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Modifiers of Endogenous Nitrosamine Synthesis and Metabolism

  • H. Bartsch
  • H. Ohshima
  • J. Nair
  • B. Pignatelli
  • S. Calmels
Part of the Basic Life Sciences book series (BLSC, volume 39)

Abstract

N-Nitroso compounds (NOCs), a class of versatile carcinogens (1,13), are formed in nature, most likely since mankind first existed on earth, whenever nitrosating agents such as nitrite or nitrosating gases encounter nitrosatable amines. To date, more than 300 NOCs have been tested in animals, and about 90% of them produced tumors in 40 animal species, including primates. Humans are exposed to NOCs from exogenous and endogenous sources through nitrosation of ingested/inhaled amino precursors. Nitrite is produced by bacterial reduction of nitrate, normally in the mouth, and the nitrosation reaction generally proceeds through an acid-catalyzed reaction in the stomach. Any nitrosation reaction occurring in vivo is, however, affected by many factors, such as the pH, precursor concentration, and the presence of catalysts and inhibitors. These various factors, some of which are difficult to measure in vivo, have complicated the estimation of nitrosation reactions occurring in humans.

Keywords

Esophageal Cancer Extrahepatic Tissue Betel Quid Beetroot Juice Endogenous Formation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Bartsch, H., and R. Montesano (1984) Relevance of nitrosamines to human cancer. Carcinogenesis 5:1381–1393.CrossRefGoogle Scholar
  2. 2.
    Bartsch, H., H. Ohshima, N. Mufioz, and S.H. Lu (1983) Measurement of endogenous nitrosatlon in humans: Potential applications of a new method and initial results. In Human Carcinogenesis, C.C. Harris and H.N. Autrup, eds. Academic Press, New York, p. 833.Google Scholar
  3. 3.
    Bartsch, H., H. Ohshima, N. Mufioz, M. Crespi, V. Cassale, V. Ramazotti, R. Lambert, Y. Minaire, J. Forichon, and C.L. Walters (1984) In- vivo nitrosation, precancerous lesions and cancers of the gastrointestinal tract. On-going studies and preliminary results. In N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer (lARC Scientific Publications No. 57), I.K. O’;Neill, R.C. von Borstel, C.T. Miller, J. Long, and H. Bartsch, eds. International Agency for Research on Cancer, Lyon, France, p. 957.Google Scholar
  4. 4.
    Bhide, S.V., A.S. Shah, J. Nair, and D. Nagarajarao (1984) Epidemiological and experimental studies on tobacco related oral cancer in India. In N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer (lARC Scientific Publications No. 57), I.K. O’;Neill, R.C. von Borstel, C.T. Miller, J. Long, and H. Bartsch, eds. International Agency for Research on Cancer, Lyon, France, p. 851.Google Scholar
  5. 5.
    Calmels, S., H. Ohshima, P. Vincent, A.M. Gounot, and H. Bartsch (1985) Screening of microorganisms for nitrosation catalysis at pH 7 and kinetic studies on nitrosamine formation from secondary amine by E, coli strains. Carcinogenesis 6:911.CrossRefGoogle Scholar
  6. 6.
    Chu, C., and P.N. Magee (1981) The metabolic fate of nitrosoproline in the rat. Cancer Res. 41:3653.Google Scholar
  7. 7.
    Dailey, R.E., R.C. Braunberg, an A.M. Blaschka (1975) The absorption, distribution and excretion of (C)-nitrosoproline by rats. Toxicology 3:23.CrossRefGoogle Scholar
  8. 8.
    Diaz-Gomez, M.I., P.F. Swann, and P.N. Magee (1977) The absorption and metabolism in rats of small oral doses of dimethyInitrosamine. Implication for the possible hazard of dimethyInitrosamine in human food. Biochem. J. 164:497–500.Google Scholar
  9. 9.
    Hawksworth, G., and M. Hill (1971) Bacteria and the N-nitrosation of secondary amines. Br. J. Cancer 25:520.CrossRefGoogle Scholar
  10. 10.
    Hoffmann, D., and K.D. Brunnemann (1983) Endogenous formation of nitrosoproline in cigarette smokers. Cancer Res. 43:5570.Google Scholar
  11. 11.
    Hoffmann, D., K.D. Brunnemann, J.D. Adams, and S.S. Hecht (1984) Formation and analysis of]N-nitrosamines in tobacco products and their endogenous formation in consumers. In N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer (lARC Scientific Publications No. 57), I.K. O’;Neill, R.C. von Borstel, C.T. Miller, J. Long, and H. Bartsch, eds. International Agency for Re-search on Cancer, Lyon, France, p. 743.Google Scholar
  12. 12.
    Hoffmann, D., and S.S. Hecht (1985) Nicotine-derived JN-nitrosamines and tobacco-related cancer: Current status and future directions. Cancer Res. 45:935.Google Scholar
  13. 13.
    International Agency for Research on Cancer (1978) Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Vol. 17. Some N-Nitroso Compounds, 365 pp.Google Scholar
  14. 14.
    International Agency for Research on Cancer (1985) Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Vol. 38. Tobacco Smoking (in press).Google Scholar
  15. 15.
    Kantor, A.F., P. Hartige, R.N. Hoover, A. Narayana, J.W. Sullivan, and J.F. Fraumeni, Jr. (1984) Urinary tract infection and risk of bladder cancer. Am. J. Epidemiol. 119:510.Google Scholar
  16. 16.
    Ladd, K.F., H.L. Newmark, and M.C. Archer (1984) N-nitrosation of proline in smokers and non-smokers. J. Natl. Cancer Inst. 73:83.Google Scholar
  17. 17.
    Lu, S.H., H. Ohshima, and H. Bartsch (1984) Recent studies on N-ni- troso compounds as possible etiological factors in oesophageal cancer.N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer (lARC Scientific Publications No. 57), I.K. O’;Neill, R.C. von Borstel, C.T. Miller, J. Long, and H. Bartsch, eds. International Agency for Research on Cancer, Lyon, France, p. 947.Google Scholar
  18. 18.
    Mirvish, S.S., O. Bulay, R.G. Runge, and K. Patil (1980) Study of the carcinogenicity of large doses of dimethylnitramine, N-nitroso-L-pro- line and sodium nitrite administered in drinking water to rats. J. Natl. Cancer Inst. 64:1435.Google Scholar
  19. 19.
    Nair, J., H. Ohshima, M. Friesen, M. Croisy, S.V. Bhide, and H. Bartsch (1985) Tobacco-specific and betel nut specific N-nitrosamino compounds: Occurrence in saliva and urine of betel quid chewers and formation in vitro by nitrosation of betel quid. Carcinogenesis 6: 295.CrossRefGoogle Scholar
  20. 20.
    Ohshima, H., and H. Bartsch (1982) Quantitative estimation of endogenous nitrosation in humans by measuring excretion of N-nitrosoproline in the urine. In Environmental Mutagens and Carcinogens, T. Sugimura, S. Kondo, and H. Takabe, eds. University of Tokyo Press, Tokyo, p. 577.Google Scholar
  21. 21.
    Ohshima, H., and H. Bartsch (1981) Quantitative estimation of endogenous nitrosation in humans by monitoring 1-nitrosoproline excreted in the urine. Cancer Res. 41:3658.Google Scholar
  22. 22.
    Ohshima, H., J.C. Bereziat, and H. Bartsch (1982) Monitoring N-nitrosa- mino acids excreted in the urine and feces of rats as an index for endogenous nitrosation. Carcinogenesis 3:115.CrossRefGoogle Scholar
  23. 23.
    Ohshima, H., M. Friesen, I.K. O’;Neill, and H. Bartsch (1983) Presence in human urine of a new K-nitroso compound, N-nitrosothiazolidine 4- carboxylic acid. Cancer Lett. 20:183.CrossRefGoogle Scholar
  24. 24.
    Ohshima, H. I.K. O’;Neill, M. Friesen, J.C. Bereziat, and H. Bartsch (1984) Occurrence in human urine of new sulphur-containing N-nitrosamino acids, N;-nitrosothiazolidine 4-carboxylic acid and its 2-methyl derivative, and their formation. J. Cancer Res. Clin. Oncol. 108:121.CrossRefGoogle Scholar
  25. 25.
    Pegg, A.E., and W. Perry (1981) Alkylatlon of nucleic acids and metabolism of small doses of dimethylnitrosamine in the rat. Cancer Res. 41:3128–3132.Google Scholar
  26. 26.
    Pignatelli, B., J.C. Bereziat, G. Descotes, and H. Bartsch (1982) Catalysis of nitrosation in vitro and in vivo in rats by catechin and resorcinol and inhibition by chlorogenic acid. Carcinogenesis 3:1045.CrossRefGoogle Scholar
  27. 27.
    Stich, H.F., H. Ohshima, B. Pignatelli, J. Michelon, and H. Bartsch (1983) Inhibitory effect of betel nut extracts on endogenous nitrosation in humans. J. Natl. Cancer Inst. 70:1047.Google Scholar
  28. 28.
    Stich, H.F., B.P. Dunn, B. Pignatelli, H. Ohshima, and E. Bartsch (1984) Dietary phenolics and betel nut extracts as modifiers on N- nitrosation in rat and man. In N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer (lARC Scientific Publications No. 57), I.K. O’;Neill, R.C. von Borstel, C.T. Miller, J. Long, and H. Bartsch, eds. International Agency for Research on Cancer, Lyon, France, p. 213.Google Scholar
  29. 29.
    Swann, P.F. (1984) Effect of ethanol on nitrosamine metabolism and distribution. Implications for the role of nitrosamines in human cancer and for the influence of alcohol consumption on cancer incidence. In N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer (lARC Scientific Publications No. 57), I.K. O’;Neill, R.C. von Borstel, C.T. Miller, J. Long, and H. Bartsch, eds. International Agency for Research on Cancer, Lyon, France, p. 501.Google Scholar
  30. 30.
    Tsuda, H., T. Hirayama, and T. Sugimura (1983) Presence of N-nitroso- L-thioproline and N-nitroso-L-methylthioproline in human urine as major li-nitroso compounds. Gann 74:331.Google Scholar
  31. 31.
    Tuyns, A.J. (1983) Protective effect of citrus fruit on esophageal cancer. Nutr. Cancer 5:195.CrossRefGoogle Scholar
  32. 32.
    Tuyus, A.J., G. Pequignot, and O.M. Jensen (1977) Le cancer de I’;oes- phage en Ille et Vilaine en fonction des niveaux de consommation d’;al- cool et de tabac. Bull. Cancer 64:45.Google Scholar
  33. 33.
    Wenke, G., and D. Hoffmann (1983) A study of betel quid carcinogenesis. 1. On the vitro N-nitrosation of arecoline. Carcinogenesis 4:169.CrossRefGoogle Scholar
  34. 34.
    Winn, D.M. (1984) Tobacco chewing and snuff dipping: An association with human cancer. In N-Nitroso Compounds; Occurrence, Biological Effects and Relevance to Human Cancer (lARC Scientific Publications No. 57), I.K. O’;Neill, R.C. von Borstel, C.T. Miller, J. Long, and H. Bartsch, eds. International Agency for Research on Cancer, Lyon, France, p. 837.Google Scholar
  35. 35.
    Yang, C.S. (1980) Research on oesophageal cancer in China: A review. Cancer Res. 40:2633.Google Scholar

Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • H. Bartsch
    • 1
  • H. Ohshima
    • 1
  • J. Nair
    • 1
  • B. Pignatelli
    • 1
  • S. Calmels
    • 1
  1. 1.Division of Environmental CarcinogenesisInternational Agency for Research on CancerLyonFrance

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