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Chemical Compound Review

AC1NV8O4     2-amino-3,5-dihydropurine-6- thione

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Disease relevance of Tioguanine


High impact information on Tioguanine

  • The inhibition of Ro5-4864 binding to high affinity binding sites by TGua appeared to be due to the binding of TGua to membranes through the formation of a mixed disulfide between the 6-thiopurine and protein thiols, since the inhibition was reversed by the presence of 2-mercaptoethanol [3].
  • We have shown that the molecular form responsible for the induction of the differentiation of HL-60 cells to mature forms by 6-thioguanine (TGua) is the free base, TGua, itself [Ishiguro, Schwartz, and Sartorelli (1984) J. Cell. Physiol., 121:383-390] [3].
  • At 48 h these included thiouric acid, 8-hydroxy-6-mercaptopurine and 6-methylmercaptopurine (median 31, 19.5 and 8.8 microM respectively), with TIMP, 6TG, thioxanthine and thioxanthine nucleotide at median concentrations of 61, 0.79, 2.11 and 0.80 microM respectively [4].
  • In regular growth medium supplemented with 10(-4) M TG (Tyr+/TG), TGr derivatives, all of which continue to express PH, occur with high frequency (approximately equal to 10(-3) [5].


  1. Deoxythioguanosine triphosphate impairs HIV replication: a new mechanism for an old drug. Krynetskaia, N.F., Feng, J.Y., Krynetski, E.Y., Garcia, J.V., Panetta, J.C., Anderson, K.S., Evans, W.E. FASEB J. (2001) [Pubmed]
  2. Thiopurine metabolism and identification of the thiopurine metabolites transported by MRP4 and MRP5 overexpressed in human embryonic kidney cells. Wielinga, P.R., Reid, G., Challa, E.E., van der Heijden, I., van Deemter, L., de Haas, M., Mol, C., Kuil, A.J., Groeneveld, E., Schuetz, J.D., Brouwer, C., De Abreu, R.A., Wijnholds, J., Beijnen, J.H., Borst, P. Mol. Pharmacol. (2002) [Pubmed]
  3. The role of benzodiazepine receptors in the induction of differentiation of HL-60 leukemia cells by benzodiazepines and purines. Ishiguro, K., Taft, W.C., DeLorenzo, R.J., Sartorelli, A.C. J. Cell. Physiol. (1987) [Pubmed]
  4. In vitro metabolism of 6-mercaptopurine by human liver cytosol. Rowland, K., Lennard, L., Lilleyman, J.S. Xenobiotica (1999) [Pubmed]
  5. DNA-mediated restoration of phenylalanine hydroxylase gene expression in enzyme-deficient derivatives of enzyme-constitutive mouse cell hybrids. Gopalakrishnan, T.V. Somat. Cell Mol. Genet. (1984) [Pubmed]
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