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Chemical Compound Review

AC1L8XSI     5H-purin-2-amine

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Disease relevance of 2-aminopurine

  • The mechanism of isomerization (basepair openings) during transcription initiation by RNA polymerase at the galP1 promoter of Escherichia coli was investigated by 2-aminopurine (2,AP) fluorescence [1].
  • We measured the in vivo incorporation of 2-aminopurine into DNA of T4 bacteriophage allelic for gene 43 (DNA polymerase), mutator (L56), 43+, and antimutator (L141) [2].
  • In this report we demonstrate that the shut-off of cellular protein synthesis by adenovirus is prevented in cells by treatment with the drug 2-aminopurine [3].
  • Detergent-treated lymphocyte nuclei undergoing a high level of EBV DNA synthesis were shown to incorporate the 2-aminopurine analog of dATP into viral DNA [4].
  • We find that treatment of mouse hepatoma Hepa-1 cells with 2-aminopurine, an inhibitor of protein kinase activity, inhibits CYP1A1 mRNA induction by TCDD as well as the concomitant increase in CYP1A1 enzyme activity [5].

High impact information on 2-aminopurine

  • 2-Aminopurine selectively inhibits the induction of beta-interferon, c-fos, and c-myc gene expression [6].
  • When this element, designated 2-APRE, is present, splicing becomes sensitive to inhibition by the PKR inhibitor, 2-aminopurine, or by coexpression of transdominant-negative mutant PKR [7].
  • In addition, the inhibition of IL-2-R-induced c-myb expression by 2-aminopurine and enhanced induction of c-myb via the TCR demonstrate that TCR activation and IL-2-R activation lead to induction of c-myb by different mechanisms [8].
  • Inhibition of PKR phosphorylation by 2-aminopurine, or deletion of the Pkr gene, led to drastic enhancement of reovirus protein synthesis in untransformed cells [9].
  • Here we show that inhibition of an early G1-phase protein kinase pathway by the addition of 2-aminopurine (2-AP) prior to the ODP arrests CHO cells in G1-phase [10].

Chemical compound and disease context of 2-aminopurine


Biological context of 2-aminopurine

  • AB formation is prevented by activation of protein kinase C by phorbol ester or by treatment with the kinase inhibitor 2-aminopurine, without any detectable effect on tyrosine phosphorylation [15].
  • 2-aminopurine override of G2 arrest imposed by VM-26 or ICRF-193, which inhibit topoisomerase II (topo II)-dependent DNA decatenation, results in the activation of p34cdc2 kinase and entry into mitosis [16].
  • These findings imply that both phorbol esters and 2-aminopurine operate, at least in part, at the level of alternative pathways that may diverge upstream of the MAP kinase and are presumably mediating the early effects of v-Src on the differentiated phenotype [15].
  • In addition, the signal transduction cascade that culminates in MAP kinase activation and its nuclear translocation is activated both by v-Src and phorbol ester, and is relatively unaffected by 2-aminopurine [15].
  • To determine the basis for this discrepancy in the correlation between carcinogenesis and mutagenesis, the ability of 2-aminopurine to induce somatic mutation and neoplastic transformation concomitantly in the same cellular system was examined [17].

Anatomical context of 2-aminopurine

  • The protein kinase inhibitor 2-aminopurine induces checkpoint override and mitotic exit in BHK cells which have been arrested in mitosis by inhibitors of microtubule function (Andreassen, P. R., and R. L. Margolis. 1991. J. Cell Sci. 100:299-310) [18].
  • In human and mouse cell lines, expression of exogenous genes was enhanced by treatment with 2-aminopurine (2-AP) [19].
  • The PKR inhibitor 2-aminopurine (2-AP) inhibited TNF-alpha/IFN-gamma-induced NF-kappaB nuclear translocation in neuronal derived cells but not in endothelial cells [20].
  • 2-Aminopurine induces spindle cell morphology in MM14 myoblasts in the absence of differentiation signals [21].
  • When HeLa cells were infected with R2-2A-2 in the presence of 2-aminopurine, a protein kinase inhibitor, much higher virus titers were produced, cleavage of p220 occurred, and host cell protein synthesis was specifically inhibited [22].

Associations of 2-aminopurine with other chemical compounds


Gene context of 2-aminopurine


Analytical, diagnostic and therapeutic context of 2-aminopurine


  1. Asynchronous basepair openings in transcription initiation: CRP enhances the rate-limiting step. Roy, S., Lim, H.M., Liu, M., Adhya, S. EMBO J. (2004) [Pubmed]
  2. 2-Aminopurine-induced mutagenesis in T4 bacteriophage: a model relating mutation frequency to 2-aminopurine incorporation in DNA. Goodman, M.F., Hopkins, R., Gore, W.C. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  3. Adenovirus inhibition of cellular protein synthesis is prevented by the drug 2-aminopurine. Huang, J.T., Schneider, R.J. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  4. Incorporation into DNA of the base analog 2-aminopurine by the Epstein-Barr virus-induced DNA polymerase in vivo and in vitro. Grossberger, D., Clough, W. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  5. Dioxin-dependent activation of murine Cyp1a-1 gene transcription requires protein kinase C-dependent phosphorylation. Carrier, F., Owens, R.A., Nebert, D.W., Puga, A. Mol. Cell. Biol. (1992) [Pubmed]
  6. 2-Aminopurine selectively inhibits the induction of beta-interferon, c-fos, and c-myc gene expression. Zinn, K., Keller, A., Whittemore, L.A., Maniatis, T. Science (1988) [Pubmed]
  7. A cis-acting element in the 3'-untranslated region of human TNF-alpha mRNA renders splicing dependent on the activation of protein kinase PKR. Osman, F., Jarrous, N., Ben-Asouli, Y., Kaempfer, R. Genes Dev. (1999) [Pubmed]
  8. Regulation of T lymphocyte proliferation. Interleukin 2-mediated induction of c-myb gene expression is dependent on T lymphocyte activation state. Churilla, A.M., Braciale, T.J., Braciale, V.L. J. Exp. Med. (1989) [Pubmed]
  9. The molecular basis of viral oncolysis: usurpation of the Ras signaling pathway by reovirus. Strong, J.E., Coffey, M.C., Tang, D., Sabinin, P., Lee, P.W. EMBO J. (1998) [Pubmed]
  10. Transformation abrogates an early G1-phase arrest point required for specification of the Chinese hamster DHFR replication origin. Wu, J.R., Keezer, S.M., Gilbert, D.M. EMBO J. (1998) [Pubmed]
  11. Ribonucleoside and deoxyribonucleoside triphosphate pools during 2-aminopurine mutagenesis in T4 mutator-, wild type-, and antimutator-infected Escherichia coli. Hopkins, R.L., Goodman, M.F. J. Biol. Chem. (1985) [Pubmed]
  12. Fluorescence-based approach for detecting and characterizing antibiotic-induced conformational changes in ribosomal RNA: comparing aminoglycoside binding to prokaryotic and eukaryotic ribosomal RNA sequences. Kaul, M., Barbieri, C.M., Pilch, D.S. J. Am. Chem. Soc. (2004) [Pubmed]
  13. Marker effects on reversion of T4rII mutants. Ronen, A., Rahat, A., Halevy, C. Genetics (1976) [Pubmed]
  14. Ligand-mediated anticodon conformational changes occur during tRNA methylation by a TrmD methyltransferase. Watts, J.M., Gabruzsk, J., Holmes, W.M. Biochemistry (2005) [Pubmed]
  15. Maintenance of the differentiated state in skeletal muscle: activation of v-Src disrupts sarcomeres in quail myotubes. Castellani, L., Reedy, M.C., Gauzzi, M.C., Provenzano, C., Alemà, S., Falcone, G. J. Cell Biol. (1995) [Pubmed]
  16. Chromosomes with two intact axial cores are induced by G2 checkpoint override: evidence that DNA decatenation is not required to template the chromosome structure. Andreassen, P.R., Lacroix, F.B., Margolis, R.L. J. Cell Biol. (1997) [Pubmed]
  17. Induction of gene mutation in and cell transformation of mammalian cells by modified purines: 2-aminopurine and 6-N-hydroxylaminopurine. Barrett, J.C. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  18. Microtubule dependency of p34cdc2 inactivation and mitotic exit in mammalian cells. Andreassen, P.R., Margolis, R.L. J. Cell Biol. (1994) [Pubmed]
  19. Enhancement of expression of exogenous genes by 2-aminopurine. Regulation at the post-transcriptional level. Kalvakolanu, D.V., Bandyopadhyay, S.K., Tiwari, R.K., Sen, G.C. J. Biol. Chem. (1991) [Pubmed]
  20. Involvement of double-stranded RNA-activated protein kinase in the synergistic activation of nuclear factor-kappaB by tumor necrosis factor-alpha and gamma-interferon in preneuronal cells. Cheshire, J.L., Williams, B.R., Baldwin, A.S. J. Biol. Chem. (1999) [Pubmed]
  21. 2-Aminopurine induces spindle cell morphology in MM14 myoblasts in the absence of differentiation signals. Palmer, D.K., Angello, J.C., Margolis, R.L. Exp. Cell Res. (1997) [Pubmed]
  22. Inhibition of translation in cells infected with a poliovirus 2Apro mutant correlates with phosphorylation of the alpha subunit of eucaryotic initiation factor 2. O'Neill, R.E., Racaniello, V.R. J. Virol. (1989) [Pubmed]
  23. Adenine and 2-aminopurine: paradigms of modern theoretical photochemistry. Serrano-Andrés, L., Merchán, M., Borin, A.C. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  24. Chemically induced premature mitosis: differential response in rodent and human cells and the relationship to cyclin B synthesis and p34cdc2/cyclin B complex formation. Steinmann, K.E., Belinsky, G.S., Lee, D., Schlegel, R. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  25. Gadd45 and Gadd153 messenger RNA levels are increased during hypoxia and after exposure of cells to agents which elevate the levels of the glucose-regulated proteins. Price, B.D., Calderwood, S.K. Cancer Res. (1992) [Pubmed]
  26. Adenoviral transfer of the melanoma differentiation-associated gene 7 (mda7) induces apoptosis of lung cancer cells via up-regulation of the double-stranded RNA-dependent protein kinase (PKR). Pataer, A., Vorburger, S.A., Barber, G.N., Chada, S., Mhashilkar, A.M., Zou-Yang, H., Stewart, A.L., Balachandran, S., Roth, J.A., Hunt, K.K., Swisher, S.G. Cancer Res. (2002) [Pubmed]
  27. The Fanconi anemia proteins functionally interact with the protein kinase regulated by RNA (PKR). Zhang, X., Li, J., Sejas, D.P., Rathbun, K.R., Bagby, G.C., Pang, Q. J. Biol. Chem. (2004) [Pubmed]
  28. Peroxisome proliferator-activated receptor gamma-independent activation of p38 MAPK by thiazolidinediones involves calcium/calmodulin-dependent protein kinase II and protein kinase R: correlation with endoplasmic reticulum stress. Gardner, O.S., Shiau, C.W., Chen, C.S., Graves, L.M. J. Biol. Chem. (2005) [Pubmed]
  29. Protein kinase R (PKR) interacts with and activates mitogen-activated protein kinase kinase 6 (MKK6) in response to double-stranded RNA stimulation. Silva, A.M., Whitmore, M., Xu, Z., Jiang, Z., Li, X., Williams, B.R. J. Biol. Chem. (2004) [Pubmed]
  30. 2-Aminopurine abolishes epidermal growth factor-stimulated phosphorylation of complexed and chromatin-associated forms of a 33 kDa phosphoprotein. Mahadevan, L.C., Targett, K., Heath, J.K. Oncogene (1989) [Pubmed]
  31. Low-energy circular dichroism of 2-aminopurine dinucleotide as a probe of local conformation of DNA and RNA. Johnson, N.P., Baase, W.A., Von Hippel, P.H. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  32. Functional roles of the conserved threonine 250 in the target recognition domain of HhaI DNA methyltransferase. Vilkaitis, G., Dong, A., Weinhold, E., Cheng, X., Klimasauskas, S. J. Biol. Chem. (2000) [Pubmed]
  33. Presteady-state analysis of a single catalytic turnover by Escherichia coli uracil-DNA glycosylase reveals a "pinch-pull-push" mechanism. Wong, I., Lundquist, A.J., Bernards, A.S., Mosbaugh, D.W. J. Biol. Chem. (2002) [Pubmed]
  34. The mouse antiphosphotyrosine immunoreactive kinase, TIK, is indistinguishable from the double-stranded RNA-dependent, interferon-induced protein kinase, PKR. Baier, L.J., Shors, T., Shors, S.T., Jacobs, B.L. Nucleic Acids Res. (1993) [Pubmed]
  35. Requirement of p38 stress-activated MAP kinase for cell death in the developing retina depends on the stage of cell differentiation. Campos, C.B., Bédard, P.A., Linden, R. Neurochem. Int. (2006) [Pubmed]
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