T.R., Axelman, J., Migeon, C.J. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  13. Regulation of the capacity for O6-methylguanine removal from DNA in human lymphoblastoid cells studied by cell hybridization. Ayres, K., Sklar, R., Larson, K., Lindgren, V., Strauss, B. Mol. Cell. Biol. (1982) [Pubmed]
  14. Intensive chemotherapy is the treatment of choice for elderly patients with acute myelogenous leukemia. Foon, K.A., Zighelboim, J., Yale, C., Gale, R.P. Blood (1981) [Pubmed]
  15. Evidence for a connection between the mismatch repair system and the G2 cell cycle checkpoint. Hawn, M.T., Umar, A., Carethers, J.M., Marra, G., Kunkel, T.A., Boland, C.R., Koi, M. Cancer Res. (1995) [Pubmed]
  16. Relationship between sister chromatid exchange and mutagenicity, toxicity and DNA damage. Bradley, M.O., Hsu, I.C., Harris, C.C. Nature (1979) [Pubmed]
  17. Do radiation-induced thioguanine-resistant mutants of cultured mammalian cells arise by HGPRT gene mutation or X-chromosome rearrangement? Cox, R., Masson, W.K. Nature (1978) [Pubmed]
  18. Generation of functional human T cell hybrids. Irigoyen, O., Rizzolo, P.V., Thomas, Y., Rogozinski, L., Chess, L. J. Exp. Med. (1981) [Pubmed]
  19. Murine lymphoma L5178Y cells resistant to purine antagonists: differences in cross-resistance to thioguanine-platinum(II) and selenoguanine-platinum(II). Kanzawa, F., Maeda, M., Sasaki, T., Hoshi, A., Kuretani, K. J. Natl. Cancer Inst. (1982) [Pubmed]
  20. Introduction of human chromosome 11 via microcell transfer controls tumorigenic expression of HeLa cells. Saxon, P.J., Srivatsan, E.S., Stanbridge, E.J. EMBO J. (1986) [Pubmed]
  21. Bloom's syndrome: evidence for an increased mutation frequency in vivo. Vijayalaxmi, n.u.l.l., Evans, H.J., Ray, J.H., German, J. Science (1983) [Pubmed]
  22. Rat bladder cell-mediated mutagenesis od Chinese hamster V79 cells and metabolism of benzo[a]pyrene. Langenbach, R., Malick, L., Nesnow, S. J. Natl. Cancer Inst. (1981) [Pubmed]
  23. Lack of effect of intravenous administration on time to respond to azathioprine for steroid-treated Crohn's disease. North American Azathioprine Study Group. Sandborn, W.J., Tremaine, W.J., Wolf, D.C., Targan, S.R., Sninsky, C.A., Sutherland, L.R., Hanauer, S.B., McDonald, J.W., Feagan, B.G., Fedorak, R.N., Isaacs, K.L., Pike, M.G., Mays, D.C., Lipsky, J.J., Gordon, S., Kleoudis, C.S., Murdock, R.H. Gastroenterology (1999) [Pubmed]
  24. Differential inhibition of nerve growth factor responses by purine analogues: correlation with inhibition of a nerve growth factor-activated protein kinase. Volonté, C., Rukenstein, A., Loeb, D.M., Greene, L.A. J. Cell Biol. (1989) [Pubmed]
  25. Role of postreplicative DNA mismatch repair in the cytotoxic action of thioguanine. Swann, P.F., Waters, T.R., Moulton, D.C., Xu, Y.Z., Zheng, Q., Edwards, M., Mace, R. Science (1996) [Pubmed]
  26. Chromosome-wide event accompanies the expression of recessive mutations in tetraploid cells. Chasin, L.A., Urlaub, G. Science (1975) [Pubmed]
  27. High incidence of secondary brain tumours after radiotherapy and antimetabolites. Relling, M.V., Rubnitz, J.E., Rivera, G.K., Boyett, J.M., Hancock, M.L., Felix, C.A., Kun, L.E., Walter, A.W., Evans, W.E., Pui, C.H. Lancet (1999) [Pubmed]
  28. High remission-induction rate in acute myeloid leukaemia. Gale, R.P., Cline, M.J. Lancet (1977) [Pubmed]
  29. Genetic analysis of mouse embryonic stem cells bearing Msh3 and Msh2 single and compound mutations. Abuin, A., Zhang, H., Bradley, A. Mol. Cell. Biol. (2000) [Pubmed]
  30. Selective radiosensitization of drug-resistant MutS homologue-2 (MSH2) mismatch repair-deficient cells by halogenated thymidine (dThd) analogues: Msh2 mediates dThd analogue DNA levels and the differential cytotoxicity and cell cycle effects of the dThd analogues and 6-thioguanine. Berry, S.E., Davis, T.W., Schupp, J.E., Hwang, H.S., de Wind, N., Kinsella, T.J. Cancer Res. (2000) [Pubmed]
  31. Defective expression of the DNA mismatch repair protein, MLH1, alters G2-M cell cycle checkpoint arrest following ionizing radiation. Davis, T.W., Wilson-Van Patten, C., Meyers, M., Kunugi, K.A., Cuthill, S., Reznikoff, C., Garces, C., Boland, C.R., Kinsella, T.J., Fishel, R., Boothman, D.A. Cancer Res. (1998) [Pubmed]
  32. Adverse drug reactions to azathioprine therapy are associated with polymorphism in the gene encoding inosine triphosphate pyrophosphatase (ITPase). Marinaki, A.M., Ansari, A., Duley, J.A., Arenas, M., Sumi, S., Lewis, C.M., Shobowale-Bakre, e.l.-.M., Escuredo, E., Fairbanks, L.D., Sanderson, J.D. Pharmacogenetics (2004) [Pubmed]
  33. Human CYP2A6 activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK): mutational specificity in the gpt gene of AS52 cells. Tiano, H.F., Wang, R.L., Hosokawa, M., Crespi, C., Tindall, K.R., Langenbach, R. Carcinogenesis (1994) [Pubmed]
  34. The thiopurine methyltransferase genetic polymorphism is associated with thioguanine-related veno-occlusive disease of the liver in children with acute lymphoblastic leukemia. Lennard, L., Richards, S., Cartwright, C.S., Mitchell, C., Lilleyman, J.S., Vora, A. Clin. Pharmacol. Ther. (2006) [Pubmed]
  35. Association of 6-thioguanine nucleotide levels and inflammatory bowel disease activity: a meta-analysis. Osterman, M.T., Kundu, R., Lichtenstein, G.R., Lewis, J.D. Gastroenterology (2006) [Pubmed]
  36. Veno-occlusive disease of the liver after chemotherapy of acute leukemia. Report of two cases. Griner, P.F., Elbadawi, A., Packman, C.H. Ann. Intern. Med. (1976) [Pubmed]
  37. Mutational spectrum at the Hprt locus in splenic T cells of B6C3F1 mice exposed to N-ethyl-N-nitrosourea. Skopek, T.R., Walker, V.E., Cochrane, J.E., Craft, T.R., Cariello, N.F. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  38. Cells from an immunodeficient patient (46BR) with a defect in DNA ligation are hypomutable but hypersensitive to the induction of sister chromatid exchanges. Henderson, L.M., Arlett, C.F., Harcourt, S.A., Lehmann, A.R., Broughton, B.C. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
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