The significance of polycyclic aromatic hydrocarbons as environmental carcinogens. 35 years research on PAH-a retrospective

Polycyclic Aromatic Compounds

Volumn 28, Issue 4-5, 2008, Pages 242-272

  Jacob, Jurgen ^a  

^a Biochemisches Institut fur Umweltcarcinogene   (Germany)

Author keywords

Animal experiments; Biomonitoring; Cell cultures; Cytochrome P450; Induction; Microsomal oxidation; PAH metabolism; Species specificity

Indexed keywords

ANTHRACENE; CELL CULTURE; CELLS; ENZYMES; PHYSIOLOGY; PYRENE; RATS;

ANIMAL EXPERIMENTS; BIOMONITORING; CARCINOGENIC PAHS; CYTOCHROMES P450; IN-VITRO; INDUCTION; MAMMALIAN CELL CULTURE; MICROSOMAL OXIDATION; PAH METABOLISM; SPECIES-SPECIFICITY;

METABOLISM;

EID: 56749173740     PISSN: 10406638     EISSN: 15635333     Source Type: Journal    
DOI: 10.1080/10406630802373772     Document Type: Conference Paper

References (40)

1. Pott, P. 1775. Chirurgical observations relative to the cataract, the polypus of the nose, the cancer of the scrotum, the different kinds of ruptures, and the mortification of the toes and feet. London: Hawes, Clark and Collins.
2. Public Health Service Publication No.149. 1951-19870. Survey of Compounds which have been tested for Carcinogenic Activity. Washington DC: Government Printing Office.
3. WHO. 1998. ICPS, Environmental Health Criteria 202, Selected Non-heterocyclic Polycyclic Aromatic Hydrocarbons. World Health Organization.
4. Jacob, J. 1996. The significance of polycyclic aromatic hydrocarbons as environmental carcinogens, Pure &Appl. Chem 68:301-308.
5. Grimmer, G. 1977. Analysis of automobile exhaust condensate. In Air pollution and cancer in man, eds. U. Mohr and L. Tomatis, 29-39. IARC Scientific Publications No. 16, Lyon, France.
6. Grimmer, G., H. Brune, R. Deutsch-Wenzel, R. Dettbarn, J. Misfeld, U. Abel, and J. Timm. 1985. The contribution of polycyclic aromatic hydrocarbon fractions with different boiling ranges to the carcinogenic impact of emission condensate from coal-fired residential furnaces as evaluated by topical application to the skin of mice, Cancer Lett. 28:203-211.
7. Jacob, J. and A. Seidel (eds). 2004. Verwendung eines auf Wirkungsäquivalenten basierenden Summenparameters für die Abschätzung der PAH-exposition und ihres Krebs erregenden Potenzials, Polycyclische aromatische Kohlenwasser-stoffe, Forschungsbericht, Deutsche Forschungsgegemeinschaft. Wiley-VCH Verlag, Weinheim, Deutschland, pp. 8-26.
8. Jacob, J. and A. Seidel. 2001/2002. Nachweis und Quantifizierung des stark karzinogenen Dibenzo[a,l]pyrens sowie weiterer isomerer Fjord-Region-PAH in der Umwelt, Abschlußbericht an die DFG, Großhansdorf. p. 35.
9. Seidel, A., H. Frank, A.Behnke, D. Schneider, and J. Jacob. 2004. Determination of dibenzo[a,l]pyrene and other fjord-region PAH isomers with m.w 302 in environmental samples. Polycycl. Arom. Comp. 24:759-771.
10. Jacob, J. A. Schmoldt, and G. Grimmer. 1981. Glass-capillary-gas chromatography/mass spectrometry data of mono- and polyhydroxylated benz[a] anthracene. Comparison with benz[a]anthracene metabolites from rat liver micosomes. HoppeSeyler's Z. Physiol.Chem. 362:1021-1030.
11. Jacob, J., G. Grimmer, and A. Schmoldt. 1981. The influence of polycyclic aromatic hydrocarbons as inducers of monooxygenases on the metabolite profile of benz[a]anthracene in rat liver micosomes. Cancer Lett. (1981): 175-185.
12. Jacob, J., G. Grimmer, and A. Schmoldt. 1979. Metabolitenprofile von polycyclischen aromatischen Kohlenwasserstoffen nach Vorbehandlung mit verschiedenen Induktoren mikrosomalerMonooxygenasen. Hoppe-Seyler's Z. Physiol. Chem. 360:1525-1534.
13. Schmoldt, A., J. Jacob, and G. Grimmer. 1981. Dose-dependent induction of rat liver microsomal aryl hydrocarbon monooxygenase by benzo[k]fluoranthene. Cancer Lett. 13:249-257.
14. Jacob, J., A. Schmoldt, and G. Grimmer. 1982. Influence of monooxygenase inducers on the metabolic profile of phenanthrene in rat liver microsomes. Toxicol. 25:333-343.
15. Jacob, J., A. Schmoldt, and G. Grimmer. 1982. Formation of carcinogenic and inactive chrysene metabolites by rat liver microsomes of various monooxygenase activities. Arch. Toxicol. 51:255-265.
16. Jacob, J., A. Schmoldt, and G. Grimmer. 1983. Benzo[e]pyrene metabolism in rat liver microsomes: dependence of the metabolite profile on the pretreatment of rats with various monooxygenase inducers. Carcinogenesis 4:905-910.
17. Jacob, J. 1986. Polycyclische aromatische Kohlenwasserstoffe - Vorkommen, Analytik und Metabolismus, Beitr gerichtl Med 46:233-242.
18. Schmoldt, A., J. Jacob, G. Grimmer, C. Augustin, and G. Raab. 1993. Species-specific liver microsomal metabolism of benz[a] anthracene in mammals, Polycyclic Aromatic Compounds: Thirteenth International Symposium, R Garrigues and M. Lamotte (Eds.), Bordeaux, France, Gordon and Breach Science Publ. pp. 1199-1206.
19. Jacob, J., G. Grimmer, and A. Schmoldt. 1982. Comparison of the metabolic profiles of pyrene and benz[a]anthracene in rat liver and lung by glass capillary gas chromatography/mass spectrometry. In Polynuclear aromatic hydrocarbons, ed. M. Cooke and A. J. Dennis, 383-388. Columbus, Ohio: Battelle-Press, Columbus/Ohio.
20. Estabrook, R. W., J. Werringloer, J. Capdevila, and R. A. Prough. 1978. The role of cytochrome P-450 and the microsomal electron transport system: The oxidative metabolism of benzo[a]pyrene. In Polycyclic hydrocarbons and cancer, vol. 1, Environment, chemistry, and metabolism, eds. H.V. Gelboin and P.O. Ts'o. pp. 285-319. New York, San Francisco, London: Academic Press.
21. T. Shimada. 2006. Xenobiotic-metabolizing enzymes involved in activation and detoxification of carcinogenic polycyclic aromatic hydrocarbons. Drug. Metab. Pharmacokinet. 21:257-276.
22. Emura, M., M. Riebe-Imre, A. Ochiai, G. Singh, S. L. Katyal, M.Aufderheide, U. Mohr, J. Jacob, and G. Grimmer. 1992. New cell culture system for pulmonary carcinogenesis and inhalation toxicology. In Environmental hygiene III, eds. N. H. Seemayer and W. Hadnagy, pp. 64-66. Berlin - Heidelberg - New York: Springer-Verlag.
23. Emura, M., J. Jacob, W. Knebel, M. Aufderheide, G. Grimmer, and U. Mohr. 1995. Establishment of in vitro systems from the respiratory tract of different species for the investigation of PAH metabolism. Exp. Toxic. Pathol. 47:434-439.
24. Jacob, J. 1997. Mammalian organism - Cell cultures - Enzymes: A comparison of in vivo and in vitro systems. In Correlation between in vitro and in vivo investigations in inhalation toxicology, eds. U. Mohr, D .L. Dungworth, K. B. Adler, C. C. Harris and C. G. Plopper. pp. 279-297. Washington, D.C.: ILSI Press.
25. Jacob, J., G. Grimmer, M. Emura, G. Raab, J.W. Knebel, and M. Aufderheide. 1995. Metabolism of polycyclic aromatic hydrocarbons in fetal human, rat and hamster epithelial cells. Exp. Toxic. Pathol. 47:428-431.
26. Jacob, J., M. Emura, G. Grimmer, J. W. Knebel, G. Raab, and U. Mohr. 1996. Requirement of monooxygenase induction in cultured lung epithelial cells for metabolism, of PAH. Polycycl. Aromat. Comp. 10:123-128.
27. Jacob, J., G. Raab, V. Soballa, W. A. Schmalix, G. Grimmer, H. Greim, J. Doehmer, and A. Seidel. 1996. Cytochrome P450-mediated activation of phenanthrene in genetically engineered V79 Chinese hamster cells. Environ. Toxicol. Pharmacol. 1:1-11.
28. Shou, M., K. R. Korzekwa, K. W. Krausz, C. L. Crespi, F. J. Gonzales, and H. V. Gelboin. 1994. Regio- and stereo-selective metabolism, of phenanthrene by twelve cDNA-expressed human, rodent, and rabbit cytochromes P-450. Cancer Lett. 83:305-313.
29. Jacob, J., J. Doehmer, G. Grimmer, V. Soballa, G. Raab, A. Seidel, and H. Greim. 1996. Metabolism of phenanthrene, benz[a]anthracene, benzo[a]pyrene, chrysene and benzo[c]phenanthrene by eight cDNA-expressed human and rat cytochromes P450. Polycycl. Aromat. Comp. 10:1-9.
30. Paul, D., J. Jacob, G. Grimmer, and G. Raab. 1987. Clonal heterogeneity of immortalized rat hepatocyte lines results in distinct profiles of polycyclic aromatic hydrocarbons. 11th Symposium on PAH, Gaithersburg/Washington D.C. pp. 687-700.
31. Shou, M., K. R. Korzekwa, C. L. Crespi, F. J. Gonzales, and H. V. Gelboin. 1994. The role of 12 cDNA-expressed human, rodent, and rabbit cytochromes P450 in the metabolism, of benzo[a]pyrene and benzo[ajpyrene trans-7,8-dihydrodiol. Mol. Carcinogen. 10:159-168.
32. Jacob, J., G. Raab, V. J. Soballa, A. Luch, G. Grimmer, H. Greim, J. Doehmer, H. L. Morrison, J. J. Stegeman, and A. Seidel. 1999. Species-dependent metabolism of benzo[c]phenanthrene and dibenzo[a,l]pyrene by various CYP450 isoforms. Polycycl. Aromat. Comp. 16:191-203.
33. Seidel, A., V. J. Soballa, G. Raab, H. Frank, H. Greim, G. Grimmer, J. Jacob, and J. Doehmer. 1998. Regio- and stereoselectivity in the metabolism of benzo[c]phenanthrene mediated by genetically engineered V79 Chinese hamster cells expressing rat and human cytochromes P450. Environ. Toxicol. Pharmacol. 5:179-196.
34. Schober, W., A. Luch, V. J. Soballa, G. Raab, J. J. Stegeman, J. Doehmer, J. Jacob, and A. Seidel. 2006. On the species-specific biotransformation of dibenzo[a,l]pyrene. Chemico.-Biol. Interact. 161:37-48.
35. Luch, A., W. Schober, V. J. Soballa, G. Raab, H. Greim., J. Jacob, J. Doehmer, and A. Seidel. 1999. Metabolie activation of dibenzo[a,l]pyrene by human cytochrome P450 1A1 and P450 1B1 expressed in V79 Chinese hamster cells. Chem. Res. Toxicol. 12:353-364.
36. Luch, A., W. Schober, H. Greim, J. Doehmer, J. Jacob, A. Seidel, and W. Baird. 2000. Metabolic activation of dibenzo[a,l]pyrene by cytochrome P450 enzymes to stable DNA adducts occurs exclusively through the formation of the (-)-trans-(11R,12R)-diol. Polycycl. Aromat. Comp. 21:87-98.
37. Jacob, J., G. Grimmer, and G. Dettbarn. 1999. Profile of urinary phenanthrene metabolites in smokers and non-smokers. Biomarkers 4:319-327.
38. Grimmer, G., G. Dettbarn, and J. Jacob. 1993. Biomonitoring of polycyclic aromatic hydrocarbons in highly exposed coke plant workers by measurement of urinary phenanthrene and pyrene metabolites (phenols and dihydrodiols). Int. Arch. Occup. Environ. Health 65:189-199.
39. Seidel, A., D. Dahmann, H. Krekeler, and J. Jacob. 2002. Biomonitoring of poly-cyclic aromatic compounds in the urine of mining workers occupationally exposed to diesel exhaust. Int. J. Hyg. Environ. Health 204:333-338.
40. Sherson, D., T. Sisgaard, E. Overgaard, S. Loft, H. Poulsen, and F. J. Jongeneelen. 1992. Interaction of smoking, uptake of polycyclic aromatic hydrocarbons, and cytochrome P450 1A2 activity among foundry workers. Brit. J. Industr. Med. 49:197-202.