Hepatic Microsomal N-Glucuronidation and Nucleic Acid Binding of N-Hydroxy Arylamines in Relation to Urinary Bladder Carcinogenesis

Cancer Research

Volumn 37, Issue 3, 1977, Pages 805-814

  Kadlubar, Fred F ^a,b   Miller, James A ^a   Miller, Elizabeth C ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL; AROMATIC AMINE; FLUORENYLACETOHYDROXAMIC ACID; N HYDROXY 2 FLUORENYLAMINE; NUCLEIC ACID;

4 (HYDROXYLAMINO)AZOBENZENE; BLADDER CARCINOGENESIS; BLADDER CARCINOMA; DOG; DRUG METABOLISM; GLUCURONIDATION; HUMAN; LIVER CELL; LIVER MICROSOME; MICROSOME; N HYDROXY 1 NAPHTHYLAMINE; N HYDROXY 2 NAPHTHYLAMINE; N HYDROXY 2 NAPHTHYLAMINE H 3; N HYDROXY 4 BIPHENYLAMINE; NORMAL HUMAN; PHARMACOKINETICS; RAT; THEORETICAL STUDY;

ANIMAL; BLADDER NEOPLASMS; DNA; DOGS; GLUCURONATES; GLUCURONIDASE; HUMAN; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; HYDROXYLAMINES; IN VITRO; MICROSOMES, LIVER; NEOPLASMS, EXPERIMENTAL; RATS; RNA; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0017365046     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (59)

1. Ashwell, G. Colorimetric Analysis of Sugars. Methods Enzymol., 3: 73-105,1957.
2. Bartsch, H., Dworkin, C., Miller, E. C., and Miller, J. A. Formation of Electrophilic N-Acetoxyarylamines in Cytosols from Rat Mammary Gland and Other Tissues by Transacetylation from the Carcinogen N-Hydroxy-4-acetylaminobiphenyl. Biochim. Biophys. Acta, 304: 42–55, 1973.
3. Bartsch, H., Dworkin, M., Miller, J. A., and Miller, E. C. Electrophilic N-Acetoxyaminoarenes Derived from Carcinogenic N-Hydroxy-N-acetylam-inoarenes by Enzymatic Deacetylation and Transacetylation in Liver. Biochim. Biophys. Acta, 286: 272–298, 1972.
4. Belman, S., and Troll, W. The Reaction of Bladder Carcinogens and Mutagens with Deoxyribonucleic Acid. In: K. F. Lampe (ed.), Bladder Cancer, pp. 58–79. Birmingham, Alabama. Aesculapius Publishing Co., 1967.
5. Belman, S., Troll, W., Teebor, G., and Mukai, F. The Carcinogenic and Mutagenic Properties of N-Hydroxy-aminonaphthalenes. Cancer Res., 28: 535–542, 1968.
6. Booth, J., and Boyland, E. The Biochemistry of Aromatic Amines. 10. Enzymic N-Hydroxylation of Arylamines and Conversion of Arylhydroxylamines into o-Aminophenols. Biochem. J., 91: 362–369, 1964.
7. Boyland, E., Busby, E. R., Dukes, C. E., Grover, P. L., and Manson, D. Further Experiments on Implantation of Materials into the Urinary Bladder of Mice. Brit. J. Cancer, 18: 575–581, 1964.
8. Boyland, E., Dukes, C. E., and Grover, P. L. Carcinogenicity of 2-Naphthylhydroxylamine and 2-Naphthylamine. Brit. J. Cancer, 17: 79–84, 1963.
9. Boyland, E., Manson, D., and Orr, S. F. D. The Biochemistry of Aromatic Amines. 2. The Conversion of Arylamines into Arylsulphonic Acids and Arylamine-N-glucosiduronic Acids. Biochem. J., 65: 417–423, 1957.
10. Brill, E., and Radomski, J. L. Comparison of the In Vitro and In Vivo N-Oxidation of the Carcinogenic Aromatic Amines. Xenobiotica, 1: 347–348, 1971.
11. Bryan, G. T., and Morris, C. R. Distribution of 14 C-labeled 8-Methyl Ether of Xanthurenic Acid in the Mouse Following Bladder Luminal, Subcutaneous and Intraperitoneal Administration under Carcinogenic Conditions. Cancer Res., 28: 186–191, 1968.
12. Bryan, G. T., Morris, C. R., and Brown, R. R. Absorption of 14 C-Labeled 3-Hydroxy-L-kynurenine and 3-Hydroxyanthranilic Acid from the Mouse Urinary Bladder under Carcinogenic Conditions. Cancer Res., 25:1432-1437, 1965.
13. Cardona, R. A., and King, C. M. Activation of the O-Glucuronide of the Carcinogen N-Hydroxy-N-2-FluorenyIacetamide by Enzymatic Deacetylation in Vitro: Formation of Fluorenylamine-tRNA Adducts. Biochem. Pharmacol., 25: 1051–1056, 1976.
14. Clayson, D. B., and Cooper, E. H. Cancer of the Urinary Tract. Advan. Cancer Res., 13: 271–381, 1970.
15. Exner, O. Derivatives of Oximes. II. Reduction of O-and N-Alkyl Oximes with Lithium Aluminum Hydride. Collection Czech. Chem. Commun., 20: 202–209, 1955.
16. Glucuronidase (Bovine Liver). In: Worthington Enzyme Manual, p. 109. Freehold, N. J.: Worthington Biochemical Corp., 1972.
17. Gornall, A. G., Bardawill, C. J., and David, M. M. Determination of Serum Proteins by Means of the Biuret Reaction. J. Biol. Chem., 177: 751–766, 1949.
18. Gorski, J. P., and Kasper, C. B. Purification and Properties of Microsomal UDP-Glucuronosyltransferase from Rat Liver. J. Biol. Chem., 252: 1336–1343, 1977.
19. Hamer, J., and Macaluso, A. Nitrones. Chem. Rev., 64: 473-495, 1964.
20. Irving, C. C. Metabolic Activation of N-Hydroxy Compounds by Conjugation. Xenobiotica, 1: 387–398, 1971.
21. Irving, C. C. Conjugates of N-Hydroxy Compounds. In: W. H. Fishman (ed.), Metabolic Conjugation and Metabolic Hydrolysis pp. 53–119. New York: Academic Press, Inc., 1973.
22. Irving, C. C., and Russell, L. T. Synthesis of the O-Glucuronide of N-2-Fluorenylhydroxylamine. Reaction with Nucleic Acids and with Guanosine 5'-Monophosphate. Biochemistry, 9: 2471–2476, 1970.
23. Irving, C. C., and Veazey, R. A. Isolation of Deoxyribonucleic Acid and Ribosomal Ribonucleic Acid from Rat Liver. Biochim. Biophys. Acta, 166: 246–248, 1968.
24. Kadlubar, F. F., Miller, J. A., and Miller, E. C. Microsomal N-Oxidation of the Hepatocarcinogen N-Methyl-4-aminoazobenzene and the Reactivity of N-Hydroxy-N-methyl-4-aminoazobenzene. Cancer Res., 36: 1196—1206, 1976.
25. Kadlubar, F. F., Miller, J. A., and Miller, E. C. Hepatic Metabolism of N-Hydroxy-N-methyl-4-aminoazobenzene and Other N-Hydroxy Arylamines to Reactive Sulfuric Acid Esters. Cancer Res., 36: 2350–2359, 1976.
26. Kamm, O. β-Phenylhydroxylamine. In: H. Gilman (ed.), Organic Syntheses, Collective pp. 445–447. New York: John Wiley & Sons, Inc., 1941.
27. Kiese, M., Renner, G., and Wiedemann, I. N-Hydroxylation of 2-Aminofluorene in the Guinea Pig and by Guinea Pig Liver Microsomes In Vitro. Naunyn-Schmiedebergs Arch. Expt. Pathol. Pharmakol., 252: 418–423, 1966.
28. King, C. M. Mechanism of Reaction, Tissue Distribution, and Inhibition of Arylhydroxamic Acid Acyltransferase. Cancer Res., 34: 1503–1515, 1974.
29. Kriek, E. On the Interaction of N-2-Fluorenylhydroxylamine with Nucleic Acids In Vitro. Biochem. Biophys. Res. Commun., 20: 793-799, 1965.
30. Kriek, E. Carcinogenesis by Aromatic Amines. Biochim. Biophys. Acta, 355: 177–203, 1974.
31. Lotlikar, P. D., Miller, E. C., Miller, J. A., and Margreth, A. The Enzymatic Reduction of the N-Hydroxy Derivatives of 2-Acetylaminofluorene and Related Carcinogens by Tissue Preparations. Cancer Res., 25: 1743–1752, 1965.
32. Maher, V. M., Miller, J. A., Miller, E. C., and Summers, W. C. Mutation and Loss of Transforming Activity of Bacillus subtilis DNA after Reaction with Esters of Carcinogenic N-Hydroxy Aromatic Amides. Cancer Res., 30: 1473–1480, 1970.
33. Manson, D. Oxidation of N-Naphthylhydroxylamines to Nitrosonaphthols by Air. J. Chem. Soc. Perkin Trans. I, 192–194, 1974.
34. McDonald, D. F., and Lund, R. R. The Role of the Urine in Vesical Neoplasm. 1. Experimental Confirmation of the Urogenous Theory of Pathogenesis. J. Urol., 71: 560–570, 1954.
35. Miller, J. A. Carcinogenesis by Chemicals: An Overview-G. H. A. Clowes Memorial Lecture. Cancer Res., 30: 559–576, 1970.
36. Miller, J. A., and Miller, E. C. The Metabolic Activation of Carcinogenic Aromatic Amines and Amides. Progr. Exptl. Tumor Res., 11: 273–301, 1969.
37. Miller, J. A., Wyatt, C. S., Miller, E. C., and Hartman, H. A. The N-Hydroxylation of 4-Acetylaminobiphenyl by the Rat and Dog and the Strong Carcinogenicity of N-Hydroxy-4-acetylaminobiphenyl in the Rat. Cancer Res., 21: 1465–1473 1961.
38. Morris, C. R., and Bryan, G. T. Absorption of 1 4 C-Labeled Tryptophan, Its Metabolites, Glycine, and Glucose by the Urinary Bladder of the Mouse. Invest. Urol. 3: 577–585, 1966.
39. Osbourne, C. A., Low, D. G., and Finco, D. R. Canine and Feline Urology. Philadelphia: W. B. Saunders Co., 1972.
40. Poirier, L. A., Miller, J. A., and Miller, E. C. The N-and Ring-Hydroxylation of 2-Acetylaminofluorene and the Failure to Detect N-Acetylation of 2-Aminofluorene in the Dog. Cancer Res., 23: 790–800, 1963.
41. Poulsen, L. L., Masters, B. S. S., and Ziegler, D. M. Mechanism of 2-Naphthylamine Oxidation Catalyzed by Pig Liver Microsomes. Xenobiotica, 6: 481–498, 1976.
42. Puhakainen, E. and Hanninen, O. Pyrophosphatase and Glucuronosyltransferase in Microsomal UDPglucuronic-Acid Metabolism in the Rat Liver. European J. Biochem., 61: 165–169, 1976.
43. Radomski, J. L., and Brill, E. Bladder Cancer Induction by Aromatic Amines: Role of N-Hydroxy Metabolites. Science, 167: 992-993,1970.
44. Radomski, J. L., Brill, E., Deichmann, W. B., and Glass, E. M. Carcinogenicity Testing of N-Hydroxy and Other Oxidation and Decomposition Products of 1-and 2-Naphthylamine. Cancer Res., 31: 1461–1467, 1971.
45. Radomski, J. L., Conzelman, G. M., Jr., Rey, A. A., and Brill, E. N-Oxidation of Certain Aromatic Amines, Acetamides, and Nitro Compounds by Monkeys and Dogs. J. Natl. Cancer Inst., 50: 989-995,1973.
46. Radomski, J. L., Rey, A. A., and Brill, E. Evidence for a Glucuronic Acid Conjugate of N-Hydroxy-4-aminobiphenyl in the Urine of Dogs Given 4-Aminobiphenyl. Cancer Res., 33: 1284-1289, 1973.
47. Sato, K., Poirier, L. A., Miller, J. A., and Miller, E. C. Studies on the N-Hydroxylation and Carcinogenicity of 4-Aminoazobenzene and Related Compounds. Cancer Res., 26: 1678–1687, 1966.
48. Scott, W. W., and Boyd, H. L. A Study of the Carcinogenic Effect of Beta-Naphthylamine on the Normal and Substituted Isolated Sigmoid Loop Bladder of Dogs. J. Urol., 70: 914-925, 1953.
49. Shindo, H., and Umezawa, B. Infrared Absorption Spectra of Aldonitrones. I. Infrared Spectra of Benzaldehyde N-Methyl and N-Phenyl Nitrones. Chem. Pharm. Bull. Tokyo, 10: 493–503, 1962.
50. Tada, M., and Tada, M. Seryl-tRNA Synthetase and Activation of the Carcinogen 4-Nitroquinoline-1-oxide. Nature, 255: 510–512, 1975.
51. Thorgeirsson, S. S., Jollow, D. J., Sasame, H. A., Green, I., and Mitchell, J. R. The Role of Cytochrome P-450 in N-Hydroxylation of 2-Acetylaminofluorene. Mol. Pharmacol., 9: 398-404, 1973.
52. Troll, W., Belman, S., and Levine, E. The Effect of Metabolites of 2-Naphthylamine and the Mutagen Hydroxylamine on the Thermal Stability of DNA and Polyribonucleotides. Cancer Res., 23: 841–847, 1963.
53. Uehleke, H. N-Hydroxylation of Carcinogenic Amines in vivo and in vitro with Liver Microsomes. Biochem. Pharmacol., 12: 219–221, 1963.
54. Uehleke, H., and Nestel, K. Hydroxylamino and Nitrosobiphenyl: Biologische Oxydations Produkte der Reduction von 4-Nitrobiphenyl. Naunyn-Schmiedebergs Arch. Exptl. Pathol. Pharmacol., 257: 151–171, 1967.
55. von Jagow, R., and Kiese, M. Isolation of N-Hydroxy-p-aminopropio-phenone from the Urine of Rabbits Injected with p-Aminopropiophenone. Biochem. Biophys. Acta, 136: 168–169, 1967.
56. Weisburger, J. H., Grantham, P. H., and Weisburger, E. K. The Metab-bolism of N-2-Fluorenylhydroxylamine in Male and Female Rats. Biochem. Pharmacol., 15: 833–839, 1966.
57. Weisburger, J. H., and Weisburger, E. K. Biochemical Formation and Pharmacological, Toxicological, and Pathological Properties of Hydroxyamines and Hydroxamic Acids. Pharmacol. Rev., 25: 1–66, 1973.
58. Willstatter, R., and Kubli, H. Uber die Reduktion von Nitroverbindungen nach der Methode von Zinin. Chem. Ber., 41: 1936–1940, 1908.
59. Zakim, D., and Vessey, D. A. Techniques for the Characterization of UDP-Glucuronosyltransferase, Glucose-6-Phosphatase, and Other Tightly-Bound Microsomal Enzymes. Methods Biochem. Anal., 21:1-37, 1973.