Biomonitoring of aromatic amines V: Acetylation and deacetylation in the metabolic activation of aromatic amines as determined by haemoglobin binding

Archives of Toxicology

Volumn 72, Issue 8, 1998, Pages 499-504

  Zwirner Baier, Iris ^a   Neumann, Hans Günter ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Acetylation; Aromatic amines; Biomonitoring; Deacetylation; Haemoglobin adducts

Indexed keywords

ACETAMIDE DERIVATIVE; AROMATIC AMINE; HEMOGLOBIN;

ACETYLATION; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOLOGICAL MONITORING; CONTROLLED STUDY; DEACETYLATION; DNA DAMAGE; DRUG PROTEIN BINDING; GENETIC POLYMORPHISM; GENOTYPE; METABOLIC ACTIVATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; TECHNIQUE;

ACETYLATION; AMINES; ANIMALS; BIOTRANSFORMATION; BLOOD PROTEINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEALKYLATION; ENVIRONMENTAL MONITORING; FEMALE; HEMOGLOBINS; MICE; MICE, INBRED C57BL; POLYMORPHISM, GENETIC; PROTEIN BINDING; RATS; RATS, WISTAR;

ANIMALIA; RATTUS NORVEGICUS;

EID: 0031858673     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002040050534     Document Type: Article

References (38)

1. Aune T, Vanderslice RR, Croft JE, Dybing E, Bend JR, Philpot RM (1985) Deacetylation to 2-aminofluorene as a major initial reaction in the microsomal metabolism of 2-acetylaminofluorene to mutagenic products in preparations from rabbit lung and liver. Cancer Res 45: 5859-5866
2. Beland FA, Kadlubar FF (1990) Metabolic activation and DNA-adducts of aromatic amines and nitroaromatic hydrocarbons. In: Cooper CS, Grover PL (eds) Handbook of experimental pharmacology, vol 94/I. Springer, Berlin, pp 267-325
3. Birner G, Albrecht W, Neumann H-G (1990) Biomonitoring of aromatic amines III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol 64: 97-102
4. Bryant MS, Vineis P, Skipper PL, Tannenbaum SR (1988) Hemoglobin adducts of aromatic amines: associations with smoking status and type of tobacco. Proc Natl Acad Sci USA 85: 9788-9791
5. Daune MP, Fuchs RP, Leng M (1981) Structural modification and protein recognition of DNA modified by N-2-fluorenylacetamide, its 7-iodo derivative, and by N-2-fluorenamine. Natl Cancer Inst Monogr 58: 201-210
6. Dolle B, Töpner W, Neumann H-G (1980) Reaction of arylnitroso compounds with mercaptans. Xenobiotica 10: 17-35
7. Ever P (1994) Reactions of oxidatively activated arylamines with thiols: reaction mechanisms and biological implications. An overview. Environ Health Perspect 102(Suppl 6): 133-136
8. Flammang TJ, Yerokun T, Bryant MS, Couch LH, Kirlin WG, Lee KJ, Ogolla F, Ferguson RJ, Talaska G, Hein DW (1992) Hemoglobin adduct and hepatic-and urinary bladder DNA adduct levels in rapid and slow acelylator Syrian inbred hamsters administered 2-aminofluorene. J Pharmacol Exp Ther 260: 865-871
9. Gant TW, Sehrenk D, Silverman JA, Thorgeirsson SS (1994) Requirement for metabolic activation of acetylaminofluorene to induce multidrug gene expression. Environ Health Perspect 102 (Suppl 6): 209-212
10. Grant DM, Mörike K, Eichelbaum M, Meyer UA (1990) Acetylation pharmacogenetics: the slow acetylator phenotype is caused by decreased or absent arylamine N-acetyltransferase in human liver. J Clin Invest 85: 968-972
11. Grunt DM, Josephy D, Lord HL, Morrison D (1992) Salmonella lyphimurium strains expressing human arylamine N-acetyltransferases: metabolism and mutagenic activation of aromatic amines. Cancer Res 52: 3961-3963
12. Grant DM, Hughes NC, Janezic SA, Goodfellow GH, Chen HJ, Gaedigk A, Yu VL, Grewal R (1997) Human acetyltransferase polymorphism. Mutat Res 376: 61-70
13. Hultin TA, Weber WW (1987) Genetic variability in deacetylation of 2-acetylaminofluorene and N-hydroxy-2-acetylaminofluorene in inbred strains of mice. Carcinogenesis 8: 1939-1941
14. Jarvinen M, Santti RS, Hopsu-Havu VK (1971) Partial purification and characterization of two enzymes from guinea pig liver microsomes that hydrolyze carcinogenic amides 2-acetylaminofluorene and N-hydroxy-2-acetylaminofluorene. Biochem Pharmacol 20: 2971-2982
15. Karreth S, Lenk W (1991) The metabolism of 4-aminobiphenyl in rat. I. Reaction of N-hydroxy-4-aminobiphenyl with rat blood in vivo. Xenobiotica 21: 417-428
16. King CM, Weber WW (1981) Formation, metabolic activation by N,O-acyltransfer, and hydrolysis of N-acyl-N-arylamine derivatives. Natl Cancer Inst Monogr 58: 117-122
17. Klöhn P-C, Neumann H-G (1997) Impairment of respiration and oxidative phosphorylation by redox cyclers 2-nitrosofluorene and menadione. Chem-Biol Interact 106: 15-28
18. Klöhn P-C, Massalha H, Neumann H-G (1995) A metabolite of carcinogenic 2-acetylaminofluorene, 2-nitrosofluorene induces redox cycling in mitochondria. Biochim Biophys Acta 1229: 363-372
19. Kriek E (1974) Carcinogenesis by aromatic amines. Biochim Biophys Acta 355: 177-203
20. Lai CC, Miller EC, Miller JA, Liem A (1988) The essential role of microsomal deacetylase activity in the metabolic activation. DNA-(deoxyguanosin-8-yl)-2-aminofluorene adduct formation and initiation of liver tumors by N-hydroxy-2-acetylaminofluorene in the livers of infant male B6C3F1 mice. Carcinogenesis 9: 1295-1302
21. Land S, Zukowski K, Lee M-S, Wang CY, King CM (1993) Purification and characterization of a rat hepatic acetyltransferase that can metabolize aromatic amine derivatives. Carcinogenesis 14: 1441-1449
22. Levy GN, Weber WW (1989) 2-Aminofluorene-DNA adduct formation in acetylator congenic mouse lines. Carcinogenesis 10: 705-709
23. Levy GN, Weber WW (1992) 2-Aminofluorene-DNA adducts in mouse urinary bladder: effect of age, sex and acetylator phenotype. Carcinogenesis 13: 159-164
24. Levy GN, Chung J-G, Weber WW (1994) 2-Aminofluorene metabolism and DNA adduct formation by mononuclear leukocytes from rapid and slow acetylator mouse strains. Carcinogenesis 15: 353-357
25. Lewalter J, Korallus U (1985) Blood protein conjugates and acetylation of aromatic amines: new findings on biological monitoring. Intern Arch Occup Environ Health 56: 179-196
26. Martell KJ, Levy GN, Weber WW (1992) Cloned mouse N-acetyltransferases: enzymatic properties of expressed NAT-1 and NAT-2 gene products. Mol Pharmacol 42: 265-272
27. Martin CN, Beland FA, Roth RW, Kadlubur FF (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: 2678-2686
28. Meerman JHN, van de Poll MLM (1994) Metabolic activation routes of arylamines and their genotoxic effects. Environ Health Perspect 102(Suppl 6): 153-159
29. Meyer U (1994) Polymorphism of human acetyltransferases. Environ Health Perspect 102(Suppl 6): 213-216
30. Morton KC, King CM, Baetke KP (1979) Metabolism of benzidine to N-hydroxy-N,N′-diacetylbenzidine and subsequent nucleic acid binding and mutagenicity. Cancer Res 39: 3107-3113
31. Neumann H-G (1984) Dosimetry and dose-response relationships. IARC Sci Publ 59: 115-126
32. Neumann H-G, Bitsch A, Klöhn P-C (1996) The dual role of 2-acetylaminofluorene in hepatocarcinogenesis: specific targets for initiation and promotion. Mutat Res 376: 169-176
33. Pereira MA, Lin L-HC, Chang LW (1981) Dose-dependence of 2-acetylaminofluorene binding to liver DNA and hemoglobin in mice and rats. Toxicol Appl Pharmacol 60: 472-478
34. Poirier MC, Yuspa SH (1981) Detection and quantification of acetylated und deacelylated N-2-fluorenylacetamide-DNA adducts by radioimmunoassay. Natl Cancer Inst Monogr 58: 211-216
35. Thorgeirsson SS, Erickson LC, Smith CL, Glowinski IB (1983) Genotoxicity of N-acetylarylamines in the Salmonella/hepatocyte system. Environ Health Perspect 49: 141-145
36. Weber WW (1987) The acetylator genes and drug response. Oxford University Press, New York
37. Zwirner-Baier I, Neumann H-G (1994) Biomonitoring of aromatic amines IV: use of hemoglobin adducts to demonstrate the bioavailability of cleavage products from diarylide azo pigments in vivo. Arch Toxicol 68: 8-14
38. Zwirner-Baier I, Kordowich F-J, Neumann H-G (1994) Hydrolysable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environ Health Perspect 102(Suppl 6): 43-45