Determination of dibenzo[a,l]pyrene and other fjord-region PAH isomers with mw 302 in environmental samples

Polycyclic Aromatic Compounds

Volumn 24, Issue 4-5, 2004, Pages 759-771

  Seidel, Albrecht ^a,b   Frank, Heinz ^a   Behnke, Andreas ^a   Schneider, Dietmar ^a   Jacob, Juergen ^a  

^a Prof Dr Gernot Grimmer Foundation   (Germany)

^b Prof Dr Gernot Grimmer Foundation   (Germany)

Author keywords

Dibenzo a,l pyrene; Environmental occurrence; GC MS analysis; Naphtho 1,2 a pyrene; Naphtho 1,2 e pyrene; Polycyclic aromatic hydrocarbons

Indexed keywords

BENZ[A]ANTHRACENE; BENZO[GHI]PERYLENE; CHRYSENE; CIGARETTE SMOKE; DIBENZ[A,H]ANTHRACENE; DIBENZO[A,L]PYRENE; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE DERIVATIVE; SILICA GEL; THIOPHENE DERIVATIVE;

CARCINOGENIC ACTIVITY; CARCINOGENICITY; CONFERENCE PAPER; EXPERIMENTAL ANIMAL; GAS CHROMATOGRAPHY; ISOMER; ISOTOPE DILUTION ASSAY; MASS SPECTROMETRY; MOLECULAR WEIGHT; MOTOR VEHICLE; MUTAGENIC ACTIVITY; ULTRAVIOLET SPECTROSCOPY;

EID: 4844220809     PISSN: 10406638     EISSN: None     Source Type: Journal    
DOI: 10.1080/10406630490472527     Document Type: Conference Paper

References (31)

1. S. Higginbotham, N. V. S. RamaKrishna, S. L. Johansson, E. G. Rogan, and E. L. Cavalieri, Tumor-Initiating Activity and Carcinogenicity of Dibenzo[a,l]pyrene Versus 7,12-Dimethylbenz[a]anthracene and Benzo[a]pyrene at Low Doses in Mouse Skin, Carcinogenesis 14 (1993):875-878.
2. A. Luch, H. R. Glatt, K. L. Platt, F. Oesch, and A. Seidel, Synthesis and Mutagenicity of the Diastereomeric Fjord-Region 11,12-Dihydrodiol 13,14-Epoxides of Dibenzo[a,l]pyrene, Carcinogenesis 15 (1994):2507.
3. S. L. Ralston, H. H. S. Lau, A. Seidel, A. Luch, K. L. Platt, and W. M. Baird, The Potent Carcinogen Dibenzo[a,l]pyrene is Metabolically Activated to Fjord-Region 11,12-Diol 13,14-Epoxides in Human Mammary Carcinoma MCF-7 Cell Cultures, Cancer Res. 54 (1994):887-890.
4. S. Ralston, A. Seidel, K. L. Platt, A. Luch, and W. M. Baird, Stereoselective Activation of Dibenzo[a,l]pyrene to (-)-anti-(11R, 12S, 13S, 14R)- and (+)-syn(11S,12R,13S,14R)-11,12-diol-13,14-epoxides Which Bind Extensively to Deoxyadenosine Residues of DNA in the Human Mammary Carcinoma Cell Line MCF-7, Carcinogenesis 16 (1995):2899-2907.
5. J. Jacob, G. Grimmer, and A. Hildebrandt, Long-Term Decline of Atmospheric and Marine Pollution by Polycyclic Aromatic Hydrocarbons (PAHs) in Germany, Chemosphere 34 (1997):2099-2108.
6. G. Grimmer, J. Jacob, and K.-W. Naujack, Atmospheric Emission of Polycyclic Aromatic Hydrocarbons in Sampling Areas of the German Environmental Specimen Bank: Method for the Precise Measurement of Gaseous and Particle-Associated Polycyclic Aromatic Hydrocarbons in the Sub-Nanogram Range Using Deuterated Internal Standards, Chemosphere 34 (1997):2213-2226.
7. H. A. Hattemer-Frey and C. C. Travis, Benzo[a]pyrene: Environmental Partitioning and Human Exposure, Toxicol. Ind. Health 7 (1991):141-157.
8. P. Muller, B. Leece, and D. Raha, Scientific Criteria Document for Multimedia Standards Development Polycyclic Aromatic Hydrocarbons (PAH). Part 1: Hazard Identification and Dose-Response Assessment, (Ontario, Canada: Ministry of Environment and Energy, 1997), Ottawa, Canada.
9. J. Jacob, The Significance of Polycyclic Aromatic Hydrocarbons as Environmental Carcinogens, Pure and Appl. Chem. 68 (1996):301-308.
10. J. Jacob, P. E. T. Dauben, P. L. Grover, R. F. Hertel, J. Kielhorn, D. W. Luebke, H. Malcolm, I. Magelsderf, E. Menichini, P. Mueller, J. L. Mumford, G. Rosher, R. Schobrel, T. Sorahah, and K. L. White, Jr., Environmental Health Criteria 202: Selected Non-Heterocyclic Polycyclic Aromatic Hydrocarbons, International Programme on Chemical Safety (IPCS), (Geneva: Inter-Organization Programme for the Sound Management of Chemicals (IOMC), World Health Organization (WHO), 1998).
11. E. Maly, A Simple Test for Exposure to Polycyclic Hydrocarbons, Bull. Environ. Contam. Toxicol. 6 (1971):422-425.
12. R. J. Young, W. J. McKay, and J. M. Evans, Coal Gasification and Occupational Health, Am. Ind. Hyg. Assoc. J. 39 (1978):985-997.
13. K. Bridbord and J. G. French, Carcinogenic and Mutagenic Risks Associated with Fossil Fuels, in Carcinogens Volume 3. Polynuclear Aromatic Hydrocarbons, ed. P. W. Jones and R. I. Freudenthal (New York: Raven Press, 1978), 451.
14. J. L. Mumford, D. B. Harris, and K. Williams, Indoor Air Sampling and Mutagenicity Studies of Emissions from Unvented Coal Combustion, Environ. Sci. Technol. 21 (1987):308-311.
15. J. L. Mumford, X. Li, F. Hu, X. B. Lu, and J. C. Chuang, Human Exposure and Dosimetry of Polycyclic Aromatic Hydrocarbons in Urine from Xuan Wei, China with High Lung Cancer Mortality Associated with Exposure to Unvented Coal Smoke, Carcinogenesis 16 (1995):3031-3036.
16. M. E. Snook, R. F. Severson, R. F. Arrendale, H. C. Higman, and O. T. Chortyk, The Identification of High Molecular Weight Polynuclear Aromatic Hydrocarbons in a Biologically Active Fraction of Cigarette Smoke Condensate, Beitr. Tabakforsch. Int. 9(1977):79-101.
17. D. Hoffmann and I. Hoffmann, Tobacco Smoke Components, Beitr. Tabakforsch. Int. 18(1998):49.
18. J.-J. Sauvain, T. VuDuc, and C. K. Huynh, Development of an Analytical Method for the Simultaneous Determination of 15 Carcinogenic Polycyclic Aromatic Hydrocarbons and Polycyclic Aromatic Nitrogen Heterocyclic Compounds: Application to Diesel Particulates, Fresenius J. Anal. Chem. 371 (2001):966-974.
19. P. Schubert, M. M. Schantz, L. C. Sander, and S. A. Wise, Determination of Polycyclic Aromatic Hydrocarbons with Molecular Weight 300 and 302 in Environmental-Matrix Standard Reference Materials by Gas Chromatography/ Mass Spectrometry, Anal. Chem. 75 (2003):234-246.
20. I. S. Kozin, C. Gooijer, and N. H. Velthorst, Direct Determination of Dibenzo[a,l] pyrene in Crude Extracts of Environmental Samples by Laser Excited Shpol'skii Spectroscopy, Anal. Chem. 67 (1995):1623-1626.
21. S. Kumar, A Convenient and General Synthesis of Cata- and Peri-Condensed Polycyclic Aromatic Hydrocarbons with a Fjord-Region, Synthesis (2001):841-844.
22. D. Desai, A. K. Sharma, J.-M. Lin, J. Krzeminski, M. Pimental, K. El-Bayoumy, S. Nesnow, and S. Amin, Synthesis, In Vitro Metabolism, Cell Transformation, Mutagenicity, and DNA Adduction of Dibenzo[c,mno]chrysene, Chem. Res. Toxicol. 15 (2002):964-971.
23. A. K. Sharma, J. Krzeminski, D. Desai, and S. Amin, Synthesis of Dihydrodiol Metabolites of Naphtho[8,1,2-ghi]chrysene and Dibenzo[c,mno] chrysene, Polycycl. Arom. Compds. 23 (2003):297-305.
24. J. Jacob, G. Grimmer, H.-P. Hanssen, and A. Hildebrandt, Extractability and Bioavailability of PAH from Soil and Air Particulate Matter, Polycycl. Arom. Compds. 5 (1994):209-217.
25. M. Funk, H. Frank, F. Oesch, and K. L. Platt, Development of Chiral Stationary Phases for the Enantiomeric Resolution of Dihydrodiols of Polycyclic Aromatic Hydrocarbons by π-Donor-Acceptor Interactions, J. Chromatogr. A 659 (1994):57-68.
26. Y. H. Kim, A. Tishbee, and E. Gil-Av, Optical Resolution of Mutagenic and Carcinogenic Derivatives of Polyaromatic Hydrocarbons by High Pressure Liquid Chromatography on a Chiral Support, J. Chem. Soc. Chem. Commun. (1981):75-76.
27. F. Mikes, G. Boshart, and E. Gil-Av, Resolution of Optical Isomers by High-Performance Liquid Chromatography Using Coated and Bonded Chiral Charge-Transfer Complexing Agents as Stationary Phases, J. Chromatogr. 122 (1976):205-221.
28. A. Rodgman, The Composition of Cigarette Smoke: Problems with Lists of Tumorigens, Beitr. Tabakforsch. Int. 20 (2003):402-437.
29. R. von Borstel, B. Georgi, and M. Bahadir, Größenselektve Probennahme von Dieselrußpartikeln und die Bestimmung der angelagerten PAH, Staub-Reinhaltung der Luft 55 (1995):199-203.
30. J. Jacob and A. Seidel, Zur Problematik der Verwendung von Benzo[a]pyren als Leitkomponente für das PAH-bedingte karzinogene Potential in Umweltmatrices, Gefahrstoffe-Reinhaltung der Luft 62 (2002):239-246.
31. C.-E. Boström, P. Gerde, A. Hanberg, B. Jernström, C. Johansson, T. Kyrklund, A. Rannug, M. Törnqvist, K. Victorin, and R. Westerholm, Cancer Risk Assessment, Indicators, and Guidelines for Polycyclic Aromatic Hydrocarbons in the Ambient Air, Environ. Health Perspec. 110 (suppl. 3) (2002):451-488.