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Chemical Compound Review

Leucenol     2-amino-3-(3-hydroxy-4-oxo- pyridin-1...

Synonyms: Lecenine, Mimosine, DL-Mimosine, Prestwick_830, SureCN41924, ...
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Disease relevance of Leucaenine

  • We applied this protocol to study the effect of the plant amino acid mimosine on the rate of replicon initiation in exponentially growing murine erythroleukemia F4N cells [1].
  • However, mimosine does not influence folate metabolism in SH-SY5Y neuroblastoma [2].
  • Our results demonstrated that mimosine inhibits DNA synthesis in mitochondrial, nuclear, and simian virus 40 (SV40) genomes to a similar extent [3].
  • Agents that produced double-strand breaks in DNA and/or inhibition of transcription caused an induction of p53 in the absence of radiation in control cells but not in ataxia-telangiectasia, but inhibitors of cell cycle progression such as mimosine and aphidicolin led to an increase in p53 in both cell types in the absence of radiation [4].
  • Mimosine-treated neural precursor cells injected into established intracerebral CNS-1 gliomas in nude mice migrated extensively throughout the tumor and into the surrounding parenchyma beyond the tumor over 3 days [5].

High impact information on Leucaenine

  • L-Mimosine suppressed the posttranslational hydroxylation of the precursors for collagen and for eukaryotic initiation factor-5A (eIF-5A) by directly inhibiting the specific protein hydroxylases involved, prolyl 4-hydroxylase (E.C. and deoxyhypusyl hydroxylase (E.C., respectively [6].
  • Cells that have escaped from mimosine G1 arrest, from hydroxyurea or aphidicolin S-phase arrest, or from VM-26-induced G2 arrest subsequently have all the hallmarks of mitosis--such as a mitotic microtubule array, nuclear envelope breakdown, and chromatin condensation [7].
  • Here we demonstrate that G(1)/S arrest by overexpression of the cyclin-dependent kinase inhibitors p16(INK4a), p21(Cip1), or p27(Kip1) or by treatment with mimosine or aphidicolin confers anoikis resistance in MCF-10A cells [8].
  • Unexpectedly, UVC treatment was also found to block the induction of p21Waf1 by various stress-inducing agents such as mimosine in the p53-deficient cells [9].
  • Mimosine, however, enhanced p21(Waf1/Cip1) expression, completely inhibited RKO cell proliferation, and exerted marked protection against a subsequent PGA2 challenge [10].

Chemical compound and disease context of Leucaenine

  • The effects of mimosine on folate metabolism were investigated in human MCF-7 cells and SH-SY5Y neuroblastoma [2].
  • pyd genes of Rhizobium sp. strain TAL1145 are required for degradation of 3-hydroxy-4-pyridone, an aromatic intermediate in mimosine metabolism [11].
  • We now report that the alpha-hydroxypyridones, specifically mimosine, a natural product, and deferiprone, an experimental drug, inhibited deoxyhypusyl hydroxylase in T-lymphocytic and promonocytic cell lines and, in a concentration-dependent manner, suppressed replication of HIV-1 [12].
  • In this study, we compared the effects of mimosine to desferrioxamine (DFO), a well-characterized iron chelator, and found that both chemicals similarly altered cell cycle progression in MDA-MB-453 human breast cancer cells [13].
  • The intraperitoneal administration of L-mimosine (200 microg/dose) to the potassium permanganate treated mice for 5 consecutive days (the first at the same time of inoculation of the KMnO4), produced a significant decrease in size and weight of the granuloma when compared to mice not treated with L-mimosine (controls) [14].

Biological context of Leucaenine


Anatomical context of Leucaenine


Associations of Leucaenine with other chemical compounds


Gene context of Leucaenine


Analytical, diagnostic and therapeutic context of Leucaenine


  1. Effect of mimosine on DNA synthesis in mammalian cells. Tsvetkov, L.M., Russev, G.C., Anachkova, B.B. Cancer Res. (1997) [Pubmed]
  2. Mimosine is a cell-specific antagonist of folate metabolism. Oppenheim, E.W., Nasrallah, I.M., Mastri, M.G., Stover, P.J. J. Biol. Chem. (2000) [Pubmed]
  3. Mimosine arrests DNA synthesis at replication forks by inhibiting deoxyribonucleotide metabolism. Gilbert, D.M., Neilson, A., Miyazawa, H., DePamphilis, M.L., Burhans, W.C. J. Biol. Chem. (1995) [Pubmed]
  4. Ionizing radiation and UV induction of p53 protein by different pathways in ataxia-telangiectasia cells. Khanna, K.K., Lavin, M.F. Oncogene (1993) [Pubmed]
  5. Neural precursor cells for delivery of replication-conditional HSV-1 vectors to intracerebral gliomas. Herrlinger, U., Woiciechowski, C., Sena-Esteves, M., Aboody, K.S., Jacobs, A.H., Rainov, N.G., Snyder, E.Y., Breakefield, X.O. Mol. Ther. (2000) [Pubmed]
  6. Specific inhibition of eIF-5A and collagen hydroxylation by a single agent. Antiproliferative and fibrosuppressive effects on smooth muscle cells from human coronary arteries. McCaffrey, T.A., Pomerantz, K.B., Sanborn, T.A., Spokojny, A.M., Du, B., Park, M.H., Folk, J.E., Lamberg, A., Kivirikko, K.I., Falcone, D.J. J. Clin. Invest. (1995) [Pubmed]
  7. 2-Aminopurine overrides multiple cell cycle checkpoints in BHK cells. Andreassen, P.R., Margolis, R.L. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  8. G1/S cell cycle arrest provides anoikis resistance through Erk-mediated Bim suppression. Collins, N.L., Reginato, M.J., Paulus, J.K., Sgroi, D.C., Labaer, J., Brugge, J.S. Mol. Cell. Biol. (2005) [Pubmed]
  9. p53-dependent elevation of p21Waf1 expression by UV light is mediated through mRNA stabilization and involves a vanadate-sensitive regulatory system. Gorospe, M., Wang, X., Holbrook, N.J. Mol. Cell. Biol. (1998) [Pubmed]
  10. Protective role of p21(Waf1/Cip1) against prostaglandin A2-mediated apoptosis of human colorectal carcinoma cells. Gorospe, M., Wang, X., Guyton, K.Z., Holbrook, N.J. Mol. Cell. Biol. (1996) [Pubmed]
  11. pyd genes of Rhizobium sp. strain TAL1145 are required for degradation of 3-hydroxy-4-pyridone, an aromatic intermediate in mimosine metabolism. Awaya, J.D., Fox, P.M., Borthakur, D. J. Bacteriol. (2005) [Pubmed]
  12. Antiretroviral effects of deoxyhypusyl hydroxylase inhibitors: a hypusine-dependent host cell mechanism for replication of human immunodeficiency virus type 1 (HIV-1). Andrus, L., Szabo, P., Grady, R.W., Hanauske, A.R., Huima-Byron, T., Slowinska, B., Zagulska, S., Hanauske-Abel, H.M. Biochem. Pharmacol. (1998) [Pubmed]
  13. Mimosine blocks cell cycle progression by chelating iron in asynchronous human breast cancer cells. Kulp, K.S., Vulliet, P.R. Toxicol. Appl. Pharmacol. (1996) [Pubmed]
  14. Effect of the compound L-mimosine in an in vivo model of chronic granuloma formation induced by potassium permanganate (KMNO4). Frydas, S., Papazahariadou, M., Papaioannou, N., Hatzistilianou, M., Trakatellis, M., Merlitti, D., Di Gioacchino, M., Grilli, A., DeLutiis, M.A., Riccioni, G., Conti, P., Vlemmas, I. International journal of immunopathology and pharmacology. (2003) [Pubmed]
  15. The plant amino acid mimosine may inhibit initiation at origins of replication in Chinese hamster cells. Mosca, P.J., Dijkwel, P.A., Hamlin, J.L. Mol. Cell. Biol. (1992) [Pubmed]
  16. Initiation of DNA replication in the dihydrofolate reductase locus is confined to the early S period in CHO cells synchronized with the plant amino acid mimosine. Dijkwel, P.A., Hamlin, J.L. Mol. Cell. Biol. (1992) [Pubmed]
  17. Negative regulation of histone H1 kinase expression by mimosine, a plant amino acid. Feldman, S.T., Schönthal, A. Cancer Res. (1994) [Pubmed]
  18. Internucleosomal DNA fragmentation is not obligatory for castration induced rat ventral prostate cell apoptosis in vivo. Zhang, X., Decarli, A.J., Buttyan, R. Cell Death Differ. (1997) [Pubmed]
  19. Dissociation of p34cdc2 complex formation from phosphorylation and histone H1 kinase activity. Eblen, S.T., Fautsch, M.P., Burnette, R.J., Snyder, M., Leof, E.B. Cancer Res. (1995) [Pubmed]
  20. Mimosine attenuates serine hydroxymethyltransferase transcription by chelating zinc. Implications for inhibition of DNA replication. Perry, C., Sastry, R., Nasrallah, I.M., Stover, P.J. J. Biol. Chem. (2005) [Pubmed]
  21. Initiation of human DNA replication in vitro using nuclei from cells arrested at an initiation-competent state. Krude, T. J. Biol. Chem. (2000) [Pubmed]
  22. Cyclin-dependent kinase 2 (Cdk2) is required for centrosome duplication in mammalian cells. Matsumoto, Y., Hayashi, K., Nishida, E. Curr. Biol. (1999) [Pubmed]
  23. Inhibition of cyclin D1 expression and phosphorylation of retinoblastoma protein by phosmidosine, a nucleotide antibiotic. Kakeya, H., Onose, R., Liu, P.C., Onozawa, C., Matsumura, F., Osada, H. Cancer Res. (1998) [Pubmed]
  24. Quercetin arrests human leukemic T-cells in late G1 phase of the cell cycle. Yoshida, M., Yamamoto, M., Nikaido, T. Cancer Res. (1992) [Pubmed]
  25. Mimosine targets serine hydroxymethyltransferase. Lin, H.B., Falchetto, R., Mosca, P.J., Shabanowitz, J., Hunt, D.F., Hamlin, J.L. J. Biol. Chem. (1996) [Pubmed]
  26. AML1/RUNX1 increases during G1 to S cell cycle progression independent of cytokine-dependent phosphorylation and induces cyclin D3 gene expression. Bernardin-Fried, F., Kummalue, T., Leijen, S., Collector, M.I., Ravid, K., Friedman, A.D. J. Biol. Chem. (2004) [Pubmed]
  27. Induction and bypass of p53 during productive infection by polyomavirus. Dey, D., Dahl, J., Cho, S., Benjamin, T.L. J. Virol. (2002) [Pubmed]
  28. p21WAF1/CIP1/SDI1 is elevated through a p53-independent pathway by mimosine. Alpan, R.S., Pardee, A.B. Cell Growth Differ. (1996) [Pubmed]
  29. Mimosine arrests proliferating human cells before onset of DNA replication in a dose-dependent manner. Krude, T. Exp. Cell Res. (1999) [Pubmed]
  30. Mimosine differentially inhibits DNA replication and cell cycle progression in somatic cells compared to embryonic cells of Xenopus laevis. Wang, Y., Zhao, J., Clapper, J., Martin, L.D., Du, C., DeVore, E.R., Harkins, K., Dobbs, D.L., Benbow, R.M. Exp. Cell Res. (1995) [Pubmed]
  31. Expression and actions of HIF prolyl-4-hydroxylase in the rat kidneys. Li, N., Yi, F., Sundy, C.M., Chen, L., Hilliker, M.L., Donley, D.K., Muldoon, D.B., Li, P.L. Am. J. Physiol. Renal Physiol. (2007) [Pubmed]
  32. Enantioseparation of chiral aromatic amino acids by capillary electrophoresis in neutral and charged cyclodextrin selector modes. La, S., Ahn, S., Kim, J.H., Goto, J., Choi, O.K., Kim, K.R. Electrophoresis (2002) [Pubmed]
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