Skip to main content
Have a personal or library account? Click to login
Oxidation of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxy-naphthalene (Sudan I) by cytochromes P450 and peroxidases: a comparative study Cover

Oxidation of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxy-naphthalene (Sudan I) by cytochromes P450 and peroxidases: a comparative study

Interdisciplinary Toxicology
Volume 2 (2009): Issue 3 (September 2009)
By: ,  ,  ,  ,  ,  ,   and    
Open Access
|Sep 2009
References

References

  1. An Y, Jiang L, Cao J, Geng C, Zhong L. (2007). Sudan I induces genotoxic effects and oxidative DNA damage in HepG2 cells.: 164-170.
    Search in Google Scholar
  2. Cameron TP, Hughes TJ, Kirby PE, Fung VA, Dunkel VC. (1987). Mutagenic activity of 27 dyes and related chemicals in the/microsome and mouse lymphoma TKassays.: 223-261.
    Search in Google Scholar
  3. Chen L, Devanesan PD, Higginbotham S, Ariese F, Jankowiak R, Small GJ, Rogan EG, Cavalieri EL. (1996). Expanded analysis of benzo[a]pyrene-DNA adducts formedand in mouse skin: their significance in tumor initiation.: 897-903.
    Search in Google Scholar
  4. Childs JJ, Clayson DS. (1966). The metabolism of 1-phenylazo-2-naphthol in the rabbit.: 1247-1258.
    Search in Google Scholar
  5. Dixit S, Khanna SK, Das M. (2008). A simple 2-directional high-performance thin-layer chromatographic method for the simultaneous determination of curcumin, metanil yellow, and sudan dyes in turmeric, chili, and curry powders.: 1387-1396.
    Search in Google Scholar
  6. Eling TE, Thompson DC, Foureman GL, Curtis JF, Hughes MF. (1990). Prostaglandin H synthase and xenobiotic oxidation.: 1-45.
    Search in Google Scholar
  7. Federal Institute for Risk Assessment. (2003). Dyes Sudan I to IV in food. In. Federal Institute for Risk Assessment, Berlin, Germany.
    Search in Google Scholar
  8. Garner RC, Martin CN, Clayson DB. (1984). Carcinogenic aromatic amines and related compounds. In, Vol., CS Monograph 182, (Searle, C. ed.), American Chemical Society, Washington, DC, pp. 175-302.
    Search in Google Scholar
  9. Gupta RC. (1985). Enhanced sensitivity ofP-postlabeling analysis of aromatic carcinogenic:DNA adducts.: 5656-5662.
    Search in Google Scholar
  10. International Agency for Research on Cancer (IARC) (1975). Sudan I. In, Vol., IARC, Lyon, France, pp. 225-231.
    Search in Google Scholar
  11. Kozuka T, Tashiro M, Sano S, Fujimoto K, Nakamura Y, Hashimoto S, Nakaminami G. (1980). Pigmented contact dermatitis from azo dyes. I. Cross-sensitivity in humans.: 330-336.
    Search in Google Scholar
  12. Liu Y, Song Z, Dong F, Zhang L. (2007). Flow injection chemiluminescence determination of Sudan I in hot chilli sauce.: 614-617.
    Search in Google Scholar
  13. Lubet RA, Connolly G, Kouri RE, Nebert DW, Bigelow SW. (1983). Biological effects of Sudan I dyes. Role of the cytosolicreceptor.: 3053-3058.
    Search in Google Scholar
  14. Martínek V, Stiborová M. (2002). Metabolism of carcinogenic azo dye Sudan I by rat, rabbit, minipig and human hepatic microsomes.: 1883-1898.
    Search in Google Scholar
  15. Mazzetti M, Fascioli R, Mazzoncini I, Spinelli G, Morelli I, Bertoli A. (2004). Determination of 1-phenylazo-2-naphthol (Sudan I) in chilli powder and in chilli-containing food products by GPC clean-up and HPLC with LC/MS confirmation.: 935-941.
    Search in Google Scholar
  16. Moller P, Wallin H. (2000). Genotoxic hazards of azo pigments and other colorants related to 1-phenylazo-2-hydroxynaphthalene.: 13-30.
    Search in Google Scholar
  17. NCI (1982). Carcinogenesis bioassay of C. I. Solvent Yellow 14 in F344/N rats and B6C3F1 mice. In, US National Cancer Institute, Bethesda.
    Search in Google Scholar
  18. Randerath K, Reddy MV, Gupta RC. (1981).P-labeling test for DNA damage.: 6126-6129.
    Search in Google Scholar
  19. Semanská M, Martínek V, Hudeček J, Hodek P, Dračínský M, Frei E, Stiborová M. (2008). A one-electron oxidation of carcinogenic non-aminoazo dye Sudan I by horseradish peroxidase.: 712-716.
    Search in Google Scholar
  20. Stiborová M, Asfaw B, Anzenbacher P, Lešetický L, Hodek P. (1988a). 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
  21. Stiborová M, Asfaw B, Anzenbacher P, Hodek P. (1988b). A new way to carcinogenicity of azo dye: the benzenediazonium ion formed from non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomal enzymes binds to deoxyguanosine residues of DNA.: 327-333.
    Open DOISearch in Google Scholar
  22. Stiborová M, Asfaw B, Anzenbacher P. (1988c). Activation of carcinogens by peroxidase. Horseradish peroxidase-mediated formation of benzenediazonium ion from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) and its binding to DNA.: 387-390.
    Open DOISearch in Google Scholar
  23. Stiborová M, Frei E, Klokow K, Wiessler M, Šafarík L, Anzenbacher P, Hradec J. (1990a). Peroxidase-mediated reaction of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene with transfer ribonucleic acid.: 1789-1794.
    Open DOISearch in Google Scholar
  24. Stiborová M, Frei E, Schmeiser HH, Wiessler M, Hradec J. (1990b). Mechanism of formation andP-postlabeling of DNA adducts derived from peroxidative activation of carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I).: 1843-1848.
    Open DOISearch in Google Scholar
  25. Stiborová M, Frei E, Anzenbacher P. (1991). Study of oxidation and binding to macromolecules of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene catalyzed by horseradish (L.) peroxidase.: 227-236.
    Search in Google Scholar
  26. Stiborová M, Frei E, Schmeiser HH, Wiessler M. (1992).P-Postlabeling analysis of adducts formed from 1-phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) with DNA and homopolydeoxyribonucleotides.: 1221-1225.
    Search in Google Scholar
  27. Stiborová M, Frei E, Schmeiser HH, Wiessler M, Hradec J. (1993). Detoxication products of the carcinogenic azodye Sudan I (Solvent Yellow 14) bind to nucleic acids after activation by peroxidase.: 43-47.
    Search in Google Scholar
  28. Stiborová M, Asfaw B, Frei E, Schmeiser HH, Wiessler M. (1994). Identification of 1-(3,4-dihydroxyphenylazo)-2-hydroxynaphthalene as the product of oxidation of 1-phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) by rat liver microsomes.: 2727-2733.
    Search in Google Scholar
  29. Stiborová M, Asfaw B, Frei E. (1995a). Peroxidase-activated carcinogenic azo dye Sudan I (Solvent Yellow 14) binds to guanosine in transfer ribonucleic acid.: 39-49.
    Search in Google Scholar
  30. Stiborová M, Asfaw B, Frei E, Schmeiser HH, Wiessler M. (1995b). Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct.: 489-498.
    Open DOISearch in Google Scholar
  31. Stiborová M, Asfaw B, Frei E, Schmeiser HH. (1996). Oxidation of azo dyes by peroxidase: additional evidence of a one-electron mechanism of oxidation of dimethylaminoazobenzene and Sudan I (Solvent Yellow 14).: 962-972.
    Search in Google Scholar
  32. Stiborová M, Schmeiser HH, Breuer A, Frei E. (1999a).P-Postlabelling analysis of DNA adducts with 1-(phenylazo)-2-naphthol (Sudan I, Solvent Yellow 14) formed in vivo in Fisher 344 rats.: 1335-1347.
    Open DOISearch in Google Scholar
  33. Stiborová M, Schmeiser HH, Frei E. (1999b). Prostaglandin H synthase mediated oxidation and binding to DNA of a detoxication metabolite of carcinogenic Sudan I 1-(phenylazo) 2,6-dihydroxynaphthalene.: 53-60.
    Open DOISearch in Google Scholar
  34. Stiborová M, Mikšanová M, Martínek V, Frei E. (2000). Heme peroxidases: structure, function, mechanism and involvement in activation of carcinogens. A review.: 297-325.
    Search in Google Scholar
  35. Stiborová M, Martínek V, Rýdlová H, Hodek P, Frei E. (2002). Sudan I is a potential carcinogen for humans: evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes.: 5678-5684.
    Search in Google Scholar
  36. Stiborová M, Martínek V, Rýdlová H, Koblas T, Hodek P. (2005). Expression of cytochrome P450 1A1 and its contribution to oxidation of a potential human carcinogen 1-phenylazo-2-naphthol (Sudan I) in human livers.: 145-154.
    Search in Google Scholar
  37. Stiborová M Martínek V Schmeiser HH, Frei E. (2006). Modulation of CYP1A1-mediated oxidation of carcinogenic azo dye Sudan I and its binding to DNA by cytochrome b.: 35-39.
    Search in Google Scholar
  38. Uematsu Y, Ogimoto M, Kabashima J, Suzuki K, Ito K. (2007). Fast cleanup method for the analysis of Sudan I-IV and para red in various foods and paprika color (oleoresin) by high-performance liquid chromatography/diode array detection: focus on removal of fat and oil as fatty acid methyl esters prepared by transesterification of acylglycerols.: 437-945.
    Search in Google Scholar
  39. Wise RW, Zenser TV, Kadlubar FF, Davis BB. (1984). Metabolic activation of carcinogenic aromatic amines by dog bladder and kidney prostaglandin H synthase.: 1893-1897.
    Search in Google Scholar
  40. Wang S, Xu Z, Fang G, Duan Z, Zhang Y, Chen S. (2007). Synthesis and characterization of a molecularly imprinted silica gel sorbent for the on-line determination of trace Sudan I in Chilli powder through high-performance liquid chromatography.: 3869-3876.
    Search in Google Scholar
  41. Wang Y, Wei D, Yang H, Yang Y, Xing W, Li Y, Deng A. (2009). Development of a highly sensitive and specific monoclonal antibody-based enzyme-linked immunosorbent assay (ELISA) for detection of Sudan I in food samples.: 1783-1789.
    Search in Google Scholar
  42. Westmoreland C, Gatehouse DG. (1991). The differential clastogenicity of Solvent Yellow 14 and FD & C Yellow No. 6 in vivo in the rodent micronucleus test (observation of species and tissues specificity).: 1403-1407.
    Search in Google Scholar
  43. Xu H, Heinze TM, Chen S, Cerniglia CE, Chen H. (2007). Anaerobic metabolism of 1-amino-2-naphthol-based azo dyes (Sudan dyes) by human intestinal microflora.: 7759-7762.
    Search in Google Scholar
  44. Yamazoe Y, Miller DW, Wies CC, Dooley KL, Zenser TV, Beland FA, Kadlubar FF. (1985). DNA adducts formed by ring-oxidation of the carcinogen 2-naphthylamine with prostaglandin H synthaseand in the dog urothelium: 1379-1387.
    Search in Google Scholar
  45. Zeiger E, Andersen B, Haworth S, Lawlor T, Mortelmans K. (1988).mutagenicity tests. IV. Results from the testing of 300 chemicals.: 1-158.
    Search in Google Scholar
  46. Zhang X, Jiang L, Geng C, Hu C, Yoshimura H, Zhong L. (2008a). Inhibition of Sudan I genotoxicity in human liver-derived HepG2 cells by the antioxidant hydroxytyrosol.: 189-195.
    Open DOISearch in Google Scholar
  47. Zhang X, Juany L, Geng C, Hu C, Yoshimura H, Zhong L. (2008b). Inhibition of Sudan I genotoxicity in human liver-derived HepG2 cells by the antioxidant hydroxytyrosol.: 189-195.
    Open DOISearch in Google Scholar
DOI: https://doi.org/10.2478/v10102-009-0017-z | Journal eISSN: 1337-9569 | Journal ISSN: 1337-6853
Journal RSS Feed
Language: English
Page range: 195 - 200
Published on: Sep 24, 2009
Published by: Slovak Academy of Sciences, Institute of Experimental Pharmacology & Toxicology, Centre of Experimental Medicine
In partnership with: Paradigm Publishing Services
Keywords:
carcinogenic azo dye,
Sudan I,
cytochrome P450,
peroxidase,
oxidative activation
Related subjects:
Medicine,
Clinical medicine,
Pharmacology, toxicology

© 2009 Marie Stiborová, Václav Martínek, Marcela Semanská, Petr Hodek, Martin Dračínský, Josef Cvačka, Heinz Schmeiser, Eva Frei, published by Slovak Academy of Sciences, Institute of Experimental Pharmacology & Toxicology, Centre of Experimental Medicine
This work is licensed under the Creative Commons License.

Volume 2 (2009): Issue 3 (September 2009)
Previous article
Next article