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Chemical Compound Review

AG-G-91589     5H-purin-6-amine

Synonyms: CTK5D8433, AC1L8V1K, 73663-96-4, 9H-Purin-6-amine,hydriodide (1:1), 1H-Purin-6-amine,monohydriodide (9CI)
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Disease relevance of adenine

  • The mechanism of DNA mismatch repair has been modeled upon biochemical studies of the E. coli DNA adenine methylation-instructed pathway where the initial recognition of mismatched nucleotides is performed by the MutS protein [1].
  • BRCA1 mutations are found in approximately 12 percent of women with breast cancer of early onset, and the specific mutation causing a deletion of adenine and guanine (185delAG), which is present in 1 percent of the Ashkenazi Jewish population, contributes to 21 percent of breast cancers among young Jewish women [2].
  • Several families have been described in which a mutation of mitochondrial DNA, the substitution of guanine for adenine (A-->G) at position 3243 of leucine transfer RNA, is associated with diabetes mellitus and deafness [3].
  • The product of the bacteriophage Mu gene mom modifies adenine residues of DNA within the consensus sequence CGAGCNPy, providing protection against various restriction endonucleases (ref. 1 and D. Kamp, personal communication cited in ref. 2). The mom gene is only expressed during lytic development of the phage [4].
  • Abnormal adenine metabolism of erythrocytes in Duchenne and myotonic muscular dystrophy [5].

Psychiatry related information on adenine


High impact information on adenine

  • We report that the wz mutation disrupts the gene Sil1 that encodes an adenine nucleotide exchange factor of BiP, a crucial ER chaperone [11].
  • Here we show that Sir2 can transfer labeled phosphate from nicotinamide adenine dinucleotide to itself and histones in vitro [12].
  • All the point mutations involved the substitution of adenine for guanine, but all were in different locations [13].
  • Adenine recognition is primarily mediated by contacts with conserved residues found in the RNP motifs of the two RRMs [14].
  • Crystal structures of complexes between the N-terminal domain of the yeast Hsp90 chaperone and ADP/ATP unambiguously identify a specific adenine nucleotide binding site homologous to the ATP-binding site of DNA gyrase B [15].

Chemical compound and disease context of adenine


Biological context of adenine


Anatomical context of adenine

  • We have now demonstrated that cultured aortic endothelial cells exposed to trypsin, thrombin or other stimuli can liberate a high proportion of their adenine nucleotides without substantial loss of lactate dehydrogenase [24].
  • Vascular endothelial and smooth muscle cells in culture selectively release adenine nucleotides [24].
  • Sarcoplasmic reticulum contains adenine nucleotide-activated calcium channels [25].
  • Induction of abnormal development and differentiation in cultured mammary glands by cyclic adenine nucleotide and prostaglandins [26].
  • The results suggest that the ribosome recognizes the codon-anticodon complex by adenine contacts to the messenger RNA backbone and provide a mechanism for molecular discrimination of correct versus incorrect codon-anticodon pairs [27].

Associations of adenine with other chemical compounds


Gene context of adenine

  • PHHI mutations have been informative on the function of SUR1 and regulation of KATP channels by adenine nucleotides [33].
  • DESIGN: DNA analysis for the IVS 4 + 4 A-->T (adenine to thymine) mutation in the FA complement C (FANCC) gene in single blastomeres, obtained by biopsy of embryos, to identify genetic status and HLA markers of each embryo before intrauterine transfer [34].
  • MSH2 and MSH6 are required for removal of adenine misincorporated opposite 8-oxo-guanine in S. cerevisiae [35].
  • The deduced amino acid sequence of cMOAT is 49% identical to that of the human multidrug resistance- associated protein (MRP) MRP1, and cMOAT and MRP1 are members of the same sub-family of adenine nucleotide binding cassette transporters [36].
  • Gene 69 is bracketed by the non-essential early gene dam (DNA adenine methylase) and the late gene soc (small outer capsid protein) [37].

Analytical, diagnostic and therapeutic context of adenine


  1. The human mismatch recognition complex hMSH2-hMSH6 functions as a novel molecular switch. Gradia, S., Acharya, S., Fishel, R. Cell (1997) [Pubmed]
  2. Differential contributions of BRCA1 and BRCA2 to early-onset breast cancer. Krainer, M., Silva-Arrieta, S., FitzGerald, M.G., Shimada, A., Ishioka, C., Kanamaru, R., MacDonald, D.J., Unsal, H., Finkelstein, D.M., Bowcock, A., Isselbacher, K.J., Haber, D.A. N. Engl. J. Med. (1997) [Pubmed]
  3. A subtype of diabetes mellitus associated with a mutation of mitochondrial DNA. Kadowaki, T., Kadowaki, H., Mori, Y., Tobe, K., Sakuta, R., Suzuki, Y., Tanabe, Y., Sakura, H., Awata, T., Goto, Y. N. Engl. J. Med. (1994) [Pubmed]
  4. Transcription initiation of Mu mom depends on methylation of the promoter region and a phage-coded transactivator. Plasterk, R.H., Vrieling, H., Van de Putte, P. Nature (1983) [Pubmed]
  5. Abnormal adenine metabolism of erythrocytes in Duchenne and myotonic muscular dystrophy. Solomons, C.C., Ringel, S.P., Nwuke, E.I., Suga, H. Nature (1977) [Pubmed]
  6. HPRT-APRT-deficient mice are not a model for lesch-nyhan syndrome. Engle, S.J., Womer, D.E., Davies, P.M., Boivin, G., Sahota, A., Simmonds, H.A., Stambrook, P.J., Tischfield, J.A. Hum. Mol. Genet. (1996) [Pubmed]
  7. Brain regional analysis of NADH-cytochrome C reductase activity in Alzheimer's disease. Zubenko, G.S., Moossy, J., Claassen, D., Martinez, A.J., Rao, G.R. J. Neuropathol. Exp. Neurol. (1990) [Pubmed]
  8. Association of mitochondrial complex I subunit gene NDUFV2 at 18p11 with bipolar disorder in Japanese and the National Institute of Mental Health pedigrees. Washizuka, S., Iwamoto, K., Kazuno, A.A., Kakiuchi, C., Mori, K., Kametani, M., Yamada, K., Kunugi, H., Tajima, O., Akiyama, T., Nanko, S., Yoshikawa, T., Kato, T. Biol. Psychiatry (2004) [Pubmed]
  9. In situ surface-enhanced infrared study of hydrogen bond pairing of complementary nucleic acid bases at the electrochemical interface. Sato, Y., Noda, H., Mizutani, F., Yamakata, A., Osawa, M. Anal. Chem. (2004) [Pubmed]
  10. Sparing of cholinergic neurons following quinolinic acid lesions of the rat striatum. Davies, S.W., Roberts, P.J. Neuroscience (1988) [Pubmed]
  11. Protein accumulation and neurodegeneration in the woozy mutant mouse is caused by disruption of SIL1, a cochaperone of BiP. Zhao, L., Longo-Guess, C., Harris, B.S., Lee, J.W., Ackerman, S.L. Nat. Genet. (2005) [Pubmed]
  12. An enzymatic activity in the yeast Sir2 protein that is essential for gene silencing. Tanny, J.C., Dowd, G.J., Huang, J., Hilz, H., Moazed, D. Cell (1999) [Pubmed]
  13. Exercise intolerance due to mutations in the cytochrome b gene of mitochondrial DNA. Andreu, A.L., Hanna, M.G., Reichmann, H., Bruno, C., Penn, A.S., Tanji, K., Pallotti, F., Iwata, S., Bonilla, E., Lach, B., Morgan-Hughes, J., DiMauro, S. N. Engl. J. Med. (1999) [Pubmed]
  14. Recognition of polyadenylate RNA by the poly(A)-binding protein. Deo, R.C., Bonanno, J.B., Sonenberg, N., Burley, S.K. Cell (1999) [Pubmed]
  15. Identification and structural characterization of the ATP/ADP-binding site in the Hsp90 molecular chaperone. Prodromou, C., Roe, S.M., O'Brien, R., Ladbury, J.E., Piper, P.W., Pearl, L.H. Cell (1997) [Pubmed]
  16. Inhibitory action of gossypol on enzymes and growth of Trypanosoma cruzi. Montamat, E.E., Burgos, C., Gerez de Burgos, N.M., Rovai, L.E., Blanco, A., Segura, E.L. Science (1982) [Pubmed]
  17. Allopurinol enhanced adenine nucleotide repletion after myocardial ischemia in the isolated rat heart. Lasley, R.D., Ely, S.W., Berne, R.M., Mentzer, R.M. J. Clin. Invest. (1988) [Pubmed]
  18. Fulminant hepatitis B: induction by hepatitis B virus mutants defective in the precore region and incapable of encoding e antigen. Kosaka, Y., Takase, K., Kojima, M., Shimizu, M., Inoue, K., Yoshiba, M., Tanaka, S., Akahane, Y., Okamoto, H., Tsuda, F. Gastroenterology (1991) [Pubmed]
  19. Base changes at position 792 of Escherichia coli 16S rRNA affect assembly of 70S ribosomes. Santer, M., Bennett-Guerrero, E., Byahatti, S., Czarnecki, S., O'Connell, D., Meyer, M., Khoury, J., Cheng, X., Schwartz, I., McLaughlin, J. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  20. Crystal structure of cryptochrome 3 from Arabidopsis thaliana and its implications for photolyase activity. Huang, Y., Baxter, R., Smith, B.S., Partch, C.L., Colbert, C.L., Deisenhofer, J. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  21. IS10 transposition is regulated by DNA adenine methylation. Roberts, D., Hoopes, B.C., McClure, W.R., Kleckner, N. Cell (1985) [Pubmed]
  22. Complete deficiency of adenine phosphoribosyltransferase. Report of a family. Van Acker, K.J., Simmonds, H.A., Potter, C., Cameron, J.S. N. Engl. J. Med. (1977) [Pubmed]
  23. Structure of an adenine-cytosine base pair in DNA and its implications for mismatch repair. Hunter, W.N., Brown, T., Anand, N.N., Kennard, O. Nature (1986) [Pubmed]
  24. Vascular endothelial and smooth muscle cells in culture selectively release adenine nucleotides. Pearson, J.D., Gordon, J.L. Nature (1979) [Pubmed]
  25. Sarcoplasmic reticulum contains adenine nucleotide-activated calcium channels. Smith, J.S., Coronado, R., Meissner, G. Nature (1985) [Pubmed]
  26. Induction of abnormal development and differentiation in cultured mammary glands by cyclic adenine nucleotide and prostaglandins. Schaefer, F.V., Custer, R.P., Sorof, S. Nature (1980) [Pubmed]
  27. Recognition of the codon-anticodon helix by ribosomal RNA. Yoshizawa, S., Fourmy, D., Puglisi, J.D. Science (1999) [Pubmed]
  28. The association of atopy with a gain-of-function mutation in the alpha subunit of the interleukin-4 receptor. Hershey, G.K., Friedrich, M.F., Esswein, L.A., Thomas, M.L., Chatila, T.A. N. Engl. J. Med. (1997) [Pubmed]
  29. Arsenical-resistant trypanosomes lack an unusual adenosine transporter. Carter, N.S., Fairlamb, A.H. Nature (1993) [Pubmed]
  30. The voltage dependence of NADPH oxidase reveals why phagocytes need proton channels. DeCoursey, T.E., Morgan, D., Cherny, V.V. Nature (2003) [Pubmed]
  31. The complete nucleotide sequence of chromosome 3 of Plasmodium falciparum. Bowman, S., Lawson, D., Basham, D., Brown, D., Chillingworth, T., Churcher, C.M., Craig, A., Davies, R.M., Devlin, K., Feltwell, T., Gentles, S., Gwilliam, R., Hamlin, N., Harris, D., Holroyd, S., Hornsby, T., Horrocks, P., Jagels, K., Jassal, B., Kyes, S., McLean, J., Moule, S., Mungall, K., Murphy, L., Oliver, K., Quail, M.A., Rajandream, M.A., Rutter, S., Skelton, J., Squares, R., Squares, S., Sulston, J.E., Whitehead, S., Woodward, J.R., Newbold, C., Barrell, B.G. Nature (1999) [Pubmed]
  32. Post-mortem changes implicate adenine nucleotides and pyridoxal-5' -phosphate in regulation of brain glutamate decarboxylase. Miller, L.P., Walters, J.R., Martin, D.L. Nature (1977) [Pubmed]
  33. Molecular biology of adenosine triphosphate-sensitive potassium channels. Aguilar-Bryan, L., Bryan, J. Endocr. Rev. (1999) [Pubmed]
  34. Preimplantation diagnosis for Fanconi anemia combined with HLA matching. Verlinsky, Y., Rechitsky, S., Schoolcraft, W., Strom, C., Kuliev, A. JAMA (2001) [Pubmed]
  35. MSH2 and MSH6 are required for removal of adenine misincorporated opposite 8-oxo-guanine in S. cerevisiae. Ni, T.T., Marsischky, G.T., Kolodner, R.D. Mol. Cell (1999) [Pubmed]
  36. Drug export activity of the human canalicular multispecific organic anion transporter in polarized kidney MDCK cells expressing cMOAT (MRP2) cDNA. Evers, R., Kool, M., van Deemter, L., Janssen, H., Calafat, J., Oomen, L.C., Paulusma, C.C., Oude Elferink, R.P., Baas, F., Schinkel, A.H., Borst, P. J. Clin. Invest. (1998) [Pubmed]
  37. Regulation of a new bacteriophage T4 gene, 69, that spans an origin of DNA replication. Macdonald, P.M., Mosig, G. EMBO J. (1984) [Pubmed]
  38. Reduction of the isoproterenol-induced alterations in cardiac adenine nucleotides and morphology by ribose. Zimmer, H.G., Ibel, H., Steinkopff, G., Korb, G. Science (1980) [Pubmed]
  39. Purine salvage networks in Giardia lamblia. Wang, C.C., Aldritt, S. J. Exp. Med. (1983) [Pubmed]
  40. Adhalin gene mutations in patients with autosomal recessive childhood onset muscular dystrophy with adhalin deficiency. Kawai, H., Akaike, M., Endo, T., Adachi, K., Inui, T., Mitsui, T., Kashiwagi, S., Fujiwara, T., Okuno, S., Shin, S. J. Clin. Invest. (1995) [Pubmed]
  41. Adenosine deaminase deficiency: disappearance of adenine deoxynucleotides from a patient's erythrocytes after successful marrow transplantation. Chen, S.H., Ochs, H.D., Scott, C.R., Giblett, E.R., Tingle, A.J. J. Clin. Invest. (1978) [Pubmed]
  42. Mechanisms of lymphocytotoxicity induced by extracorporeal photochemotherapy for cutaneous T cell lymphoma. Marks, D.I., Rockman, S.P., Oziemski, M.A., Fox, R.M. J. Clin. Invest. (1990) [Pubmed]
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