Mechanism of peroxidase-mediated oxidation of carcinogenic o-anisidine and its binding to DNA

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 500, Issue 1-2, 2002, Pages 49-66

  Stiborová, Marie ^a   Mikšanová, Markéta ^a   Havlíček, Vladimír ^b   Schmeiser, Heinz H ^c   Frei, Eva ^c  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^c GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

32P postlabeling; Deoxyguanosine; DNA adducts; o Anisidine; Peroxidase mediated oxidation; Prostaglandin H synthase

Indexed keywords

ANILINE DERIVATIVE; ANISOLE; BUTANOL; CARBON 14; DEOXYGUANOSINE 3' MONOPHOSPHATE; DEOXYGUANOSINE DERIVATIVE; DIMER; DNA; HORSERADISH PEROXIDASE; IMINE; LACTOPEROXIDASE; MICROCOCCAL NUCLEASE; ORTHO ANISIDINE; PEROXIDASE; PHOSPHODIESTERASE; PHOSPHORUS 32; POLYDEOXYRIBONUCLEOTIDE; PROSTAGLANDIN SYNTHASE; QUINONE DERIVATIVE; RADICAL; TRANSFER RNA; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BLADDER; BLADDER CARCINOGENESIS; CARCINOGENICITY; CATALYSIS; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; COVALENT BOND; DNA ADDUCT; DNA BINDING; DNA MODIFICATION; ENZYME ACTIVITY; ENZYME METABOLISM; GENOTOXICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; ISOTOPE LABELING; METABOLITE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN FUNCTION; QUANTITATIVE ANALYSIS; SHEEP; SPLEEN; TANDEM MASS SPECTROMETRY;

ARMORACIA RUSTICANA; MAMMALIA; RODENTIA;

EID: 0037139223     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(01)00295-0     Document Type: Article

References (54)

1. Carcinogenic aromatic amines and related compounds
2. Ortho- and para-anisidine and their hydrochlorides
3. Reproducibility of microbial mutagenicity assays
4. Chemical structure. Salmonella mutagenicity and extend of carcinogenicity as indicator of genotoxic carcinogenesis among 222 chemicals tested in rodents by the US NCI/NTP
5. 32P bladder DNA adduction
6. Reactive intermediates formed during the peroxidative oxidation of anisidine isomers
7. Enhanced mutagenicity of anisidine isomers in bacterial strains containing elevated N-acetyltransferase activity
8. Chromosome aberrations and sister chromatid exchanges in Chinese hamster ovary cells, evaluations of 108 chemicals
9. Mouse lymphoma L5178Y thymidine kinase locus assay of 50 compounds
10. The aromatic amine carcinogens o-toluidine and o-anisidine induce free radicals and intrachromosomal recombination in Saccharomyces cerevisiae
11. Organ-specific genotoxicity of the potent rodent bladder carcinogens o-anisidine and p-cresidine
12. Mutational specificity of o-anisidine in the bladder of Big Blue™ mice
13. The non-genotoxicity to rodents of the potent rodent bladder carcinogens carcinogens o-anisidine and p-cresidine
14. Evaluation of the rodent micronucleus assays in the screening of IARC carcinogens (groups 1, 2A and 2B). The summary report of the 6th collaborative study by CSGMT/JEMS-MMS
15. The metabolism of p-phenetidine (p-ethoxyaniline) with some observations on the anisidines (methoxyanilines)
16. Influence of substrates on the microsomal dealkylation of aromatic N-, O- and S-alkyl compounds
17. Prostaglandin H synthase and xenobiotic oxidation
18. Xenobiotic metabolism by prostaglandin H synthase
19. Isolation of mammalian transfer RNA
20. 32P-postlabelling analysis of DNA adducts formed by aristolochicacid in tissues from patients with Chinese herbs nephropathy
21. 32P-postlabelling: Evidence for reductive activation by peroxidases
22. Prostaglandin synthetase dependent co-oxidation of (+)benzo[a]pyrene-7,8-dihydrodiol by human lung and mammalian tissues
23. A rapid sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
24. Statistical analysis of the enzyme kinetic data
25. Peroxidase-mediated reaction of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene with transfer ribonucleic acid
26. 32P-postlabeling of DNA adducts derived from peroxidative activation of carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I)
27. Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct
28. Mechanism of formation and structural characterization of DNA adducts derived from peroxidative activation of benzidine
29. 32P-postlabeling analysis of nonradioactive aromatic carcinogen-DNA adducts
30. 32P-postlabelling test for structurally diverse DNA adducts
31. 32P-adduct assay comparativerecoveries of structurally diverse DNA adducts in the various enhancement procedures
32. 32P-postlabeling analysis of DNA adduct formation
33. DNA adduction by phenol, hydroquinone, or benzpquinone in vitro but not in vivo
34. 32P-postlabelling analysis of DNA adducts with 1-(phenylazo)-2-naphthol (Sudan I, solvent yellow 14) formed in vivo in Fisher 344 rats
35. Radical formation during the peroxidase catalyzed metabolism of carcinogens and xenobiotics: The reactivity of these radicals with, GSH, DNA, and unsaturated lipid
36. Inactivation of prostaglandin endoperoxide synthase by acylating derivatives of indomethacin
37. The generation and subsequent fate of glutathionyl radicals in biological systems
38. Prostaglandin H synthase mediated oxidation and binding to DNA of a detoxication metabolite of carcinogenic Sudan I 1-(phenylazo)-2,6-dihydroxynaphthalene
39. Reaction of four-substituted phenols with benzidine in a peroxidase system
40. Heme peroxidases: Structure, function, mechanism and involvement in activation of carcinogens. A review
41. 32P-postlabeling methods for DNA adduct detection: Overview and critical evaluation
42. Structural origins of bulky oxidative DNA adducts (type II I-compounds) as deduced by oxidation of oligonucleotides of known sequence
43. 32P-postlabeling analysis of adducts formed from 1-phenylazo-2-hydroxynaphthalene (Sudan I, solvent yellow 14) with DNA and homopolydeoxyribonucleotides
44. 32P-postlabeling: A sensitive technique for the detection of DNA adducts
45. Comparative cytotoxic effects of N-acetyl-p-benzoquinone imine and two dimethylated analogoues
46. Reactive products formed by peroxidase catalyzed oxidation of p-phenetidine
47. The oxidation of p-phenetidine by horseradish peroxidase and prostaglandin H synthase and the fate of glutathione during such oxidation
48. Cellular effects of N-(4-ethoxyphenyl)-p-benzoquinone imine. A p-phenetidine metabolite formed during peroxidative reactions
49. 2-methyl-9-hydroxy-ellipticinium acetate (NSC 264137) on RNA and poly A in vitro
50. Prostaglandin H synthase and horseradish peroxidase catalyzed DNA-binding of p-phenetidine
51. Benzidine binding to nucleic acids mediated by the peroxidative activity of prostaglandin endoperoxide synthetase
52. Cellular and molecular mechanisms of multistep carcinogenesis: Relevance to carcinogen risk assesment
53. Peroxyl free radicals: Potential mediators of tumor initiation and promotion