The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Epoxybutene     2-ethenyloxirane

Synonyms: Vinyloxirane, Ethenyloxirane, PubChem23575, NSC-8023, CCRIS 2614, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Epoxybutene

  • The influence of 3,4-epoxybutene (EB), the primary metabolite of 1,3-butadiene, on the colony-forming response of hematopoietic progenitor cells (HPCs) from C57BL/6, Sl, and W mice was investigated in order to elucidate the role of altered HPC regulation in the pathogenesis of 1,3-butadiene toxicity [1].
  • In the lower concentration range where first order metabolism applies (up to about 500 ppm) epoxybutene is metabolized by mice at higher rates compared to rats (metabolic clearance per kg body weight, mice: 24,900 ml X h-1, rats: 13,400 ml X h-1) [2].

High impact information on Epoxybutene


Biological context of Epoxybutene

  • EB pretreatment in vitro and butadiene exposure in vivo mimic hematopoietic defects seen in W and Sl mice, suggesting that the pleotypic pathologies encountered in these murine models may be largely due to a common defect in primitive HPCs [1].
  • It predicts that inhalation uptake of butadiene and formation and retention of epoxybutene are controlled to a much greater extent by physiological parameters than by biochemical parameters and that storage in the fat represents a significant fraction of the retained butadiene [6].
  • Induction of sister chromatid exchange by 1,2-epoxy-3-butene in cultured human lymphocytes: influence of GSTT1 genotype [7].
  • The same two compounds I and II in a similar (54:46) ratio have been identified after acidic or thermal hydrolysis of DNA which had been reacted with 3,4-epoxy-1-butene under similar conditions [8].
  • If formed in sufficient amounts, DEB and MEB may produce chromosome damage of the type found in leukemia following exposure to butadiene [9].

Anatomical context of Epoxybutene


Associations of Epoxybutene with other chemical compounds


Gene context of Epoxybutene


Analytical, diagnostic and therapeutic context of Epoxybutene


  1. Chemical suppression of a subpopulation of primitive hematopoietic progenitor cells: 1,3-butadiene produces a hematopoietic defect similar to steel or white spotted mutations in mice. Colagiovanni, D.B., Stillman, W.S., Irons, R.D. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  2. Inhalation pharmacokinetics of 1,2-epoxybutene-3 reveal species differences between rats and mice sensitive to butadiene-induced carcinogenesis. Kreiling, R., Laib, R.J., Filser, J.G., Bolt, H.M. Arch. Toxicol. (1987) [Pubmed]
  3. 1,3-Butadiene oxidation by human myeloperoxidase. Role of chloride ion in catalysis of divergent pathways. Duescher, R.J., Elfarra, A.A. J. Biol. Chem. (1992) [Pubmed]
  4. Palladium-catalyzed DYKAT of butadiene monoepoxide: enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G. Trost, B.M., Horne, D.B., Woltering, M.J. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  5. Structure of an oligodeoxynucleotide containing a butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adduct in the human N-ras codon 61 sequence. Scholdberg, T.A., Merritt, W.K., Dean, S.M., Kowalcyzk, A., Harris, C.M., Harris, T.M., Rizzo, C.J., Lloyd, R.S., Stone, M.P. Biochemistry (2005) [Pubmed]
  6. Species differences in the production and clearance of 1,3-butadiene metabolites: a mechanistic model indicates predominantly physiological, not biochemical, control. Kohn, M.C., Melnick, R.L. Carcinogenesis (1993) [Pubmed]
  7. Induction of sister chromatid exchange by 1,2-epoxy-3-butene in cultured human lymphocytes: influence of GSTT1 genotype. Bernardini, S., Hirvonen, A., Pelin, K., Norppa, H. Carcinogenesis (1998) [Pubmed]
  8. The reaction of 3,4-epoxy-1-butene with deoxyguanosine and DNA in vitro: synthesis and characterization of the main adducts. Citti, L., Gervasi, P.G., Turchi, G., Bellucci, G., Bianchini, R. Carcinogenesis (1984) [Pubmed]
  9. Induction of chromosome-specific aneuploidy and micronuclei in human lymphocytes by metabolites of 1,3-butadiene. Xi, L., Zhang, L., Wang, Y., Smith, M.T. Carcinogenesis (1997) [Pubmed]
  10. Oxidation of 1,2-epoxy-3-butene to 1,2:3,4-diepoxybutane by cDNA-expressed human cytochromes P450 2E1 and 3A4 and human, mouse and rat liver microsomes. Seaton, M.J., Follansbee, M.H., Bond, J.A. Carcinogenesis (1995) [Pubmed]
  11. Identification and quantitation of DNA adducts from calf thymus DNA exposed to 3,4-epoxy-1-butene. Tretyakova, N., Lin, Y., Sangaiah, R., Upton, P.B., Swenberg, J.A. Carcinogenesis (1997) [Pubmed]
  12. Mutagenicity of butadiene and its epoxide metabolites: II. Mutational spectra of butadiene, 1,2-epoxybutene and diepoxybutane at the hprt locus in splenic T cells from exposed B6C3F1 mice. Cochrane, J.E., Skopek, T.R. Carcinogenesis (1994) [Pubmed]
  13. Molecular analysis of lacI mutants from transgenic fibroblasts exposed to 1,2-epoxybutene. Saranko, C.J., Pluta, L.J., Recio, L. Carcinogenesis (1998) [Pubmed]
  14. Disposition of butadiene monoepoxide and butadiene diepoxide in various tissues of rats and mice following a low-level inhalation exposure to 1,3-butadiene. Thornton-Manning, J.R., Dahl, A.R., Bechtold, W.E., Griffith, W.C., Henderson, R.F. Carcinogenesis (1995) [Pubmed]
  15. Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats and mice. Csanády, G.A., Guengerich, F.P., Bond, J.A. Carcinogenesis (1992) [Pubmed]
  16. Characterization of four N-3-thymidine adducts formed in vitro by the reaction of thymidine and butadiene monoxide. Selzer, R.R., Elfarra, A.A. Carcinogenesis (1997) [Pubmed]
  17. Influence of GSTM1 genotype on sister chromatid exchange induction by styrene-7,8-oxide and 1,2-epoxy-3-butene in cultured human lymphocytes. Uusküla, M., Järventaus, H., Hirvonen, A., Sorsa, M., Norppa, H. Carcinogenesis (1995) [Pubmed]
  18. Inhalation exposure of rats and mice to 1,3-butadiene induces N6-adenine adducts of epoxybutene detected by 32P-postlabeling and HPLC. Koivisto, P., Adler, I.D., Sorsa, M., Peltonen, K. Environ. Health Perspect. (1996) [Pubmed]
  19. Genetic susceptibility, biomarker respones, and cancer. Norppa, H. Mutat. Res. (2003) [Pubmed]
  20. Mutagenicity of the racemic mixtures of butadiene monoepoxide and butadiene diepoxide at the Hprt locus of T-lymphocytes following inhalation exposures of female mice and rats. Meng, Q., Henderson, R.F., Walker, D.M., Bauer, M.J., Reilly, A.A., Walker, V.E. Mutat. Res. (1999) [Pubmed]
  21. Absence of detectable P450 2E1 in bone marrow of B6C3F1 mice: relevance to butadiene-induced bone marrow toxicity. Genter, M.B., Recio, L. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1994) [Pubmed]
  22. Butadiene monoxide and deoxyguanosine alkylation products at the N7-position. Neagu, I., Koivisto, P., Neagu, C., Kostiainen, R., Stenby, K., Peltonen, K. Carcinogenesis (1995) [Pubmed]
  23. Germ cell mutagenicity of three metabolites of 1,3-butadiene in the rat: induction of spermatid micronuclei by butadiene mono-, di-, and diolepoxides in vivo. Lähdetie, J., Peltonen, K., Sjöblom, T. Environ. Mol. Mutagen. (1997) [Pubmed]
  24. Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry. Tretyakova NYu, n.u.l.l., Chiang, S.Y., Walker, V.E., Swenberg, J.A. Journal of mass spectrometry : JMS. (1998) [Pubmed]
  25. Somatic and germ cell effects in rats and mice after treatment with 1,3-butadiene and its metabolites, 1,2-epoxybutene and 1,2,3,4-diepoxybutane. Anderson, D., Dobrzyńka, M.M., Jackson, L.I., Yu, T.W., Brinkworth, M.H. Mutat. Res. (1997) [Pubmed]
  26. Macromolecular adducts of butadiene. Tretyakova NYu, n.u.l.l., Lin, Y.P., Upton, P.B., Sangaiah, R., Swenberg, J.A. Toxicology (1996) [Pubmed]
WikiGenes - Universities