Styrene metabolism, genotoxicity, and potential carcinogenicity

Drug Metabolism Reviews

Volumn 38, Issue 4, 2006, Pages 805-853

  Vodicka, Pavel ^a   Koskinen, Mikko ^b   Naccarati, Alessio ^a   Oesch Bartlomowicz, Barbara ^c   Vodickova, Ludmila ^a,d   Hemminki, Kari ^e,f   Oesch, Franz ^c  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Czech Republic)

^b Orion Pharma ^*  (Finland)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

^d NATIONAL INSTITUTE OF PUBLIC HEALTH   (Czech Republic)

^e GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

^f KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Biotransformation; DNA and chromosomal damage; DNA repair; Genetic polymorphisms; Styrene

Indexed keywords

CYTOCHROME P450 2E1; ISOENZYME; NUCLEIC ACID; STYRENE; STYRENE OXIDE;

BIOTRANSFORMATION; CARCINOGENICITY; CELL CULTURE; CHROMOSOME ABERRATION; CONFERENCE PAPER; CYTOGENETICS; DETOXIFICATION; DNA ADDUCT; DNA DAMAGE; DNA REPAIR; DNA STRAND BREAKAGE; ENVIRONMENTAL EXPOSURE; GENE MUTATION; GENETIC POLYMORPHISM; GENOTOXICITY; GLUTATHIONE METABOLISM; HUMAN; HYDROLYSIS; HYDROXYLATION; MICRONUCLEUS; MUTAGENICITY; NONHUMAN; OCCUPATIONAL EXPOSURE; OXIDATION; RESPIRATORY SYSTEM; RISK FACTOR; SISTER CHROMATID EXCHANGE; TOXICOKINETICS; URINARY EXCRETION;

ANIMALS; BIOTRANSFORMATION; CARCINOGENS; DNA; DNA ADDUCTS; DNA DAMAGE; HUMANS; MUTAGENS; STYRENES;

EID: 33845410719     PISSN: 03602532     EISSN: 10979883     Source Type: Journal    
DOI: 10.1080/03602530600952222     Document Type: Conference Paper

References (199)

1. Anwar, W. A., Shamy, M. Y. (1995). Chromosomal aberrations and micronuclei in reinforced plastics workers exposed to styrene. Mutat. Res. 327:41-47.
2. Arand, M., Muller, P., Mecky, A., Hinz, W., Urban, P., Pompon, D., Kellner, R., Oesch, F. (1999). Catalytic triad of microsomal epoxide hydrolase: Replacement of Glu404 with Asp lead to a strongly increased turnover rate. Biochem. J. 337:37-43.
3. Artuso, M., Angotzi, G., Bonassi, S., Bonatti, S., De Ferrari, M., Gargano, D., Lastrucci, L., Milici, L., Sbrana, C., Abbondandolo, A. (1995). Cytogenetic biomonitoring of styrene-exposed plastic boatbuilders. Arch. Environ. Contam. Toxicol. 29:270-274.
4. Bakke, O. M., Scheline, R. R. (1970). Hydroxylation of aromatic hydrocarbons in the rat. Toxicol. Appl. Pharmacol. 16:691-700.
5. Bardodej, Z., Bardodejova, E. (1970). Biotransformation of ethyl benzene, styrene, and alpha-methylstyrene in man. Am. Ind. Hyg. Assoc. J. 31:206-209.
6. Barlow, T., Dipple, A. (1999). Formation of deaminated products in styrene oxide reactions with deoxycytidine. Chem. Res. Toxicol. 12:883-886.
7. Bastlova, T., Podlutsky, A. (1996). Molecular analysis of styrene oxide-induced hprt mutation in human T-lymphocytes. Mutagenesis 11:581-591.
8. Bastlova, T., Vodicka, P., Peterkova, K., Hemminki, K., Lambert, B. (1995). Styrene oxide-induced HPRT mutations, DNA adducts and DNA strand breaks in cultured human lymphocytes. Carcinogenesis 16:2357-2362.
9. Begemann, P., Sram, R.J., Neumann, H.-G. (2001). Haemoglobin adducts of epoxybutene in workers occupationally exposed to 1,3-butadiene. Arch. Toxicol. 74:680-687.
10. Bernardini, S., Hirvonen, A., Järventaus, H., Norppa, H. (2002). Influence of GSTM1 and GSTT1 genotypes on sister chromatid exchange induction by styrene in cultured human lymphocytes. Carcinogenesis 23:893-897.
11. Bigbee, W. L., Grant, S. G., Langlois, R. G., Jensen, R. H., Antilla, A., Pfaffli, P., Pekari, K., Norppa, H. (1996). Glycophorin: A somatic cell mutation frequencies in Finnish reinforced plastics workers exposed to styrene. Cancer Epidemiol. Biomarkers Prevent. 5:801-810.
12. Biro, A., Pallinger, E., Major, J., Jakab, M.G., Klápl, T., Falus, A., Tompa, A. (2002). Lymphocyte phenotype analysis and chromosome aberration frequency of workers occupationally exposed to styrene, benzene, polycyclic aromatic hydrocarbons or mixed solvents. Immunol. Lett. 81:133-140.
13. Bjorge, C., Brunnborg, G., Wiger, R., Holme, J. A., Scholz, T., Dybing, E., Soderlund, E. J. (1996). A comparative study of chemically induced DNA damage in isolated human and rat testicular cells. Reprod. Toxicol. 10:509-519.
14. 14C]styrene in rats and mice exposed by recirculating nose-only inhalation. Toxicol. Sci. 58:161-172.
15. 14C- styrene by nose-only inhalation. Toxicol. Sci. 57:203-216.
16. Brenner, D. D., Jeffrey, A. M., Latriano, L., Wazneh, L., Warburton, D., Toor, M., Pero, R. W., Andrews, L. R., Walles, S., Perera, F. P. (1991). Biomarkers in styrene-exposed boatbuilders. Mutat. Res. 261:225-236.
17. Buschini, A., De Palma, G., Poli, P., Martiono, A., Rossi, C., Mozzoni, P., Scotti, E., Buzio, L., Bergamaschi, E., Mutti, A. (2003). Genetic polymorphism of drug-metabolizing enzymes and styrene-induced DNA damage. Environ. Mol. Mutagen. 41:243-252.
18. Carlson, G. P. (1997). Effects of inducers and inhibitors on the microsomal metabolism of styrene to styrene oxide in mice. J. Toxicol. Environ. Health 51:477-488.
19. Carlson, G. P., Hynes, D. E., Mantick, N. A. (1998). Effects of inhibitors of CYP1A and CYP1B on styrene metabolism in mouse liver and lung microsomes. Toxicol. Lett. 98:131-137.
20. Carlson, G. P., Mantick, N. A., Powley, M. W. (2000). Metabolism of styrene by human liver and lung. J. Toxicol. Environ. Health A59:591-595.
21. Carlson, G. P., Perez Rivera, A. A., Mantick, N. A. (2001). Metabolism of the styrene metabolite 4-vinylphenol by rat and mouse liver and lung. J. Toxicol. Environ. Health 63:541-551.
22. Carlson, G. P., Ullman, M., Mantick, N. A., Snyder, P. W. (2002). 4-Vinylphenol-induced pneumotoxicity and hepatotoxicity in mice. Toxicol Pathol. 30:565-569.
23. Cerny, S., Mraz, J., Flek, J., Tichy, M. (1990). Effect of ethanol on the urinary excretion of mandelic acid and phenyl glyoxylic acid. Int. Arch. Occup. Environ. Health 62:243-247.
24. Chakrabarti, S., Duhr, M. A., Sennecal-Quevillon, M., Richer C. L. (1993). Dose-dependent genotoxic effects of styrene on human blood lymphocytes and the relationship to its oxidative and metabolic effects. Environ. Mol. Mutagen. 22:85-92.
25. Chakrabarti, S., Zhang, X. X., Richer, C. L. (1997). Influence of duration of exposure to styrene oxide on sister chromatid exchanges and cell-cycle kinetics in cultured human blood lymphocytes in vitro. Mutat. Res. 395:37-45.
26. Chen, S., Tang, D., Xue, K., Xu, L., Ma, G., Hsu, Y., Cho, S. S. (2002). DNA repair gene XRCC1 and XPD polymorphisms and risk of lung cancer in a Chinese population. Carcinogenesis 23:1321-1325.
27. Christakopoulos, A., Bergmark, E., Zorcec, V., Norppa, H., Mäki-Paakkanen, J., Osterman-Golkar, S. (1993). Monitoring occupational exposure to styrene from haemoglobin adducts and metabolites in blood. Scand. J. Work Environ. Health 19:255-263.
28. Christmann, M., Tomicic, M. T., Roos, W. P., Kaina, B. (2003). Mechanisms of human DNA repair: An update. Toxicology 193:3-34.
29. Coccini, T., Maestri, L., Robustelli della Cuna, F. S., Bin, L., Costa, L. G., Manzo, L. (1996). Urinary mercapturic acid diastereomers in rats subchronically exposed to styrene and alcohol. Arch. Toxicol. 70:736-741.
30. Cohen, J. T., Carlson, G., Charnley, G., Coggon, D., Delzell, E., Graham, J. D., Greim, H, Krewski, D., Medinski, M., Monson, R., Paustenbach, D., Petersen, B., Rappoport, S., Rhomberg, I., Ryan. P. B., Thompson, K. (2002). A comprehensive evaluation of the potential health risks associated with occupational and environmental exposure to styrene. J. Toxicol. Environ. Health 5:1-265.
31. Cole, J., Skopek, T. R. (1994) Somatic mutant frequency, mutation rates and mutational spectra in the human population in vivo. Mutat. Res. 304:33-105.
32. Collins, A. R. (1998). Molecular epidemiology in cancer research. Mol. Aspects Med. 19:359-432.
33. Collins, A. R., Dobson, V. L., Dusinska, M., Kennedy, G., Stetina, R. (1997). The comet assay: What it can tell us? Mutat. Res. 375:183-193.
34. Cruzan, G., Carlson, G. P., Johnson, K. A., Andrews, L. S., Banton, M. I., Bevan, C., Cushman, J. R. (2002). Styrene respiratory tract toxicity and mouse lung tumors are mediated by CYP2F-generated metabolites. Regul. Toxicol. Pharmacol. 35:308-319.
35. Cruzan, G., Carlson, G. P., Turner, M., Mellert, W. (2005). Ring-oxidized metabolites of styrene contribute to styrene-induced Clara-cell toxicity in mice. J. Toxicol. Environ. Health A. 68:229-237.
36. Cruzan, G., Cushman, J. R., Andrews, L. S., Granwille, G. C., Johnson, K. A., Bevan, C., Hardy, C. J., Coombs, D. W., Mullins, P. A., Brown, W. R. (2001). Chronic toxicity/oncogenicity study of styrene in CD-1 mice by inhalation exposure for 104 weeks. J. Appl. Toxicol. 21:185-198.
37. Delbressine, L. P., van Bladeren, P. J., Smeets, F. L., Seutter-Berlage, F. (1981). Stereoselective oxidation of styrene to styrene oxide in rats as measured by mercapturic acid excretion. Xenobiotica 11: 589-594.
38. De Palma, G., Manini, P., Mozzoni, P., Andreoli, R., Bergamaschi, E., Cavazzini, S., Franchini, I., Mutti, A. (2001). Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids. Chem. Res. Toxicol. 14:1393-1400.
39. Diodovich, C., Bianchi, M. G., Bowe, G., Acquati, F., Taramelli, R., Parent-Massin, D., Gribaldo, L. (2004). Response of human cord blood cells to styrene exposure: Evaluation of its effects on apoptosis and gene expression by genomic technology. Toxicology 200:145-157.
40. Divine, K. K., Gilliland, F. D., Crowell, R. E., Stidley, C. A., Bocklage, T. J., Cook, D. L., Belinsky, S. A. (2001). The XRCC1 399 glutamine allele is a risk factor for adenocarcinoma of the lung. Mutat. Res. 461:273-278.
41. Dypbukt, J. M., Costa, L. G., Manzo, L., Orrenius, S., Nicotera, P. (1992). Cytotoxic and genotoxic effects of styrene 7,8-oxide in neuroadrenerdic Pc 12 cells. Carcinogenesis 13:417-424.
42. Elovaara, E., Engström, K., Nakajima, T., Park, S. S., Gelboin, H. V., Vainio, H. (1991). Metabolism of inhaled styrene in acetone-, phenobarbital- and 3-methylcholanthrene-pretreated rats: Stimulation and stereochemical effects by induction of cytochromes P450IIE1, P450IIB and P450IA. Xenobiotica 21:651-661.
43. Engelhardt, G., Gamer, A., Vodicka, P., Barta, I., Hoffmann, H. D., Veenstra, G. (2003). A re-assessment of styrene-induced clastogenicity in mice in a subacute inhalation study. Arch. Toxicol. 77:56-61.
44. Farmer, P. B., Sepai, O., Lawrence, R., Autrup, H., Sabro Nielsen, Vestergard, A. B., Waters, R., Leuratti, C., Jones, N. J., Stone, J., Baan, R. A., Van Delft, J. H. M., Steenwinkel, M. J. S. T., Kyrtopoulos, S., Souliotis, V. L., Theodorakopoulos, N., Bacalis, N. C., Natarajan, A. T., Tates, A. D., Haugen, A., Andreassen, A., Ovrebo, S., Shuker, D. E. G., Amaning, K. S., Schouft, A., Ellol, A., Garner, R. C., Dingley, K. H., Abbondandolo, A., Merlo, F., Cole, J., Aldrich, K., Beare, D., Capulas, E., Rowley, G., Waugh, A. P. W., Povey, A. C., Haque, K., Kirsch-Volders, M., Van Hummelen, P., Castelain, P. (1996). Biomonitoring human exposure to environmental carcinogenic chemicals. Mutagenesis 11:363-381.
45. Filser, J. G., Kessler, W., Csanády, G. A. (2002). Estimation of a possible tumorigenic risk of styrene from daily intake via food and ambient air. Toxicol. Lett. 126:1-18.
46. Foureman, G. L., Harris, C., Guengerich, F. P., Bend, J. R. (1989). Stereoselectivity of styrene oxidation in microsomes and in purified cytochromes P-450 enzymes from rat liver. J. Pharmacol. Exp. Therap. 248:492-497.
47. Gadberry, M. G., DeNicola, D. B., Carlson, G. P. (1996). Pneumotoxicity and hepatotoxicity of styrene and styrene oxide. J. Toxicol. Environ. Health 48:273-294.
48. Gamer, A. O., Leibold, E., Deckardt, K., Kittel, B., Kaufmann, W., Tennekes, H. A., Van Ravenzwaay, B. (2004). The effects of styrene on lung cells in female mice and rats. Food Chem. Toxicol. 42:1655-1667.
49. Godderis, L., Aka, P., Mateuca, R., Kirsch-Volders, M., Lison, D., Veulemans, R. (2006). Dose-dependent influence of genetic polymorphisms on DNA damage induced by styrene oxide, ethylene oxide and gamma-radiation. Toxicology, 219:220-229.
50. Godderis, L., De Boeck, M., Haufroid, V., Emmery, M., Mateuca, R., Gardinal, S., Kirsch-Volders, M., Veulemans, H., Lison, D. (2004). Influence of genetic polymorphisms on biomarkers of exposure and genotoxic effects in styrene-exposed workers. Environ. Molec. Mutagen. 44:293-303.
51. Green, T., Lee, R., Toghill, A., Meadowcroft, S., Lund, V., Foster, J. R. (2001a). The toxicity of styrene to the nasal epithelium of mice and rats. Chem. Biol. Interact. 137:185-202.
52. Green, T., Toghill, A., Foster, J. R. (2001b). The role of cytochrome P-450 in styrene-induced pulmonary toxicity and carcinogenicity. Toxicology 169:107-117.
53. Guengerich, F. P., Kim, D.-H., Iwasaki, M. (1991). Role of human cytochrome IIE1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol. 4:168-179.
54. Guillemin, M. P., Bauer, D. (1979). Human exposure to styrene. III. Elimination kinetics of urinary mandelic and phenylglyoxylic acids after single experimental exposure. Int. Arch. Occup. Environ. Health 44:249-263.
55. Hagmar, L., Stromberg, U., Bonassi, S., Hansteen, I. L., Knudsen, L. E., Lindholm, C., Norppa, H. (2004). Impact of types of lymphocyte chromosomal aberrations on human cancer risk: Results from Nordic and Italian cohorts. Cancer Res. 64:2258-2263.
56. Hallier, E., Goergens, H. W., Hallier, K., Bolt, H. M. (1994). Intervention study on the influence of reduction of occupational exposure to styrene on sister chromatid exchanges in lymphocytes. Int. Arch. Occup. Environ. Health 66:167-172.
57. Hassett, C., Aicher, L., Sidhu, J. S., Omiecinski, C. J. (1994). Human microsomal epoxide hydrolase genetic polymorphism and functional expression in vitro of amino acid variants. Hum. Mol. Genet. 3:421-428.
58. Haufroid, V., Buchet, J. P., Gardinal, S., Ghittori, S., Imbriania, M., Hirvonen, A., Lison, D. (2001). Importance of genetic polymorphisms of drug metabolising enzymes for the interpretation of biomarkers of exposure to styrene. Biomarkers 6:236-249.
59. Haufroid, V., Jakubowski, M., Janasik, B., Ligocka, D., Buchet, J. P., Bergamaschi, E., Manini, P., Mutti, A., Ghittori, S., Arand, M., Hangen, N., Oesch, F., Hirvonen, A., Lison, D. (2002). Interest in genotyping and phenotyping of drug-metabolizing enzymes for the interpretation of biological monitoring of exposure to styrene. Pharmacogenetics 12:691-702.
60. Hemminki, K., Hesso, A. (1984). Reaction products of styrene oxide with guanosine in aqueous media. Carcinogenesis 5:601-607.
61. Hemminki, K., Koskinen, M., Rajaniemi, H., Zhao, C. (2000). DNA adducts, mutations and cancer 2000. Regulat. Toxicol. Pharmacol. 32:264-275.
62. Henderson, L. M., Speit, G. (2005). Review of the genotoxicity of styrene in humans. Mutat Res. 589:158-191.
63. Herrero, M. E., Arand, M., Hengstler, J. G., Oesch, F. (1997). Recombinant expression of human microsomal epoxide hydrolase protects V79 Chinese hamster cells from styrene oxide- but not from ethylene oxide-induced DNA strand breaks. Environ. Mol. Mutagen. 30:429-439.
64. Holz, O., Scherer, G., Brodtmeier, S., Koops, F., Warncke, K., Krause, T., Austen, A., Angerer, J., Tricker, A. R., Adlkofer, F. (1995). Determination of low level exposure to volatile aromatic hydrocarbons and genotoxic effects in workers at a styrene plant. Occup. Environ. Med. 52:420-428.
65. 32P-postlabelling detection of DNA adducts in mononuclear cells of workers occupationally exposed to styrene. Carcinogenesis 15:1309-1315.
66. Hou, S. M., Fält, S., Angelini, S., Yang, K., Nyberg, F., Lambert, B., Hemminki, K. (2002). The XPD variant alleles are associated with increased aromatic DNA adduct level and lung cancer risk. Carcinogenesis 23:599-603.
67. Hou, S. M., Fält, S., Steen, A. M. (1995). HPRT mutant frequency and GSTM1 genotype in non-smoking healthy individuals. Environ. Molec. Mutagen. 25:97-105.
68. Hynes, D. E., DeNicola, D. B., Carlson, G. P. (1999). Metabolism of styrene in mouse and rat isolated lung cells. Toxicol. Sci. 51:195-201.
69. IARC (International Agency for Research on Cancer). (1979). IARC Monographs on the Evaluation of the Carcinogenic Risks of Chemicals to Humans: Some Monomers, Plastics and Synthetic Elastomers, and Acrolein, Volume 19, WHO, International Agency for Research on Cancer.
70. IARC (International Agency for Research on Cancer). (1994). IARC Monographs on the Evaluation of the Carcinogenic Risks in Humans: Some Industrial Chemicals, Volume 60, WHO, International Agency for Research on Cancer.
71. IARC (International Agency for Research on Cancer). (2002). Monographs on the Evaluation of Carcinogenic Risks to Humans: Some Traditional Herbal Medicines, Some Mycotoxins, Naphthalene and Styrene, Volume 82, WHO, International Agency for Research on Cancer.
72. 6-alkylguanine in hprt mutagenesis in T-lymphocytes of rats exposed in vivo to ethylmethanesulfonate, N-(2-hydroxyethyl)-N-nitrosourea, or N-ethyl-N-nitrosourea. Cancer Res. 55:1875-1882.
73. Johanson, G., Ernstgard L., Gullstrand, E., Osterman-Golkar, S., Williams, C. C., Sumner, S. C. (2000). Styrene oxide in blood, hemoglobin adducts, and urinary metabolites in human volunteers exposed to (13)C(8)-styrene vapors. Toxicol. Appl. Pharmacol. 168:36-49.
74. Karakaya, A. E., Karahalil, B., Yilmazer, M., Aygun, N., Sarda, S., Burgas, S. (1997). Evaluation of genotoxic potential of styrene in furniture workers using unsaturated polyester resins. Mutat. Res. 392:261-268.
75. Kessler, W., Jiang, X., Filser, J. (1992). Pharmakokinetik von Styrol-7,8-Oxid bei Maus und Ratte. In: R. Kreutz, C. Piekarski (Eds.) Arbeitsmedizinische Aspekte der Arbeits(-zeit)organisation-Skeletterkrankungen und Beruf-Arbeitsmedizinisches Kolloquium der gewerblichen Berufsgenossenschaften, Stuttgart, Germany: Gentner Verlag, pp. 622-626.
76. Kim, H., Wang, R. S., Elovaara, E., Raunio, H., Pelkonen, O., Aoyama, T., Vainio, H., Nakajima, T. (1997). Cytochrome P450 isozymes responsible for the metabolism of toluene and styrene in human liver microsomes. Xenobiotica 27:657-665.
77. Kligerman, A. D., Allen, J. W., Bryant, M. F., Campbell, B. W., Collins, B. W., Doerr, C. L., Erexson, G. L., Kwanyuen, P., Morgan, D. L. (1992). Cytogenetic studies of mice exposed to styrene by inhalation. Mutat. Res. 280:35-43.
78. Kligerman, A. D., Allen, J. W., Erexson, G. L., Morgan, D. L. (1993). Cytogenetic studies of rodents exposed to styrene by inhalation. In: Sorsa, M., Peltonen, K., Vainio, H., and Hemminki, K. (Eds.) Butadiene and Styrene: Assessment of Health Hazards (IARC Sci. Publ. No. 127), Lyon, France: IARC, pp. 217-224.
79. Korn, M., Gfrorer, W., Filser, J. G., Kessler, W. (1994). Styrene 7,8-oxide in blood of workers exposed to styrene. Arch. Toxicol. 68:524-527.
80. Korn, M., Wodarz, R., Drysch, K., Schoknecht, W., Schmal, F. W. (1985). Stereometabolism of styrene in man: Gas chromatographic determination of phenylethyleneglycol enantiomers and phenylethanol isomers in the urine of occupationally-exposed persons. Arch. Toxicol. 58:110-114.
81. Koskinen, M., Calebiro, D., Hemminki, K. (2000a). Styrene oxide-induced 2′-deoxycytidine adducts: implications for the mutagenicity of styrene oxide. Chem. Biol. Interact. 126:201-213.
82. Koskinen, M., Plna, K. (2000). Specific DNA adducts induced by some mono-substituted epoxides. Chem. Biol. Interact. 129:209-229.
83. Koskinen, M., Schweda, E. K. H., Hemminki, K. (1999). Alkylation of anionic DNA bases by styrene-7,8-oxide. J. Chem. Soc. Perkin Trans. 2:2441-2446.
84. Koskinen, M., Vodicka, P., Hemminki, K. (2000b) Adenine N3 is a main alkylation site of styrene oxide in double-stranded DNA. Chem. Biol. Interact. 124:13-27.
85. Koskinen, M., Vodicka, P., Hemminki, K. (2001a). Identification of 1-adenine DNA adducts in workers occupationally exposed to styrene. J. Occup. Environ. Med. 43:694-700.
86. Koskinen, M., Vodickova, L., Vodicka, P., Warner, S. C., Hemminki, K. (2001b). Kinetics of formation of specific styrene oxide adducts in double-stranded DNA. Chem. Biol. Interact. 138:111-124.
87. Kumar, R., Höglund, L., Zhao, C., Försti, A., Snellman, E., Hemminki, K. (2003). Single nucleotide polymorphisms in the XPG gene: Determination of role in DNA repair and breast cancer risk. Int. J. Cancer 103:671-675.
88. Kuricova, M., Naccarati, A., Kumar, R., Koskinen, M., Dusinska, M., Tulinska, J., Vodickova, L., Liskova, A., Jahnova, E., Fuortes, L., Haufroid, V., Hemminki, K., Vodicka, P. (2004). DNA repair and cyclin D1 polymorphisms and styrene-induced genotoxicity and immunotoxicity. Toxicol. Appl. Pharmacol, 207:S302-S309.
89. Laffon, B., Passaro, E., Mendez, J. (2001). Effects of styrene-7,8-oxide over p53, p21, bcl-2 and bax expression in human lymphocyte cultures. Mutagenesis 16:127-132.
90. Laffon, B., Pasaro, E., Mendez, J. (2002a). DNA damage and repair in human leucocytes exposed to styrene-7,8-oxide measured by comet assay. Toxicol. Lett. 126:61-68.
91. Laffon, B., Pasaro, E., Mendez, J. (2002b). Evaluation of genotoxic effects in a group of workers exposed to low levels of styrene. Toxicology 171:175-186.
92. Laffon, B., Perez-Cadahia, B., Pasaro, E., Mendez, J. (2003a). Individual sensitivity to DNA damage induced by styrene in vitro: Influence of cytochrome P450, epoxide hydrolase and glutathione S-transferase genotypes. Toxicology 15:131-141.
93. Laffon, B., Perez-Cadahia, B., Psaro, B., Mendez, J. (2003b). Effect of epoxide hydrolase and glutathione S-transferase genotypes on the induction of micronuclei and DNA damage by styrene 7,8-oxide. Mutat. Res. 536:49-59.
94. 6 is dependent on both the chirality of the lesion and the local sequence context. J. Biol. Chem. 268:23427-23434.
95. Lazutka, J. R., Lekevicius, R., Dedonyte, V., Maciuleviciute-Gervers, L., Mierauskiene, J., Rudaitiene, S., Slapsyte, G. (1999). Chromosomal aberrations and sister-chromatid exchanges in Lithuanian populations: Effects of occupational and environmental exposures. Mutat. Res. 445:225-239.
96. Leavens, T. L., Farris, G. M., James, R. A., Shah, R., Wong, V. A., Marshall, M. W., Bond, J. A. (1997). Genotoxicity and cytotoxicity in male B6C3F1 mice following exposure to mixtures of 1,3-butadiene and styrene. Environ. Molec. Mutagen. 29:335-345.
97. Lee, S. H., Norppa, H. (1995). Effects of indomethacin and arachidonic acid on sister chromatid exchange induction by styrene and styrene-7,8-oxide. Mutat. Res. 348:175-181.
98. Leibman, K., Ortiz, E. (1970). Epoxide intermediates in microsomal oxidation of olefins to glycols. J. Pharmacol. Exp. Therap. 173:242-246.
99. Loeb, L. A., Preston, B. D. (1986). Mutagenesis by apurinic/apyrimidinic sites. Annu. Rev. Genet. 20:201-230.
100. Ma, M., Umemura, T., Mori, Y., Gong, Y., Saijo, Y., Sata, F., Kawai, T., Kishi, R. (2005). Influence of genetic polymorphisms of styrene-metabolizing enzymes and smoking habits on levels of urinary metabolites after occupational exposure to styrene. Toxicol. Lett. 160:84-91.
101. Maestri, L., Imbriani, I., Ghittori, S., Capadoglio, E., Gobba, F., Cavalleri, A. (1997). Excretion of N-acetyl-S-(1-phenyl-2-hydroxyethyl)-cysteine and N-acetyl-S-(2-phenyl-2-hydroxyethyl)-cysteine in workers exposed to styrene. Sci. Total Environ. 199:13-22.
102. Manini, P., Buzio, L., Andreoli, R., Goldoni, M., Bergamaschi, E., Jakubowski, M., Vodicka, P., Hirvonen, A., Mutti, A. (2003). Assessment of biotransformation of the arene moiety of styrene in volunteers and occupationally exposed workers. Toxicol. Appl. Pharmacol. 189:160-169.
103. Manini, P., De Palma, G., Mozzoni, P., Andreoli, R., Poli, D., Bergamaschi, E., Franchini, I., Mutti, A. (2002). GSTM1 polymorphism and styrene metabolism: insights from an acute accidental exposure. Toxicol. Lett. 134:201-208.
104. Marczynski, B., Peel, M., Baur, X. (2000). New aspects in genotoxic risk assessment of styrene exposure-a working hypothesis. Med Hypotheses. 54: 619-623.
105. Marczynski, B., Rozynek, H., Ellichausen, J., Korn, M., Bauer, X. (1997). Detection of 8-hydroxydeoxyguanosine, a marker of oxidative DNA damage, in white blood cells of workers occupationally exposed to styrene. Arch. Toxicol. 71:496-500.
106. Mayer, C., Popanda, O, Zelezny, O., von Brevem, M.C., Bach, A., Bartsch, H., Schmezer, P. (2002). DNA repair capacity after γ-irradiation and expression profiles of DNA repair genes in resting and proliferating human peripheral blood lymphocytes. DNA Repair 1:237-250.
107. Mendrala, A. L., Langvardt, P. W., Nitschke, K. D., Quast, J. F., Nolan, R. J. (1993). In vitro kinetics of styrene and styrene oxide metabolism in rat, mouse and human. Arch. Toxicol. 67:18-27.
108. Migliore, L., Naccarati, A., Zanello, A., Scarpato, R., Bramanti, L., Mariani, M. (2002). Assessment of sperm DNA integrity in workers exposed to styrene. Hum. Reprod. 17:2912-2918.
109. Mohrenweiser, H. W., Xi, T., Vazquez-Matias, J., Jones, I. M. (2002). Identification of 127 amino acid substitution variants in screening 37 DNA repair genes in humans. Cancer Epidemiol. Biomarkers Prev. 11:1054-1064.
110. 6-substituted guanosine products resulting from reaction of guanosine with styrene oxide. J. Org. Chem. 51:2952-2955.
111. Naccarati, A., Soucek, P., Stetina, R., Haufroid, V., Kumar, R., Vodickova, L., Trtkova, K., Dusinska, M., Hemminki, K., Vodicka, P. (2006). Genetic polymorphisms and possible gene-gene interactions in metabolic and DNA repair genes: Effects on DNA damage. Mutat Res. 593:22-31.
112. Nakajima, T., Elovaara, E., Gonzales, F. J., Gelboin, H. V., Raunio, H., Pelkonen, O., Vainio, H., Aoyama, T. (1994a). Styrene metabolism by cDNA-expressed human hepatic and pulmonary cytochromes P450. Chem. Res. Toxicol. 7:891-896.
113. Nakajima, T., Wang, R.-S., Elovaara, E., Gonzales, F. J., Gelboin, H. V., Vainio, H., Aoyama, T. (1994b). CYP2C11 and CYP2B1 are major cytochrome P450 forms involved in styrene oxidation in liver and lung from untreated rats, respectively. Biochem. Pharmacol. 48:637-642.
114. Natarajan, A. T. (2002). Chrosome aberrations: past, present and future. Mutat. Res. 504:3-16.
115. Nestmann, E. R., Lynch, B. S., Ratpan, F. (2005). Perspective on the genotoxic risks of styrene. J. Toxicol. Environ. Health B Crtit. Rev. 8:95-107.
116. Nishi, Y., Hasegawa, M. M., Taketomi, M., Ohkawa, Y., Inui, N. (1984). Comparison of 6-thioguanine-resistant mutation and sister chromatid exchanges in Chinese hamster V79 cells with forty chemical and physical agents. Cancer Res. 44:3270-3279.
117. Norppa, H. (2003). Genetic susceptibility, biomarker responses, and cancer. Mutat. Res. 544:339-348.
118. Norppa, H. (2004). Cytogenetic biomarkers and genetic polymorphisms. Toxicol. Lett. 149:309-334.
119. Nylander-French, L. A., Kupper, L., Rappaport, S. M. (1999). An investigation of factors contributing to styrene and styrene-7,8-oxide exposures in the reinforced-plastics industry. Ann. Occup. Hyg. 43:99-109.
120. Oberheitmann, B., Frentzel-Beyme, R., Hoffmann, W. (2001). An application of the challenge aasay in boat builders exposed to low levels of styrene-a feasibility study of a possible biomarker for acquired susceptibility. Int. J. Hyg. Environ. Health 204:23-29.
121. Oesch, F. (1973). Mammalian epoxide hydrases: Inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds. Xenobiotica 3:305-340.
122. Oesch, F., Bentley, P. (1976). Antibodies against homogeneous epoxide hydratase provide evidence for a single enzyme hydrating styrene oxide and benzo[α]pyrene 4,5-oxide. Nature 259:53-55.
123. Oesch, F., Glatt, H. R., Schmassmann, H. U. (1977). The apparent ubiquity of epoxide hydratase in rat organs. Biochem. Pharmacol. 26:603-607.
124. Oesch, F., Herrero, M. E., Hengstler, J. G., Lohmann, M., Arand, M. (2000). Metabolic detoxification: Implications for thresholds. Toxicol. Pathol. 28:382-387.
125. 3H] styrene oxide. Biochim. Biophys. Acta 227:685-691.
126. Oesch, F., Jerina, D. M., Daly, J. W., Rice, J. (1973). Induction, activation and inhibition of epoxide hydrase: An anomalous prevention of chlorobenzene-induced hepatotoxicity by an inhibitor of epoxide hydrase. Chem. Biol. Interact. 6:189-202.
127. Oesch, F., Schmassmann, H. U., Ohnhaus, E., Althaus, U., Lorenz, J. (1980). Monooxygenase, epoxide hydrolase, and glutathione S-transferase activities in human lung: Variations between groups of bronchogenic carcinoma and non-cancer patients and interindividual differences. Carcinogenesis 1:827-835.
128. Oesch, F., Thoenen, H., Fahrländer, H. J. (1974). Epoxide hydrase in human liver biopsy specimens: Assay and properties. Biochem. Pharmacol. 23:1307-1317.
129. Ollikainen, T., Hirvonen, A., Norppa, H. (1998). Influence of GSTT1 genotype on sister chromatid exchange induction by styrene-7,8-oxide in cultured human lymphocytes. Environ. Molec. Mutagen. 31:311-315.
130. 6-position of guanine. Chem. Res. Toxicol. 12:93-99.
131. Otteneder, M., Lutz, U., Lutz, W. K. (2002). DNA adducts of styrene 7,8-oxide in target and non-target organs for tumor induction in rat and mouse after repeated inhalation exposure to styrene. Mutat. Res. 500:111-116.
132. Pagano, D. A., Yagen, B., Hernandez, O., Bend, J. R., Zeiger, E. (1982). Mutagenicity of (R) and (S) styrene 7,8-oxide and the intermediary mercapturic acid metabolites formed from styrene 7,8-oxide. Environ. Mutagen. 4:575-584.
133. Pantarotto, C., Fanelli, R., Bidoli, F., Morazzoni, P., Szczawinska, K. (1978). Arene oxides in styrene metabolism, a new perspective in styrene toxicity? Scand. J. Work Environ. Health 4:67-77.
134. Pauwels, W., Vodicka, P., Severi, M., Plna, K., Veulemans, H., Hemminki, K. (1996). Adduct formation on DNA and haemoglobin in mice intraperitoneally administered with styrene. Carcinogenesis 17:2673-2680.
135. 6-benzylguanine. Biochemistry 16:11998-20006.
136. 6-alkylguanine. FASEB J. 6:2302-2310.
137. Perera, F. P., Weinstein, I. B. (2000). Molecular epidemiology: recent advances and future directions. Carcinogenesis 21:517-524.
138. Pfäffli, P., Hesso, A., Vainio, H., Hyvonen, M. (1981). 4-Vinylphenol excretion suggestive of arene oxide formation in workers occupationally exposed to styrene. Toxicol. Appl. Pharmacol. 60:85-90.
139. Phillips, D. H., Farmer, P. B. (1994.) Evidence for DNA and protein binding by styrene and styrene oxide. Crit. Rev. Toxicol. 24:S35-46.
140. Pilger, A., Rudiger, H. W. (2006). 8-Hydroxy-2′-deoxyguanosine as a marker of oxidative DNA damage related to occupational and environmental exposures. Int. Arch. Occup. Environ. Health 80:1-15.
141. 6-substituted adenine and 3-substituted cytosine/uracil: Formation and persistence in vitro and in vivo. Carcinogenesis 20:2025-2032.
142. Preston, J. R., Abernathy, D. J. (1993). Studies on the induction of chromosomal aberrations and sister chromatid exchange in rats exposed to styrene by inhalation. In: Sorsa, M., Peltonen, K., Vainio, H,. and Hemminki, K. (Eds.) Butadiene and Styrene: Assessment of Health Hazards (IARC Sci. Publ. No. 127), Lyon, France: IARC, pp. 225-233.
143. 6-positions. Chem. Res. Toxicol. 8:389-395.
144. Rappaport, S. M., Yeowell-O'Connell, K., Bodell, W., Yager, J. W., Symanski, E. (1996). An investigation of multiple biomarkers among workers exposed to styrene and styrene-7,8-oxide. Cancer Res. 56:5410-5416.
145. Rossner, P., Boffetta, P., Ceppi, M., Bonassi, S., Smerhovsky, Z., Landa, K., Juzova, D., Sram, R. J. (2005). Chromosomal aberrations in lymphocytes of healthy subjects and risk of cancer. Environ Health Perspect. 113:517-520.
146. Ruder, A. M., Ward, E. M., Dong, M., Okun, A. H., Davis-King, K. (2004). Mortality patterns among workers exposed to styrene in the reinforced plastic boatbuilding industry: An update. Am. J. Ind. Med. 45:165-176.
147. Sasaki, Y. F., Izumiyama, F., Nishidate, E., Matsusaka, N., Tsuda, S. (1997). Detection of rodent liver carcinogen genotoxicity by the alkaline single-cell gel electrophoresis (Comet) assay in multiple mouse organs (liver, lung, spleen, kidney and bone marrow). Mutat. Res. 391:201-214.
148. Sato, A., Nakajima, T. (1985). Enhanced metabolism of volatile hydrocarbons in rat liver following food deprivation, restricted carbohydrate intake, and administration of ethanol, phenobarbital, polychlorinated biphenyl and 3-methylcholanthrene: A comparative study. Xenobiotica 15:67-75.
149. Savela, K., Hesso, A., Hemminki, K. (1986). Characterization of reaction products between styrene oxide and deoxynucleosides and DNA. Chem. Biol. Interact. 60:235-246.
150. Scott, D., Preston, R. J. (1994). A re-evaluation of the cytogenetic effects of styrene. Mutat. Res. 318:175-203.
151. Seutter-Berlage, F., Delbressine, L. P. C., Smets, F. I., Ketlaars, H. C. J. (1978). Identification of three sulphur-containing metabolites of styrene in the rat. Xenobiotica 8:413-418.
152. Shamy, M. Y., Osman, H. H., Kandeel, K. M., Abdel-Moneim, N. M., El Said, K. F. (2002). DNA single strand breaks induced by low levels of occupational exposure to styrene. J. Environ. Path. Toxicol. Oncol. 21:57-61.
153. Shield, A. J., Sanderson, B. J. (2001). Role of glutathione S-transferase μ (GSTM1) in styrene-7,8-oxide toxicity and mutagenicity. Environ. Molec. Mutagen. 37:285-289.
154. Shield, A. J., Sanderson, B. J. (2004). A recombinant model for assessing the role of GSTM1 in styrene-7,8-oxide toxicity and mutagenicity. Toxicology 195:61-68.
155. Shields, P. G., Harris, C. C. (2000). Cancer risk and low-penetrance susceptibility genes in gene-environment interactions. J. Clin. Oncol. 18:2309-2315.
156. Simula, A. P., Priestly, B. G. (1992). Species differences in the genotoxicity of cyclophosphamide and styrene in three in vivo assays. Mutat. Res. 271:49-58.
157. Sinsheimer, J. E., Chen, R., Das, S. K., Hooberman, H. Osorio, S., You, Z. (1993). The genotoxicity of enantiomeric aliphatic epoxides. Mutat. Res. 298:197-206.
158. Somorovska, M., Jahnova, E., Tulinska, J., Zamecnikova, M., Sarmanova, J., Terenova, A., Vodickova, L., Liskova, A., Vallova, B., Soucek, P., Hemminki, K., Norppa, H., Hirvonen, A., Tates, A. D., Fuortes, L., Dusinska, M., Vodicka, P. (1999). Biomonitoring of occupational exposure to styrene in a plastics lamination plant. Mutat. Res. 428:255-269.
159. Speit, G., Henderson, L. (2005). Review of the in vivo genotoxicity tests performed with styrene. Mutat. Res. 589:67-79.
160. Sumner, S. J., Fennell, T. R. (1994). Review of the metabolic fate of styrene. Crit. Rev. Toxicol. 24:S11-33.
161. Tates, A. D., Grummt, T., Törnqvist, M., Farmer, P. B., van Damm, F. J., van Mossel, H., Schoemaker, H. M., Osterman-Golkar, S., Uebel, C., Tang, Y. S., Zwinderman, A. H., Natarajan, A. T., Ehrenberg, L. (1991). Biological and chemical monitoring of occupational exposure to ethylene oxide. Mutat. Res. 250:483-497.
162. Tates, A. D., Grummt, T., van Damm, F. J., de Zwart, F., Kasper, F. J., Rothe, R., Stirn, H., Zwinderman, A. H., Natarajan, A. T. (1994). Measurement of frequencies of HPRT mutants, chromosomal aberrations, micronuclei, sister-chromatid exchanges and cells with high frequencies of SCEs in styrene/dichloromethane-exposed workers. Mutat. Res. 313:249-262.
163. Teixeira, J. P., Gaspar, J., Silva, S., Torres, J., Silva, S. N., Conceicao Azevedo, M., Neves, P., Laffon, B., Mendez, J., Goncalves, C., Mayan, O., Farmer, P. B., Rueff, J. (2004). Occupational exposure to styrene: Modulation of cytogenetic damage and levels of urinary metabolites of styrene by polymorphisms in genes CYP2E1, EPHX1, GSTM1, GSTT1 and GSTP1. Toxicology 195:231-242.
164. Thilly, W. G. (2003). Have environmental mutagens caused oncomutations in people? Nature Genet. 34:255-259.
165. Tornero-Velez, R., Rappaport, S. M. (2001). Physiological modeling of the relative contributions of styrene-7,8-oxide derived from direct inhalation and from styrene metabolism to the systemic dose in humans. Toxicol. Sci. 64:151-161.
166. Tsuda, S., Matsusaka, N., Madarame, H., Miyamae, Y., Ishida, K., Satoh, M., Sekihashi, K., Sasaki, Y. F. (2000). The alkaline single cell electrophoresis assay with eight mouse organs: Results with 22 mono-functional alkylating agents (including 9 dialkyl N-nitrosoamines) and 10 DNA crosslinkers. Mutat. Res. 467:83-98.
167. Turner, M., Mantick, N. A., Carlson, G. P. (2005). Comparison of the depletion of glutathione in mouse liver and lung following administration of styrene and its metabolites styrene oxide and 4-vinylphenol. Toxicology 206:383-388.
168. Tzeng, H. F., Laughlin, L. T., Armstrong, R. N. (1998). Semifunctional site-specific mutants affecting the hydrolytic half-reaction of microsomal epoxide hydrolase. Biochemistry 37:2905-2911.
169. Uusküla, M., Järventaus, H., Hirvonen, A., Sorsa, M., Norppa, H. (1995). Influence of GSTM1 genotype on sister chromatid exchange induction by styrene-7,8-oxide and 1,2-epoxy-3-butene in cultured human lymphocytes. Carcinogenesis 16:947-950.
170. Vaghef, H., Hellman B. (1998). Detection of styrene and styrene oxide-induced DNA damage in various organs of mice using the comet assay. Pharmacol. Toxicol. 83:69-74.
171. Van Hummelen, P., Severi, M., Pauwels, W., Roosels, D., Veulemans, H., Kirsch-Volders, M. (1994). Cytogenetic analysis of lymphocytes from fiberglass-reinforced plastics workers occupationally exposed to styrene. Mutat Res. 310:157-165.
172. Vettori, M. V., Caglieri, A., Goldoni, M., Castoldi, A. F., Dare, E., Alinovi, R., Ceccatelli, S., Mutti, A. (2005). Analysis of oxidative stress in SK-N-MC neurons exposed to styrene-7,8-oxide. Toxicol. In Vitro 19:11-20.
173. 6-guanine DNA adducts, DNA strand breaks and mutant frequencies in the hypoxanthine guanine phosphoribosyltransferase gene in T-lymphocytes. Carcinogenesis 16:1473-1481.
174. 32P-postlabelling of DNA adducts in styrene oxide-modified DNA and in workers exposed to styrene. In M. Sorsa, K. Peltonen, H. Vainio, K. Hemminki (eds.), Butadiene and Styrene: Assessment of Health Hazards, Vol. 127, Lyon, France: IARC Sci. Publ., pp. 109-118.
175. Vodicka, P., Koskinen, M., Arand, M., Oesch, F., Hemminki, K. (2002a). Spectrum of styrene-induced DNA adducts: The relationship to other biomarkers and prospects in human biomonitoring. Mutat. Res. 511:239-254.
176. Vodicka, P., Koskinen, M., Stetina, R., Soucek, P., Vodickova, L., Matousu, Z., Kuricova, M., Hemminki, K. (2003). The role of various biomarkers in the evaluation of styrene genotoxicity. Cancer Detect. Prevent. 27:275-284.
177. Vodicka, P., Koskinen, M., Vodickova, L., Stetina, R., Smerak, P., Barta, I., Hemminki, K. (2001a). DNA adducts, strand breaks and micronuclei in mice exposed to styrene by inhalation. Chem. Biol. Interact. 137:213-227.
178. 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., Norrpa, H. M, Buchancova, J., Hemminki, K. (2004a). Markers of individual susceptibility and DNA repair rate in workers exposed to xenobiotics in a tire plant. Environ. Molec. Mutagen. 44:283-292.
179. Vodicka, P., Kumar, R., Stetina, R., Sanyal, S., Soucek, P., Haufroid, V., Dusinska, M., Kuricova, M., Zamecnikova, M., Musak, L., Buchancova, J., Norppa, H., Hirvonen, A., Vodickova, L., Naccarati, A., Matousu, Z., Hemminki, K. (2004b). Genetic polymorphisms in DNA repair genes and possible links with DNA repair rates, chromosomal aberrations and single-strand breaks in DNA. Carcinogenesis 25:757-763.
180. Vodicka, P. E., Linhart, I., Novak, J., Koskinen, M., Vodickova, L., Hemminki, K. (2006). 7-Alkylguanine adduct levels in urine, lungs and liver of mice exposed to styrene by inhalation. Toxicol. Appl. Pharmacol. 2010:1-8.
181. 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. (2001b). Association between genetic polymorphisms and biomarkers in styrene-exposed workers. Mutat. Res. 482:91-105.
182. Vodicka, P., Stetina, R., Koskinen, M., Soucek, P., Vodickova, L., Hlavac, P., Kuricova, M., Necasova, R., Hemminki, K. (2002b). New aspects in the biomonitoring of occupational exposure to styrene. Int. Arch. Occup. Environ. Health 75:75-85.
183. 32P- postlabelling in DNA and human embryonal lung fibroblasts (HEL). Carcinogenesis 17:801-808.
184. Vodicka, P., Tuimala, J., Stetina, R., Kumar, R., Manini, P., Naccarati, A., Maestri, L., Vodickova, L., Kuricova, M., Järventaus, H., Majvaldova, Z., Hirvonen, A., Imbriani, M., Mutti, A., Migliore, L., Norppa, H., Hemminki, K. (2004c). Cytogenetic markers, DNA single-strand breaks, urinary metabolites and DNA repair rates in styrene-exposed lamination workers. Environ. Health Perspect. 112:867-871.
185. Vodicka, P., Tvrdik, T., Osterman-Golkar, S., Vodickova, L., Peterkova, K., Soucek, P., Sarmanova, J., Farmer, P. B., Granath, F., Lambert, B., Hemminki, K. (1999). An evaluation of styrene genotoxicity using several biomarkers in a 3-year follow-up study of hand-lamination workers. Mutat. Res. 445:205-224.
186. 32P- postlabelling of DNA adducts of styrene-exposed lamination workers. Carcinogenesis 14:2059-2061.
187. 32P-postlabelling. Carcinogenesis 15:1949-1953.
188. Walles, S. A. S., Edling, C., Anundi, H., Johanson, G. (1993). Exposure dependent increase in DNA single strand breaks in leucocytes from workers exposed to low concentrations of styrene. Br. J. Ind. Med. 50:570-574.
189. Watabe, T., Hiratsuka, A., Sone, T., Ishihama, T., Endoh, K. (1984). Hepatic microsomal oxidation of styrene to 4-hydroxystyrene 7,8-glycol via 4-hydroxystyrene and its 7,8-oxide as short-lived intermediates. Biochem. Pharmacol. 3:3101-3103.
190. Watabe, T., Isobe, M., Yoshikawa, K., Takabatake, E. (1978). Studies on the metabolism and toxicity of styrene. I. Biotransformation of styrene to styrene glycol via styrene oxide by rat liver microsomes. J. Pharm. Dyn. 1:98-104.
191. Watabe, T., Ozawa, N., Yoshikawa, K. (1981). Stereochemistry in the oxidative metabolism of styrene by hepatic microsomes. Biochem. Pharmacol. 30:1695-1698.
192. Watabe, T., Ozawa, N., Yoshikawa, K. (1982). Studies on the metabolism and toxicity of styrene. V. The metabolism of styrene, racemic, (R)-(+)-, and (S)-(-)-phenyloxiranes in the rat. J. Pharm. Dyn. 5:129-133.
193. Wenker, M. A. M., Kecic, S., Monster, A. C., de Wolff, F. A. (2000). Metabolism of styrene-7,8-oxide in human liver in vitro: Interindividual variation and stereochemistry. Toxicol. Appl. Pharmacol. 169:52-58.
194. Wenker, M. A. M., Kecic, S., Monster, A. C., de Wolff, F. A. (2001). Metabolism of styrene in human liver in vitro: Interindividual variation and enantioselectivity. Xenobiotica 31:61-72.
195. Wilson, H. K., Robertson, S. M., Waldron, H. A., Gompertz, D. (1983). Effect of alcohol on the kinetics of mandelic acid excretion in volunteers exposed to styrene vapour. Br. J. Ind. Med. 40:75-80.
196. Winsey, S. L., Haldar, N. A., Marsh, H. P., Bunce, M., Marshall, S. E., Harris, A. L., Wojnarowska, F., Welsh, K. I. (2000). A variant within the DNA repair gene XRCC3 is associated with the development of melanoma skin cancer. Cancer Res. 60:5612-5616.
197. Yeowell-O'Connell, K., Jin, Z., Rappaport, S. M. (1996). Determination of albumin and hemoglobin adducts in workers exposed to styrene and styrene oxide. Cancer Epid. Biomarkers Prevent. 5:205-215.
198. Zhang, W., Johnson, F., Grollman, A. P., Shibutani, S. (1995). Miscoding by the exocyclic and related DNA adducts 3,N4-etheno-2′-deoxycytidine, 3,N4-ethano-2′-deoxycytidine, and 3-(2-hydroxyethyl)-2′- deoxyuridine. Chem. Res. Toxicol. 8:157-163.
199. Zhao, C., Vodicka, P., Sram, R. J., Hemminki, K. (2000). Human DNA adducts of 1,3-butadiene, an important environmental carcinogen. Carcinogenesis 21:107-111.