The polar PAC network Print
Recent studies have shown that semi-polar polycyclic aromatic compounds (PACs), such as oxy-PAHs, azaarens, nitro-PAHs and hydroxy-PAHs, are accompanying PAHs at many contaminated sites, and may constitute an additional risk. The semi-polar PACs have slightly different properties than the PAHs, which influences their environmental behavior and thereby the risk they pose to humans and environment. For example, semi-polar PACs may have higher mobility in soil than PAHs, as a result of their higher water solubility. Furthermore, many semi-polar PACs are shown to be toxic, mutagenic and carcinogenic, and sometimes the effects caused by the semi-polar fractions of soil extracts are stronger than those cause by the fractions containing the PAHs. Despite these facts, semi-polar PACs are seldom included in risk assessment programs.

PolarPACs

Within the polar PAC network we want to elucidate whether polar and semi-polar polycyclic aromatic compounds (PACs) need to be considered during risk assessment of contaminated soils. We are doing this by collecting and evaluating the present knowledge in the field, and by building a network of experts, decision-making authorities and companies that will facilitate information exchange and stimulate discussions on the subject.

If you are interested, you are welcome to join the network and share your knowledge on polar PACs with us. Please contact the project leader.


Project leader: Staffan Lundstedt, Umeå University
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Phone: +46-90-7866654.

Project time frame: Jan 2009- June 2011.
Budget: 48 000 €


*What are your thoughts about polar PACs as soil contaminants?
Do you think these compounds contribute significantly to the risk?

*Please let us know about new findings and interesting publications.


Related Companies/Universities




Staffan Lundstedt (PhD), project leader
Department of Chemistry, Umeå University, Sweden
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Adj.Prof. Paul A. White (PhD)
Genetic Toxicology Group, Health Canada, Ottawa, Canada
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Christine Lemieux (MSc)
Genetic Toxicology Group, Health Canada, Ottawa, Canada
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Prof. Iain Lambert (PhD)
Biology Department, Carleton University, Ottawa, Canada
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Prof. Wolfgang Wilcke (PhD)
Soil Science Group, Geographic Institute, University of Berne, Berne, Switzerland
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Benjamin Bandowe (PhD)
Soil Science Group, Geographic Institute, University of Berne, Berne, Switzerland
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Werner Brack (PhD)
Department of Effect-Directed Analysis
Helmholtz Centre for Environmental Research- UFZ, Leipzig, Germany
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Mahmoud Bataineh (PhD)
Abu Dhabi Men's College, Abu Dhabi, United Arab Emirates
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Jose Luis Gomez-Eyles (MSc)
Department of Soil Science, School of Human and Environmental Sciences,
The University of Reading, Whiteknights, Reading, United Kingdom
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Chris Collins (PhD)
Department of Soil Science, School of Human and Environmental Sciences
The University of Reading, Whiteknights, Reading, United Kingdom
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Mark A. Lampi (PhD)
Toxicology & Environmental Sciences, ExxonMobile Biomedical Sciences, Inc., Annadale, NJ, USA
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Ass. Prof. Ulla Stenius (PhD)
Institute of Environmental Medicine, Karolinska Institutet, Stockholm, Sweden
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Klas Köhler (MSc) national co-coordinator for contaminated sites
The County Administrative Boards of Sweden, Umeå, Sweden
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Karin Söderström, co-ordinator of contaminated sites
Västerbotten County Administrative Board, Umeå, Sweden
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Nadja Lundgren (PhD), Environmental Consultant
Tyrens, Environmental Geotechnology, Umeå, Sweden
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Christian Maurice (PhD), Environmental Consultant
Ramböll Sweden, Luleå, Sweden
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Per Ivarsson (PhD), Laboratory Manager
ALS Laboratory Group, ALS Scandinavia AB, Stockholm, Sweden
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Miriam Leon Paumen (PhD), Environmental Scientist
Toxicology & Environmental Sciences Division,
ExxonMobil Petroleum and Chemical, Machelen, Belgium
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Jocelyne Hellou (PhD)
Bedford Institute of Oceanography, Fisheries and Oceans Canada, Dartmouth, Canada
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Ass. Prof. Jan H. Christensen (PhD)
Department of Basic Sciences and Environment, University of Copenhagen, Fredriksberg, Denmark
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Esther Boll (MSc)
Department of Basic Sciences and Environment, University of Copenhagen, Fredriksberg, Denmark
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Stine N. Schmidt (MSc)
Department of Environmental Chemistry and Microbiology
National Environmental Research Institute, Roskilde, Denmark
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Thomas Letzel (PhD)
Technical University of Munich, Analytical Research Group, Freising, Germany
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Prof. Juliane Hollender (PhD)
Eawag, Swiss Federal Institute of Aquatic Science and Technology
Department of Environmental Chemistry, Dübendorf, Switzerland
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Prof. Pim de Voogt (PhD)
Institute for Biodiversity and Ecosystem Dynamics - Earth Surface Sciences
University of Amsterdam, Amsterdam, Netherlands
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Anna Rotander (MSc)
Man-Technology-Environment Research Centre, Örebro University, Örebro, Sweden
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Maria Larsson (MSc)
Man-Technology-Environment Research Centre, Örebro University, Örebro, Sweden
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Ass. prof. Kåre B. Jørgensen (PhD)
Department of Mathematics and Natural Science, University of Stavanger, Stavanger, Norway
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Prof. Magdalena Grifoll Ruiz (PhD)
Department of Microbiology, University of Barcelona, Barcelona, Spain
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Joaquim Vila (PhD)
Department of Microbiology, University of Barcelona, Barcelona, Spain
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Coralie Biache (PhD)
CNRS / UMR, LIEC, University of Lorraine, Nancy, France
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Ass. prof. Laurence Mansuy-Huault (PhD)
CNRS / UMR, LIEC, University of Lorraine, Nancy, France
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Pierre Faure (PhD)
CNRS /  UMR, LIEC, University of Lorraine, Nancy, France
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Christophe Mouvet (PhD)
BRGM, Environment and Processes Division, Orleans, France
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Alain Saada (PhD)
BRGM, Environment and Processes Division, Orleans, France
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Stefan Colombano (Ir)
BRGM, Environment and Processes Division, Orleans, France
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Bruno Lemiere (PhD)
BRGM, Environment and Processes Division, Orleans, France
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Elke Fries (PhD)
BRGM, Water, Environment and Eco-technologies Division, Orleans, France
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Marja Tuomela (PhD)
Department of Food and Environmental Sciences, University of Helsinki, Finland
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Christophe Walgraeve (PhD)
Faculty of Bioscience Engineering Research Group EnVOC, Ghent University, Belgium
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Prof. Kim Anderson (PhD)
Department of Environmental and Molecular Toxicology, Oregon State University, Corvallis, Oregon,USA
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Below, please find a list of publications on different aspects of polar PACs.
Note that the publications are grouped in several categories relevant for the polar-PAC network.

Analysis of polar PACs
Bandowe B. A. M., Wilcke W.(2010) Analysis of Polycyclic Aromatic Hydrocarbons and Their Oxygen-Containing Derivatives and Metabolites in Soils. Journal of Environmental Quality 39(4): 1349-58.
Bataineh M., Luebcke-Von Varel U., Hayen H., Brack W. (2010) HPLC/APCI-FTICR-MS as a tool for identification of partial polar mutagenic compounds in effect-directed analysis. Journal of the American society for mass spectrometry.21(6): 1016-1027.
Grosse S., Letzel T. (2007) Liquid chromatography / atmospheric pressure ionization mass spectrometry with post-column liquid mixing for the efficient determination of partially oxidized polycyclic aromatic hydrocarbons. Journal of Chromatography A , 1139: 75-83.
Letzel T., PöschlU., Rosenberg E., Grasserbauer M., Niessner R.(1999) In-source fragmentation of partially oxidized mono- and polycyclic aromatic hydrocarbons in atmospheric pressure chemical ionization mass spectrometry coupled with liquid chromatography. Rapid Communications in Mass Spectrometry 13: 2456-2468.
Letzel T., Rosenberg E., Wissiack R., Grasserbauer M., Niessner R. (1999) Separation and identification of polar degradation products of benzo[a]pyrene with ozone by atmospheric pressure chemical ionization – mass spectrometry after optimized column chromatographic clean-up. Journal of Chromatography A, 855: 501-514.
Letzel, T., Poschl U., Wissiack R., Rosenberg E., Grasserbauer M. and Niessner R. 2001. Phenyl-modified reversed-phase liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry: A universal method for the analysis of partially oxidized aromatic hydrocarbons. Anal. Chem. 73, 1634-1645.
Lundstedt, S., Haglund P. and Oberg L. 2006. Simultaneous extraction and fractionation of polycyclic aromatic hydrocarbons and their oxygenated derivatives in soil using selective pressurized liquid extraction. Anal. Chem. 78, 2993-3000.
Meyer, S., Cartellieri S. and Steinhart H. 1999. Simultaneous determination of PAHs, hetero-PAHs (N, S, O), and their degradation products in creosote-contaminated soils. Method development, validation, and application to hazardous waste sites. Anal. Chem. 71, 4023-4029.
Mundt, M; Hollender, J. 2005. Simultaneous determination of NSO-heterocycles, homocycles and their metabolites in groundwater of tar oil contaminated sites using LC with diode array UV and fluorescence detection. J. Chromatogr A 1065 (2): 211-218.
Niederer, M. 1998. Determination of polycyclic aromatic hydrocarbons and substitutes (nitro-, oxy-PAHs) in urban soil and airborne particulate by GC-MS and NCI-MS/MS. Environ. Sci. Pollut. Res. 5, 209-216.
Walgraeve, C., Demeestere, K., De Wispelaere P., Dewulf J., Lintelmann J., Fischer K., Van Langenhove, H. 2012. Selective accurate.mass.based analysis of 11 oxy-PAHs on atmospheric particulate matter by pressurized liquid extraction followed by high-performance liquid chromatography and magnetic sector mass spectrometry. Anal. Bioanal. Chem 402:1697-1711.
Zdrahal, Z., Karasek P., Lojkova L., Buckova M., Vecera Z. and Vejrosta J. 2000. Pressurised liquid extraction of ketones of polycyclic aromatic hydrocarbons from soil. J. Chromatogr. A 893, 201-206.
Occurrence of polar PACs at contaminated sites
Bandowe B. A. M., Shukurov N., Kersten M., Wilcke W.(2010) Polycyclic Aromatic Hydrocarbons (PAHs) and their oxygen-containing derivatives (OPAHs) in soils from the Angeren industrial area, Uzbekistan. Environmental Pollution 158: 2888-2899.
Blotevogel, J; Reineke, AK; Hollender, J; Held, T. 2008. Identification of NSO-heterocyclic priority substances for investigating and monitoring creosote-contaminated sites. Grundwasser 13 (3): 147-157. (In German)
Brooks, L.R., Hughes T.J., Claxton L.D., Austern B., Brenner R. and Kremer F. 1998. Bioassay-directed fractionation and chemical identification of mutagens in bioremediated soils. Environ. Health Perspect. 106, 1435-1440.
Eriksson, M., Dalhammar G. and Borg-Karlsson A.K. 2000. Biological degradation of selected hydrocarbons in an old PAH/creosote contaminated soil from a gas work site. Appl. Microbiol. Biotechnol. 53, 619-626.
Johansen, SS, Hansen AB, Mosbæk H and Arvin E. (1997) Identification of Heteroaromatic and other Organic Compounds in Ground Water at Creosote-Contaminated Sites in Denmark. Ground Wat. Monitor. Rem. 17(2):106-115.
Lundstedt, S., Haglund P. and Öberg L.G. 2003. Degradation and formation of polycyclic aromatic compounds during bio-slurry treatment of an aged gasworks soil. Environ. Toxicol. Chem. 22, 1413-1420.
Lundstedt S, White PA, Lemieux CL, Lynes KD, Lambert IB, Öberg L, Haglund P, Tysklind M (2007) Sources, fate and toxic hazards of oxy-PAHs at PAH-contaminated sites. Ambio, 36(6):475-485.
Matscheko N, Lundstedt S, Svensson L, Harju M, Tysklind M (2002) Accumulation and elimination of 16 polycyclic aromatic compounds in the earthworm (Eisenia fetida). Environmental Toxicology and Chemistry, 21(8), 1724-1729.
Meyer, S., Cartellieri S. and Steinhart H. 1999. Simultaneous determination of PAHs, hetero-PAHs (N, S, O), and their degradation products in creosote-contaminated soils. Method development, validation, and application to hazardous waste sites. Anal. Chem. 71, 4023-4029.
Neuwoehner, J; Reineke, AK; Hollender, J; Eisentraeger, A. 2009. Ecotoxicity of quinoline and hydroxylated derivatives and their occurrence in groundwater of a tar-contaminated field site. Ecotoxicol. Environ. Safety 72 (3): 819-827.
Niederer, M. 1998. Determination of polycyclic aromatic hydrocarbons and substitutes (nitro-, oxy-PAHs) in urban soil and airborne particulate by GC-MS and NCI-MS/MS. Environ. Sci. Pollut. Res. 5, 209-216
Reineke, AK; Goen, T; Preiss, A; Hollender, J. 2007. Quinoline and derivatives at a tar oil contaminated site: Hydroxylated products as indicator for natural attenuation?. Environ. Sci. Technol. 41 (15): 5314-5322.

Reineke A.-K., Preiss A., Elend M., Hollender J. (2008) Detection of methylquinoline transformation products in microcosm experiments and in tar oil contaminated groundwater using LC-NMR. Chemopshere 70; 2118-2126.
Saponaro, S., Bonomo L., Petruzzelli G., Romele L. and Barbafieri M. 2002. Polycyclic aromatic hydrocarbons (PAHs) slurry phase bioremediation of a manufacturing gas plant (MGP) site aged soil. Water, Air, Soil Pollut. 135, 219-236.

Toxicity of polar PACs
Alexander, R.R., Tang J.X. and Alexander M. 2002. Genotoxicity is unrelated to total concentration of priority carcinogenic polycyclic aromatic hydrocarbons in soils undergoing biological treatment. J. Environ. Qual. 31, 150-154.
Belkin, S., Stieber M., Tiehm A., Frimmel F.H., Abeliovich A., Werner P. and Ulitzur S. 1994. Toxicity and Genotoxicity Enhancement During Polycyclic Aromatic Hydrocarbons Biodegradation. Environ. Toxicol. Water Qual. 9, 303-309.
Bleeker E.A.J., Van der Geest H.G., Klamer H.J.C., de Voogt P., Wind E., Kraak M.H.S. (1999) Toxic and genotoxic effects of azaarenes: isomers and metabolites. Polycycl. Arom. Comp. 13(2): 191-203.
Bleeker E.A.J., Wiegman S., de Voogt P., Kraak M.H.S., Leslie H.A., de Haas E.M., Admiraal W. (2002) Toxicity of Azaarenes - A Review. Rev. Environ. Contam. Toxicol. 173: 39-84
Bolton, J.L., Trush M.A., Penning T.M., Dryhurst G. and Monks T.J. 2000. Role of quinones in toxicology. Chem. Res. Toxicol. 13, 135-160.
Brack, W., Altenburger R., Kuster E., Meissner B., Wenzel K.D. and Schuurmann G. 2003. Identification of toxic products of anthracene photomodification in simulated sunlight. Environ. Toxicol. Chem. 22, 2228-2237.
Chesis, P.L., Levin D.E., Smith M.T., Ernster L. and Ames B.N. 1984. Mutagenicity of quinones: Pathways of metabolic activation and detoxification. Proc. Natl. Acad. Sci. USA 81, 1696-1700.
Durant, J.L., Busby W.F., Lafleur A.L., Penman B.W. and Crespi C.L. 1996. Human cell mutagenicity of oxygenated, nitrated and unsubstituted polycyclic aromatic hydrocarbons associated with urban aerosols. Mutat. Res.-Genet. Toxicol. 371, 123-157.
Huang, X.D., Dixon D.G. and Greenberg B.M. 1993. Impacts of UV Radiation and Photomodification on the Toxicity of PAHs to the Higher Plant Lemna gibba (Duckweed). Environ. Toxicol. Chem. 12, 1067-1077.
Huang, X.D., Dixon D.G. and Greenberg B.M. 1995. Increased Polycyclic Aromatic Hydrocarbon Toxicity Following Their Photomodification in Natural Sunlight - Impacts on the Duckweed Lemna-Gibba l G-3. Ecotoxicol. Environ. Saf. 32, 194-200.
Kubatova, A., Dronen L.C., Picklo M.J. and Hawthorne S.B. 2006. Midpolarity and nonpolar wood smoke particulate matter fractions deplete glutathione in RAW 264.7 macrophages. Chem. Res. Toxicol. 19, 255-261.
Kumagai, Y., Koide S., Taguchi K., Endo A., Nakai Y., Yoshikawa T. and Shimojo N. 2002. Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles. Chem. Res. Toxicol. 15, 483-489.
Kurihara, R., Shiraishi F., Tanaka N. and Hashimoto S. 2005. Presence and estrogenicity of anthracene derivatives in coastal Japanese waters. Environ. Toxicol. Chem. 24, 1984-1993.
Lampi, M.A., Gurska J., McDonald K.I., Xie F., Huang X.D., Dixon D.G. and Greenberg B.M. 2006. Photoinduced toxicity of polycyclic aromatic hydrocarbons to Daphnia magna: ultraviolet-mediated effects and the toxicity of polycyclic aromatic hydrocarbon photoproducts. Environ. Toxicol. Chem. 25, 1079-1087.
Leary, J.A., Lafleur A.L., Liber H.L. and Blemann K. 1983. Chemical and toxicologic characterization of fossil fuel combustion product Phenalen-1-one. Anal. Chem. 55, 758-761.
Lemieux CL, Lynes KD, White PA, Lundstedt S, Öberg L, Lambert IB (2009) Mutagenicity of an aged gasworks soil during bioslurry treatment. Environmental and Molecular Mutagenesis, 50(5):404-412.

Lemieux CL, Lambert IB, Lundstedt S, Tysklind M, White PA (2008) Mutagenic hazards of complex PAH mixtures in contaminated soil. Environmental Toxicology and Chemistry, 27(4), 978-990.
Leon-Paumen M., de Voogt P., van Gestel C.A.M., Kraak M.H.S. (2009) Comparative chronic toxicity of homo- and heterocyclic aromatic compounds to aquatic and terrestrial invertebrates: generalizations and exceptions. Science of the Total Environment 407: 4605-4609
Machala, M., Ciganek M., Blaha L., Minksova K. and Vondrack J. 2001. Aryl hydrocarbon receptor-mediated and estrogenic activities of oxygenated polycyclic aromatic hydrocarbons and azaarenes originally identified in extracts of river sediments. Environ. Toxicol. Chem. 20, 2736-2743.
Mallakin, A., McConkey B.J., Miao G.B., McKibben B., Snieckus V., Dixon D.G. and Greenberg B.M. 1999. Impacts of structural photomodification on the toxicity of environmental contaminants: Anthracene photooxidation products. Ecotoxicol. Environ. Saf. 43, 204-212.
Mattsson Å, Lundstedt S, Stenius U (2009) Exposure of HepG2 cells to low levels of PAH-containing extracts from contaminated soils results in unpredictable genotoxic stress responses. Environmental and Molecular Mutagenesis 50(4):337-348.
McConkey, B.J., Duxbury C.L., Dixon D.G. and Greenberg B.M. 1997. Toxicity of a PAH photooxidation product to the bacteria Photobacterium phosphoreum and the duckweed Lemna gibba: Effects of phenanthrene and its primary photoproduct, phenanthrenequinone. Environ. Toxicol. Chem. 16, 892-899.
Moller, M., Hagen I. and Ramdahl T. 1985. Mutagenicity of polycyclic aromatic compounds (PAC) identified in source emissions and ambient air. Mutat. Res. 149-156.
Morelli, I.S., Vecchioli G.I., Del Panno M.T. and Painceira M.T. 2001. Effect of petrochemical sludge concentrations on changes in mutagenic activity during soil bioremediation process. Environ. Toxicol. Chem. 20, 2179-2183.
Pitts, J.N., Lokensgard D.M., Harger W., Fisher T.S., Mejia V., Schuler J.J., Scorziell G.M. and Katzenstein Y.A. 1982. Mutagens in diesel exhaust particulate identification and direct activities of 6-nitrobenzo[a]pyrene, 9-nitroanthracene, 1-nitropyrene and 5H-phenanthro[4,5-bcd]pyran-5-one. Mutat. Res. 103, 241-249.
Ren, L., Zeiler L.F., Dixon D.G. and Greeberg B.M. 1996. Photoinduced effects of polycyclic aromatic hydrocarbons on Brassica napus (Canola) during germination and early seedling development. Ecotoxicol. Environ. Saf. 33, 73-80.
Sakai, M., Yoshida D. and Mizusaki S. 1985. Mutagenicity of polycyclic aromatic hydrocarbons and quinones on Salmonella typhimurium TA97. Mutat. Res. 156, 61-67.
Sasek, V., Bhatt M., Cajthaml T., Malachova K. and Lednicka D. 2003. Compost-mediated removal of polycyclic aromatic hydrocarbons from contaminated soil. Arch. Environ. Contam. Toxicol. 44, 336-342.
Shimada, H., Oginuma M., Hara A. and Imamura Y. 2004. 9,10-phenanthrenequinone, a component of diesel exhaust particles, inhibits the reduction of 4-benzoylpyridine and all-trans-retinal and mediates superoxide formation through its redox cycling in pig heart. Chem. Res. Toxicol. 17, 1145-1150.
Winters, K., Batterton J.C. and van Baalen C. 1977. Phenalen-1-one: Occurrence in a fuel oil and toxicity to microalgae. Environ. Sci. Technol. 11, 270-272.
Xie, F., Koziar S.A., Lampi M.A., Dixon D.G., Warren N.P., Borgmann U., Huang X.D. and Greenberg B.M. 2006. Assessment of the toxicity of mixtures of copper, 9,10-phenanthrenequinone, and phenanthrene to Daphnia magna: evidence for a reactive oxygen mechanism. Environ. Toxicol. Chem. 25, 613-622.
Zhu, H., Li Y.B. and Trush M.A. 1995. Characterization of Benzo[A]Pyrene Quinone-Induced Toxicity to Primary Cultured Bone-Marrow Stromal Cells from Dba/2 Mice - Potential Role of Mitochondrial Dysfunction. Toxicol. Appl. Pharmacol. 130, 108-120.

Formation of polar PACs and accumulation during PAH-transformation
Andersson, B.E.and Henrysson T. 1996. Accumulation and degradation of dead-end metabolites during treatment of soil contaminated with polycyclic aromatic hydrocarbons with five strains of white-rot fungi. Appl. Microbiol. Biotechnol. 46, 647-652.
Andersson, B.E., Lundstedt S., Tornberg K., Schnurer Y., Öberg L.G. and Mattiasson B. 2003. Incomplete degradation of polycyclic aromatic hydrocarbons in soil inoculated with wood-rotting fungi, and their effect on the indigenous soil bacteria. Environ. Toxicol. Chem. 22, 1238-1243.
Arias L., Bauzá J., Tobella J., Vila J., Grifoll M. (2007) A microcosm system and an analytical protocol to assess PAH degradation and metabolite formation in soils. Biodegradation 19(3): 425-434.

Biache, C., Mansuy-Huault L., Faure P., Munier-Lamy C., Leyval C. (2008). Effects of thermal desorption on the composition of two coking plant soils: Impact on solvent extractable organic compounds and metal bioavailability. Environmental Pollution 156: 671-677.
Biache, C., Ghislain T., Faure P., Mansuy-Huault L. (2011). Low temperature oxidation of a coking plant soil organic matter and its major constituents: An experimental approach to simulate a long term evolution. Journal of hazardous Materials 188: 221-230.
Cerniglia, C.E. 1992. Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 3, 351-368.
Cerniglia, C.E. 1997. Fungal metabolism of polycyclic aromatic hydrocarbons: Past, present and future applications in bioremediation. J. Ind. Microbiol. Biotechnol. 19, 324-333.
de Voogt P., Bleeker E.A.J., van Vlaardingen P.L.A., Fernández A., Slobodník J., Wever H., Kraak M.H.S. (1999) Formation and identification of azaarene trans­form­ation products from aquatic invertebrate metabolism. J. Chromatogr. B 724(2): 265-274
Grifoll M., Selifonov S.A., Gatlin C.V., Chapman P.J. (1995) Actions of versatile fluorene-degrading bacterial isolate on polycyclic aromatic compounds. Applied and Environmental Microbiology 61(10): 3711-3723.

Kanaly, R.A. and Harayama S. 2000. Biodegradation of high-molecular-weight polycyclic aromatic hydrocarbons by bacteria. J. Bacteriol. 182, 2059-2067.
Koeber, R., Bayona J.M. and Niessner R. 1997. Analysis of ozonolysis products of benzo[a]pyrene with capillary gas chromatography mass spectrometry and liquid chromatography mass spectrometry. Int. J. Environ. Anal. Chem. 66, 313-325.
Kochany, J. and Maguire R.J. 1994. Abiotic transformations of polynuclear aromatic hydrocarbons and polynuclear aromatic nitrogen heterocycles in aquatic environments. Sci. Total Environ. 144, 17-31.
Kotzias, D. and Brussol C. 1999. Fate of polycyclic aromatic hydrocarbons (PAHs) in ambient air. Fresenius Environ. Bull. 8, 518-522.
Lee, B.D., Hosomi M. and Murakami A. 1998. Fenton oxidation with ethanol to degrade anthracene into biodegradable 9,10-anthraquinon: A pretreatment method for anthracene-contaminated soil. Water Sci. Technol. 38, 91-97.
Lee, B.D.and Hosomi M. 2001. A hybrid Fenton oxidation-microbial treatment for soil highly contaminated with benz(a)anthracene. Chemosphere 43, 1127-1132.
López Z., Vila J., Ortega-Calvo J.-J., Grifoll M. (2008) Simultaneous biodegradation of creosote-polycyclic aromatic hydrocarbons by pyrene-degrading Mycobacterium. Appl. Microbiol. Biotechnol. 78:165-172.

Lundstedt, S., Persson Y. and Oberg L. 2006. Transformation of PAHs during ethanol-Fenton treatment of an aged gasworks' soil. Chemosphere 65, 1288-1294.
Mallakin, A., Dixon D.G. and Greenberg B.M. 2000. Pathway of anthracene modification under simulated solar radiation. Chemosphere 40, 1435-1441.
Meyer, S.and Steinhart H. 2001. Fate of PAHs and hetero-PAHs during biodegradation in a model soil/compost-system: Formation of extractable metabolites. Water, Air, Soil Pollut. 132, 215-231.
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