The Protective Role of 11β-Hydroxysteroid Dehydrogenase/Carbonyl Reductase Against Tobacco-Smoke Related Lung Cancer

  • Edmund Maser
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 463)

Abstract

Lung cancer is one of the most common cancers worldwide and has the highest mortality rate among malignant tumors in the United States (Boring et al., 1994). More than 85 % of l cancers may be attributed directly to cigarette smoking (Wynder and Hoffmann, 1994). e of the most potent carcinogens in tobacco products is the nitrosamine 4-(methyl- nitrosamino)-l-(3-pyridyl)-l-butanone (NNK) (Rivenson et al., 1988) which is formed by nitrosation of nicotine during the processing of tobacco (Burton et al., 1989) (Figure 1).

Keywords

Cortisol Nicotine Carbonyl Glucocorticoid Flavonoid 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adams, J. D., La Voie, E. J., and Hoffmann, D., 1985, On the pharmacokinetics of tobacco-specific N-nitrosamines in Fisher rats, Carcinogenesis, 6: 509–511.PubMedCrossRefGoogle Scholar
  2. Adams, J. D., LaVoie, E. J., O’Mara-Adams, K. J., Hoffmann, D., Carey, K. D., and Marshall, M. V., 1985, Pharmacokinetics of N-nitrosonornicotine and 4-methylnitrosamino-l-(3-pyridyl)-l-butanone in laboratory animals, Cancer Lett, 28: 195–201.PubMedCrossRefGoogle Scholar
  3. Boring, C. C., Squires, T. S., Tong, T., and Montgomery, S., 1994, Cancer Statistics, 1994, CA Cancer J. Clin., 44: 7–26.PubMedCrossRefGoogle Scholar
  4. Burton, H. R., Childs, G. H., Anderson, R. A., and Fleming, P. D., 1989, Changes in chemical composition of Burley tobacco during senescence and curing. 3. Tobacco specific nitrosamines, J. Agric. Food Chem., 37: 426–430.CrossRefGoogle Scholar
  5. Carmella, S. G., Akerkar, S. A., Richie, J. P., and Hecht, S. S., 1995, Intraindividual and interindividual differences in metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone (NNK) in smoker’s urine, Cancer Epidemiol. Biomarkers & Prev., 4: 635–652.Google Scholar
  6. Carmella, S. G., Borukhova, A., Akerkar, S. A., and Hecht, S. S., 1997, Analysis of human urine for pyridine-N-ox-ide metabolites of 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone, a tobacco-specific lung carcinogen, Cancer Epidemiol. Biomarkers Prev., 6: 113–120.PubMedGoogle Scholar
  7. Crespi, C. L., Penman, B. W., Gelboin, H. V., and Gonzalez, F. J., 1991, A tobacco smoke-derived nitrosamine, 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone, is activated by multiple human cytochrome P450s including the polymorphic human cytochrome P4502D6, Carcinogenesis, 12: 1197–1201.PubMedCrossRefGoogle Scholar
  8. Hecht, S. S., 1994, Metabolic activation and detoxification of tobacco-specific nitrosamines-a model for cancer prevention strategies, Drug Metab. Rev., 26: 373–390.PubMedCrossRefGoogle Scholar
  9. Hecht, S. S., Carmella, S. G., Murphy, S. E., Akerkar, S., Brunnemann, K. D., and Hoffmann, D., 1993, A tobacco-specific lung carcinogen in the urine of men exposed to cigarette smoke, N. Engl. J. Med., 329: 1543–1546.PubMedCrossRefGoogle Scholar
  10. Hecht, S. S. and Hoffmann, D., 1988, Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke, Carcinogenesis, 9: 875–884.PubMedCrossRefGoogle Scholar
  11. Hecht, S. S. and Hoffmann, D., 1989, The relevance of tobacco-specific nitrosamines to human cancer, Cancer Surv., 8: 273–294.PubMedGoogle Scholar
  12. Hecht, S. S., Trushin, N., Reid Quinn, C. A., Burak, E. S., Jones, A. B., Southers, J. L., Gombar, C. T., Carmella, S. G., Anderson, L. M., and Rice, J. M., 1993, Metabolism of the tobacco-specific nitrosamine 4-(methylni-trosamino)-l-(3-pyridyl)-l-butanone in the patas monkey: pharmacokinetics and characterization of glu-curonide metabolites, Carcinogenesis, 14: 229–236.PubMedCrossRefGoogle Scholar
  13. Hecht, S. S., Young, R., and Chen, C. B., 1980, Metabolism in the F344 rat of 4-(N-methyl-N-nitrosamino)-l-(3-pyridyl)-1-butanone, a tobacco-specific carcinogen, Cancer Res., 40: 4144–4150.PubMedGoogle Scholar
  14. Maser, E., 1995, Xenobiotic carbonyl reduction and physiological steroid oxidoreduction-the pluripotency of several hydroxysteroid dehydrogenases, Biochem. Pharmacol, 49: 421–440.PubMedCrossRefGoogle Scholar
  15. Maser, E., 1996, llβ-Hydroxysteroid dehydrogenase acts as carbonyl reductase in microsomal phase I drug metabolism, Exp. Toxic. Pathol, 48: 266–273.Google Scholar
  16. Maser, E., 1997, Stress, hormonal changes, alcohol, food constituents and drugs: factors that advance the incidence of tobacco smoke-related cancer?, Trends Pharmacol. Sci., 18: 270–275.PubMedGoogle Scholar
  17. Maser, E., 1998, 1 lβ-Hydroxysteroid dehydrogenase responsible for carbonyl reduction of the tobacco-specific nitrosamine 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone in mouse lung microsomes, Cancer Res.,(in press)Google Scholar
  18. Maser, E. and Bannenberg, G., 1994a, The purification of llβ-hydroxysteroid dehydrogenase from mouse liver microsomes, J. Steroid Biochem. Molec. Biol.,4: 257–26CrossRefGoogle Scholar
  19. Maser, E. and Bannenberg, G., 1994b, llβ-Hydroxysteroid dehydrogenase mediates reductive metabolism of xenobiotic carbonyl compounds, Biochem. Pharmacol, 47: 1805–1812.PubMedCrossRefGoogle Scholar
  20. Maser, E., Friebertshäuser, J., and Mangoura, S. A., 1994, Ontogenic pattern of carbonyl reductase activity of 1 lβ-hydroxysteroid dehydrogenase in mouse liver and kidney, Xenobiotica, 24: 109–117.PubMedCrossRefGoogle Scholar
  21. Maser, E. and Oppermann, U. C. T., 1997, Role of type-1 11 β-hydroxysteroid dehydrogenase in detoxification processes, Eur. J. Biochem., 249: 356–369.CrossRefGoogle Scholar
  22. Maser, E., Richter, E., and Friebertshauser, J., 1996, The identification of 11 beta-hydroxysteroid dehydrogenase as carbonyl reductase of the tobacco-specific nitrosamine 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone, Eur J. Biochem., 238: 484–89.PubMedCrossRefGoogle Scholar
  23. Meger, M., Meger-Kossien, I., Dietrich, M., Tricker, A. R., Scherer, G., and Adlkofer, F., 1996, Metabolites of 4-(N-methylnitrosamino)-l-(3-pyridyl)-l-butanone in urine of smokers, Eur. J. Cancer Prev., 5 (Suppl. l): 121–12PubMedGoogle Scholar
  24. Murphy, S. E., Palomino, A., Hecht, S. S., and Hoffmann, D., 1990, Dose-response study of DNA and hemoglobin adduct formation by 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone in F344 rats, Cancer Res., 50: 5446–5452.PubMedGoogle Scholar
  25. Oppermann, U. C. T., Netter, K. J., and Maser, E., 1995, Cloning and primary structure of murine 11 β-hydroxysteroid dehydrogenase/microsomal carbonyl reductase, Eur. J. Biochem., 227: 202–208.PubMedCrossRefGoogle Scholar
  26. Rekka, E. A., Soldan, M., Belai, I., Netter, K. J., and Maser, E., 1996, Biotransformation and detoxification of in-secticidal metyrapone analogues by carbonyl reduction in the human liver, Xenobiotica, 26: 1221–1229.PubMedCrossRefGoogle Scholar
  27. Riddle, M. C. and McDaniel, P. A., 1993, Acute reduction of renal 11 beta-hydroxysteroid dehydrogenase activity by several antinatriuretic stimuli, Metabolism, 42: 1370–1374.PubMedCrossRefGoogle Scholar
  28. Rivenson, A., Hoffmann, D., Prokopczyk, B., Amin, S., and Hecht, S. S., 1988, Induction of lung and exocrine pancreas tumors in F344 rats by tobacco-specific and Areca-derived N-nitrosamines, Cancer Res., 48: 6912–6917.PubMedGoogle Scholar
  29. Seckl, J. R., 1993, 11 β-Hydroxysteroid dehydrogenase isoforms and their implications for blood pressure regulation, Eur. J. Clin. Invest., 23: 589–601.PubMedCrossRefGoogle Scholar
  30. Valentino, R., Tommaselli, A. P., Savastano, S., Stewart, P. M., Ghiggi, M. R., Galletti, F., Mariniello, P., Lombardi, G., and Edwards, C. R., 1995, Alcohol inhibits 11-beta-hydroxysteroid dehydrogenase activity in rat kidney and liver, Horm. Res., 43: 176–180.PubMedCrossRefGoogle Scholar
  31. Wynder, E. L. and Hoffmann, D., 1994, Smoking and lung cancer: scientific challenges and opportunities, Cancer Res., 54: 5284–5295.PubMedGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1999

Authors and Affiliations

  • Edmund Maser
    • 1
  1. 1.Department of Pharmacology and ToxicologyPhilipps-UniversityMarburgGermany

Personalised recommendations