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Chemical Compound Review

METHYLTHIOINOSINE     (2R,3S,4R,5R)-2- (hydroxymethyl)-5-(6...

Synonyms: MMPR, Me6MPR, CHEMBL388931, SureCN672035, NCI-C04784, ...
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Disease relevance of METHYLTHIOINOSINE


High impact information on METHYLTHIOINOSINE


Chemical compound and disease context of METHYLTHIOINOSINE

  • Thus, 6-MMPR, which blocks the de novo pathway of purine nucleotide biosynthesis, caused a pronounced decrease in the intracellular pools of GTP in Sarcoma 180 cells; this phenomenon was accompanied by a marked reduction in the incorporation of radiolabelled mannose into cellular glycoproteins and their dolichol-linked oligosaccharide precursors [2].
  • Four sulphur-containing purine nucleoside analogues: 6MP, 6-thioinosine, 6-methylthioinosine and 6-ethylthioinosine, were examined for antiviral activity against some RNA viruses [8].

Biological context of METHYLTHIOINOSINE


Anatomical context of METHYLTHIOINOSINE


Associations of METHYLTHIOINOSINE with other chemical compounds



  • This study examined thiopurine methyltransferase (TPMT) and the relationship to thioguanine nucleotides (TGN) and methylthioinosine monophosphate (meTIMP) in a large Swedish patient population [16].
  • Metabolites of 6-TG included thio-XMP, thio-GMP, thio-GDP and thio-GTP, while MMPR-MP was the only major metabolite of MMPR, MMPR (25 microM, 4 h) induced a 16-fold increase in P-Rib-PP and 6-MP (25 microM, 4 h) induced a delayed 5.2-fold increase [9].

Analytical, diagnostic and therapeutic context of METHYLTHIOINOSINE

  • An isocratic reversed-phase high-performance liquid chromatographic (HPLC) method for the determination of methylmercaptopurine riboside (MMPR) in human plasma and urine is reported [17].


  1. Purine analogue 6-methylmercaptopurine riboside inhibits early and late phases of the angiogenesis process. Presta, M., Rusnati, M., Belleri, M., Morbidelli, L., Ziche, M., Ribatti, D. Cancer Res. (1999) [Pubmed]
  2. Inhibition of mannose incorporation into glycoproteins and dolichol-linked intermediates of Sarcoma 180 cells by 6-methylmercaptopurine ribonucleoside. Sokoloski, J.A., Sartorelli, A.C. Int. J. Cancer (1987) [Pubmed]
  3. Phase II trial of PALA and 6-methylmercaptopurine riboside (MMPR) in combination with 5-fluorouracil in advanced pancreatic cancer. Redei, I., Green, F., Hoffman, J.P., Weiner, L.M., Scher, R., O'Dwyer, P.J. Investigational new drugs. (1994) [Pubmed]
  4. Feedback inhibition by 6-methylthioinosine 3',5'-cyclic monophosphate in tumor cells resistant to the nucleoside. Epps, D., Chang, I.M., Sherwood, E., Kimball, A.P. Proc. Soc. Exp. Biol. Med. (1975) [Pubmed]
  5. Apoptosis induced in advanced CD8F1-murine mammary tumors by the combination of PALA, MMPR and 6AN precedes tumor regression and is preceded by ATP depletion. Nord, L.D., Stolfi, R.L., Alfieri, A.A., Netto, G., Reuter, V., Sternberg, S.S., Colofiore, J.R., Koutcher, J.A., Martin, D.S. Cancer Chemother. Pharmacol. (1997) [Pubmed]
  6. Stimulation of tyrosine aminotransferase degradation by methylthioinosine. Koontz, J.W., Wicks, W.D. J. Biol. Chem. (1984) [Pubmed]
  7. 6-Methylmercaptopurine riboside is a potent and selective inhibitor of nerve growth factor-activated protein kinase N. Volonté, C., Greene, L.A. J. Neurochem. (1992) [Pubmed]
  8. Inhibitory effect of sulphur-containing purine nucleoside analogues on replication of RNA viruses: selective antiviral activity against influenza viruses. Yamamoto, K., Hasobe, M., Saneyoshi, M. Acta Virol. (1988) [Pubmed]
  9. Metabolic effects of thiopurine derivatives against human CCRF-CEM leukaemia cells. Shi, R.Z., Lyons, S.D., Christopherson, R.I. Int. J. Biochem. Cell Biol. (1998) [Pubmed]
  10. Effects on transmethylation by high-dose 6-mercaptopurine and methotrexate infusions during consolidation treatment of acute lymphoblastic leukemia. Keuzenkamp-Jansen, C.W., De Abreu, R.A., Blom, H.J., Bökkerink, J.P., Trijbels, J.M. Biochem. Pharmacol. (1996) [Pubmed]
  11. Induction of meiotic maturation in mouse oocytes by adenosine analogs. Downs, S.M., Chen, J. Mol. Reprod. Dev. (2006) [Pubmed]
  12. Thiopurine methyltransferase: a review and a clinical pilot study. Keuzenkamp-Jansen, C.W., Leegwater, P.A., De Abreu, R.A., Lambooy, M.A., Bokkerink, J.P., Trijbels, J.M. J. Chromatogr. B, Biomed. Appl. (1996) [Pubmed]
  13. Superactivity of human phosphoribosyl pyrophosphate synthetase due to altered regulation by nucleotide inhibitors and inorganic phosphate. Becker, M.A., Losman, M.J., Wilson, J., Simmonds, H.A. Biochim. Biophys. Acta (1986) [Pubmed]
  14. Uptake and metabolism of adenosine mediate a meiosis-arresting action on mouse oocytes. Downs, S.M. Mol. Reprod. Dev. (1999) [Pubmed]
  15. Differences between children and adults in thiopurine methyltransferase activity and metabolite formation during thiopurine therapy: possible role of concomitant methotrexate. Pettersson, B., Almer, S., Albertioni, F., Söderhäll, S., Peterson, C. Therapeutic drug monitoring. (2002) [Pubmed]
  16. Assessment of thiopurine methyltransferase and metabolite formation during thiopurine therapy: results from a large Swedish patient population. Hindorf, U., Peterson, C., Almer, S. Therapeutic drug monitoring. (2004) [Pubmed]
  17. Chromatographic analysis of methylmercaptopurine riboside in human plasma and urine. Tinsley, P.W., O'Dwyer, P.J., LaCreta, F.P. J. Chromatogr. (1991) [Pubmed]
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