Human N-acetylation of benzidine: Role of NAT1 and NAT2

Cancer Research

Volumn 56, Issue 17, 1996, Pages 3941-3947

  Zenser, Terry V ^a,c   Lakshmi, Vijaya M ^a   Rustan, Timothy D ^b   Doll, Mark A ^b   Deitz, Anne C ^b   Davis, Bernard B ^a   Hein, David W ^b  

^a SAINT LOUIS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF NORTH DAKOTA SCHOOL OF MEDICINE AND HEALTH SCIENCES   (United States)

^c VETERANS AFFAIRS MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL COENZYME A; ACYLTRANSFERASE; BENZIDINE; BENZIDINE DERIVATIVE;

ADULT; AGED; ARTICLE; CATALYSIS; DRUG ACETYLATION; FEMALE; HUMAN; HUMAN TISSUE; LIVER METABOLISM; MALE; MICHAELIS CONSTANT; PRIORITY JOURNAL;

ACETYLATION; ARYLAMINE N-ACETYLTRANSFERASE; BASE SEQUENCE; BENZIDINES; FEMALE; GENOTYPE; HUMANS; ISOENZYMES; KINETICS; LIVER; MALE; MIDDLE AGED; MOLECULAR SEQUENCE DATA; PHENOTYPE; RECOMBINANT PROTEINS;

EID: 0029835661     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (59)

1. Weber, W W., and Hein, D. W N-Acetylation pharmacogenetics Pharmacol. Rev , 37: 25-79, 1985.
2. Hein, D. W. Acetylator genotype and arylamine-induced carcinogenesis. Biochim. Biophys. Acts. 948: 37-66, 1988
3. Evans, D. P. N-acetyltransferase. Pharmacol. Ther., 42: 157-234, 1989.
4. Grant, D M., Blum, M , Beer, M., and Meyer, U A. Monomorphic and polymorphic human arylamine N-acetyltransferases A comparison of liver isozymes and expressed products of two cloned genes Mol Pharmacol , 39: 184-191, 1991
5. Ohsako, S., and Deguchi, T Cloning and expression of cDNAs for polymorphic and monomorphic arylamine N-acetyltransferases from human liver J. Biol. Chem., 265, 4630-4634, 1990
6. Blum, M , Demierre, A., Grant, D. M., Heim, M., and Meyer, U. A. Molecular mechanism of slow acetylation of drugs and carcinogens in humans. Proc Natl. Acad. Sci USA, 88 5237-5241, 1991.
7. Deguchi, T , Mashimo, M., and Suzuki, T Correlation between acetylator phenotypes and genotypes of polymorphic arylamine N-acetyltransferase m human liver J Biol Chem , 265 12757-12760, 1990
8. Hem, D W., Ferguson, R J , Doll, M A., Rustan, T. D., and Gray, K. Molecular genetics of human polymorphic N-acetyltransferase: enzymatic analysis of 15 recombinant wild-type, mutant, and chimeric NAT2 allozymes. Hum. Mol Genet, 3: 729-734, 1994.
9. Hem, D W , Doll, M A , Rustan, T D , and Ferguson, R. J. Metabolic activation of N-hydroxyarylamines and N-hydroxyarylamides by 16 recombinant human NAT2 allozymes. Effects of seven specific NAT2 nucleic acid substitutions. Cancer Res., 55: 3531-3536, 1995.
10. Vatsis, K P , and Weber, W. W. Structural heterogeneity of Caucasian N-acetyltransferase at the NAT1 locus. Arch Biochem. Biophys., 301: 71-76, 1993.
11. Hughes, N. C , McQueen, K. L., Janezic, S. A., Jewett, M. A. S., and Grant, D. M. Identification and characterization of variant alleles of human acetyltransferase NAT1 with defective function using p-ammosalicylate as an in vivo/in vitro probe Pharmacogenetics, in press, 1996.
12. Bell D A , Badawi, A. F., Lang, N. P., Ilett, K. F., Kadlubar, F. F., and Hirvonen, A Polymorphism in the N-acetyltransferase 1 (NAT1) polyadenylation signal: association of NAT1-10 allele with higher N-acetylation activity in bladder and colon tissue. Cancer Res., 55: 5226-5229, 1995.
13. Hein, D. W., Doll, M A , Rustan, T. D , Gray, K , Feng, Y , Ferguson, R J., and Grant, D. M. Metabolic activation and deactivation of arylamme carcinogens by recombinant human NAT1 and polymorphic NAT2 acetyltransferases. Carcinogenesis (Lond.), 14: 1633-1638, 1993
14. Miller, J A. Carcinogenesis by chemicals an overview. Cancer Res , 30, 559-576, 1970
15. Miller, J A., and Miller, E. C. The concept of reactive electrophihc metabolites in chemical carcinogenesis, recent results with aromatic amines, safrole, and aflatoxin B1. In D J Jollow, J. J Kocsis, R. Snyder, and H Vainio (eds.), Biological Reactive Intermediates, pp 6-24. New York: Plenum Publishing Corp., 1977
16. Kadlubar, F F., Miller, J A., and Miller, E. C. Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines m relation 10 urinary bladder carcinogenesis. Cancer Res., 37: 805-814, 1977
17. Vineis, P., Caporaso, N , Tannenbaum, S. R., Skipper, P. L., Glogowski, J , Bartsch, H., Coda, M., Talaska, G , and Kadlubar, F. Acetylation phenotype, carcinogenhemoglobin adducts, and cigarette smoking Cancer Res., 50: 3002-3004, 1990.
18. Vineis, P., Bartsch, H., Caporaso, N , Harrington, A M., Kadlubar, F. F , Landi, M. T , Malaveule, C., Shields, P. G , Skipper, P , Talaska, G., and Tannenbaum, S. R Genetically based N-acetyltransferase metabolic polymorphism and low-level environmental exposure to carcinogens. Nature (Lond.), 369: 154-156, 1994
19. Yu. M. C., Skipper, P. L., Taghizadeh, K., Tannenbaum, S. R., Chan, K. C , Henderson, B. E., and Ross, R. K. Acetylator phenotype, aminobiphenyl-hemoglobin adduct levels, and bladder cancer risk in White, Black, and Asian men in Los Angeles, California. J. Natl. Cancer Inst , 86: 712-716, 1994.
20. Mommsen, S., Barfod, N. M., and Aagaard, J. N-Acetyltransferase phenotypes in the urinary bladder carcinogenesis of a low risk population. Carcinogenesis (Lond.), 6: 199-201, 1985.
21. Lower, G. M., Jr, Nilsson, T., Nelson, C. E., Wolf, H., Gamsky, T. E., and Bryan, G T N-Acetyltransferase phenotype and risk in urinary bladder cancer: approaches in molecular epidemiology. Preliminary results in Sweden and Denmark. Environ. Health Perspect., 29: 71-79, 1979.
22. Flammang, T. J., and Kadlubar, F. F. Acetyl coenzyme A-dependent metabolic activation of N-hydroxy-3,2′-dimethyl-4-aminobiphenyl and several carcinogenic N-hydroxy arylamines in relation to tissue and species differences, other acy1 donors, and arylhydroxamic acid-dependent acyltransferases. Carcinogenesis (Lond.), 7: 919-926, 1986.
23. Badawi, A. F., Hirvonen, A., Bell, D. A., Lang, N P., and Kadlubar, F. F. Role of aromatic amine acetyltransferases, NAT1 and NAT2, in carcinogen-DNA adduct formation in the human urinary bladder. Cancer Res., 55 5230-5237, 1995.
24. Qian, G., Ross, R. K., Yu, M. C., Yuan, J., Gao, Y., Henderson, B. E., Wogan, G. N., and Groopman, J. D. A follow-up study of urinary markers of aflatoxin exposure and liver cancer risk in Shanghai, People's Republic of China. Cancer Epidemiol , Biomarkers & Prev., 3: 3-10, 1994
25. Tang, D , Santella, R. M., Blackwood, A. M., Young, T., Mayer, J., Jaretzki, A., Grantham, S., Tsai, W., and Perera, F. P A case control molecular epidemiologic study of lung cancer. Cancer Epidemiol., Biomarkers & Prev., 4: 341-346, 1995.
26. Hemminki, K DNA adducts: mutations and cancer Carcinogenesis (Lond.), 14: 2007-2012, 1993.
27. Case, R. A. M., Hosker, M. W., McDonald, D B., and Pearson, J T. Tumors of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates m the British chemical industry. Br. J. Ind Med., 11 75-104, 1954.
28. Zavon, M R., Hoegg, U., and Bingham, E. Benzidine exposure as a cause of bladder tumors. Arch Environ. Health, 27: 1-7, 1973.
29. Bi, W , Hayes, R. B., Feng, P , Qi, Y , You, X , Zhen, J , Zhang, M , Qu, B., Fu, Z , Chen, M., Co Chien, H. T., and Blot, W. J. Mortality and incidence of bladder cancer in benzidine-exposed workers in China. Am. J. Ind. Med., 21: 481-489, 1992
30. Grant, D. M., Josephy, P. D., Lord, H. L., and Morrison, L. D. Salmonella typkimurium strains expressing human arylamine N-acetyltransferases: metabolism and mutagenic activation of aromatic amines Cancer Res., 52: 3961-3964, 1992
31. Martin, C. N., Beland, F. A., Roth, R. W , and Kadlubar, F. F. 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, 1982.
32. Kennelly, J. C., Beland, F. A., Kadlubar, F. F., and Martin, C. N. Binding of N-acetylbenzidme and N,N′-diacetylbenzidine to hepatic DNA of rat and hamster m vivo and in vitro. Carcinogenesis (Lond.), 5: 407-412, 1984.
33. Frederick, C. B., Weis, C. C., Flammang, T J , Martin, C. N., and Kadlubar, F. F. Hepatic N-oxidation, acetyl-transfer and DNA-binding of the acetylated metabolites of the carcinogen, benzidine. Carcinogenesis (Lond), 6: 959-965, 1985.
34. Babu, S. R., Lakshmi, V. M , Hsu, F. F., Kane, K. E., III, Zenser, T. V., and Davis, B B. N-Acetylbenzidine-N′-glucuronidation by human, dog, and rat liver. Carcinogenesis (Lond), 14: 2605-2611, 1993.
35. Babu, S. R., Lakshmi, V. M., Zenser, T V , and Davis, B. B Glucuronidation of N′-acetylbenzidine by human liver. Drug Metab. Dispos, 22: 922-927, 1994
36. Cartwright, R., Glasham, R., Rogers, H., Ahmad, R., Barham-Hall, D., Higgins, E., and Khan, M. Role of N-acetyltransferases phenotypes in bladder carcinogenesis: a pharmacogenetic epidemiological approach to bladder cancer. Lancet, 2: 842-846, 1982
37. Hayes, R. B., Bi, W., Rothman, N., Broly, F., Caporaso, N , Feng, P., You, X., Yin, S , Woosley, R , and Meyer, U. A. N-Acetylation phenotype and genotype and risk of bladder cancer, in benzidine-exposed workers Carcinogenesis (Lond.), 14: 675-678, 1993.
38. Rothman, N., Bhatnager, V. K., Hayes, R B , Zenser, T. V , Kashyap, S. K., Butler, M. A., Bell, D. A., Lakshmi, V , Jaeger, M , Kashyap, R , Hirvonen, A , Schulte, P A., Dosemeci, M., Hsu, F., Parikh, D. J., Davis, B. B , and Talaska, G. The impact of interindividual variation in NAT2 activity on benzidine urinary metabolites and urothelial DNA adducts in exposed workers. Proc. Natl. Acad. Sci. USA, 93: 5084-5089, 1996.
39. Lakshmi, V M., Bell, D. A., Watson, M. A , Zenser, T. V , and Davis, B. B. N-Acetylbenzidine and N,N′-diacetylbenzidine formation by rat and human liver slices exposed to benzidine. Carcinogenesis (Lond.), 16: 1565-1571, 1995.
40. Lakshmi, V M , Mattammal, M. B., Spry, L. A., Kadlubar, F. F., Zenser, T. V., and Davis, B. B. Metabolism and disposition of benzidme in the dog Carcinogenesis (Lond.), 11: 139-144, 1990.
41. Sanger, F., Niklen, S., and Coulson, R. DNA sequencing with chain terminating inhibitors. Proc. Natl. Acad. Sci USA, 74: 5463-5467, 1977.
42. Trinidad, A., Kirlin, W. G., Ogolla, F , Andrews, A. F., Yerokun, T., Ferguson, R. J., Bradj, P K., and Hem, D. W. Kinetic characterization of acetylator genotype-dependent and -independent N-acetyltransferase isozymes in homozygous rapid and slow acetylator inbred hamster liver cytosol. Drug Metab. Dispos., 17: 238-247, 1989.
43. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye banding. Anal. Biochem., 72: 248-254, 1976.
44. Doll, M. A., Fretland, A. J., Deitz, A. C., and Hein, D. W Determination of human NAT2 acetylator genotype by restriction fragment length polymorphism and allele-specific amplification. Anal. Biochem., 231: 413-420, 1995.
45. Vatsis, K. P., Weber, W., Bell, D. A., Dupret, J-M., Evans, D. A P , Grant, D. M , Hem, D. W , Lin, H. J , Meyer, U. A., Relling, M. V., Sim, E., Suzuki, T., and Yamazoe, Y. Nomenclature for N-acetyltransferases. Pharmacogenetics, 5: 1-17, 1995.
46. Deitz, A. C., Doll, M. A., and Hein, D. W. Development of a human NAT1 genotype assay methodology and application for molecular epidemiological studies. Proc. N. D. Acad Sci , 50 15, 1996.
47. Babu, S. R., Lakshmi, V. M., Hsu, F. F., Zenser, T. V., and Davis, B. B. Role of N-glucuronidation in benzidine-induced bladder cancer in dog Carcinogenesis (Lond), 13: 1235-1240, 1992.
48. Babu, S. R., Wongsurawat, V. J., Zenser, T. V., and Davis, B. B. Benzidine glucuronidation in dog liver. Carcinogenesis (Lond.), 14: 893-897, 1993.
49. Gupta, R. C., Earley, K , and Sharma, S. Use of human peripheral blood lymphocytes to measure DNA binding capacity of chemical carcinogens. Proc. Natl. Acad. Sci. USA, 85: 3513-3517, 1988.
50. Kilbane, A. J., Petroff, T , and Weber, W. W. Kinetics of acetyl CoA. Arylamine N-acetyltransferase from rapid and slow acetylator human liver. Drug Metab. Dispos., 19: 503-507, 1991.
51. Babu, S. R., Lakshmi, V. M., Owens, I. S., Zenser, T. V , and Davis, B B. Human liver glucuronidation of benzidine. Carcinogenesis (Lond.), 15: 2003-2007, 1994.
52. Dupret, J., and Grant, D. M. Site-directed mutagenesis of recombinant human arylamine N-acetyltransferase expressed in Escherichia coli. J. Biol. Chem , 267: 7381-7385, 1992.
53. Weber, W. W., and Cohen, S. N. N-Acetylation of drugs, isolation and properties of an N-acetyltransferase from rabbit liver. Mol. Pharmacol. 3: 266-273, 1967.
54. Weber, W. W , and Cohen, S. N. The mechanism of isoniazid acetylation by human N-acetyltransferase. Biochim. Biophys Acta. 151: 276-278, 1968.
55. Lynn, R. K., Garvie-Gould, C. T., Milam, D. F., Scon, K F , Eastman, C L., Ilias, A M., and Rodgers, R. M. Disposition of the aromatic amine, benzidine, in the rat: characterization of mutagenic urinary and biliary metabolites. Toxicol. Appl. Pharmacol., 72: 1-14, 1984.
56. Lynn, R. K., Garvie-Gould, C., Milam, D. F., Scott, K. F., Eastman, C. L., and Rodgers, R. M. Metabolism of the human carcinogen, benzidine, in the isolated perfused rat liver. Drug Metab. Dispos., 11: 109-114, 1983.
57. Lakshmi, V. M., Zenser, T. V , Goldman, H D., Spencer, G. G., Gupta, R. C , Hsu, F. F., and Davis, B. B. The role of acetylation in benzidine metabolism and DNA adduct formation in dog and rat liver. Chem. Res. Toxicol., 8: 711-720, 1995.
58. Frederickson, S. M., Hatcher, J. F., Reznikoff, C. A., and Swaminathan, S. Acetyl transferase-mediated metabolic activation of N-hydroxy-4-armnobiphenyl by human uroepithelial cells. Carcinogenesis (Lond.), 13: 955-961, 1992.
59. Hsu, F , Lakshmi, V., Rothman, N., Bhatnager, V. K., Hayes, R. B , Kashyap. R , Parikh, D J., Kashyap, S K , Turk, J., Zenser, T., and Davis, B. Determination of benzidine, N-acetylbeitzidine and N,N′-diacetylbenzidine in human urine by capillary gas chromatography/negative ion chemical ionization mass spectrometry. Anal. Biochem., 234: 183-189, 1996.