Bacterial mutagenicity of dicyclopenta-fused pyrene congeners in FVT-pyrolysates: Partial combustion exhaust mimics

Polycyclic Aromatic Compounds

Volumn 24, Issue 4-5, 2004, Pages 567-582

  Otero Lobato, M J ^a   Jenneskens, L W ^a   Seinen, W ^b  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Ames assay; Combustion exhausts mimics; Dicyclopenta fused pyrenes; Ethynyl PAH; Flash vacuum thermolysis (FVT); Strain TA98

Indexed keywords

PYRENE DERIVATIVE;

AMES TEST; BACTERIAL MUTATION; BACTERIAL STRAIN; COMBUSTION; CONFERENCE PAPER; MOLECULAR INTERACTION; MUTAGENIC ACTIVITY; MUTAGENICITY; NONHUMAN; SALMONELLA TYPHIMURIUM;

EID: 4844226070     PISSN: 10406638     EISSN: None     Source Type: Journal    
DOI: 10.1080/10406630490471690     Document Type: Conference Paper

References (37)

1. U. E. Wiersum and L. W. Jenneskens, The Formation of Polyaromatic Hydrocarbons, Fullerenes and Soot in Combustion: Pyrolytic Mechanisms and the Industrial and Environmental Connection, in Gas Phase Reactions in Organic Synthesis, ed. Y. Vallée (New York: Gordon and Breach Science, 1997), 143-194.
2. A. M. Mastral, M. S. Callen, and T. García, Toxic Organic Emissions from Coal Combustion, Fuel Processing Technology 67 (2000):1-10.
3. J. Jacob, The significance of PAH as Environmental Carcinogens, Pure and Applied Chemistry 68 (1996):301-308.
4. E. Eisenstadt and A. Gold, Cyclopenta[cd]pyrene: A Highly Mutagenic PAH, Proceedings of the National Academy of Sciences of the USA 75 (1978):1667-1669.
5. M. J. Kohan, R. Sangaiah, L. M. Ball, and A. Gold, Bacterial Mutagenicity of Aceanthrylene: A Novel CP-PAH of Low Molecular Weight, Mutation Research 155 (1985):95-98.
6. L. M. Ball, S. H. Warren, R. Sangaiah, and A. Gold, Bacterial Mutagenicity of Two Cyclopentafused Isomers of Benzpyrene, Mutation Research 260 (1991):271-279.
7. P. P. Fu, F. A. Beland, and S. K. Yang, CP-PAH: Potential Carcinogens and Mutagens, Carcinogenesis 1 (1980):725-727.
8. A. L. Lafleur, J. P. Longwell, L. Shirname-More, P. A. Monchamp, W. A. Peters, and E. F. Plummer, Chemical Characterization and Bacterial Mutagenicity Testing of Ethylene Combustion Products from a Jet-Stirred/Plug-Flow Reactor, Energy and Fuels 4 (1990):307-319.
9. 10 Cyclopenta-Fused PAH, Journal of the Chemical Society, Chemical Communications (1995):2415-2416.
10. L. T. Scott and A. Necula, Synthesis and Characterization of the Three Dicyclopentapyrenes, Journal of Organic Chemistry 61 (1996):386-388.
11. 10 Dicyclopentapyrenes in Flames: Correlation with Corannulene and Fullerene Formation, Journal of Physical Chemistry 100 (1996):17421-17428.
12. A. L. Lafleur, J. B. Howard, E. F. Plummer, K. Taghizadeh, A. Necula, L. T. Scott, and K. C. Swallow, Identification of Some Novel Cyclopenta-Fused PAH in Ethylene Flames, Polycyclic Aromatic Compounds 12 (1998):223-237.
13. E. B. Ledesma, M. A. Kalish, M. J. Wornat, P. F. Nelson, and J. C. Mackie, Observation of Cyclopenta-Fused and Ethynyl-Substituted PAH During the Fuel-Rich Combustion of Primary Tar from a Bituminous Coal, Energy and Fuels 13 (1999):1167-1172.
14. M. J. Otero Lobato, L. W. Jenneskens, and W. Seinen, Bacterial Mutagenicity of the Three Isomeric Dicyclopenta-Fused Pyrenes: The Effects of Dicyclopenta Topology, Mutation Research 559 (2004):105-119.
15. H. Wang and M. Freklach, A Detailed Kinetic Modeling Study of Aromatics Formation in Laminar Premixed Acetylene and Ethylene Flames, Combustion and Flame 110 (1997):173-221.
16. A. Necula and L. T. Scott, High Temperature Behavior of Alternant and Non-Alternant PAH, Journal of Analytical and Applied Pyrolysis 54 (2000):65-87.
17. C. W. Bauschlicher Jr. and A. Ricca, Mechanism for PAH Growth, Chemical Physics Letters 326 (2000):283-287.
18. For a popular treatise: L. W. Jenneskens, E. J. Vlietstra, M. Sarobe, and S. N. R. Ponzano, High Temperature Chemistry of (Non)-Alternant PAH: The Flash Vacuum Thermolysis Approach, International Society of Polycyclic Aromatic Compounds Newsletter 10 (1999).
19. L. W. Jenneskens and M. Sarobe, Prevalent CP-PAH Combustion Effluents. Build-Up and Conversion Under High Temperature Conditions in the Gas Phase, Polycyclic Aromatic Compounds 14-15 (1999):169-178.
20. A. L. Lafleur, J. J. Gagel, J. P. Longwell, and P. A. Monchamp, Identification of Aromatic Alkynes and Acyclic Polyunsaturated Hydrocarbons in the Output of a Jet-Stirred Combustor, Energy and Fuels 2 (1988):709-716.
21. U.S. Environmental Protection Service (U.S. Environmental Protection Agency, Philadelphia, PA, USA). http://www.epa.gov, Selecting Exposure Routes and Contaminants of Concern by Risk-Based Screening, EPA/903/R-93-001 (1993).
22. K. C. Donnelly, L. D. Claxton, H. J. Huebner, and J. L. Capizzi, Mutagenic Interactions of Model Chemical Mixtures, Chemosphere 37 (1998):1253-1261.
23. M. Hermann, Synergistic Effects of Individual PAH on the Mutagenicity of Their Mixtures, Mutation Research 90 (1981):399-409.
24. P. R. Ortiz de Montellano, and N. O. Reich, Inhibition of Cytochrome P-450 Enzymes, in Cytochrome P-450: Structure, Mechanism, and Biochemistry, ed. P. R. Ortiz de Montellano (New York: Plenum Press, 1986), 273-314.
25. L.-S. L. Gan, A. L. Acebo, and W. L. Alworth, 1-Ethynylpyrene, a Suicide Inhibitor of Cytochrome P-450 Dependent Benzo[a]pyrene Hydroxylase Activity in Liver Microsomes, Biochemistry 23 (1984):3827-3836.
26. M. Sarobe, Polycyclic Aromatic Hydrocarbons under High Temperature Conditions. Consequences for Carbon Build up During Combustion and Fullerene Formation Processes (Ph.D. Thesis, Utrecht University, Utrecht, The Netherlands 1998), 208.
27. R. F. C. Brown, Pyrolytic Methods in Organic Chemistry, Organic Chemistry Monographs 41 (New York: Academic Press, 1980).
28. M. Sarobe, J. W. Zwikker, J. D. Snoeijer, U. E. Wiersum, and L. W. Jenneskens, Preparative Flash Vacuum Thermolysis: A Short Synthesis of Cyclopenta[cd]-pyrene, Journal of the Chemical Society, Chemical Communications (1994):89-90.
29. M. Sarobe, S. Flink, L. W. Jenneskens, J. W. Zwikker, and J. W. Wessseling, Flash Vacuum Thermolysis of 6-(1-Chloroethenyl)acenaphthene: A Short Synthesis of Pyracylene and Its Behavior Under High Temperature Conditions, Journal of the Chemical Society, Perkin Transaction 2 (1996):2125-2131.
30. M. Sarobe, J. D. Snoeijer, L. W. Jenneskens, M. Q. Slagt, and J. W. Zwikker, Cyclopenta[cd]fluoranthene: Acefluoranthylene, Tetrahedron Letters 36 (1995): 8489-8492.
31. M. Sarobe, R. van Heerbeek, L. W. Jenneskens, and J. W. Zwikker, Unexpected High Temperature Behavior of 2,2′-Diethynylbiphenyl in the Gas Phase - A Precursor for Acephenanthrylene Instead of Pyrene, Liebigs Annalen/Recueil (1997):2499-2503.
32. D. M. Maron and B. N. Ames, Revised Methods for the Salmonella Mutagenicity Test, Mutation Research 113 (1983):173-215.
33. O. H. Lowry, N. J. Rosebrough, A. L. Farr, and R. J. Randall, Protein Measurement with the Folin Phenol Reagent, Journal of Biological Chemistry 193 (1951):265-275.
34. H. M. Wortelboer, C. A. de Kruif, A. A. J. van Iersel, H. E. Falke, J. Noordhoek, and B. J. Blaauboer, The Isoenzyme Pattern of Cytochrome P450 in Rat Hepatocytes in Primary Culture, Comparing Different Enzyme Activities in Microsomal Incubations and Intact Monolayers, Biochemical Pharmacology 40 (1990):2525-2534.
35. B. S. Kim and B. H. Margolin, Statistical Methods for the Ames Salmonella Assay: A Review, Mutation Research 436 (1999):113-122.
36. M. Sarobe, H. C. Kwint, T. Fleer, R. W. A. Havenith, L. W. Jenneskens, E. J. Vlietstra, J. H. van Lenthe, and J. W. Wessseling, Flash Vacuum Thermolysis of Acenaphtho[1,2-a]acenaphthylene, Fluoranthene, Benzo[k]- and Benzo[j]fluoranthene - Homolytic Scission of Carbon-Carbon Single Bonds of Internally Fused Cyclopenta Moieties at T > 1000°C, European Journal of Organic Chemistry (1999):1191-1200.
37. M. Hall, D. K. Parker, P. L. Grover, J.-Y. L. Lu, N. E. Hopkins, and W. L. Alworth, Effects of 1-Ethynylpyrene and Related Inhibitors of P450 Isozymes upon Benzo[a]pyrene Metabolism by Liver Microsomes, Chemico-Biological Interactions, 76 (1990):181-192.