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Cytochrome P450-mediated metabolism of N-(2-methoxyphenyl)-hydroxylamine, a human metabolite of the environmental pollutants and carcinogens o-anisidine and o-nitroanisole Cover

Cytochrome P450-mediated metabolism of N-(2-methoxyphenyl)-hydroxylamine, a human metabolite of the environmental pollutants and carcinogens o-anisidine and o-nitroanisole

Interdisciplinary Toxicology
Volume 1 (2008): Issue 3-4 (December 2008)
By: ,  ,  ,  ,  ,  ,  ,   and    
Open Access
|Nov 2010
References

References

  1. Balaban AT, Garfield RE, Lesko MJ, Seitz WA. (1998) Synthesis and spectral data of some new N-nitroso-N-phenylhydroxylamine (cupferron) derivatives.: 439-446.
    Open DOISearch in Google Scholar
  2. Beland FA, Fullerton NF, Heflich RH. (1984) Rapid isolation, hydrolysis and chromatography of formaldehyde-modified DNA.: 121-131.
    Open DOISearch in Google Scholar
  3. Branner B, Kutzer C, Zwickenpflug W, Scherer G, Heller W-D, Richter E. (1998) Haemoglobin adducts from aromatic amines and tobacco-specific nitrosamines in pregnant smoking and non-smoking women.: 35-47.
    Open DOISearch in Google Scholar
  4. Brennan RJ, Schiestl RH. (1997). Aniline and its metabolite generate free radicals in yeast.: 215-220.
    Search in Google Scholar
  5. Brennan RJ, Schiestl RH. (1999) The aromatic amine carcinogens-toluidine and-anisidine induce free radicals and intrachromosomal recombination in Saccharomyces cerevisiae.: 37-45.
    Search in Google Scholar
  6. Cheng G, Shi Y, Sturla S, Jalas J, McIntee EJ, Villalta PW, Wang M, Hecht SS. (2003) Reactions of formaldehyde plus acetaldehyde with deoxyguanosine and DNA: Formation of cyclic deoxyguanosine adducts and formaldehyde cross-links.: 145-152.
    Open DOISearch in Google Scholar
  7. Dhareshwar SS, Stella VJ. (2008) Your prodrug releases formaldehyde: Should you be concerned? No!97: 4184-4193.
    Open DOISearch in Google Scholar
  8. Falter B, Kutzer C, Richter E. (1994) Biomonitoring of hemoglobin adducts: aromatic amines and tobacco-specific nitrosamines.: 364-371.
    Open DOISearch in Google Scholar
  9. Garner RC, Martin CN, Clayson DB (1984) (2nd ed. Searle C, Ed.) Carcinogenic aromatic amines and related compounds. Chemical Carcinogens,182, Vol. 1: pp. 175-302, American Chemical Society, Washington, DC.
    Search in Google Scholar
  10. Hauthal HG. (1993) Rosenmontag und die Folgen die Störfälle der Hoechst AG.: 440.
    Search in Google Scholar
  11. Hodek P, Jansčák P, Anzenbacher P, Burkhard J, Janků J, Vodička L. (1988) Metabolism of diamantane by rat-liver microsomal-cytochromes P-450.: 1109-1118.
    Open DOISearch in Google Scholar
  12. Huang H, Hopkins PB. (1993) DNA interstrand cross-linking by formaldehyde: nucleotide sequence preference and covalent structure of the predominant cross-link formed in synthetic oligonucleotides.: 9402-9408.
    Open DOISearch in Google Scholar
  13. Imaoka S, Osada M, Minamiyama Y, Yukimura T, Toyokuni S, Takemura S, Hiroi T, Funae Y. (2004) Role of phenobarbital-inducible cytochrome P450s as a source of active oxygen species in DNA-oxidation.: 117-125.
    Open DOISearch in Google Scholar
  14. IARC (1982) Ortho- and para-anisidine and their hydrochlorides. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, No. 27, IARC, Lyon.
    Search in Google Scholar
  15. IARC (2006) Formaldehyde, 2-butoxyethanol and 1-terc-butoxypropan-2-ol. IARC Monographs on the Evaluation of Carcinogenic Risk to Humans, Vol. 88, pp. 39-325, IARC, Lyon.
    Search in Google Scholar
  16. Kim D, Kadlubar FF, Teitel CH, Guengerich FP. (2004) Formation and reduction of aryl and heterocyclic nitroso compounds and significance in the flux of hydroxylamines.: 529-536.
    Open DOISearch in Google Scholar
  17. Kirchner G, Bayer U. (1992) Genotoxic activity of the aminophenols as evidenced by the induction of sister chromatid exchanges.: 387-392.
    Search in Google Scholar
  18. Mikšanová M, Novák P, Frei E, Stiborová M. (2004) Metabolism of carcinogenic 2-nitroanisole by rat, rabbit, porcine and human hepatic cytosol.: 589-602.
    Open DOISearch in Google Scholar
  19. Naiman K, Dračínská H, Martínková M, Šulc M, Dračínský M, Kejíková L, Hodek P, Hudeček J, Liberda J, Schmeiser HH, Frei E, Stiborová M. (2008) Redox cycling in the metabolism of the environmental pollutant and suspected human carcinogen-anisidine by rat and rabbit hepatic microsomes.: 1610-1621.
    Open DOISearch in Google Scholar
  20. NTP (1978) Bioassay of o-anisidine hydrochloride for possible carcinogenicity. NTP Technical Report 89, National Institute of Health, US Department of Health and Human Services, Bethesda, MD.
    Search in Google Scholar
  21. NTP (1993) Toxicology and Carcinogenesis. Studies of 2-nitroanisole. NTP Technical Report 416, National Institute of Health, US Department of Health and Human Services, Bethesda, MD.
    Search in Google Scholar
  22. Okhuma Y, Kawanishi S. (2001) Oxidative DNA damage induced by a metabolite of carcinogenic o-anisidine: enhancement of DNA damage and alteration in its sequence specificity by superoxide dismutase.: 49-56.
    Search in Google Scholar
  23. Omura T, Sato R. (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature.: 2370-2378.
    Search in Google Scholar
  24. Richter E, Rosler S, Scherer G, Gostomzyk JG, Grubl A, Kamer U, Behrendt H. (2001) Haemoglobin adducts from aromatic amines in children in relation to area of residence and exposure to environmental tobacco smoke.: 421-428.
    Open DOISearch in Google Scholar
  25. Rýdlová H, Mikšanová M, Ryšlavá H, Stiborová M. (2005) Carcinogenic pollutants-nitroanisole and-anisidine are substrates and inducers of cytochromes P450.: 441-447.
    Open DOISearch in Google Scholar
  26. Sasaki YF, Nishidate E, Su YQ, Matsusaka N, Tsuda S, Susa N, Furukawa Y, Ueno S. (1998) Organ-specific genotoxicity of the potent rodent bladder carcinogens-anisidine and-cresidine.: 155-160.
    Open DOISearch in Google Scholar
  27. Seidenfaden W. (1971) Methoden der Organischen Chemie (Houben-Weyl), Band X/1, Georg Thieme Verlag, Stuttgart, p. 1058.
    Search in Google Scholar
  28. Sottocasa GL, Kuylenstierna I, Ernster I, Bergstrand A. (1967) An electron transport system associated with the outer membrane of liver mitochondria.: 415-438.
    Open DOISearch in Google Scholar
  29. Stabbert R, Schäfer K-H, Biefel C, Rustemeier K. (2003) Analysis of aromatic amines in cigarette smoke.: 2125-2132.
    Open DOISearch in Google Scholar
  30. Stiborová M, Asfaw B, Anzenbacher P, Lešetický L, Hodek P. (1988) The first identification of the benzenediazonium ion formation from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomes of rat livers.: 319-326.
    Open DOISearch in Google Scholar
  31. Stiborová M, Asfaw B, Frei E, Schmeiser HH, Wiessler M. (1995) Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct.: 489-498.
    Open DOISearch in Google Scholar
  32. Stiborová M, Mikšanová M, Havlíček V, Schmeiser HH, Frei E. (2002) Mechanism of peroxidase-mediated oxidation of carcinogenic-anisidine and its binding to DNA.: 49-66.
    Open DOISearch in Google Scholar
  33. Stiborová M, Mikšanová M, Smrček S, Bieler CA, Breuer A, Klokow KA, Schmeiser HH., Frei E. (2004) Identification of a genotoxic mechanism for 2-nitroanisole carcinogenicity and of its carcinogenic potential for humans.: 833-840.
    Search in Google Scholar
  34. Stiborová M, Mikšanová M, Šulc M, Rýdlová H, Schmeiser HH, Frei E. (2005) Identification of a genotoxic mechanism for the carcinogenicity of the environmental pollutant and suspected human carcinogen-anisidine.: 667-678.
    Open DOISearch in Google Scholar
  35. Stiborová M, Schmeiser HH, Breuer A, Frei E. (2001) Evidence for activation of carcinogenic-anisidine by prostaglandin H synthase:P-postlabelling analysis of DNA adducts formation.: 267-279.
    Search in Google Scholar
  36. Stiborová M, Schmeiser HH, Frei E. (1998) To the mechanism of 2-nitroanisole carcinogenicity: in vitro metabolism of 2-nitroanisole mediated by peroxidases and xanthine oxidase.: 857-869.
    Open DOISearch in Google Scholar
  37. Traupe H, Menge G, Kandt J, Karmaus W. (1997) Higher frequency of atopic dermatitis and decrease in viral warts among children exposed to chemicals liberated in a chemical accident in Frankfurt, Germany.: 112-118.
    Open DOISearch in Google Scholar
  38. U. S. Department of Health and Human Services (2004) 11Report on Carcinogens, U. S. Government Printing Office, Washington, DC.
    Search in Google Scholar
  39. Weiss T, Angerer J. (2003) Simultaneous determination of various aromatic amines and metabolites of aromatic nitro compounds in urine for low level exposure using gas chromatography-mass spectrometry.: 179-192.
    Search in Google Scholar
  40. Wiechelman KJ, Braun RD, Fitzpatrick JD. (1988) Investigation of the bicinchoninic acid protein assay: identification of the groups responsible for color formation.: 231-237.
    Open DOISearch in Google Scholar
  41. Yang CS, Tu YY, Koop DR, Coon MJ. (1985) Metabolism of nitrosamines by purified rabbit liver cytochrome P-450 isozymes.: 1140-1145.
    Search in Google Scholar
DOI: https://doi.org/10.2478/v10102-010-0045-8 | Journal eISSN: 1337-9569 | Journal ISSN: 1337-6853
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Language: English
Page range: 218 - 224
Published on: Nov 1, 2010
Published by: Slovak Academy of Sciences, Institute of Experimental Pharmacology & Toxicology, Centre of Experimental Medicine
In partnership with: Paradigm Publishing Services
Keywords:
o-anisidine,
N-(2-methoxyphenyl)hydroxylamine,
metabolism,
oxidation,
cytochrome P450
Related subjects:
Medicine,
Clinical medicine,
Pharmacology, toxicology

© 2010 Karel Naiman, Helena Dračínská, Martin Dračínský, Markéta Martínková, Václav Martínek, Petr Hodek, Martin Štícha, Eva Frei, Marie Stiborová, published by Slovak Academy of Sciences, Institute of Experimental Pharmacology & Toxicology, Centre of Experimental Medicine
This work is licensed under the Creative Commons License.

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