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Chemical Compound Review

MOLI001236     ethenylbenzene

Synonyms: AC1L9P44
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Disease relevance of styrene

  • Probing structure/function relationships of HIV-1 reverse transcriptase with styrene oxide N2-guanine adducts [1].
  • There appear to be many similarities between the toxicity and metabolism of styrene in rodents and humans [2].
  • 2. Styrene oxide was carcinogenic to the forestomach of both sexes of rats and mice after gavage exposure and was associated with an increase in liver neoplasms in male mice in one study [3].
  • Copolymers of vinyl bases with acrylic acid and styrene or 1-vinyluracil with maleic acid were found to stimulate in vitro polyphenylalanine synthesis using a system extracted from Escherichia coli MRE600 [4].
  • Kinetic mechanism of the enantioselective conversion of styrene oxide by epoxide hydrolase from Agrobacterium radiobacter AD1 [5].

Psychiatry related information on styrene


High impact information on styrene

  • Early data showed that styrene oxide hydrolase activity was associate with the microsomal subcellular fraction [11].
  • Antibodies against homogeneous epoxide hydratase provide evidence for a single enzyme hydrating styrene oxide and benz(a)pyrene 4,5-oxide [12].
  • Composed of a glycidylmethacrylate (GMA) and styrene copolymer core with a GMA polymer surface, the beads minimize nonspecific protein binding and maximize purification efficiency [13].
  • Biochemistry, genetics and physiology of microbial styrene degradation [14].
  • The compound is of major importance in the petrochemical and polymer-processing industries, which can contribute to the pollution of natural resources via the release of styrene-contaminated effluents and off-gases [14].

Chemical compound and disease context of styrene


Biological context of styrene


Anatomical context of styrene

  • This level of induction correlates well with the 5-fold induction in catalytic activity of epoxide hydrolase (using styrene 7,8-oxide as substrate) in microsomes isolated from phenobarbital-treated rats [24].
  • The results show that erythrocytes are essential for the activation of styrene in the lymphocyte test system [21].
  • Addition of 1 mM styrene oxide caused 75-100% and 4-8-fold increase in AFB1-DNA binding in control and treated hepatocytes, respectively, with corresponding decreases in thiol conjugation [25].
  • There is preliminary evidence for the presence of DNA adducts and for adducts in hemoglobin and albumin in blood cells of styrene-exposed workers [26].
  • Styrene oxide, like many intermediate metabolites of foodstuffs, is genotoxic and, if introduced directly into the stomachs of rodents in high doses/concentrations, gives rise to cancers of the forestomach [27].

Associations of styrene with other chemical compounds


Gene context of styrene

  • PHEMAs cannot be recommended as biomarkers of exposure to styrene, unless the GSTM1 genotype is considered in data interpretation [32].
  • These data indicate that several human hepatic and/or pulmonary P450 forms are capable of metabolizing styrene, albeit at different rates [16].
  • Multifactorial regression analysis indicated that SSB in DNA were significantly associated with styrene exposure and with heterozygosity in CYP2E1 (5'-flanking region and intron 6; r(2)=0.614) [33].
  • The field survey confirms that styrene exposure is associated with increased DNA damage and indicates a modulating role for GSTM1 and GSTT1 genotypes [34].
  • When the combined influence of the CYP2B6 genotype and the predicted activity of EPHX1 were examined, urinary metabolites in subjects with low enzyme activity were lower than in those with medium or high activity after high styrene exposure (>or=50 ppm) [35].

Analytical, diagnostic and therapeutic context of styrene


  1. Probing structure/function relationships of HIV-1 reverse transcriptase with styrene oxide N2-guanine adducts. Forgacs, E., Latham, G., Beard, W.A., Prasad, R., Bebenek, K., Kunkel, T.A., Wilson, S.H., Lloyd, R.S. J. Biol. Chem. (1997) [Pubmed]
  2. Review of the toxicology of styrene. Bond, J.A. Crit. Rev. Toxicol. (1989) [Pubmed]
  3. Review of styrene and styrene oxide long-term animal studies. McConnell, E.E., Swenberg, J.A. Crit. Rev. Toxicol. (1994) [Pubmed]
  4. Mechanims of stimulation of in vitro protein synthesis by some copolymers of styrene, vinyluracil, and vinyladenine with maleic acid and acrylic acid. Boguslawski, S., Olson, P.E., Mertes, M.P. Biochemistry (1976) [Pubmed]
  5. Kinetic mechanism of the enantioselective conversion of styrene oxide by epoxide hydrolase from Agrobacterium radiobacter AD1. Rink, R., Janssen, D.B. Biochemistry (1998) [Pubmed]
  6. The neuroepidemiology of styrene: a critical review of representative literature. Rebert, C.S., Hall, T.A. Crit. Rev. Toxicol. (1994) [Pubmed]
  7. Toxicity of styrene vapor in hepatocyte monolayers at low oxygen tensions. Costa, A.K., Trudell, J.R. Environ. Health Perspect. (1990) [Pubmed]
  8. Influence of occupational styrene exposure on memory and attention. Schoenhuber, R., Gentilini, M. Neurotoxicology and teratology. (1989) [Pubmed]
  9. Effects of acute styrene and simultaneous noise exposure on auditory function in the guinea pig. Fechter, L.D. Neurotoxicology and teratology. (1993) [Pubmed]
  10. Alcohol consumption and tolerance of workers exposed to styrene in relation to level of exposure and psychological symptoms and signs. Lindström, K., Härkönen, H., Mantere, P. Scandinavian journal of work, environment & health. (1978) [Pubmed]
  11. Epoxide hydrolase activity in the mitochondrial fraction of mouse liver. Gill, S.S., Hammock, B.D. Nature (1981) [Pubmed]
  12. Antibodies against homogeneous epoxide hydratase provide evidence for a single enzyme hydrating styrene oxide and benz(a)pyrene 4,5-oxide. Oesch, F., Bentley, P. Nature (1976) [Pubmed]
  13. High-performance affinity beads for identifying drug receptors. Shimizu, N., Sugimoto, K., Tang, J., Nishi, T., Sato, I., Hiramoto, M., Aizawa, S., Hatakeyama, M., Ohba, R., Hatori, H., Yoshikawa, T., Suzuki, F., Oomori, A., Tanaka, H., Kawaguchi, H., Watanabe, H., Handa, H. Nat. Biotechnol. (2000) [Pubmed]
  14. Biochemistry, genetics and physiology of microbial styrene degradation. O'Leary, N.D., O'Connor, K.E., Dobson, A.D. FEMS Microbiol. Rev. (2002) [Pubmed]
  15. The in vitro induction of sister chromatid exchanges and chromosome aberrations in human lymphocytes by styrene derivatives. Norppa, H. Carcinogenesis (1981) [Pubmed]
  16. Styrene metabolism by cDNA-expressed human hepatic and pulmonary cytochromes P450. Nakajima, T., Elovaara, E., Gonzalez, F.J., Gelboin, H.V., Raunio, H., Pelkonen, O., Vainio, H., Aoyama, T. Chem. Res. Toxicol. (1994) [Pubmed]
  17. Towards a biocatalyst for (S)-styrene oxide production: characterization of the styrene degradation pathway of Pseudomonas sp. strain VLB120. Panke, S., Witholt, B., Schmid, A., Wubbolts, M.G. Appl. Environ. Microbiol. (1998) [Pubmed]
  18. Stereospecific dihydroxylation of the styrene vinyl group by purified naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Lee, K., Gibson, D.T. J. Bacteriol. (1996) [Pubmed]
  19. Purification and characterization of phenylacetaldehyde reductase from a styrene-assimilating Corynebacterium strain, ST-10. Itoh, N., Morihama, R., Wang, J., Okada, K., Mizuguchi, N. Appl. Environ. Microbiol. (1997) [Pubmed]
  20. An investigation of multiple biomarkers among workers exposed to styrene and styrene-7,8-oxide. Rappaport, S.M., Yeowell-O'Connell, K., Bodell, W., Yager, J.W., Symanski, E. Cancer Res. (1996) [Pubmed]
  21. Metabolic activation of styrene by erythrocytes detected as increased sister chromatid exchanges in cultured human lymphocytes. Norppa, H., Vainio, H., Sorsa, M. Cancer Res. (1983) [Pubmed]
  22. Molecular dosimetry of polycyclic aromatic hydrocarbon epoxides and diol epoxides via hemoglobin adducts. Day, B.W., Naylor, S., Gan, L.S., Sahali, Y., Nguyen, T.T., Skipper, P.L., Wishnok, J.S., Tannenbaum, S.R. Cancer Res. (1990) [Pubmed]
  23. Induction of cell proliferation in the forestomach of F344 rats following subchronic administration of styrene 7,8-oxide and butylated hydroxyanisole. Cantoreggi, S., Dietrich, D.R., Lutz, W.K. Cancer Res. (1993) [Pubmed]
  24. Effect of phenobarbital on the level of translatable rat liver epoxide hydrolase mRNA. Pickett, C.B., Lu, A.Y. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  25. Effect of butylated hydroxyanisole pretreatment on aflatoxin B1-DNA binding and aflatoxin B1-glutathione conjugation in isolated hepatocytes from rats. Jhee, E.C., Ho, L.L., Tsuji, K., Gopalan, P., Lotlikar, P.D. Cancer Res. (1989) [Pubmed]
  26. Evidence for DNA and protein binding by styrene and styrene oxide. Phillips, D.H., Farmer, P.B. Crit. Rev. Toxicol. (1994) [Pubmed]
  27. Styrene: toxicity studies--what do they show? Roe, F.J. Crit. Rev. Toxicol. (1994) [Pubmed]
  28. The formation of styrene glutathione adducts catalyzed by prostaglandin H synthase. A possible new mechanism for the formation of glutathione conjugates. Stock, B.H., Bend, J.R., Eling, T.E. J. Biol. Chem. (1986) [Pubmed]
  29. The roles of His-64, Tyr-103, Tyr-146, and Tyr-151 in the epoxidation of styrene and beta-methylstyrene by recombinant sperm whale myoglobin. Rao, S.I., Wilks, A., Ortiz de Montellano, P.R. J. Biol. Chem. (1993) [Pubmed]
  30. The obligatory intermediacy of 16,17 alpha- and 16,17 beta-epoxides in the biotransformation of androsta-5,16-dien-3 beta-ol to androst-5-ene-3 beta, 16 alpha, 17 beta- and -3 beta, 16 beta, 17 alpha-triols by male rat liver microsomes. Watabe, T., Komatsu, T., Kobayashi, K., Isobe, M., Ozawa, N., Saitoh, Y. J. Biol. Chem. (1985) [Pubmed]
  31. Monooxygenase activity of cytochrome c peroxidase. Miller, V.P., DePillis, G.D., Ferrer, J.C., Mauk, A.G., Ortiz de Montellano, P.R. J. Biol. Chem. (1992) [Pubmed]
  32. Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids. De Palma, G., Manini, P., Mozzoni, P., Andreoli, R., Bergamaschi, E., Cavazzini, S., Franchini, I., Mutti, A. Chem. Res. Toxicol. (2001) [Pubmed]
  33. Association between genetic polymorphisms and biomarkers in styrene-exposed workers. Vodicka, P., Soucek, P., Tates, A.D., Dusinska, M., Sarmanova, J., Zamecnikova, M., Vodickova, L., Koskinen, M., de Zwart, F.A., Natarajan, A.T., Hemminki, K. Mutat. Res. (2001) [Pubmed]
  34. Genetic polymorphism of drug-metabolizing enzymes and styrene-induced DNA damage. Buschini, A., De Palma, G., Poli, P., Martino, A., Rossi, C., Mozzoni, P., Scotti, E., Buzio, L., Bergamaschi, E., Mutti, A. Environ. Mol. Mutagen. (2003) [Pubmed]
  35. Influence of genetic polymorphisms of styrene-metabolizing enzymes and smoking habits on levels of urinary metabolites after occupational exposure to styrene. Ma, M., Umemura, T., Mori, Y., Gong, Y., Saijo, Y., Sata, F., Kawai, T., Kishi, R. Toxicol. Lett. (2005) [Pubmed]
  36. Rat and mouse forestomach tumors induced by chronic oral administration of styrene oxide. Lijinsky, W. J. Natl. Cancer Inst. (1986) [Pubmed]
  37. A ferret model of acute multifocal gastrointestinal infarction. Hudson, M., Piasecki, C., Sankey, E.A., Sim, R., Wakefield, A.J., More, L.J., Sawyerr, A.M., Dhillon, A.P., Pounder, R.E. Gastroenterology (1992) [Pubmed]
  38. Glutathione-S-epoxide transferase activity during development and the effect of partial hepatectomy. Mukhtar, H., Bresnick, E. Cancer Res. (1976) [Pubmed]
  39. Epidemiological studies of styrene-exposed populations. Coggon, D. Crit. Rev. Toxicol. (1994) [Pubmed]
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