Polycyclic AromaticCompounds

SYNTHESIS, PROPERTIES,ANALYTICAL MEASUREMENTS,

OCCURRENCE ANDBIOLOGICAL EFFECTS

Proceedings of theTHIRTEENTH INTERNATIONAL SYMPOSIUM ON

POLYNUCLEAR AROMATIC HYDROCARBONSBordeaux, FranceOctober 1-4, 1991

Edited by

Philippe Garriguesand

Michel LamotteUniversite de Bordeaux I

France

GORDON AND BREACH SCIENCE PUBLISHERSSwitzerland • Australia • Belgium • France • Germany • Great Britain

India • Japan • Malaysia • Netherlands • Russia • Singapore • USA

CONTENTS

Preface xix

List of Committee Members xxi

Acknowledgements xxiii

The PAH-Story of Gernot Grimmer—Thirty Years of PAH Researchat B.I.U 1G. Grimmer

Relevance of Polycyclic Aromatic Hydrocarbons asEnvironmental Carcinogens 31G. Grimmer

STANDARD REFERENCE MATERIALS AND METHODS

R e f e r e n c e Mate r i a l s a n d Spect ra l D a t a for Po lycyc l i c A r o m a t i c C o m p o u n d s . . . . 4 3W. Karcher, JJ. Belliardo and J. Jacob

Development and Application of Isotope Dilution Internal Standard Solutionsfor the Chromatographic/Mass Spectrometric Determination of PolycyclicAromatic Compounds in Complex Mixtures 55P.G. Sim, MA. Quilliam, MD. Leblanc and S. Karunanithy

BCR Reference Materials for Polycyclic Aromatic Hydrocarbons (PAHs)in Foods—Recent Developments and Outlook 65H.A.M.G. Vaessen, C.G. van de Kamp and AA. Jekel

A Graphic Data Base on PAC for PC-Computers 77A.L. Colmsjo and CM. Ostman

Fluorinated Internal Standards for the Quantitation of Polycyclic AromaticCompounds in a Chimney Ash Sample 85JJ. Andersson and U. Weis

PAH TRANSFORMATION AND DEGRADATION

Photooxidations of 6-Methylbenzo[a]pyrene and Related Compounds 93E. Lee-Ruff and C. Wang

vi CONTENTS

Photochemical Oxidation of PAH and Heteroaromatic Analoguesin Different Model Conditions 103U. Kirso, L. Paalme, H. Uibopuu, N. Irha, E. Urbas and P.C. Jacquignon

Photodegradation of Polycyclic Aromatic Hydrocarbons in Hexadecaneand Methoxyphenols I l lSJi. McDow, QR. Sun, M. Vartiainen, Y.S. Hong, YL. Yao,EA. Hayes and RM. Kamens

Uptake of PAHs by Carrots Grown in Sewage Sludge Amended Soils 119SJi. Wild and K.C. Jones

Phototransformation of PAHs Adsorbed on SiO2 in Aqueous Suspension 127B. David and P. Boule

Methods for Degradation of Polycyclic Heterocyclic Compoundsin Laboratory Wastes 135M. Castegnaro, M. De Mio, M. Laget and G. Dumenil

On the Synthesis and Properties of Very Large Peri-condensedPolycyclic Aromatic Hydrocarbons 143M. Zander

Synthesis of Methylene-bridged Polycyclic Hydrocarbons 151C. Yang and R.G. Harvey

Synthesis and Mutagenicity of Nitro-, Nitroso- and Amino-Fluoranthenes 159CJ. van Haeringen, J. Cornelisse, J. Lugtenburg, F.C.J. Wierckx,AJM. Timmers-Reker, GJ. Mulder and J.HN. Meerman

Synthesis and Mutagenicity of Cyclopenta[cd]pyrene and ItsMonomethyl Derivatives 167R. Sangaiah, A. Gold and L.M. Ball

Synthesis of Biologically Active Dihydrodiol and Diol EpoxideMetabolites of Cyclopenta[a]phenanthrenes 175R J. Young, C. Cortez, E. Luna, H. Lee and R.G. Harvey

Combinational Directed Ortho and Remote Metalation Route to CondensedFluorenones. A Study of Haller-Bauer Cleavage of Substituted Fluorenones . . . . 183B.-P. Zhao and V. Snieckus

Stereospecific Synthesis of the Diastereomeric "Reverse" DihydrodiolEpoxides of Chrysene and Picene 191C. Wameling, HJt. Glatt, F. Oesch and A. Seidel

Regiospecific Carrier-free Radiosynthesis of (5,12-14C)Dibenz[a,h]anthracene . . . 199KL. Platt, F. Setiabudi and F. Oesch

Synthesis and Characterization of Glutathione Conjugates ofDiastereomeric Bay- and Fjord-Region Dihydrodiol Epoxides 207M. Funk, H. Frank, KL. Platt, F. Oesch and A. Seidel

CONTENTS vn

4,5-Difluorobenzo[a]pyrene: Synthesis and Characterization 215S.C. Agarwal, G. Lambert, W. Padgett and S. Nesnow

Synthesis of Polycyclic Aromatic Hydrocarbons Adducts Attachedto the Exocyclic Amino Group of 2'-Deoxyguanosine viaNucleophilic Substitution 223T. Steinbrecher, C. Wameling, F. Oesch and A. Seidel

MOLECULAR MODELING AND THEORY

Structure/Property Relationships in the Field of PAHs/BasicPrinciples and Examples • 231M. Zander

Study of Fluorenoid/Fluoranthenoid Hydrocarbons 239JR. Dias

Mechanism of Carcinogenesis Revealed through the TheoreticalTreatment on Structure-Carcinogenic Activity Relationshipof Polycyclic Aromatic Hydrocarbons 247D. Qianhuan

Modeling the Biological Activity of PAH by Neural Networks 257/ . Devillers and B. Cambon

Predicting n-OctanoI/Water Partition Coefficients by Molecular Topology:Heterocyclic and Substituted Polycyclic Aromatic Hydrocarbons 267H. Gusten and A. Sabljid

Prediction of Distribution Properties of Substituted Mono- andPolycyclic Aromatic Compounds 277HA.J. Govers, A.G. van Haelst and R. Luijk

Predictive Study of the Intercalation Geometry and Dynamics ofDNA-Naphthodifuran Complexes 285P. Vigny, J.-Ph. Demaret, A. Brunissen, C. Bilger, J.-L. Soulierand P. Demerseman

Interaction of Quinone Metabolites of Benzo[a]pyrene withMicrotubule Proteins 293R. Aulenbacher, E. Pfeiffer and M. Metzler

Role of Molecular Structure of Polycyclic Aromatic Hydrocarbons inActivation Mechanisms Leading to DNA Alterations Responsible forMutagenesis and Carcinogenesis 299M. Duquesne, S. Lecoq, H. Strapelias, B. Jolles, J.-F. Gourvest,O. Chalvet, J. Einhorn and P. Demerseman

Structure-Environmental Fate Relationships for PAHs: A Graphical Approach . . 305/ . Devillers, W. Karcher, D. Domine, M. Chastrette and Ph. Garrigues

viii CONTENTS

PAH-ANALYSIS, METHODOLOGY

Dual Detection (PID-FID) in Gas Chromatography for theIdentification of PAH 313A.L. Colmsjo and A.K. Bemgdrd

Application of Multidimensional Chromatographic/MassSpectrometric Techniques to the Analysis of Complex Mixtures ofPolycyclic Aromatic Compounds (PAC) 321P.G. Sim, MA. Quilliam, S. Pleasance, J. Anacleto, H. Perreault,L. Ramaley and FM. Benoit

Analysis of Aromatic Compounds by Capillary GasChromatography/Fourier Transform Infrared Spectroscopy 329H. Budzinski, C. Pierard, Ph. Garrigues and J. Bellocq

Trace Enrichment and HPLC Analysis of PAHs in Edible Oils andFat Products Using Liquid Chromatography on Electron AcceptorStationary Phases in Connection with Reverse Phaseand Fluorescence Detection 337J.L. Perrin, N. Poirot, P. Liska, C. Hanras, A. Thienpont and G. Filix

A Fast Clean-up Method for Chlorinated PAHs in Environmental Samples 347U.L. Nilsson and A.L. Colmsjo

Carbon Dioxide Enhanced Negative Chemical Ionizan'onMass Spectrometry of Polycyclic Aromatic Hydrocarbons 355Y.L. Tan and A. Kong

Instrumentation for Analysis of Trace-Level PAHs byShpoPskii High-Resolution Spectrofluorometry 363A. Saber, L. Paturel, J. Jarosz, J. Suptil and M. Martin-Bouyer

PAH ANALYSIS IN AQUATIC SYSTEMS AND GEOLOGICAL SAMPLES

Oxy-Substituted PAHs in Urban Atmospheric Particulatesand Coastal Marine Sediments 371JM. Bayona, P. Fernandez and J. Albaiges

Aquatic Distribution and Origin of PAH in Coastal Deltaic Waters 379/. Bouloubassi and A. Saliot

Occurrence and Fate of PAH in Zooplankton Faecal Pelletsand Sediments Traps at 200 Meters in the Western Mediterranean Sea 389E. Lipiatou, A. Saliot and J.C. Marty

Presence of PAHs in Coastal Environments of the South-East Gulf of Mexico . . 397A.V. Botello. G.G. Diaz, SF1. Villanueva and SL. Salazar

CONTENTS ix

The Use of Silicalite for Removal of Species which Interferein Trace Analysis of Polycyclic Aromatic Hydrocarbons in Biota 405SJ. Fisher, R. Alexander and R.I. Kagi

The Content of Polycyclic Aromatic Hydrocarbons (PAH)in Municipal Sludges from Different Cities in Finland 415E. Sandell, R. Levinen and A. Kiviranta

Correlation between PAH Concentrations Measured in Air, BiologicalPassive Samplers and in Corresponding Soil Samples in Germany 427/ . Jacob, G. Grimmer and A. Hildebrandt

Separation by HPLC of Functionalized Complex PolyaromaticsPresent in Fossil Materials 435/ . Kister and AM. Siouffi

Mechanism Model of Polycyclic Aromatic HydrocarbonsContamination of Marine Coastal Sediments from the Mediterranean Sea 443C.Y. Raoux and Ph. Garrigues

A Novel Aromatic Triterpene Hydrocarbon in Eocene Messel Shale:A New Aromatisation Pathway of Hopanoid Hydrocarbons? 451V. Hauke, JM. Trendel and P. Albrecht

Luminescence Spectroscopy of Polynuclear Aromatic Compoundson Soil Surfaces 459M.U. Kumke, H.-G. Lohmannsroben and Th. Roch

Chromatographic Retention Behaviour of Trimethylphenanthrenesand Their Identification by GC-FTTR in Geological Samples 467M. Radke, H. Budzinski, C. Pierard, H. Willsch and Ph. Garrigues

PAH Levels and Significance in the Orbetello Lagoon 475AM. Caricchia, S. Chiavarini, C. Cremisini, R. Morabito and A. Monti

PAH ANALYSIS IN EMISSION SOURCES AND IN AMBIENT AIR

On-Line LC-GC for the Analysis of PAH in Small Sample Volumes 485C. Ostman, H. Carlsson, A. Bemgdrd and A. Colmsjo

An Interseasonal Study of Mutagens on Airborne Particulates 493A. Greenberg, J.-H. Lwo, T. Atherholt, R. Rosen, T. Hartman, J. Butlerand J. Louis

A Methodology for Modeling the Formation and Decay ofNitro-PAH in the Atmosphere 501RM. Kamens, F. Zhi-Hua, Y. Yi-Lin, M. Vartiainen, EA. Hayesand SR. McDow

CONTENTS

Vapor and Particle Phase Measurements of Polycyclic AromaticCompounds (PAC) in Ambient Air 511DA. Lane and N.D. Johnson

Occurrence and Sources of Atmospheric Polycyclic Aromatic Hydrocarbonsat an International Airport 519T. Nielsen, K. Pilegaard and AJ3. Jensen

Year-Round Measurements of PAH and Oxidized-PAH in Urban Airin Relation to Temperature and Solar Energy 527T. Vu-Duc and C.K. Huynh

Long Range Transport of Polycyclic Aromatic Hydrocarbons: Evaluationof Background Concentrations in Arctic Regions (Greenland) 535P. Masclet, J.L. Jaffrezo, H. Wortham, S. Beyne and G. Mouvier

The Particle Size Distribution of Polycyclic Aromatic Hydrocarbonsin the Marine Atmosphere 543E. Lipiatou, J.O. Grimalt, M. Colom-Altes, R. Simo and J. Albaiges

Determination of Aromatic Hydrocarbons in Combustion Products UsingResonant Two-Photon Ionization Time-of-Flight Mass Spectrometry 551M. Loepfe, H. Burtscher and H.C. Siegmann

HPLC Analysis of Indoor Air PAHs Trapped in Active Carbonand XAD-8 Filters 557P. Pibarot, P. Clair and J. Cassan

Prediction of the Gas Chromatographic Retention Behaviourof Polybrominated Dibenzo-p-Dioxins: Preliminary Results 565R. Luijk, K. Dorland, P. Smit and HAJ. Govers

Long-Term Sampling of Air for the Determination of PolycylicAromatic Hydrocarbons 573R. Niehaus and G. Kloster

Measurement of Polycyclic Aromatic Hydrocarbons in theAmbient Air of Quebec, Canada 579A. Germain and C. Gonthier

The Determination of Nitro-polycyclic Aromatic Hydrocarbonsin the Ash of a Sanitary Waste Incinerator 587V. Librando, A. Liberatori and S.D. Fazzino

PAHS IN COAL AND PETROLEUM

Characterization of Bitumen Upgrading and Coprocessing Products 595R. Otson and E. Peake

Gas Chromatographic Analysis of PAHs with Molecular Weight

CONTENTS xi

Exceeding 300 Dalton 603A.K. Bemgdrd, B.O. Lundmark and A. Colmsjo

Identification of Alkylated Dibenzothiophenes: Applicationto Organic Geochemistry 611H. Budzinski, Ph. Garrigues, J. Connan and J. Bellocq

Polycyclic Aromatic Hydrocarbons in Fossil Fuel Extracts.1—The Puertollano Oil Shale 621J.C. Del Rio, J. Garcia-Molla, FJ. Gonzalez-Vila and F. Martin

Tetramethylnaphthalenes in Crude Oils 629R. Alexander, T.P. Bastow, S.J. Fisher and R.I. Kagi

3-Methyltriaromatic Steroids in Sediments. Molecular Fossilswith Unknown Precursors 635E. Lichtfouse, P. Albrecht and F. Behar

Rapid Determination of Coal Rank by Synchronous LuminescenceSpectroscopy 639/ . Kister, P. Doumenq, G. Mille, P. Landais and JJ. Pis

METABOLIC ACTIVITY, MUTAGENICITY

The Relationship between PAC Emissions and Mutagenicity:A Multivariate Analysis of Diesel Particulates 647H. Li, M. Sjogren, U. Rannug and R. Wester holm

Role of Cytosolic DT-Diaphorase on the Metabolism andMutagenic Expression of Dinitropyrenes 655A.KD. Hajos and G.W. Winston

Characterization of Monoclonal Anti-idiotypic Antibody, InternalImage of Conjugated Benzo[a]pyrene 663J.-L. Chagnaud, S. Faiderbe, I. Gosset and M. Geffard

Effects of Methyl Substitution on the Metabolism and DNABinding of Benz[e]acephenanthrylene 673EM. Weyand, S. Amin, R. Sodhi and EJ. LaVoie

Studies on Stereoselective Metabolism of (-)-Benzo[a]pyrene-7,8-diolby Human Lung Microsomes and Peripheral Blood Lymphocytes:Effect of Smoking 681M. Rojas, A.-M. Camus, K. Alexandrov, K. Husgafvel-Pursiainen,S. Anttila, H. Vainio and H. Bartsch

Various Rat Liver UDP-Glucuronosyltransferases Involved inRegiospecific Conjugations of Hydroxy-PAH 687C. Augustin, A. Schmoldt, HR. Glatt and A. Seidel

xii CONTENTS

Carcinogenic Benzo[a]pyrene and Non-carcinogenic Benzo[e]pyreneDiscriminated by Dictyosteliwn discoideum Cells through Internalization 695/. Tatischeff, F. Lavialle, C. de Paillerets, H. Weintraub,G. Tham and A. Alfsen

Sulfate Conjugation of Various Hydroxy-PAH by Rat Liver Sulfotransferases . . . 703A. Johannes, A. Schmoldt, A. Seidel and HR. Glatt

Biotransformation of 7H-Dibenzo[c,g]carbazole and Dibenzo[a,j]acridinein the Mouse Following Topical Application 711D. Warshawsky, J. Dietz, J. Schnieder, R. Reilman, M. Schamer,W. Xue, K. LaDow, J. Roh and G. Talaska

Prediction of the Carcinogenic Potential by Computer-optimizedMolecular Parametric Analysis of Chemical Toxity (COMPACT)via Cytochrome P450 Interactions 719D.F.V. Lewis, C. Foannides and D.V. Parke

DNA-ADDUCTS. MECHANISMS, CHARACTERIZATION

Mechanisms of Benzo[a]pryene and 7,12-Dimethylbenz[a]anthraceneActivation: Qualitative Aspects of the Stable and DepurinationDNA Adducts Obtained from Radical Cations and Diol Epoxides 725EL. Cavalieri, E.G. Rogan, N.V.S. RamaKrishna and PD. Devanesan

Mechanisms of Benzo[a]pyrene and 7,12-Dimethylbenz[a]anthraceneActivation: Quantitative Aspects of the Stable and DepurinationDNA Adducts Obtained from Radical Cations and Diol Epoxides 733E.G. Rogan, E.L. Cavalieri, N.V.S. RamaKrishna and PD. Devanesan

Fluorescence Line Narrowing: High Resolution Window onDNA Damage from Benzo[a]pyrene and 7,12-Dimethylbenz[a] anthracene 741GL. Small, R. Jankowiak, H. Jeong and GA. Marsch

Structure Determination of DNA Adducts of Benzo[a]pyreneand 7,12-Dimethylbenz[a]anthracene by Using Tandem Four-SectorMass Spectrometry 749ML. Gross and R.L. Cerny

Trace Analysis of Benzo[a]pyrene Metabolites in Fish BileUsing Laser-excited ShpoFskii Spectroscopy (LESS) 757F. Ariese, SJ. Kok, C. Gooijer, NJi. Velthorst and J.W. Hofstraat

Laser-Based Fiberoptic Immunosensors for DNA-adducts Measurements 765T. Vo-Dinh, J.P. Alarie, F. Hyder and M.J. Sepaniak

Two-Dimensional Gel Electrophoretic Analysis of Cytoplasmic

CONTENTS xiii

Proteins from Mouse Embryonic Fibroblasts Treated with 3H-Benzo[a]pyrene . . . 773Chaoying He.BA. Merrick and J.K. Selkirk

Antigens Prepared from Cyclopenta[a]phenanthrenes 781MB. Jones and MM. Coombs

DNA-BINDING, METABOLIC ACTIVATION

Induction of Specific Cytochrome P450 Isozymes in the Metabolic Activationof Benzo[a]pyrene to DNA-Binding Metabolites in Cells in Culture 791WM. Baird, R. Polzer, J. Eberhart, S.S. Meera, C. Marcus, S.S Parkand H.V. Gelboin

DNA Binding Characteristics of Complex Mixtures ofPolycyclic Aromatic Hydrocarbons 799D.H. Phillips, PL. Carmichael, W. Pfau, N.C. Hughes, M. Ni SM,G. Grimmer and J. Jacob

Chemistry of DNA Adduct Formation by Dihydrodiol Epoxidesof Polycyclic Aromatic Hydrocarbons 807A. Dipple, K. Peltonen, S.C. Cheng and B.D. Hilton

Multiple Routes of Metabolic Activation of Benz[j]aceanthrylenein C3H10T1/2CL8 Cells 817S. Nesnow, J. Lasley, S. Curti, J. Ross, G. Nelson, R. Sangaiah and A. Gold

On the Metabolic Activation of Benzo[j]fluoranthene 825EJ. LaVoie, Z.-M. He, JM. Rice, Y. Wu and EM. Weyand

Quantum Mechanical Studies of the Binding ofCyclopenta-polynuclear Aromatic Hydrocarbons to Nucleophiles 833JR. Rabinowitz, S.B. Little and RE. Venegas

Theoretical Studies of the Structure of Crowded PolycyclicAromatic Hydrocarbons 841RE. Venegas, PM. Reggio and JR. Rabinowitz

Passage-Dependent Characteristics of PAH-Metabolismand PAH-induced Transformation in Airway Epithelial Cells in vitro 849M. Riebe-lmre, C. Peiser, M. Emura, M. Aufderheide, J. Jacob,G. Grimmer and G. Raab

Potential Tumor Initiating Agents for Skin: Binding to DNAand Induction of DNA Single-Strand Breaks Measured by Nick Translation . . . 857L. Steeb, H. Friesel, T. Schneider and E. Hecker

Investigation of the Sequence Specificity of Carcinogen Bindingto DNA Using an Exonuclease 863M. Osborne

xiv CONTENTS

Formation and Persistence of Polycyclic Aromatic Hydrocarbons-DNAAdducts in Peripheral Blood Lymphocytes of Psoriatic PatientsTreated with Coal Tar 871S. Pavanello and A.G. Levis

"Reverse" Diol-Epoxides of Chrysene: Genotoxicity Characteristics 879HR. Glatt, C. Wameling, S. Elsberg, H. Thomas, H. Marquardt, A. Hewer,DM. Phillips, F. Oesch and A. Seidel

Synthesis of 11 Benzylic Sulfate Esters, Their Bacterial Mutagenicityand Its Modulation by Chloride, Bromide and Acetate Anions 887N. Enders, A. Seidel, S. Monnerjahn and HR. Glatt

Stereoselective Formation of Picene trans-3,4-dihydrodiolby Rat Liver Microsomes and by a Cell Line which Stably ExpressesCytochrome P450c (P4501A1) 895S. Reichert, J. Doehmer, H. Frank, F. Oesch and KL. Platt

Effect of Retinol and Tocopherol on Metabolism and MutagenicActivation of Benzo[a]pyrene in Rat Liven Involvement of Enzymaticand Non-enzymatic Mechanisms 905S. Decoudu, J.C. Garcin, MM. Bani, X. Michel, P. Cassandand J.F. Narbonne

Comparison of the Metabolic Activation of Various Methoxy and/orNitro Derivatives of Naphthofurans 913H. Strapelias, J.-P. Buisson, P. Demerseman, S. Lecoq, H. Pezerat,R. Zalma and M. Duquesne

Comparison of the Metabolic Activation of Dibenz[a,h]anthraceneand Picene Using 32P-Postlabelling 921S. Lecoq, E. Pfau, MM Ni SM, KL. Platt, A. Seidel, F. Oesch,DM. Phillips and PL. Grover

Comparative Analysis of the Formation and Persistence ofDNA Adducts of Benzo[b]fluoranthene and Benzo[a]pyrene in Rat Tissues . . . . 929J. Ross, G. Nelson, K. Holden, G. Erexson, K. Earley, A. Beach,A. Kligerman, R.C. Gupta and S. Nesnow

Isolation of Polycyclic Aromatic Hydrocarbons-DNA Adductsfrom Human Lung 937A. Weston, P.G. Shields and E.D. Bowman

A Rapid Method to Isolate DNA From Mouse Epidermis 945R. Krauss, R. Schmidt and E. Hecker

DNA and Protein Binding in Mouse Skin Following TopicalApplication of Tritiated Benzo[a]pyrene in Acetone or Mineral Oilsof Differing Viscosity 953A J. Ingram and J.C. Phillips

CONTENTS xv

PAH EXPOSURE, BIOMONITORING

Differences in the Phenanthrene Metabolism of Tumor-freeand Tumor-bearing Rats 961G. Grimmer, U. Heinrich, J. Jacob, G. Dettbarn and K.-W. Naujack

Relationship between Pulmonary DNA-Adduct Levels Measuredby 32P-Post-labelling and Arylhydrocarbon Hydroxylase Activity in LungParenchyma of Smokers and Ex-smokers 969M. Castegnaro, A.-M. Camus, A. Schouft, A. Karjalainen, S. Anttila,H. Vaino and H. Bartsch

Occupational Exposure to Polycyclic Aromatic Hydrocarbons Relatedto the Use of Cutting, Hardening and Extruding Oils 977P. Apostoli, M. Crippa, L. Alessio, D. Cottica and L. Pozzoli

Biochemical Effects of Coal Tar in Mice Following Ingestion 985EM. Weyand, Y. Wu, S. Patel, B.B. Taylor and DM. Mauro

The Influence of Fuel Type on the Emission of PAH and MutagenicActivity from Small Wood Stoves 993PA. Nielsen, A. Grove and H. Olsen

PAH Concentrations in Forest Floor Invertebrates in the Vicinityof a Blast Furnace Plant 1001NM. van Straalen, RA. Verweij and T.C. van Brummelen

(Bio)chemical Approaches to Monitoring of Levels and Effectsof PAHs in the Marine Environment—Preliminary Investigations 1007J.W. Hofstraat, ML. Eggens, A. Bergman, F. Ariese, C. Gooijer,NM. Velthorst, M.- J.S.T. Steenwinkel, RA. Baan and JJ3. Boon

Assessment of Occupational PAH Exposure by Biological Monitoringof Metabolites in Urine 1015AM. Hansen, O.M. Poulsen, J.M. Christensen and SM. Hansen

The Determination of 1-Hydroxypyrene in Urine as a Toolfor the Biological Monitoring of PAH-exposed Persons \ 1023KM. Schaller, J. Angerer and N. Hausmann

In Situ Bioaccumulation of PAH in Freshwater Isopods in Relationto Partitioning between Sediments and Water 1031MJ. Curto, B. van Hattum andJJ7. Cid

Monitoring of PAH Exposure Levels in the Marine EnvironmentUsing Synchronous Scanning Fluorescence Analysis of 1-Hydroxypyrenein Fish Bile 1039F. Ariese, SJK. Kok, M. Verkaik, C. Gooijer, NM. Velthorstand J.W. Hofstraat

xvi CONTENTS

COMPARATIVE METABOLISM OF B[a]P

Mechanistic Aspects of Benzo[a]pyrene Metabolism 1047EL. Cavalieri, E.G. Rogan, WJ. Murray and N.V.S. RamaKrishna

Metabolism of Benzo[a]pyrene by the Sea Star Asteria rubens L 1055PJ. den Besten, P. Lemaire, S.CM. OMara and DR. Livingstone

In vivo Metabolism and Identification of Some Metabolitesof Benzo[a]pyrene by the Stone Loach (Noemacheilus barbatulus),the Gastropod (Limnaea peregra) and the Leech (Glossiphonia complanata) . . . 1063RA. Gill, KM. Evans, P.W.J. Robotham and BM. Taylor

Metabolism of Benzo[a]pyrene by Microsomes from Mussel DigestiveGland and Sea Bass Liver 1071XR. Michel, PM. Cassand, D.G. Ribera andJ.-F. Narbonne

In vitro Studies of Benzo[a]pyrene Metabolism by Representativesof the Class Crustacea 1079G.W. Winston, M.O. James and C.S.E. Jewell

Comparative Metabolism of Benzo[a]pyrene by the Liver Microsomesand Freshly Isolated Hepatocytes of Brown Bullhead and Carp 1087H.C. Sikka, AR. Steward, J. Zaleski, C. Kandaswami, JJ3. Rutkowski,S. Kumar and R.C. Gupta

Benzo[a]pyrene Metabolism by the American Alligator Alligatormississippiensis: Effect of 3-Methylcholanthrene-Pretreatment 1095MA. Kirchin, JA. Nunez and G.W. Winston

Metabolism and Inductive Effect of Benzo[a]pyrene in the Newt 1103/ . Marty and J.P. Cravedi

Comparative Biotransformation of Benzo[a]pyrene in TCDD InducedChondrostei and Teleost Fish 1111E. Perdu, N. Gasc, J.P. Cravedi and J. Tulliez

Comparison of in vivo Administration of Benzo[a]pyrene andMonoclonal Anti-idiotypic Antibody, Internal Image of Benzo[a]pyrene toSprague-Dawley Female Rats 1119JL. Chagnaud, S. Faiderbe and M. Geffard

Activation of Benzo[a]pyrene into DNA-Damaging Speciesby Liver Microsomes from Control and Benzo[a]pyrene-treated Trout:Relationship with Erod Activity 1127JJF. Masfaraud, A. Pfohl-Leszkowicz, M. Castegnaro, A. Devaux,C. Malaveille and G. Monod

Comparative Metabolism of Benzo[a]pyrene by Microsomes of Hepatopancreasof the Shore Crab Carcinus maenas L. and Digestive Gland of the Common

CONTENTS xvii

Mussel Mytilus edulis L 1133P. Lemaire, PJ. den Besten, S.CM. O'Hara and DR. Livingstone

BIOACTIVATION, METABOLITES

Bisdihydrodiol Epoxides Play a Dominant Role in the StereoselectiveBiotransformation of Dibenz(a,h)anthracene to Genotoxic Metabolites 1141KL. Platt, M. Schollmeier, H. Frank and F. Oesch

Thermodynamics of Helix-Coil Transitions in Stereospecific Benzo[a]pyreneDiol Epoxide-Oligonucleotide Adducts 1151M. Cosman, N.E. Geacintov and S. Amin

Bioactivation of Quinoline to a Hepatocarcinogen 1159E J. LaVoie, J. Defauw, CA. McQueen, CL. Meschter and EM. Weyand

Stable Expression of Heterologous Cytochromes P450 in V79 Cells:Mutagenicity Studies with Polycyclic Aromatic Hydrocarbons 1167HR. Glatt, K. Pauly, C. Wolfel, S. Dogra, A. Seidel, H. Lee, R.G. Harvey,F. Oesch and J. Doehmer

Metabolic Activation of Chrysene and Benzo[a]pyrene in Hamster, Ratand Human in vitro Lung Cell Cultures 1175/ . Jacob, G. Grimmer, V. Mohr, M. Emura, M. Riebe-Imre, G. Raaband J. Knebel

Influence of Some Carcinogenesis Inhibitors upon Benzofa]-pyrene Metabolism 1183/. Niculescu-Duvaz, I. Colovai, G. Stoica, S. Cinca and N. Voiculetz

Influence of PAH-Pretreatment on MFO-related Metabolic Featuresin Airway Epithelial Cells in vitro 1191M. Riebe-Imre, M. Emura, U. Hilbsch, M. Aufderheide, J. Jacob,G. Grimmer and G. Raab

Species-Specific Liver Microsomal Metabolism of Benz[a]anthrancenein Mammals 1199A. Schmoldt, J. Jacob, G. Grimmer, C. Augustin and G. Raab

Preliminary Data on Bioconcentration Factors of Tetrachlorobenzyltoluenes(TCBTs) in the Guppy (Poecilia reticulatus) 1207A.G. van Haelst, H.E.WM. Loonen, F.WM. van der Wielenand HAJ. Govers

The Effect of Polycyclic Aromatic Hydrocarbons on the Measurementof TCDD-like Toxic Potency in Chick Embryo Livers 1215M. Machala, R. Ulrich, I. Holoubek, J. ddslavskf, A. Ko£an, J. Petrik,J. Chovancovd, K. Btlikovd, F. Filip and V. GajddSkovd

xviii CONTENTS

Inhibition of Rat Hepatic Nuclear RNA Synthesis in vivoand in vitro by Benzo[a]pyrene . 1223GM. Shah and R.K. Bhattacharya

List of Participants 1231

Keywords 1253

Index of Authors 1259