Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 41, 2011 - Issue 1
240
Views
7
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

In vitro metabolism, glutathione conjugation, and CYP isoform specificity of epoxidation of 4-vinylphenol

, , , , , & show all
Pages 6-23 | Received 22 Jul 2010, Accepted 10 Sep 2010, Published online: 07 Oct 2010

References

  • Bakke OM. (1969a). Urinary simple phenols in rats fed diets containing different amounts of casein and 10 per cent tyrosine. J Nutr 98:217–221.
  • Bakke OM. (1969b). Urinary simple phenols in rats fed purified and nonpurified diets. J Nutr 98:209–216.
  • Bakke OM, Scheline RR. (1970). Hydroxylation of aromatic hydrocarbons in the rat. Toxicol Appl Pharmacol 16:691–700.
  • Bratton SB, Lau SS, Monks TJ. (1997). Identification of quinol thioethers in bone marrow of hydroquinone/phenol-treated rats and mice and their potential role in benzene-mediated hematotoxicity. Chem Res Toxicol 10:859–865.
  • Carlson G. (2004). Influence of selected inhibitors on the metabolism of the styrene metabolite 4-vinylphenol in wild-type and CYP2E1 knockout mice. J Toxicol Environ Health Part A 67:905–909.
  • Carlson GP. (2002). Effect of the inhibition of the metabolism of 4-vinylphenol on its hepatotoxicity and pneumotoxicity in rats and mice. Toxicology 179:129–136.
  • Carlson GP, Perez Rivera AA, Mantick NA. (2001). Metabolism of the styrene metabolite 4-vinylphenol by rat and mouse liver and lung. J Toxicol Environ Health Part A 63:541–551.
  • Carlson GP, Ullman M, Mantick NA, Snyder PW. (2002). 4-Vinylphenol-induced pneumotoxicity and hepatotoxicity in mice. Toxicol Pathol 30:565–569.
  • Dehal SS, Kupfer D. (1996). Evidence that the catechol 3,4-Dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins. Cancer Res 56:1283–1290.
  • Devanesan P, Santen RJ, Bocchinfuso WP, Korach KS, Rogan EG, Cavalieri E. (2001). Catechol estrogen metabolites and conjugates in mammary tumors and hyperplastic tissue from estrogen receptor-alpha knock-out (ERKO)/Wnt-1 mice: implications for initiation of mammary tumors. Carcinogenesis 22:1573–1576.
  • Fustinoni S, Manini P, Campo L, De Palma G, Andreoli R, Mutti A, Bertazzi PA, Rappaport SM. (2010). Assessing variability and comparing short-term biomarkers of styrene exposure using a repeated measurements approach. Toxicol Lett 192:40–44.
  • Gemechu-Hatewu M, Platt KL, Oesch F, Hacker HJ, Bannasch P, Steinberg P. (1997). Metabolic activation of aflatoxin B1 to aflatoxin B1-8,9-epoxide in woodchucks undergoing chronic active hepatitis. Int J Cancer 73:587–591.
  • Guengerich FP. (1982). Microsomal Enzymes involved in Toxicology-Analysis and separation. Principles and Methods of Toxicology (AW Hayes, ed.). Raven Press, New York, 609–634.
  • Himmelstein MW, Carpenter SC, Hinderliter PM. (2004). Kinetic modeling of beta-chloroprene metabolism: I. In vitro rates in liver and lung tissue fractions from mice, rats, hamsters, and humans. Toxicol Sci 79:18–27.
  • Hiramatsu M, Kumagai Y, Unger SE, Cho AK. (1990). Metabolism of methylenedioxymethamphetamine: formation of dihydroxymethamphetamine and a quinone identified as its glutathione adduct. J Pharmacol Exp Ther 254:521–527.
  • Johnson BM, Qiu SX, Zhang S, Zhang F, Burdette JE, Yu L, Bolton JL, van Breemen RB. (2003). Identification of novel electrophilic metabolites of piper methysticum Forst (Kava). Chem Res Toxicol 16:733–740.
  • Linhart I, Mráz J, Scharff J, Krouzelka J, Dusková S, Nohová H, Vodicková L. (2010). New urinary metabolites formed from ring-oxidized metabolic intermediates of styrene. Chem Res Toxicol 23:251–257.
  • López R, Aznar M, Cacho J, Ferreira V. (2002). Determination of minor and trace volatile compounds in wine by solid-phase extraction and gas chromatography with mass spectrometric detection. J Chromatogr A 966:167–177.
  • Manini P, Andreoli R, Poli D, De Palma G, Mutti A, Niessen WM. (2002). Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat. Rapid Commun Mass Spectrom 16:2239–2248.
  • Peppercorn MA, Goldman P. (1972). Caffeic acid metabolism by gnotobiotic rats and their intestinal bacteria. Proc Natl Acad Sci USA 69:1413–1415.
  • Pfäffli P, Hesso A, Vainio H, Hyvönen M. (1981). 4-Vinylphenol excretion suggestive of arene oxide formation in workers occupationally exposed to styrene. Toxicol Appl Pharmacol 60:85–90.
  • Reinke LA, Moyer MJ. (1985). p-Nitrophenol hydroxylation. A microsomal oxidation which is highly inducible by ethanol. Drug Metab Dispos 13:548–552.
  • Schlosser PM, Bond JA, Medinsky MA. (1993). Benzene and phenol metabolism by mouse and rat liver microsomes. Carcinogenesis 14:2477–2486.
  • Schnellmann RG. (1989). 2-Bromohydroquinone-induced toxicity to rabbit renal proximal tubules: evidence against oxidative stress. Toxicol Appl Pharmacol 99:11–18.
  • Schwarz M, Wabnitz TC, Winterhalter P. (2003). Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wines. J Agric Food Chem 51:3682–3687.
  • Shen L, Pisha E, Huang Z, Pezzuto JM, Krol E, Alam Z, van Breemen RB, Bolton JL. (1997). Bioreductive activation of catechol estrogen-ortho-quinones: aromatization of the B ring in 4-hydroxyequilenin markedly alters quinoid formation and reactivity. Carcinogenesis 18:1093–1101.
  • Simmonds AC, Reilly CA, Baldwin RM, Ghanayem BI, Lanza DL, Yost GS, Collins KS, Forkert PG. (2004). Bioactivation of 1,1-dichloroethylene to its epoxide by CYP2E1 and CYP2F enzymes. Drug Metab Dispos 32:1032–1039.
  • Simpson CJ, Fitzhenry MJ, Stamford NP. (2005). Preparation of vinylphenols from 2- amd 4-hydroxybenzaldehydes. Tetrahedron Lett 46:6893–6896.
  • Solomon EI, Chen P, Metz M, Lee SK, Palmer AE. (2001). Oxygen Binding, Activation, and Reduction to Water by Copper Proteins. Angew Chem Int Ed Engl 40:4570–4590.
  • Takasu A, Bando T, Morimoto Y, Shibata Y, Hirabayashi T. (2005). Asymmetric epoxidation of alpha-olefins having neighboring sugar chiral templates and alternating copolymerization with dicarboxylic anhydrides. Biomacromolecules 6:1707–1712.
  • Vidyasagar T, Sujatha N, Sashidhar RB. (1997). Direct synthesis of aflatoxin B1-N7 guanine adduct: a reference standard for biological monitoring of dietary aflatoxin exposure in molecular epidemiological studies. Food Addit Contam 14:457–467.
  • 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 33:3101–3103.
  • Zhang F, Chen Y, Pisha E, Shen L, Xiong Y, van Breemen RB, Bolton JL. (1999). The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone. Chem Res Toxicol 12:204–213.
  • Zhang F, Fan PW, Liu X, Shen L, van Breeman RB, Bolton JL. (2000). Synthesis and reactivity of a potential carcinogenic metabolite of tamoxifen: 3,4-dihydroxytamoxifen-o-quinone. Chem Res Toxicol 13:53–62.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.