Synthesis, characterization, and comparative 32P-postlabeling efficiencies of 2,6-dimethylaniline-DNA adducts

Chemical Research in Toxicology

Volumn 14, Issue 2, 2001, Pages 165-174

  Goncalves L L ^a   Beland, F A ^b   Marques, M M ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIMETHYLANILINE; ANILINE DERIVATIVE; BENZO[A]PYRENE; DEOXYGUANOSINE; DNA; GUANOSINE DERIVATIVE; NUCLEOTIDE; PHOSPHORUS 32; POLYNUCLEOTIDE 5' HYDROXYL KINASE; UNCLASSIFIED DRUG;

ARTICLE; CARCINOGENICITY; CHEMICAL STRUCTURE; DNA ADDUCT; POLLUTANT; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

ANILINE COMPOUNDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; ISOTOPE LABELING; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS RADIOISOTOPES; PHOSPHORYLATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

NICOTIANA TABACUM; RODENTIA;

EID: 0035101458     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0002031     Document Type: Article

References (46)

1. Chemical studies on tobacco smoke LXIV. On the analysis of aromatic amines in cigarette smoke
2. Primary aromatic amines from side-stream cigarette smoke are common contaminants of indoor air
3. The tissue distribution, metabolism and excretion of lidocaine in rats, guinea pigs, dogs and man
4. Toxicology and carcinogenesis studies of 2,6-xylidine (2,6-dimethylaniline) (CAS No. 87-62-7) in Charles River CD rats (feed studies)
5. Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons
6. DNA adducts of carcinogenic aromatic amines
7. Carcinogenic aromatic amines and amides
8. Structure of the single stable hemoglobin adduct formed by 4-aminobiphenyl in vivo
9. Methaemoglobin formation by aromatic amines
10. Contribution of aniline metabolites to aniline-induced methemoglobinemia
11. Hemoglobin adducts of aromatic amines: Associations with smoking status and type of tobacco
12. 2,6-Dimethylaniline-hemoglobin adducts from lidocaine in humans
13. Methaemoglobinaemia following lignocaine
14. Methemoglobin levels following intravenous lidocaine administration
15. Bacterial mutagenicity and mammalian cell DNA damage by several substituted anilines
16. Genotoxicity of aniline derivatives in various short-term tests
17. Mutations in Salmonella typhimurium and inactivation of Bacillus subtilis transforming DNA induced by phenylhydroxylamine derivatives
18. Effect of substitution site upon the oxidation potentials of alkylanilines, the mutagenicities of N-hydroxyalkylanilines, and the conformations of alkylaniline-DNA adducts
19. Formation of N-(deoxyguanosin-8-yl)aniline in the in vitro reaction of N-acetoxyaniline with deoxyguanosine and DNA
20. N-Aryl-O-(α-aminoacyl)hydroxylamine: Modellreaktionen mit Desoxyguanosin, Guanosin und 5′-Guanosinmonophosphat zur Aktivierung monocyclischer aromatischer Amine (z.B. Phenacetin) zu ultimaten Carcinogenen
21. Synthesis, characterization, and conformational analysis of DNA adducts from methylated anilines present in tobacco smoke
22. Synthesis and analysis of DNA adducts of arylamines
23. 6-aryl 2′-deoxyadenosine analogues
24. New syntheses of DNA adducts from methylated anilines present in tobacco smoke
25. 32P-postlabeling assay
26. Standardization and validation of DNA adduct postlabelling methods: Report of interlaboratory trials and production of recommended protocols
27. Methods of DNA adduct determination and their application to testing compounds for genotoxicity
28. 32P-Postlabeling of N-(deoxyguanosin-8-yl)arylamine adducts: A comparative study of labeling efficiencies
29. Reactions of polycyclic aromatic hydrocarbons with DNA
30. Conformation of DNA modified with a dihydrodiol epoxide derivative of benzo[α]pyrene
31. Relationships between the DNA adducts and the mutations and sister-chromatid exchanges produced in Chinese hamster ovary cells by N-hydroxy-2-aminofluorene, N-hydroxy-N′-acetylbenzidine and 1-nitrosopyrene
32. Synthesis of 2-substituted 2′-deoxyguanosines and 6-O-allylguanines via the activation of C-2 by a trifluoromethanesulfonate group
33. 6-arylation of DNA by the carcinogen N-hydroxy-1-naphthylamine
34. 6 atom of adenine
35. Hydrolysis reactions of N-sulfonatooxy-N-acetyl-1-aminonaphthalene and N-sulfonatooxy-N-acetyl-2-aminonaphthalene: Limited correlation of nitrenium ion azide/solvent selectivities with mutagenicities of the corresponding amines
36. Correlation of azide/solvent selectivities for nitrenium ions with ab initio hydration energies: Understanding the kinetic lability of nitrenium ions in aqueous solution
37. Cyclohexadienes from the rearrangement of O-aroyl-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamines. Reaction in aqueous solution to meta- and para-substituted 2,6-dimethylacetanilides
38. Nature of nitrenium: Carboxylate ion pair intermediates in the hydrolysis of O-aroyl-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamines
39. 32P-Postlabeling test for covalent DNA binding of chemicals in vivo: Application to a variety of aromatic carcinogens and methylating agents
40. 32P-Postlabeling analysis of DNA adducts persisting for up to 42 weeks in the skin, epidermis and dermis of mice treated topically with 7,12-dimethylbenz[α]anthracene
41. 32P-Analysis of DNA adducts in somatic and reproductive tissues of rats treated with the anticancer antibiotic, mitomycin C
42. 32P-postlabelling
43. Synthesis, characterization, and quantitation of a 4-aminobiphenyl-DNA adduct standard