Synthesis and quantification of DNA adducts of 4,4'-methylenedianiline

Chemical Research in Toxicology

Volumn 9, Issue 7, 1996, Pages 1103-1112

  Schütze, Dietrich ^a   Sagelsdorff, Peter ^b   Sepai, Ovnair ^c   Sabbioni, Gabriele ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b CIBA GEIGY LTD   (Switzerland)

^c NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4,4' METHYLENEDIANILINE; DNA; GUANINE DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; COVALENT BOND; DNA ADDUCT; DNA BINDING; FEMALE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIVER; MASS SPECTROMETRY; NONHUMAN; RAT;

ANILINE COMPOUNDS; ANIMALS; CARCINOGENS; DEOXYGUANOSINE; DNA ADDUCTS; FEMALE; HYDROLYSIS; LIVER; RATS; RATS, WISTAR;

ANIMALIA; RATTUS NORVEGICUS;

EID: 0029912106     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950194+     Document Type: Article

References (47)

1. National Institute for Occupational Health and Safety (1976) Background information on 4,4′-diaminodiphenylmethane (DDM). Am. Ind. Hyg. Assoc. J. 37, 26-27.
2. Lamb, J. C., Huff, J. E., Haseman, J. K., Murthy, A. S. K., and Lilja, H. (1986) Carcinogenesis studies of 4,4′-methylenedianiline dihydrochloride given in drinking water to F344/N rats and B6C3F1 mice. J. Tcxicol. Environ. Health 18, 325-337.
3. Deichman, W. B., MacDonald, W. E., Coplan, M., Woods, F., and Blum, E. (1978) Di-(4-aminodiphenyl)-methane (DDM): 4-7 year dog feeding study. Toxicology 11, 185-188.
4. McGill, D. B., and Motto, J. D. (1974) An industrial outbreak of toxic hepatitis due to methylenedianiline. N. Engl. J. Med. 291, 278-282.
5. Tanaka, K., Ino, T., Sawahata, T., Marui, S., Igaki, H., and Yashima, H. (1985) Mutagenicity of N-acetyl and N,N'-diacetyl derivatives of 3 aromatic amines used as epoxy-hardeners. Mutat. Res. 143, 11-15.
6. IARC Monographs on the Evaluation of Carcinogenic Risk to Humans (1987) Overall evaluations of carcinogenicity: an updating of IARC Monographs, Volumes 1 to 42, Suppl. 7, p 66, International Agency for Research on Cancer, Lyon, France.
7. Cocker, J., Boobis, A. R., and Davies, D. S. (1988) Determination of the N-acetyl metabolites of 4,4′-methylenedianiline and 4,4′-methylene-bis(2-chloroaniline) in urine. Biomed. Environ. Mass Spectrom. 17, 161-167.
8. Schütze, D., Sepai, O., Lewalter, J., Miksche, L., Henschler, D., and Sabbioni, G. (1995) Biomonitoring of workers exposed to 4,4′-methylenedianiline and 4,4′-methylenediphenyl diisocyanate. Carcinogenesis 16, 573-582.
9. Tiljander, A., Skarping, G., and Dalene, M. (1989) Chromatographic determination of amines in biological fluids with special reference to the biological monitoring of isocyanates and amines: III. Determination of 4,4′-methylenedianiline in hydrolysed hu- man urine using derivatization and capillary gas chromatography with selected ion monitoring. J. Chromatogr. 479, 145-152.
10. Bailey, E., Brooks, A. G., Bird, I., Farmer, P. B., and Street, B. (1990) Monitoring exposure to methylenedianiline by the gas chromatography-mass spectrometry determination of adducts to hemoglobin. Anal. Biochem. 190, 175-181.
11. Kadlubar, F. F. (1994) DNA adducts of carcinogenic aromatic amines. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) IARC Monographs, pp 196-216, International Agency for Research on Cancer, Lyon, France.
12. Beland, F. A., and Kadlubar, F. F. (1990) Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In Chemical Carcinogenesis and Mutagenesis I (Cooper, C. S., and Cover, P. L., Eds.) pp 267-325, Springer Verlag, Heidelberg.
13. Segerbäck, D., and Kadlubar, F. F. (1992) Characterization of 4,4′-methylenebis(2-chloroaniline)-DNA adducts formed in vivo and in vitro. Carcinogenesis 13, 1587-1592.
14. Silk, N. A., Lay, J. O., Jr., and Martin, C. N. (1989) Covalent binding of 4,4′-methylenebis(2-chloroaniline) (MOCA) to rat liver DNA in vivo and of its N-hydroxylated derivative to DNA in vitro. Biochem. Pharmacol. 38, 279-287.
15. Lin, D., Lay, J. O., Bryant, M. S., Malaveille, C., Friesen, M., Bartsch, H., Lang, N. P., and Kadlubar, F. F. (1994) Analysis of 4-aminobiphenyl-DNA adducts in human urinary bladder and lung by alkaline hydrolysis and negative ion gas chromatography-mass spectrometry. Environ. Health Perspect. 102 (Suppl. 6), 11-16.
16. 32P-postlabeling. Chem. Res. Toxicol. 7, 733-739.
17. Tsekhanskii, R. S.(1961) Preparation of 4-amino-4′-nitrodiphenylmethane. Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol. 4, 691-692; Chem. Abstr. (1962) 3383h.
18. Tsekhanskii, R. S.(1961) Preparation of 4-amino-4′-nitrodiphenylmethane. Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol. 4, 691-692; Chem. Abstr. (1962) 3383h.
19. Morgott, D. A. (1984) The in vivo biotransformation and acute hepatotoxicity of methylenedianiline, Ph.D. Thesis, University of Michigan.
20. Bamberger, E., and Rising, A. (1901) Einflusa von Methyl auf die Reactionsgeschwindigkeit der Arylhydroxylamine. Liebigs Ann. Chem. 316, 257-292.
21. Gupta, R. C. (1984) Nonrandom binding of the carcinogen N-hydroxy-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo. Proc. Natl Acad. Sci. U.S.A. 81, 6943-6947.
22. 32P-postlabeling assay. Carcinogenesis 13, 1053-1074.
23. Sagelsdorff, P., Lutz, W. K., and Schlatter, C. (1983) The relevance of covalent binding to mouse liver DNA to the carcinogenic action of hexachlorocyclohexane isomers. Carcinogenesis 4, 1267-1273.
24. Sagelsdorff, P., Lutz, W. K., and Schlatter, C. (1988) DNA methylation in rat liver by daminocide, 1,1-dimethylhydrazine, and dimethylnitrosoamine. Fundam. Appl. Toxicol. 11, 723-730.
25. 32P-postlabeling analysis of aromatic carcinogen: DNA adducts. Cancer Res. 45, 5656-5662.
26. Meier, C., and Boche, G. (1990) N-Aryl-O-(α-aminoacyl)hydroxylamine: Modellreaktionen mit Desoxyguanosin, Guanosin und 5′-Guanosinmonophosphat zur Aktivierung monocyclischer aromatischer Amine (z.B. Phenacetin) zu ultimaten Carcinogenen. Chem. Ber. 123, 1699-1705.
27. Lobo, A. M., Marques, M. M., Prabhakar, S., and Rzepa, H. S. (1985) Tetrahedral intermediates formed during acyl transfer reactions of acetyl cyanide. J. Chem. Soc., Chem. Commun., 1113-1115.
28. Prabhakar, S., Lobo, A. M., and Marques, M. M. (1982) Reactions between hydroxylamines and aroyl cyanides. Tetrahedron Lett. 23, 1391-1394.
29. Famulok, M., Bosold, F., and Boche, G. (1989) Synthesis of O-acetyl-N-(4-biphenyl)hydroxylamine ('N-acetoxy-4-aminobiphenyl'), an ultimate metabolite of carcinogenic 4-aminobiphenyl, and its reaction with deoxyguanosine. Angew. Chem., Int. Ed. Engl. 28, 337-338.
30. Famulok, M., and Boche, G. (1989) Formation of N-(deoxyguanosin-8-yl)aniline in the in vitro reaction of N-acetoxyamline with deoxyguanosine and DNA. Angew. Chem., Int. Ed. Engl. 28, 468-469.
31. Meier, C., and Boche, G. (1991) The modification of guanine nucleosides and nucleotides by the borderline arylamine carcinogens 4-methyl- and 4-methoxyaniline: chemistry and structural characterization. Carcinogenesis 12, 1633-1640.
32. Martin, C. N., Beland, F. A., Roth, R. W., and Kadlubar F. F. (1982) Covalent binding of benzidine and N-acetylbenzidine to DNA at the C-8 atom of deoxyguanosine in vivo and in vitro. Cancer Res. 42, 2678-2696.
33. Swaminathan, S., Frederickson, S. M., and Hatcher, J. F. (1994) Metabolic activation of N-hydroxy-4-acetylaminobiphenyl by cultured human breast epithelial cell line MCF 10A. Carcinogenesis 15, 611-617.
34. 32P-postlabeling analysis. Carcinogenesis 16, 295-301.
35. Schütze, D. (1993) Expositionsnachweis und Risikoermittlung bei Bis(4-aminophenylmethanen und davon abgeleiteten Industriechemikalien, Ph.D. Thesis, University of Würzburg, Germany.
36. 1 mice and characterization of N-(deoxyguanosin-8-yl)-4-aminoazobenzene as the major persistent hepatic DNA-bound dye in these mice. Cancer Res. 44, 2540-2550.
37. Kadlubar, F. F., Beland, F. A., Beranek, D. T., Dooley, K. L., Heflich, R. H., and Evans, F. E. (1982) Arylamine-DNA adduct formation in relation to urinary bladder carcinogenesis and Salmonella thyphimurium mutagenesis. In Environmental Mutagens and Carcinogens (Sugimura, T., Kondo, S., and Takebe, H., Eds.) pp 385-396, A. R. Liss, New York.
38. Flammang, T. J., Westra, J. G., Kadlubar, F. F., and Beland, F. A. (1985) DNA adducts formed from the probable proximate carcinogen, N-hydroxy-3,2′-dimethyl-4-aminobiphenyl, by acid catalysis or S-acetyl coenzyme A-dependent enzymatic esterification. Carcinogenesis 6, 251-258.
39. Famulok, M., Bosold, F., and Boche, G. (1989) Synthesis of N-acetoxy-2-aminonaphthalene, an ultimate carcinogen of the carcinogenic 2-naphthylamine, and its in vitro reactions with (bio)nucleophiles. Tetrahedron Lett. 30, 321-324.
40. Kriek, E., and Westra, J. G.(1980) Structural identification of the pyrimidine derivatives formed from N-(deoxyguanosin-8-yl)-2-aminofluorene in aqueous solution at alkaline pH. Carcinogenesis 1, 459-468.
41. Gupta, R. C., Earley, K., Fullerton, N. F., and Beland, F. A. (1989) Formation and removal of DNA adducts in target and nontarget tissues of rats administered multiple doses of 2-acetylaminofluorene. Carcinogenesis 10, 2025-2033.
42. Beyerbach, A., Farmer, P. B., and Sabbioni, G. (1996) Synthesis and analysis of DNA adducts of arylamines. Biomarkers 1, 9-20.
43. Marques, M. M., Mourato, L. L. G., Santos, M. A., and Beland, F. A. (1996) Synthesis, characterization, and conformational analysis of DNA adducts from methylated anilines present in tobacco smoke. Chem. Res. Toxicol. 8, 99-108.
44. 13C-NMR-Konformation-sanalysen und Minimal-Potential-Energie-Rechnungen an Desoxyguanosin-, Guanosin- und 5′-Guanosinmonophosphat-Addukten des Grenzcarzinogens 4-Methylanilin. Chem. Ber. 123,1707-1713.
45. 2-(2′-deoxyguanosin-8-yl)-PhIP. Carcinogenesis 13, 629-635.
46. 32P-adduct assay: comparative recoveries of structurally diverse DNA adducts in the various enhancements procedures. Carcinogenesis 9, 1687-1693.
47. Lutz, W. K. (1979) In vivo covalent binding of organic chemicals to DNA as a quantitative indicator in the process of chemical Carcinogenesis. Mutat. Res. 65, 289-356.