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Chemical Compound Review

BUTADIENE     buta-1,3-diene

Synonyms: Butadien, Bivinyl, Butadieen, Divinyl, Erythrene, ...
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Disease relevance of BUTADIENE


High impact information on BUTADIENE


Chemical compound and disease context of BUTADIENE


Biological context of BUTADIENE


Anatomical context of BUTADIENE


Associations of BUTADIENE with other chemical compounds


Gene context of BUTADIENE

  • Seven of these mutations were a G-->C transversion in Hras1 codon 13, consistent with a 1,3-butadiene-specific Kras2 mutation previously reported in several other tumor types [27].
  • Different genetic pathways may be involved in the development of these chemically induced tumours since we have previously shown that mutations in p53 and ras genes are common in 1,3-butadiene- but not 2',3'-dideoxycytidine-induced lymphomas [28].
  • In contrast, homozygous deletions spanning the p16INK4a and p15INK4b loci were observed in only two of 31 1,3-butadiene-induced tumours [28].
  • Lack of increased genetic damage in 1,3-butadiene-exposed Chinese workers studied in relation to EPHX1 and GST genotypes [29].
  • In addition, the expression of CYP2E1, a gene playing a key role in BD metabolism, was determined by real-time PCR in peripheral blood lymphocytes, and the capacity of lymphocytes to repair gamma-ray-induced SSBs and to convert 8-oxoguanine in HeLa cell DNA into SSBs was assessed using in vitro assays [30].

Analytical, diagnostic and therapeutic context of BUTADIENE


  1. Induced and spontaneous diabetes mellitus and suppression of cell-mediated immunologic responses. Granuloma formation, delayed dermal reactivity and allograft rejection. Mahmoud, A.A., Rodman, H.M., Mandel, M.A., Warren, K.S. J. Clin. Invest. (1976) [Pubmed]
  2. Identification of a vinyl reductase gene for chlorophyll synthesis in Arabidopsis thaliana and implications for the evolution of Prochlorococcus species. Nagata, N., Tanaka, R., Satoh, S., Tanaka, A. Plant Cell (2005) [Pubmed]
  3. Divinyl ether fatty acid synthesis in late blight-diseased potato leaves. Weber, H., Chételat, A., Caldelari, D., Farmer, E.E. Plant Cell (1999) [Pubmed]
  4. Multiple organ carcinogenicity of 1,3-butadiene in B6C3F1 mice after 60 weeks of inhalation exposure. Huff, J.E., Melnick, R.L., Solleveld, H.A., Haseman, J.K., Powers, M., Miller, R.A. Science (1985) [Pubmed]
  5. Mutagens from heated Chinese and U.S. cooking oils. Shields, P.G., Xu, G.X., Blot, W.J., Fraumeni, J.F., Trivers, G.E., Pellizzari, E.D., Qu, Y.H., Gao, Y.T., Harris, C.C. J. Natl. Cancer Inst. (1995) [Pubmed]
  6. Occupational exposure to 1,3-butadiene. Davis, D.L. Lancet (1987) [Pubmed]
  7. Multiplication of antenna genes as a major adaptation to low light in a marine prokaryote. Garczarek, L., Hess, W.R., Holtzendorff, J., van der Staay, G.W., Partensky, F. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  8. Genetic alterations of p53 and ras genes in 1,3-butadiene- and 2',3'-dideoxycytidine-induced lymphomas. Zhuang, S.M., Cochran, C., Goodrow, T., Wiseman, R.W., Söderkvist, P. Cancer Res. (1997) [Pubmed]
  9. Characterization of a Plant-like Protochlorophyllide a Divinyl Reductase in Green Sulfur Bacteria. Chew, A.G., Bryant, D.A. J. Biol. Chem. (2007) [Pubmed]
  10. Species and tissue differences in the microsomal oxidation of 1,3-butadiene and the glutathione conjugation of butadiene monoxide in mice and rats. Possible role in 1,3-butadiene-induced toxicity. Sharer, J.E., Duescher, R.J., Elfarra, A.A. Drug Metab. Dispos. (1992) [Pubmed]
  11. Species and tissue differences in the toxicity of 3-butene-1,2-diol in male Sprague-Dawley rats and B6C3F1 mice. Sprague, C.L., Phillips, L.A., Young, K.M., Elfarra, A.A. Toxicol. Sci. (2004) [Pubmed]
  12. Protection of rats against 3-butene-1,2-diol-induced hepatotoxicity and hypoglycemia by N-acetyl-l-cysteine. Sprague, C.L., Elfarra, A.A. Toxicol. Appl. Pharmacol. (2005) [Pubmed]
  13. Carcinogenicity of 1,3-butadiene in C57BL/6 x C3H F1 mice at low exposure concentrations. Melnick, R.L., Huff, J., Chou, B.J., Miller, R.A. Cancer Res. (1990) [Pubmed]
  14. Point mutations and deletions in the znfn1a1/ikaros gene in chemically induced murine lymphomas. Karlsson, A., Söderkvist, P., Zhuang, S.M. Cancer Res. (2002) [Pubmed]
  15. Activation of K-ras by codon 13 mutations in C57BL/6 X C3H F1 mouse tumors induced by exposure to 1,3-butadiene. Goodrow, T., Reynolds, S., Maronpot, R., Anderson, M. Cancer Res. (1990) [Pubmed]
  16. Chloroplast biogenesis. Detection of divinyl protochlorophyllide in higher plants. Belanger, F.C., Rebeiz, C.A. J. Biol. Chem. (1980) [Pubmed]
  17. Altered monovinyl and divinyl protochlorophyllide pools in bchJ mutants of Rhodobacter capsulatus. Possible monovinyl substrate discrimination of light-independent protochlorophyllide reductase. Suzuki, J.Y., Bauer, C.E. J. Biol. Chem. (1995) [Pubmed]
  18. 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]
  19. 1,3-Butadiene: exposure estimation, hazard characterization, and exposure-response analysis. Hughes, K., Meek, M.E., Walker, M., Beauchamp, R. Journal of toxicology and environmental health. Part B, Critical reviews. (2003) [Pubmed]
  20. Chromosome aberrations in mouse bone marrow cells following in vivo exposure to 1,3-butadiene. Irons, R.D., Oshimura, M., Barrett, J.C. Carcinogenesis (1987) [Pubmed]
  21. 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]
  22. 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]
  23. Molecular analysis of lacI mutants from transgenic fibroblasts exposed to 1,2-epoxybutene. Saranko, C.J., Pluta, L.J., Recio, L. Carcinogenesis (1998) [Pubmed]
  24. Both K-ras and H-ras protooncogene mutations are associated with Harderian gland tumorigenesis in B6C3F1 mice exposed to isoprene for 26 weeks. Hong, H.L., Devereux, T.R., Melnick, R.L., Eldridge, S.R., Greenwell, A., Haseman, J., Boorman, G.A., Sills, R.C. Carcinogenesis (1997) [Pubmed]
  25. High frequency of codon 61 K-ras A-->T transversions in lung and Harderian gland neoplasms of B6C3F1 mice exposed to chloroprene (2-chloro-1,3-butadiene) for 2 years, and comparisons with the structurally related chemicals isoprene and 1,3-butadiene. Sills, R.C., Hong, H.L., Melnick, R.L., Boorman, G.A., Devereux, T.R. Carcinogenesis (1999) [Pubmed]
  26. Irreversible inactivation of trypanothione reductase by unsaturated Mannich bases: a divinyl ketone as key intermediate. Lee, B., Bauer, H., Melchers, J., Ruppert, T., Rattray, L., Yardley, V., Davioud-Charvet, E., Krauth-Siegel, R.L. J. Med. Chem. (2005) [Pubmed]
  27. Frequent mutations of the Trp53, Hras1 and beta-catenin (Catnb) genes in 1,3-butadiene-induced mammary adenocarcinomas in B6C3F1 mice. Zhuang, S.M., Wiseman, R.W., Söderkvist, P. Oncogene (2002) [Pubmed]
  28. Inactivations of p16INK4a-alpha, p16INK4a-beta and p15INK4b genes in 2',3'-dideoxycytidine- and 1,3-butadiene-induced murine lymphomas. Zhuang, S.M., Schippert, A., Haugen-Strano, A., Wiseman, R.W., Söderkvist, P. Oncogene (1998) [Pubmed]
  29. Lack of increased genetic damage in 1,3-butadiene-exposed Chinese workers studied in relation to EPHX1 and GST genotypes. Zhang, L., Hayes, R.B., Guo, W., McHale, C.M., Yin, S., Wiencke, J.K., Patrick O'Neill, J., Rothman, N., Li, G.L., Smith, M.T. Mutat. Res. (2004) [Pubmed]
  30. Markers of individual susceptibility and DNA repair rate in workers exposed to xenobiotics in a tire plant. Vodicka, P., Kumar, R., Stetina, R., Musak, L., Soucek, P., Haufroid, V., Sasiadek, M., Vodickova, L., Naccarati, A., Sedikova, J., Sanyal, S., Kuricova, M., Brsiak, V., Norppa, H., Buchancova, J., Hemminki, K. Environ. Mol. Mutagen. (2004) [Pubmed]
  31. Analysis of diepoxide-specific cyclic N-terminal globin adducts in mice and rats after inhalation exposure to 1,3-butadiene. Boysen, G., Georgieva, N.I., Upton, P.B., Jayaraj, K., Li, Y., Walker, V.E., Swenberg, J.A. Cancer Res. (2004) [Pubmed]
  32. 32P-postlabelling/HPLC assay reveals an enantioselective adduct formation in N7 guanine residues in vivo after 1,3-butadiene inhalation exposure. Koivisto, P., Sorsa, M., Pacchierotti, F., Peltonen, K. Carcinogenesis (1997) [Pubmed]
  33. Resin hemoperfusion in dogs intoxicated with ethychlorvynol (Placidyl). Zmuda, M.J. Kidney Int. (1980) [Pubmed]
  34. Future directions in epidemiologic studies of 1,3-butadiene-exposed workers. Acquavella, J.F. Environ. Health Perspect. (1990) [Pubmed]
  35. In vitro and in vivo genotoxicity of 1,3-butadiene and metabolites. Arce, G.T., Vincent, D.R., Cunningham, M.J., Choy, W.N., Sarrif, A.M. Environ. Health Perspect. (1990) [Pubmed]
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