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Chemical Compound Review

THIOGUANOSINE     2-amino-9-[(2R,3R,4S,5R)-3,4- dihydroxy-5...

Synonyms: CHEMBL283078, SureCN608145, BSPBio_000413, NSC-29422, SRI 759, ...
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Disease relevance of THIOGUANOSINE

  • Dynamics of RNA-protein interactions in the HIV-1 Rev-RRE complex visualized by 6-thioguanosine-mediated photocrosslinking [1].
  • BACKGROUND & AIMS: Azathioprine is the gold standard for immunosuppressive therapy in Crohn's disease (CD) and its molecular mechanism of action is caused by the metabolite 6-thioguanosine triphosphate (TGTP) [2].

High impact information on THIOGUANOSINE

  • 6-TG given alone reduced GTP levels and DNA synthesis rates in HL-60 cells, while a major intracellular 6-TG metabolite, 6-thioguanosine 5'-monophosphate, accumulated to high levels (approximately 100 microM) [3].
  • Measurement of PRPP amidotransferase activity using cell homogenates revealed altered kinetics for the enzyme from TGuo-30-2 cells, which included significant loss of sensitivity to feedback inhibition by 6-thioguanosine 5'-phosphate and greater catalytic activity at low concentrations of PRPP [4].
  • During incubation with TG, the monophosphorylated form of thioguanosine was transported by both MRP4 and MRP5; the highest transport rate was for MRP4 [5].
  • In contrast, induction of TPMT produced a 1.6-fold decrease in sensitivity to 6-TG, a decrease in levels of DNA-TGN, and an increase in levels of methylated thioguanosine monophosphate [6].
  • Here, we present results of photocross-linking analysis of native and minimal hammerheads containing photoreactive nucleobases 6-thioguanosine, 2,6-diaminopurine, 4-thiouridine, and pyrrolocytidine, introduced at specific sites within the catalytic core [7].

Biological context of THIOGUANOSINE


Anatomical context of THIOGUANOSINE


Associations of THIOGUANOSINE with other chemical compounds


Gene context of THIOGUANOSINE


Analytical, diagnostic and therapeutic context of THIOGUANOSINE


  1. Dynamics of RNA-protein interactions in the HIV-1 Rev-RRE complex visualized by 6-thioguanosine-mediated photocrosslinking. Ping, Y.H., Liu, Y., Wang, X., Neenhold, H.R., Rana, T.M. RNA (1997) [Pubmed]
  2. 6-thioguanosine diphosphate and triphosphate levels in red blood cells and response to azathioprine therapy in Crohn's disease. Neurath, M.F., Kiesslich, R., Teichgräber, U., Fischer, C., Hofmann, U., Eichelbaum, M., Galle, P.R., Schwab, M. Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association. (2005) [Pubmed]
  3. Modulation of 6-thioguanine activity by guanine in human promyelocytic leukemia HL-60 cells. Cheng, H.W., Armstrong, R.D., Sadée, W. Cancer Res. (1988) [Pubmed]
  4. Altered 5-phosphoribosyl 1-pyrophosphate amidotransferase activity in 6-thioguanine-resistant HL-60 human acute promyelocytic leukemia cells. Ishiguro, K., Sartorelli, A.C. Cancer Res. (1984) [Pubmed]
  5. 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]
  6. The effect of thiopurine methyltransferase expression on sensitivity to thiopurine drugs. Coulthard, S.A., Hogarth, L.A., Little, M., Matheson, E.C., Redfern, C.P., Minto, L., Hall, A.G. Mol. Pharmacol. (2002) [Pubmed]
  7. Three conserved guanosines approach the reaction site in native and minimal hammerhead ribozymes. Lambert, D., Heckman, J.E., Burke, J.M. Biochemistry (2006) [Pubmed]
  8. Investigation of 6-thiodeoxyguanosine alkylation products and their role in the potentiation of BCNU cytotoxicity. Bodell, W.J. IARC Sci. Publ. (1986) [Pubmed]
  9. The quantitative determination of metabolites of 6-mercaptopurine in biological materials. VII. Chemical synthesis by phosphorylation of 6-thioguanosine 5'-monophosphate, 5'-diphosphate and 5'-triphosphate, and their purification and identification by reversed-phase/ion-pair high-performance liquid chromatography and by various enzymatic assays. Breter, H.J., Mertes, H. Biochim. Biophys. Acta (1990) [Pubmed]
  10. S-(N-dansylaminoethyl)-6-mercaptoguanosine as a fluorescent probe for the uridine transport system in human erythrocytes. Shohami, E., Koren, R. Biochem. J. (1979) [Pubmed]
  11. Magnesium ion dependent rabbit skeletal muscle myosin guanosine and thioguanosine triphosphatase mechanism and a novel guanosine diphosphatase reaction. Eccleston, J.F., Trentham, D.R. Biochemistry (1979) [Pubmed]
  12. Isolation of the newly synthesized DNA of HeLa cells containing beta-2'-deoxy-6-thioguanylate on an organomercurial agarose column. Yoshida, S., Morita, T., Saneyoshi, M. Biochim. Biophys. Acta (1980) [Pubmed]
  13. The interaction of chromophoric nucleotides with subfragment 1 of myosin. Eccleston, J.F., Trentham, D.R. Biochem. J. (1977) [Pubmed]
  14. Determination of mercaptopurine and its four metabolites by large-volume sample stacking with polarity switching in capillary electrophoresis. Wang, C.C., Chiou, S.S., Wu, S.M. Electrophoresis (2005) [Pubmed]
  15. HPLC analysis of azathioprine metabolites in red blood cells, plasma and urine in renal transplant recipients. Weller, S., Thürmann, P., Rietbrock, N., Gossmann, J., Scheuermann, E.H. International journal of clinical pharmacology and therapeutics. (1995) [Pubmed]
  16. RNA-protein interactions in the Tat-trans-activation response element complex determined by site-specific photo-cross-linking. Wang, Z., Rana, T.M. Biochemistry (1998) [Pubmed]
  17. Reassessment of the interactions of guanylate kinase and 6-thioguanosine 5'-phosphate. Miller, R.L., Adamczyk, D.L., Spector, T. Biochem. Pharmacol. (1977) [Pubmed]
  18. Thioguanine, mercaptopurine: their analogs and nucleosides as antimetabolites. Elgemeie, G.H. Curr. Pharm. Des. (2003) [Pubmed]
  19. On the biochemical modulation of 6-mercaptopurine by methotrexate in murine WEHI-3b leukemia cells in vitro. Liliemark, J., Pettersson, B., Peterson, C. Leuk. Res. (1992) [Pubmed]
  20. Preparation of 6-thioguanosine phosphoramidite for oligoribonucleotide synthesis. Wang, Y., Lattmann, E., Zheng, Q. Nucleosides Nucleotides Nucleic Acids (2003) [Pubmed]
  21. Affinity chromatography of thiol-containing purines and ribonucleic acid. Melvin, W.T., Keir, H.M. Biochem. J. (1977) [Pubmed]
  22. Synthesis of 4-thiouridine, 6-thioinosine, and 6-thioguanosine 3',5'-O-bisphosphates as donor molecules for RNA ligation and their application to the synthesis of photoactivatable TMG-capped U1 snRNA fragments. Kadokura, M., Wada, T., Seio, K., Sekine, M. J. Org. Chem. (2000) [Pubmed]
  23. Conversion of 6-mercaptopurine to 6-thioguanylic acid in L-1210 cells and human leukemia cells. Uchida, M., Nakamura, T., Uchino, H. Jpn. J. Cancer Res. (1985) [Pubmed]
  24. Incorporation of 6-thioguanosine and 4-thiouridine into RNA. Application to isolation of newly synthesised RNA by affinity chromatography. Melvin, W.T., Milne, H.B., Slater, A.A., Allen, H.J., Keir, H.M. Eur. J. Biochem. (1978) [Pubmed]
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