Prostaglandin H synthase-mediated oxidation and binding to DNA of a detoxication metabolite of carcinogenic Sudan I, 1-(phenylazo)-2,6-dihydroxynaphthalene

Cancer Letters

Volumn 146, Issue 1, 1999, Pages 53-60

  Stiborová, Marie ^a   Schmeiser, Heinz H ^b   Frei, Eva ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

32P postlabeling; Azo dye; Detoxification activation of carcinogens; DNA binding; Prostaglandin H synthase; Protein binding; Sudan I

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; PROSTAGLANDIN SYNTHASE; SUDAN I;

ANIMAL TISSUE; ARTICLE; BLADDER CARCINOMA; CARCINOGENESIS; CONTROLLED STUDY; COVALENT BOND; DETOXIFICATION; DNA BINDING; HYDROXYLATION; LIVER CANCER; NONHUMAN; OXYGEN CONSUMPTION; PRIORITY JOURNAL; PROTEIN BINDING;

ANIMALS; CARCINOGENS; DNA; DNA ADDUCTS; MALE; METABOLIC DETOXICATION, DRUG; NAPHTHALENES; NAPHTHOLS; OXIDATION-REDUCTION; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; SHEEP;

EID: 0032883097     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-3835(99)00226-8     Document Type: Article

References (26)

1. Sudan I. IARC Monographs, vol. 8. 1975;IARC, Lyon. pp. 225-231.
2. Garner R.C., Martin D.N., Clayson D.B. Carcinogenic aromatic amines and related compounds. Searle C.E. Chemical Carcinogens, vol. 1, ACS Monograph No. 182. 3 :1984;175-302 American Chemical Society, Washington, DC.
3. Westmoreland C., Gatehouse D.G. The differential clastogenicity of Solvent Yellow 14 and FD & C Yellow No. 6 in vivo in the rodent micronucleus test (observation of species and tissue specificity). Carcinogenesis. 12:1991;1403-1407.
4. Carcinogenesis bioassay of C.I. Solvent Yellow 14 in F344/N rats and B6C3F1 mice.Technical Report No. 226. 1982;US National Cancer Institute, Bethesda, MD.
5. Childs J.J., Clayson D.S. The metabolism of 1-phenylazo-2-naphthol in the rabbit. Biochem. Pharmacol. 15:1966;1247-1258.
6. Chung K.T. The significance of azo-reduction in the mutagenesis and carcinogenesis of azo dyes. Mutat. Res. 114:1983;265-281.
7. Stiborová M., Asfaw B., Anzenbacher P., Lešetickú L., Hodek P. The first identification of the benzenediazonium ion formation from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomes of rat livers. Cancer Lett. 40:1988;319-326.
8. Stiborová M., Asfaw B., Anzenbacher P., Hodek P. 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. Cancer Lett. 40:1988;327-333.
9. Stiborová M., Asfaw B., Frei E., Schmeiser H.H., Wiessler M. Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct. Chem. Res. Toxicol. 8:1995;489-498.
10. 32P-postlabeling of DNA adducts derived from peroxidative activation of carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I). Carcinogenesis. 11:1990;1843-1848.
11. 32P-postlabeling analysis of adducts formed from 1-phenylazo-2-hydroxynaphthalene (Sudan I Solvent Yellow 14) with DNA and homopolydeoxyribonucleotides. Carcinogenesis. 13:1992;1221-1225.
12. Stiborová M., Frei E., Schmeiser H.H., Wiessler M., Hradec J. Detoxification products of the carcinogenic azodye Sudan I (Solvent Yellow 14) bind to nucleic acids after activation by peroxidase. Cancer Lett. 68:1993;43-47.
13. Stiborová M., Frei E., Anzenbacher P. Study of oxidation and binding to macromolecules of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene catalyzed by horseradish (Armoracia rusticana L.) peroxidase. Biochem. Physiol. Pflanzen. 187:1991;227-236.
14. Eling T.E., Thompson D.C., Foureman G.L., Curtis J.F., Hughes M.F. Prostaglandin H synthase and xenobiotic oxidation. Annu. Rev. Pharmacol. Toxicol. 30:1990;1-45.
15. Eling T.E., Curtis J.F. Xenobiotic metabolism by prostaglandin H synthase. Pharm. Ther. 53:1992;261-273.
16. Sivarajah K., Lasker J.M., Eling T.E. Prostaglandin synthetase dependent co-oxidation of (+)benzo[a]pyrene-7,8-dihydrodiol by human lung and mammalian tissues. Cancer Res. 41:1981;1834-1839.
17. Bradford M.M. A rapid sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248-254.
18. Cleland W.W. Statistical analysis of the enzyme kinetic data. Purich D.L. Methods in Enzymology. vol. 63:1983;103-138 Academic Press, New York.
19. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis. 7:1986;1543-1551.
20. 32P-Labeling test for DNA damage. Proc. Natl. Acad. Sci. USA. 78:1981;6126-6129.
21. O'Brien P. Radical formation during the peroxidase catalyzed metabolism of carcinogens and xenobiotics: the reactivity of these radicals with GSH, DNA, and unsaturated lipid. Free Radic. Biol. Med. 4:1988;169-183.
22. Wells I., Marnett L.J. Inactivation of prostaglandin endoperoxide synthase by acylating derivatives of indomethacin. Biochemistry. 32:1993;2710-2716.
23. Yamazoe Y., Zenser T.V., Miller D.W., Kadlubar F.F. Mechanism of formation and structural characterization of DNA adducts derived from peroxidative activation of benzidine. Carcinogenesis. 9:1988;1635-1641.
24. Barret J.C., Wiseman R.W. Cellular and molecular mechanisms of multistep carcinogenesis: relevance to carcinogen risk assessment. Environ. Health Perspect. 76:1987;65-70.
25. Stiborová M., Schmeiser H.H., Breuer A., Frei E. 32P-Postlabeling analysis of DNA adducts with 1-(phenylazo)-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) formed in vivo in Fisher 344 rats. Collect. Czech. Chem. Commun. 1999.
26. Marnett L. Peroxyl free radicals: potential mediators of tumor initiation and promotion. Carcinogenesis. 8:1987;1365-1373.