Aquatic Toxicity of Dioxins and Related Chemicals

Polychlorinated dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs), and biphenyls (PCBs) belong to a family of lipophilic halogenated aromatic hydrocarbons that have similar structures, resist chemical and biological degradation, and persist in the environment posing a potential risk to fish, wildlife, and human health. There are more than 400 possible polychlorinated dioxins, dibenzofuran, and biphenyl congeners; however, only 21 are considered highly toxic.1,2 The more potent congeners are planar or coplanar molecules with lateral chlorine substitutions, approximate isostereomers of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), the most potent PCDD, PCDF, or PCB congener.3 In mammals, TCDD and TCDD-like dioxin, dibenzofuran, and biphenyl congeners evoke similar patterns of toxic responses within a given species, and share a common mechanism of action mediated by binding the cellular aryl hydrocarbon (Ah) receptor and altering gene transcription.3,4 The ability of TCDD and TCDD-like congeners to produce toxicity in mammalian species correlates with their Ah receptor binding affinity and their ability to induce cytochrome P450IA enzyme activity, a gene subfamily that catalyzes monooxygenase reactions and whose expression is regulated by the Ah receptor.4−6

[1]  G. Mannering,et al.  Hepatic cytochrome P-450-dependent monooxygenase systems of the trout, frog and snake--III. Induction. , 1982, Comparative biochemistry and physiology. B, Comparative biochemistry.

[2]  R. Kociba,et al.  2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD): results of a 13-week oral toxicity study in rats. , 1976, Toxicology and applied pharmacology.

[3]  J. Stegeman,et al.  Cytochrome P450E (P450IA) induction and inhibition in winter flounder by 3,3′,4,4′‐tetrachlorobiphenyl: Comparison of response in fish from georges bank and narragansett bay , 1991 .

[4]  J. Giesy,et al.  Effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on the epidermal growth factor receptor in hepatic plasma membranes of rainbow trout. , 1993, Toxicology and applied pharmacology.

[5]  A Poland,et al.  2,3,7,8-tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. , 1982, Annual review of pharmacology and toxicology.

[6]  A. Opperhuizen,et al.  Bioaccumulation and biotransformation of polychlorinated dibenzo‐p‐dioxins and dibenzofurans in fish , 1990 .

[7]  R. A. Neal,et al.  Toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin in the golden Syrian hamster. , 1980, Toxicology and applied pharmacology.

[8]  D. Rice,et al.  Effects of organic contaminants on reproduction of the starry flounder Platichthys stellatus in San Francisco Bay , 1988 .

[9]  H. Rosenthal,et al.  Chlorinated hydrocarbons and hatching success in Baltic herring spring spawners , 1985 .

[10]  S. Safe,et al.  Comparative analysis of polychlorinated dibenzo-'p'-dioxin and dibenzofuran congeners in Great Lakes fish extracts by gas chromatography-mass spectrometry and in-vitro enzyme induction activities , 1989 .

[11]  E. Glover,et al.  Chlorinated biphenyl induction of aryl hydrocarbon hydroxylase activity: a study of the structure-activity relationship. , 1977, Molecular pharmacology.

[12]  F A Smith,et al.  Three-generation reproduction study of rats given 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the diet. , 1979, Toxicology and applied pharmacology.

[13]  D. Hansen,et al.  Chronic toxicity, uptake, and retention of aroclor® 1254 in two estuarine fishes , 1971, Bulletin of environmental contamination and toxicology.

[14]  R. Peterson,et al.  Morphologic lesions and acute toxicity in rainbow trout (Salmo gairdneri) treated with 2,3,7,8-tetrachlorodibenzo-p-dioxin. , 1988, Journal of toxicology and environmental health.

[15]  R. Peterson,et al.  Characterization of the enhanced paw edema response to carrageenan and dextran in 2,3,7,8-tetrachlorodibenzo-p-dioxin-treated rats. , 1984, The Journal of pharmacology and experimental therapeutics.

[16]  J. Giesy,et al.  Relationships Between Chlorinated Hydrocarbon Concentrations and Rearing Mortality of Chinook Salmon (Oncorhynchus Tshawytscha) Eggs from Lake Michigan , 1986 .

[17]  P. Thomas.  Effects of Aroclor 1254 and cadmium on reproductive endocrine function and ovarian growth in atlantic croaker , 1989 .

[18]  Robert W. Moore,et al.  In utero and lactational exposure of male rats to 2,3,7,8-tetrachlorodibenzo-p-dioxin. 3. Effects on spermatogenesis and reproductive capability. , 1992, Toxicology and applied pharmacology.

[19]  M. Clayton,et al.  An egg injection method for assessing early life stage mortality of polychlorinated dibenzo- p -dioxins, dibenzofurans, and biphenyls in rainbow trout, (Oncorhynchus mykiss) , 1992 .

[20]  T. Fujita,et al.  PCBs: structure–function relationships and mechanism of action , 1985, Environmental health perspectives.

[21]  R. Hites,et al.  Environmental fate of combustion-generated polychlorinated dioxins and furans. , 1984, Environmental science & technology.

[22]  B. J. Puma,et al.  Screening of fresh water fish extracts for enzyme-inducing substances by an aryl hydrocarbon hydroxylase induction bioassay technique. , 1983, Journal - Association of Official Analytical Chemists.

[23]  L. Norris,et al.  Chronic Oral Toxicity of 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) to Rainbow Trout , 1977 .

[24]  M. E. Hahn,et al.  Effects of ortho- and non-ortho-substituted polychlorinated biphenyl congeners on the hepatic monooxygenase system in scup (Stenotomus chrysops). , 1989, Toxicology and applied pharmacology.

[25]  R. Peterson,et al.  Interactions of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) with immune responses of rainbow trout. , 1986, Veterinary immunology and immunopathology.

[26]  J. Whitlock,et al.  Genetic and molecular aspects of 2,3,7,8-tetrachlorodibenzo-p-dioxin action. , 1990, Annual review of pharmacology and toxicology.

[27]  R. Peterson,et al.  Cardiovascular teratogenicity of 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin in the chick embryo. , 1981, Toxicology and applied pharmacology.

[28]  S. Safe.  Determination of 2,3,7,8-TCDD toxic equivalent factors (TEFs): support for the use of the in vitro AHH induction assay , 1987 .

[29]  R. Miller,et al.  The toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in Guppies (Poecilia reticulatus Peters) , 1974, Bulletin of environmental contamination and toxicology.

[30]  U. Borgmann,et al.  DDE, PCB, and Mercury Concentration Trends in Lake Ontario Rainbow Smelt (Osmerus Mordax) and Slimy Sculpin (Cottus Cognatus): 1977 to 1988 , 1992 .

[31]  Neidermyer Wj,et al.  Chronology of organochlorine compounds in Lake Michigan fish, 1929-66. , 1976 .

[32]  N. Johansson,et al.  Metabolic effects of PCB (polychlorinated biphenyls) on the brown trout (Salmo trutta). , 1972, Comparative and general pharmacology.

[33]  G. Perdew,et al.  Detection of the Ah receptor in rainbow trout: use of 2-azido-3-[125I]iodo-7,8-dibromodibenzo-p-dioxin in cell culture. , 1991, Toxicology letters.

[34]  C. Rappe,et al.  Evaluation of baltic herring and icelandic cod liver oil for embryo toxicity, using the japanese medaka (oryzias latipes) embryo larval assay , 1991 .

[35]  L. Birnbaum,et al.  Comparative ability of various PCBs, PCDFs, and TCDD to induce cytochrome P450 1A1 and 1A2 activity following 4 weeks of treatment. , 1993, Fundamental and applied toxicology : official journal of the Society of Toxicology.

[36]  Robert W. Moore,et al.  In utero and lactational exposure of male rats to 2,3,7,8-tetrachlorodibenzo-p-dioxin. 1. Effects on androgenic status. , 1992, Toxicology and applied pharmacology.

[37]  T. Colborn,et al.  Chemically-induced alterations in sexual and functional development : the wildlife/human connection , 1992 .

[38]  B. Bengtsson.  Long-term effects of PCB (Clophen A50) on growth, reproduction and swimming performance in the minnow, Phoxinus phoxinus , 1980 .

[39]  M. Romkes,et al.  Polychlorinated dibenzofurans (PCDFs): correlation between in vivo and in vitro structure-activity relationships. , 1985, Toxicology.

[40]  W. Dunn,et al.  Polychlorinated dibenzofurans and polychlorinated dibenzo‐p‐dioxins in great lakes fish: A baseline and interlake comparison , 1989 .

[41]  D. Nebert,et al.  Trout P450IA1: cDNA and deduced protein sequence, expression in liver, and evolutionary significance. , 1988, DNA.

[42]  L. Hudson,et al.  Regulation of epidermal growth factor binding in a human keratinocyte cell line by 2,3,7,8-tetrachlorodibenzo-p-dioxin. , 1985, Toxicology and applied pharmacology.

[43]  J. Zinkl,et al.  Toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in C57B1/6 mice. , 1974, Toxicology and applied pharmacology.

[44]  G. Veith,et al.  Effects of Aroclor® 1248 and 1260 on the Fathead Minnow (Pimephales promelas) , 1978 .

[45]  Richard A. Miller,et al.  The Response of Coho Salmon and Guppies to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in Water , 1979 .

[46]  J. Giesy,et al.  Characterization of the H4IIE rat hepatoma cell bioassay as a tool for assessing toxic potency of planar halogenated hydrocarbons in environmental samples , 1991 .

[47]  T. Helder.  Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on early life stages of the pike (Esox lucius L.) , 1980 .

[48]  C. Metcalfe,et al.  Relative induction of aryl hydrocarbon hydroxylase by 2,3,7,8‐TCDD and two coplanar PCBs in rainbow trout (oncorhynchus mykiss) , 1991 .

[49]  A. J. Niimi.  Biological and Toxicologtcal Effects of Environmental Contaminants in Fish and Their Eggs , 1983 .

[50]  S. Safe,et al.  Binding of polychlorinated biphenyls classified as either phenobarbitone-, 3-methylcholanthrene- or mixed-type inducers to cytosolic Ah receptor. , 1982, Chemico-biological interactions.

[51]  M. Luster,et al.  CHAPTER 10 – Immune alterations , 1989 .

[52]  R. Peterson,et al.  Translocation of 2,3,7,8-Tetrachlorodibenzo-p-dioxin from Adult Female Lake Trout (Salvelinus namaycush) to Oocytes: Effects on Early Life Stage Development and Sac Fry Survival , 1994 .

[53]  J. L. Zajicek,et al.  National contaminant biomonitoring program: Residues of organochlorine chemicals in U.S. Freshwater Fish, 1976–1984 , 1990, Archives of environmental contamination and toxicology.

[54]  M Meselson,et al.  An analytical method for detecting TCDD (dioxin): levels of TCDD in samples from Vietnam. , 1973, Environmental health perspectives.

[55]  F. Matsumura,et al.  Effects of in vivo-administered 2,3,7,8-tetrachlorodibenzo-p-dioxin on receptor binding of epidermal growth factor in the hepatic plasma membrane of rat, guinea pig, mouse, and hamster. , 1984, Proceedings of the National Academy of Sciences of the United States of America.

[56]  H. E. Johnson,et al.  Acute Toxicities of a Polychlorinated Biphenyl (PCB) and DDT Alone and in Combination to Early Life Stages of Coho Salmon (Oncorhynchus kisutch) , 1974 .

[57]  T. Helder.  Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on early life stages of rainbow trout (Salmo Gairdneri, Richardson) , 1981 .

[58]  G. Monod,et al.  Egg mortality of lake geneva charr (Salvelinus alpinus L.) contaminated by PCB and DDT derivatives , 1985, Bulletin of environmental contamination and toxicology.

[59]  A. Nebeker,et al.  Effect of Polychlorinated Biphenyl Compounds on Survival and Reproduction of the Fathead Minnow and Flagfish , 1974 .

[60]  R. Peterson,et al.  The enhancing effect of spawning on elimination of a persistent polychlorinated biphenyl from female yellow perch. , 1985, Fundamental and applied toxicology : official journal of the Society of Toxicology.

[61]  R. Peterson,et al.  2,3,7,8-Tetrachlorodibenzo-p-dioxin toxicity in yellow perch (Perca flavescens). , 1988, Journal of toxicology and environmental health.

[62]  R. Osborne,et al.  2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) enhances terminal differentiation of cultured human epidermal cells. , 1985, Toxicology and applied pharmacology.

[63]  V. K. Rowe,et al.  Toxicology of chlorinated dibenzo-p-dioxins. , 1973, Environmental health perspectives.

[64]  M. Denison.  The molecular mechanism of action of 2,3,7,8-tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons , 1991 .

[65]  J. Giesy,et al.  Maternal transfer of bioactive polychlorinated aromatic hydrocarbons in spawning chinook salmon (Oncorhynchus tschawytscha) , 1989 .

[66]  Wayne G. Landis,et al.  Environmental toxicology and risk assessment , 1993 .

[67]  J. D. Wisk,et al.  Comparison of the toxicity of several polychlorinated dibenzo-p-dioxins and 2,3,7,8-tetrachlorodibenzofuran in embryos of the Japanese medaka (Oryzias latipes) , 1990 .

[68]  B. Gladen,et al.  Neurotoxicology of PCBs and related compounds. , 1992, Neurotoxicology.

[69]  D. Whittle,et al.  The status of selected organics in the Laurentian Great Lakes: an overview of DDT, PCBs, dioxins, furans, and aromatic hydrocarbons , 1988 .

[70]  W. Adams,et al.  Toxicity and Bioconcentration of 2,3,7,8-TCDD to fathead minnows () , 1986 .

[71]  G. Blau,et al.  Bioconcentration kinetics of 2,3,7,8-tetrachlorodibenzo-p-dioxin in rainbow trout , 1985 .

[72]  D. Rice,et al.  Effects of organic contaminants on reproduction of the starry flounder Platichthys stellatus in San Francisco Bay , 1988 .

[73]  R. Peterson,et al.  Species differences in 2,3,7,8-tetrachlorodibenzo-p-dioxin toxicity and biotransformation in fish. , 1988, Fundamental and applied toxicology : official journal of the Society of Toxicology.

[74]  Barry G. Oliver,et al.  Trophodynamic analysis of polychlorinated biphenyl congeners and other chlorinated hydrocarbons in the Lake Ontario ecosystem , 1988 .

[75]  D. Schrenk,et al.  Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on reproduction and oogenesis in zebrafish (Brachydanio rerio) , 1992 .

[76]  L. Hudson,et al.  2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) modulates epidermal growth factor (EGF) binding to basal cells from a human keratinocyte cell line. , 1986, Toxicology and applied pharmacology.

[77]  R. Peterson,et al.  Toxic equivalency factors of polychlorinated dibenzo-p-dioxin, dibenzofuran and biphenyl congeners based on early life stage mortality in rainbow trout (Oncorhynchus mykiss) , 1995 .

[78]  R. Miller,et al.  Toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in aquatic organisms. , 1973, Environmental health perspectives.

[79]  Ray R. Lassiter,et al.  Modelling Bioaccumulation of Organic Pollutants in Fish with an Application to PCBs in Lake Ontario Salmonids , 1991 .

[80]  J. Goldstein,et al.  Mechanism of action and structure-activity relationships for the chlorinated dibenzo- p- dioxins and related compounds , 1989 .

[81]  J. Stegeman,et al.  Induction of aryl hydrocarbon hydroxylase activity in embryos of an estuarine fish , 1980 .

[82]  R. Peterson,et al.  Potencies of polychlorinated dibenzo-p-dioxin, dibenzofuran, and biphenyl congeners, relative to 2,3,7,8-tetrachlorodibenzo-p-dioxin, for producing early life stage mortality in rainbow trout (Oncorhynchus mykiss) , 1991 .

[83]  J. Giesy,et al.  Relationships Among Concentrations of Individual Polychlorinated Biphenyl (PCB) Congeners, 2,3,7,8-Tetrachlorodibenzo-P-Dioxin Equivalents (TCDD-EQ), and Rearing Mortality of Chinook Salmon (Oncorhynchus Tshawytscha) Eggs from Lake Michigan , 1992 .

[84]  R. Peterson,et al.  Effects of 2,3,7,8‐tetrachlorodibenzo‐p‐dioxin (TCDD) or Aroclor 1254 on the resistance of rainbow trout, Salmo gairdneri Richardson, to infectious haematopoietic necrosis virus , 1988 .

[85]  E. Little,et al.  Toxicity and bioconcentration of 2,3,7,8-tetrachlorodibenzodioxin and 2,3,7,8-tetrachlorodibenzofuran in rainbow trout , 1988 .

[86]  D. Firestone.  Etiology of chick edema disease. , 1973, Environmental health perspectives.

[87]  M. E. Hahn,et al.  The Ah receptor in marine animals: phylogenetic distribution and relationship to cytochrome P4501A inducibility , 1992 .

[88]  J. Huckins,et al.  Carbon–Foam Chromatographic Separation of Non-o,o´-Chlorine Substituted PCBs from Aroclor Mixtures , 1980 .

[89]  J. D. Wisk,et al.  The stage specific toxicity of 2,3,7,8‐tetrachlorodibenzo‐p‐dioxin in embryos of the japanese medaka (Oryzias latipes) , 1990 .

[90]  T. Yano,et al.  Stimulatory effect of PCB on the metabolism of sex hormones in carp hepatopancreas. , 1986 .

[91]  Schmidtke.  Toxic Contamination in Large Lakes , 1988 .

[92]  Jurgen H. Exner,et al.  Solving hazardous waste problems : learning from dioxins , 1987 .

[93]  J. Allen,et al.  Morphological changes in monkeys consuming a diet containing low levels of 2,3,7,8-tetrachlorodibenzo-p-dioxin. , 1977, Food and cosmetics toxicology.

[94]  C. Elcombe,et al.  The effect of various types of inducing agents on hepatic microsomal monooxygenase activity in rainbow trout. , 1981, Toxicology and applied pharmacology.

[95]  D. Kuehl,et al.  Uptake and depuration studies of PCDDs and PCDFs in freshwater fish , 1986 .

[96]  R. Peterson,et al.  Pathologic alterations in early life stages of lake trout, Salvelinus namaycush, exposed to 2,3,7,8-tetrachlorodibenzo- p-dioxin as , 1991 .

[97]  A. Goksøyr,et al.  The cytochrome P-450 system in fish, aquatic toxicology and environmental monitoring , 1992 .

[98]  E. Gruger,et al.  Sublethal effects of structurally related tetrachloro-, pentachloro-, and hexachlorobiphenyl on juvenile coho salmon , 1976 .

[99]  J. Piskorska-Pliszczynska,et al.  Polychlorinated dibenzo-p-dioxins: quantitative in vitro and in vivo structure-activity relationships. , 1986, Toxicology.

[100]  R. Sonstegard,et al.  Proximate composition and organochlorine and heavy metal contamination of eggs from Lake Ontario, Lake Erie and Lake Michigan coho salmon (oncorhynchus kisutch walbaum) in relation to egg survival , 1985 .

[101]  U. Brinkman,et al.  Production, properties and usage of polychlorinated biphenyls , 1989 .

[102]  Michael A. Gallo,et al.  Biological Basis for Risk Assessment of Dioxins and Related Compounds , 1991 .

[103]  Robert W. Moore,et al.  In utero and lactational exposure of male rats to 2,3,7,8-tetrachlorodibenzo-p-dioxin. 2. Effects on sexual behavior and the regulation of luteinizing hormone secretion in adulthood. , 1992, Toxicology and applied pharmacology.

[104]  J. Duinker,et al.  Complete characterization of polychlorinated biphenyl congeners in commercial Aroclor and Clophen mixtures by multidimensional gas chromatography-electron capture detection , 1989 .

[105]  J. Steeves,et al.  A Short-Term Test for Dioxin Teratogenicity Using Chicken Embryos , 1993 .

[106]  M. Evans,et al.  Toxic contaminants and ecosystem health : a Great Lakes focus , 1988 .

[107]  G. E. Jones,et al.  Distribution and toxicity of TCDD and 2,4,5-T in an aquatic model ecosystem , 1978 .

[108]  A. Burlingame,et al.  Identification of chlorinated dibenzofurans in American polychlorinated biphenyls , 1975, Nature.

[109]  W. McNulty.  Toxicity and fetotoxicity of TCDD, TCDF and PCB isomers in rhesus macaques (Macaca mulatta). , 1985, Environmental health perspectives.

[110]  P. Bergqvist,et al.  Chemical physiological and morphological studies of feral baltic salmon (Salmo salar) suffering from abnormal fry mortality , 1993 .

[111]  D. Hansen,et al.  Effects of Aroclor(R) 1016 on Embryos, Fry, Juveniles, and Adults of Sheepshead Minnows (Cyprinodon variegatus) , 1975 .

[112]  W. Williams,et al.  The effects of polychlorinated biphenyls on plasma steroid levels and hepatic microsomal enzymes in fish , 1978 .

[113]  J. Stegeman.  Cytochrome P450 forms in fish: catalytic, immunological and sequence similarities. , 1989, Xenobiotica; the fate of foreign compounds in biological systems.

[114]  M. E. Hahn,et al.  Immunohistochemical localization of cytochrome P-450IA1 induced by 3,3',4,4'-tetrachlorobiphenyl and by 2,3,7,8-tetrachlorodibenzoafuran in liver and extrahepatic tissues of the teleost Stenotomus chrysops (scup). , 1991, Drug metabolism and disposition: the biological fate of chemicals.

[115]  M. Nilsen-Hamilton.  Growth factors and development , 1990 .

[116]  Lawrence M. Smith,et al.  Determination and occurrence of AHH-active polychlorinated biphenyls, 2,3,7,8-tetrachloro-p-dioxin and 2,3,7,8-tetrachlorodibenzofuran in Lake Michigan sediment and biota. The question of their relative toxicological significance , 1990 .

[117]  D. Stalling,et al.  Toxicities of PCBs to Fish and Environmental Residues , 1972, Environmental health perspectives.

[118]  H. Sanders,et al.  Residue dynamics and biological effects of polychlorinated biphenyls in aquatic organisms , 1977, Archives of environmental contamination and toxicology.

[119]  W. McNulty,et al.  Fetotoxicity of 2,3,7,8‐tetrachlorodibenzo‐p‐dioxin (TCDD) for rhesus macaques (Macaca mulatta) , 1984, American journal of primatology.

[120]  E. Glover,et al.  Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase. , 1976, The Journal of biological chemistry.

[121]  J. Waid.  PCBs and the environment , 1986 .

[122]  W. Seinen,et al.  A dose / response study with 2,3,7,8 - TCDD in the rainbow trout , 1990 .

[123]  A. Okey,et al.  Detection and characterization of [3H]2,3,7,8-tetrachlorodibenzo-p-dioxin binding to Ah receptor in a rainbow trout hepatoma cell line. , 1990, Toxicology and applied pharmacology.

[124]  F. Mayer,et al.  Effects of the Polychlorinated Biphenyl Aroclor® 1254 on Growth, Survival, and Bone Development in Brook Trout (Salvelinus fontinalis) , 1978 .

[125]  K. Ballschmiter,et al.  Analysis of polychlorinated biphenyls (PCB) by glass capillary gas chromatography , 1980 .

[126]  J. Giesy,et al.  The effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on epidermal growth factor binding and protein kinase activity in the RTH-149 rainbow trout hepatoma cell line , 1992 .

[127]  C. Rice,et al.  The biomagnification of polychlorinated biphenyls, toxaphene, and DDT compounds in a Lake Michigan offshore food web , 1991, Archives of environmental contamination and toxicology.

[128]  A. Partanen.  2 Epidermal Growth Factor and Transforming Growth Factor-α in the Development of Epithelial—Mesenchymal Organs of the Mouse , 1990 .

[129]  J. Nriagu,et al.  Contaminant effects on fisheries , 1984 .

[130]  R. Peterson,et al.  Effects of egg and sperm maturation and spawning on the distribution and elimination of a polychlorinated biphenyl in rainbow trout (Salmo gairdneri). , 1979, Toxicology and applied pharmacology.

[131]  C. M. Kaya,et al.  Effects of Prolonged Exposure to Ammonia on Fertilized Eggs and Sac Fry of Rainbow Trout (Salmo gairdneri) , 1977 .

[132]  M. Mac,et al.  Environmental contaminants and the reproductive success of lake trout in the Great Lakes: an epidemiological approach. , 1991, Journal of toxicology and environmental health.

[133]  R. Peterson,et al.  2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) Toxicity during Early Life Stage Development of Lake Trout (Salvelinus namaycush) , 1991 .

[134]  R. Kimbrough,et al.  Biological Mechanisms of Dioxin Action , 1985 .

[135]  S. Safe,et al.  Polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs), and related compounds: environmental and mechanistic considerations which support the development of toxic equivalency factors (TEFs). , 1990, Critical reviews in toxicology.

[136]  D. Hansen,et al.  Effects of Aroclor(R) 1254 on Laboratory‐Reared Embryos and Fry of Sheepshead Minnows (Cyprinodon variegatus) , 1974 .

[137]  R. Stickney.  Culture of nonsalmonid freshwater fishes , 1988 .

[138]  H. Sanders,et al.  AN EXPANDED APPROACH TO THE STUDY AND MEASUREMENT OF PCBs AND SELECTED PLANAR HALOGENATED AROMATIC ENVIRONMENTAL POLLUTANTS * , 1979, Annals of the New York Academy of Sciences.

[139]  R. Peterson,et al.  Enhancement of carrageenan and dextran-induced edemas by 2,3,7,8-tetrachlorodibenzo-p-dioxin and related compounds. , 1983, The Journal of pharmacology and experimental therapeutics.

[140]  W. Ernst,et al.  Bioaccumulating substances and reproductive success in baltic flounder platichthys flesus , 1981 .

[141]  D. Hansen,et al.  Aroclor 1016: Toxicity to and uptake by estuarine animals , 1974 .

[142]  George Eadon,et al.  Calculation of 2,3,7,8-TCDD equivalent concentrations of complex environmental contaminant mixtures , 1986, Environmental health perspectives.

[143]  S. Safe,et al.  Polychlorinated biphenyls: correlation between in vivo and in vitro quantitative structure-activity relationships (QSARs). , 1985, Journal of toxicology and environmental health.

[144]  E. G. Jensen,et al.  Response of xenobiotic metabolizing enzymes of rainbow trout (Oncorhynchus mykiss) to the mono-ortho substituted polychlorinated PCB congener 2,3′,4,4′,5-pentachlorobiphenyl, PCB-118, detected by enzyme activities and immunochemical methods , 1991, Archives of environmental contamination and toxicology.