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Organic Pollutants as Endocrine Disruptors: Organometallics, PAHs, Organochlorine, Organophosphate and Carbamate Insecticides, Phthalates, Dioxins, Phytoestrogens, Alkyl Phenols and Bisphenol A

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Part of the book series: Environmental Chemistry for a Sustainable World ((ECSW))

Abstract

Several natural or anthropogenic substances have endocrine disrupting properties that can modify the endocrine system of living organisms. This has led to increasing concern of the public. Results from animal models, human clinical observations, and epidemiological studies incriminate endocrine disrupting substances as a significant concern to public health. Estimation of health impacts of endocrine disruptors is complicated because some of these chemicals contribute to the occurrence of common diseases of multifactorial etiology such as infertility, cancer and neurobehavioral deficits. The difficulty of assessing public health effects is increased by the fact that people are typically exposed to multiple endocrine disruptors simultaneously.

We review here natural and anthropogenic endocrine disrupting substances occurring in the environment. We discuss the potential effects of exposure to endocrine disruptors in humans and wildlife. This review focus on toxicity, environmental fate, ecological effects and metabolism of organometallic compounds, polycyclic aromatic hydrocarbons, organochlorine, organophosphate and carbamate insecticides, phthalates, dioxins, phytoestrogens, alkyl phenols and bisphenol A. Recent studies show that nonylphenol, bisphenol-A, flavonoids, isoflavonoids and some chlorinated pesticides modify thyroid hormone systems. Androgen mimicking chemicals in the environment can bioaccumulate and evolve through the food web. Exposure to androgenic substances can alter reproduction of all species including humans. Research should be focused on the identification of the life stages and species that are more vulnerable to the effects of endocrine disrupting compounds and how this mechanism of disruption affects populations and communities.

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References

  • Afifi NA, Ramadan A, Abd-El-Aziz MI, Saki EE (1991) Influence of dimethoate on testicular and epididymal organs, testosterone plasma level and their tissue residues in rats. Deutsche Tieraerztliche Wochenschrift 98:419–420

    CAS  Google Scholar 

  • Ahel M, Giger W (1993) Partitioning of alkylphenols and alkylphenol polyethoxylates between water and organic solvents. Chemosphere 26:1471–1478

    Article  CAS  Google Scholar 

  • Ahel M, Giger W, Koch M (1994a) Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment – Occurrence and transformations in sewage treatment. Water Res 28:1131–1142

    Article  CAS  Google Scholar 

  • Ahel M, Hrsak D, Giger W (1994b) Aerobic transformation of short-chain alkylphenol polyethoxylates by mixed bacterial cultures. Arch Environ Contam Toxicol 26:540–548

    Article  CAS  Google Scholar 

  • Ahel M, Scully FE, Hoigné J, Giger W (1994c) Photochemical degradation of nonylphenol and nonylphenol polyethoxylates in natural waters. Chemosphere 28:1361–1368

    Article  CAS  Google Scholar 

  • Ahel M, Schaffner C, Giger W (1996) Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment: III. Occurrence and elimination of their persistent metabolites during infiltration of river water to groundwater. Water Res 30:37–46

    Article  CAS  Google Scholar 

  • Aldridge WN, Magos L (1978) Carbamates, thiocarbamates, dithiocarbamates, Luxembourg, Commission of the European Communities, report no V/F/1/78/75 EN

    Google Scholar 

  • Aly OM, El-Dib MA (1972) Persistence of some carbamate insecticides in the aquatic environment. In: Faust SD, Hunter JV (eds) Fate of organic pesticides in the environment, Advances in chemistry series III. American Chemical Society, Washington, DC, pp 210–243

    Chapter  Google Scholar 

  • Andersson A, Linder CE, Olsson M, Reutergardh L, Uvemo UB, Widequist U (1988) Spatial differences and temporal trends of organochlorine compounds in biota from the Northwestern hemisphere. Arch Environ Contam Toxicol 17:755–765

    Article  CAS  Google Scholar 

  • Anon (1998) Sex on the brain. New Scientist, 4

    Google Scholar 

  • Argese E, Marcomini A, Miana P, Bettiol C, Perin G (1994) Submitochondrial particle response to linear alkylbenzene sulfonates, nonylphenol polyethoxylates and their biodegradation derivatives. Environ Toxicol Chem 13:737–742

    Article  CAS  Google Scholar 

  • Arukwe A, Celius T, Walther BT, Goksoyr A (2000) Effects of xenoestrogen treatment on zona radiata protein and vitellogenin expression in Atlantic salmon (Salmo Salar). Aquat Toxicol 49:159

    Article  CAS  Google Scholar 

  • ASTDR (Agency for Toxic Substances and Disease Registry) (1998) Toxicological profile for chlorinated dibenzo-p-dioxins. US department of health and human services, Atlanta

    Google Scholar 

  • Ball HA, Reinhard M, McCarty PL (1989) Biotransformation of halogenated and nonhalogenated octylphenol polyethoxylate residues under aerobic and anaerobic conditions. Environ Sci Technol 23:951–961

    Article  CAS  Google Scholar 

  • Barter RA, Klaassen CD (1992) UDP-glucuronosyltransferase inducers reduce thyroid hormone levels in rats by an extrathyroidal mechanism. Toxicol Appl Pharmacol 113:36–42

    Article  CAS  Google Scholar 

  • Beck H, Eckart K, Mathar W, Wittkowski R (1989) PCDD and PCDF body burden from food intake in the Federal Republic of Germany. Chemosphere 18:417–424

    Article  Google Scholar 

  • Berg M, Cédric AG, Müller SR, Mühlemann J, Schwarzenbach RP (2001) Sorption and desorption behavior of organotin compounds in sediment  −  pore water systems. Environ Sci Technol 35(15):3151–3157

    Article  CAS  Google Scholar 

  • Bergman A, Olsson M (1985) Pathology of Baltic grey seal and ringed seal females with special reference to adrenocortical hyperplasia: Is environmental pollution the cause of a widely distributed disease syndrome? Finnish Game Res 44:47–62

    Google Scholar 

  • Berlin M (1986) Mercury. In Handbook on the Toxicology of Metals. 2nd ed. Friberg, L, Nordberg, GF (eds.) Elsevier, Amsterdam 3:386–445

    Google Scholar 

  • Bignert A, Litzén K, Odsjö T, Olsson M, Persson W, Reutergårdh L (1995) Time-related factors influence the concentrations of DDT, PCBs and shell parameters in eggs of Baltic guillemot (Uria aalge), 1961–1989. Environ Pollut 89:27–36

    Article  CAS  Google Scholar 

  • Biles JE, McNeal TP, Begley TH (1997) Determination of bisphenol a migrating from epoxy can coatings to infant formula liquid concentrates. J Agric Food Chem 45:4697–4700

    Article  CAS  Google Scholar 

  • Birmingham B, Thorpe B, Frank R, Clement R, Tosine H, Fleming G, Ashman J, Wheeler J, Ripley BD, Ryan JJ (1989) Dietary intake of PCDD and PCDF from food in Ontario, Canada. Chemosphere 19:507–512

    Article  Google Scholar 

  • Bishop CA, Collins B, Mineau P, Burgess NM, Read WF, Risley C (2000) Reproduction of cavity nesting birds in pesticide sprayed apple orchards in southern Ontario, Canada, 1988–1994. Environ Toxicol Chem 19:588

    CAS  Google Scholar 

  • Blaber SJM (1970) The occurrence of a penis-like outgrowth behind the right tentacle in spent females of Nucella lapillus. Proc Malacol Soc Lond 39:231–233

    Google Scholar 

  • Blask DE, Brainard GC, Dauchy RT, Hanifin JP, Davidson LK, Krause JA, Sauer LA, Rivera-Bermudez MA, Dubocovich ML, Jasser SA, Lynch DT, Rollag MD, Zalatan F (2005) Melatonin-depleted blood from premenopausal women exposed to light at night stimulates growth of human breast cancer xenografts in nude rats. Cancer Res 65:11174–11184

    Article  CAS  Google Scholar 

  • Blount BC, Milgram KE, Silva MJ, Malek NA, Reidy JA, Needham LL, Brock JW (2000a) Quantitative detection of eight phthalate metabolites in human urine using HPLC-APCIMS/MS. Anal Chem 72:4127–4134

    Article  CAS  Google Scholar 

  • Blount BC, Silva MJ, Caudill SP, Needham LL, Pirkle JL, Sampson EJ, Lucier GW, Jackson RJ, Brock JW (2000b) Levels of seven urinary phthalate metabolites in a human reference population. Environ Health Perspect 108:979–982

    Article  CAS  Google Scholar 

  • Boening DW (2000) Ecological effects, transport, and fate of mercury: a general review. Chemosphere 40(12):1335–1351

    Article  CAS  Google Scholar 

  • Bolger R, Wiese TE, Ervin K, Nestich S, Checovich W (1998) Rapid screening of environmental chemicals for estrogen receptor binding capacity. Environ Health Perspect 106:551–557

    Article  CAS  Google Scholar 

  • Bowerman WW, Best DA, Grubb TG, Sikarskie JG, Giesy JP (2000) Assessment of environmental endocrine disruptors in bald eagles of the Great Lakes. Chemosphere 41:1569

    Article  CAS  Google Scholar 

  • Boyer IJ (1989) Toxicity of dibutyltin, tributyltin and other organotin compounds to humans and to experimental animals. Toxicology 55:253–298

    Article  CAS  Google Scholar 

  • Branca F, Lorenzetti S (2005) Health effects of phytoestrogens. Forum Nutr 57:100–111

    Article  Google Scholar 

  • Brotons JA, Olea-Serrano MF, Villalobos M, Pedraza V, Olea N (1995) Xenoestrogens released from lacquer coatings in food cans. Environ Health Perspect 103:608–612

    Article  CAS  Google Scholar 

  • Bryan GW, Gibbs PE, Hummerstone LG, Burt GR (1986) The decline of the gastropod Nucella lapillus around south-west England: evidence for the effect of tributyltin from antifouling paints. J Mar Biol Assoc UK 66:611–640

    Article  CAS  Google Scholar 

  • Celius T, Haugen TB, Grotmol T, Walther BT (1999) A sensitive zonagenetic assay for rapid in vitro assessment of estrogenic potency of xenobiotics and mycotoxins. Environ Health Perspect 107:63–68

    Article  CAS  Google Scholar 

  • CERHR (2007) Interm NTP-CERHR report on the reproductive and developmental toxicity of bisphenol A, http://cerhr.niehs.nih.gov/chemicals/bisphenol/BPA Interim DraftRpt.pdf

  • Cerniglia CE (1984) Microbial metabolism of polycyclic aromatic hydrocarbons. Adv Appl Microbiol 30:31–71

    Article  CAS  Google Scholar 

  • Cerniglia CE (1992) Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 3:351–368

    Article  CAS  Google Scholar 

  • Cerniglia CE, Heitkamp MA (1989) Microbial degradation of polycyclic aromatic hydrocarbons (PAH) in the aquatic environment. In: Varanasi U (ed) Metabolism of polycyclic aromatic hydrocarbons in the aquatic environment. CRC Press, Inc., Boca Raton, pp 41–68

    Google Scholar 

  • CES (1993) Uses, fate and entry to the environment of nonylphenol ethoxylates. Consultants in Environmental Sciences Ltd (for the Department of the Environment), London

    Google Scholar 

  • Cheek AO, Vonier PM, Oberdorste rE, Burow BC, McLachlan JA (1998) Environmental signaling: A biological context for endocrine disruption. Environ Health Perspect 106(1):5–10

    Article  CAS  Google Scholar 

  • Cheung JKH, Lam RKW, Shi MY, Gu JD (2007) Environmental fate of endocrine-disrupting dimethyl phthalate esters (DMPE) under sulfate-reducing condition. Sci Total Environ 381(1–31):26–133

    Google Scholar 

  • Christensen L, Korsgaard B, Bjerregaard P (1999) The Effect of 4-Nonylphenol on the Synthesis of Vitellogenin in the Flounder Platichthys Flesus. Aquat Toxicol 46:211

    Article  CAS  Google Scholar 

  • Christiansen T, Korsgaard B, Jespersen A (1998) Effects of nonylphenol and 17B-Oestradiol on vitellogenin synthesis, testicular structure and cytology in male eelpout Zoarces Viviparus. J Exp Biol 201:179

    CAS  Google Scholar 

  • Clarkson TW, Magos L (2006) The toxicology of mercury and its chemical compounds. Crit Rev Toxicol 36:609–662

    Article  CAS  Google Scholar 

  • Clotfelter ED, Rodriguez AC (2006) Behavioral changes in fish exposed to phytoestrogens. Environ Pollut 144:833–839

    Article  CAS  Google Scholar 

  • COC (Committee on Toxicity of Chemicals in Food Consumer Products and the Environment) (2001) Statement on the tolerable daily intake for dioxins and dioxin-like polychlorinated biphenyls

    Google Scholar 

  • Colborn T (1995) Pesticides – How research has succeeded and failed to translate science into policy: endocrinological effects on wildlife. Environ Health Perspect Suppl 103(Suppl 6):81–86

    Article  Google Scholar 

  • Colborn T, Smolen MJ (1996) Epidemiological analysis of persistent organochlorine contaminants. Rev Environ Contam Toxicol 146:91–172

    CAS  Google Scholar 

  • Colborn T, vom Saal FS, Soto AM (1993) Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect 101:378–384

    Article  CAS  Google Scholar 

  • Cooke GM (2002) Effect of organotins on human aromatase activity in vitro. Toxicol Lett 126:121–130

    Article  CAS  Google Scholar 

  • Cooper RL, Kavlok RJ (1997) Endocrine disrupters and reproductive development: a weight-of-evidence overview. J Endocrinol 152:159–166

    Article  CAS  Google Scholar 

  • Cummings AM, Harris ST, Rehnberg GL (1990) Effects of methylbenzimidazolecarbamate during early pregnancy in the rat. Fundam Appl Toxicol 15:528–535

    Article  CAS  Google Scholar 

  • Cummings AM, Ebron-McCoy MT, Rogers JM, Barbee BD, Harris ST (1992) Developmental effects of methyl benzimidazolecarbamate following exposure during early pregnancy. Fundam Appl Toxicol 18:288–293

    Article  CAS  Google Scholar 

  • Curtis LR (2001) Organophosphate antagonism of the androgen receptor. Toxicol Sci 60:1–2

    Article  CAS  Google Scholar 

  • Czeizel AE (1996) Human germinal mutagenic effects in relation to intentional and accidental exposure to toxic agents. Environ Health Perspect 104(suppl 3):615–617

    Article  CAS  Google Scholar 

  • D’Alessandro TL, Boersma-Maland BJ, Peterson TG, Sfakianos J, Prasain JK, Patel RP, Darley-Usma rVM, Botting NP, Barnes S (2005) Metabolism of phytoestrogen conjugates. Methods Enzymol 400:316–342

    Article  CAS  Google Scholar 

  • Dauterman WC (1971) Biological and nonbiological modifications of organophosphorus compound. Bull World Health Organ 44:133–150

    CAS  Google Scholar 

  • de March BGE, de Wit CA, Muir DCG (1998) Persistent organic pollutants. In: Assessment report: arctic pollution issues. Arctic Monitoring and Assessment Programme (AMAP), Oslo, pp 183–371

    Google Scholar 

  • De Mora SJ (1996) Tributyltin: case study of an environmental contaminant in. Campbell PCC, Galloway JN Harrison RM (ed) Cambridge environmental chemistry Series No. 8, Cambridge University Press, Cambridge

    Google Scholar 

  • De Waal EJ, Schuurman HJ, Van Loveren H, Vos JG (1997) Differential effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin, bis(tri-nbutyltin) oxide and cyclosporine on thymus histophysiology. Crit Rev Toxicol 27:381–430

    Article  Google Scholar 

  • D’Itri FM (1972) The environmental mercury problem. CRC Press, Inc., Boca Raton

    Google Scholar 

  • Dodds EC, Lawson W (1938) Molecular structure in relation to oestrogenic activity. Compounds without a phenanthrene nucleus. Proc R Soc Lon B 125:222–232

    Article  CAS  Google Scholar 

  • Dreze V, Monod G, Cravedi JP, Biagianti-Risbourg S, Le Gac F (2000) Effects of 4-Nonylphenol on Sex Differentiation and Puberty in Mosquitofish (Gambusia Holbrooki). Ecotoxicology 9:93–103

    Article  CAS  Google Scholar 

  • Eadon GA, Kaminsky L, Silkworth J, Aldous KM, Hilker DR, O’Keefe P, Smith R, Gierthy JF, Hawley J, Kim NK, Decaprio A (1986) Calculation of 2,3,7,8-TCDD equivalent concentrations of complex environmental contaminant mixtures. Environ Health Perspect 70:221–227

    Article  CAS  Google Scholar 

  • Eisler R (1987) Polycyclic aromatic hydrocarbon hazards to fish, wildlife, and invertebrates: a synoptic review. U.S. Fish Wildlife Service. Biology Report, Laurel, 85(1.11)

    Google Scholar 

  • ENDS (1995) Public exposed to oestrogen risks from food cans. ENDS report 246, p3

    Google Scholar 

  • ENDS (1998) WHO to slash dioxin safety limits. ENDS report 281, pp 4–5

    Google Scholar 

  • ENDS (1999) Industry glimpses new challenges as endocrine science advances. ENDS report 290, pp 26–30

    Google Scholar 

  • Eto M (1974) Organophosphorus pesticides. CRC, Cleveland

    Google Scholar 

  • Fisher JS, Turner KJ, Brown D, Sharpe RM (1999) Effect of neonatal exposure to estrogenic compounds on development of the excurrent ducts of the rat testis through puberty to adulthood. Environ Health Perspect 107:397–405

    Article  CAS  Google Scholar 

  • Flouriot G, Pakdel F, Ducouret B, Valotaire Y (1995) Influence of xenobiotics on rainbow trout liver estrogen receptor and vitellogenin gene expression. J Mol Endocrinol 15:143

    Article  CAS  Google Scholar 

  • Foster PMD (1997) Assessing the effects of chemicals on male reproduction: lessons learned from di-n-butyl phthalate. Chemical Industry Institute of Toxicology, Durham

    Google Scholar 

  • Fox JE (2004) Chemical communication threatened by endocrine-disrupting chemicals. Environ Health Perspect 112(6):648–653

    Article  CAS  Google Scholar 

  • Fox JE, Starcevic M, Jones PE, Burow ME, McLachlan JA (2004) Phytoestrogen signaling and symbiotic gene activation are disrupted by endocrine-disrupting chemicals. Environ Health Perspect 112(6):672–677

    Article  CAS  Google Scholar 

  • Fukuto TR (1972) Metabolism of carbamate insecticides. Drug Metab Rev 1:117–151

    Article  Google Scholar 

  • Fukuto TR (1990) Mechanism of action of organophosphorus and carbamate insecticides. Environ Health Perspect 87:245–254

    Article  CAS  Google Scholar 

  • Gadd GM (2000) Microbial interactions with tributyltin compounds: detoxification, accumulation, and environmental fate. Sci Total Environ 258(1–2):119–127

    Article  CAS  Google Scholar 

  • Gaido K, Leonard L, Lovell S, Gould J, Babai D, Portier C, McDonnell D (1997) Evaluation of chemicals with endocrine modulating activity in a yeast-based steroid hormone receptor gene transcription assay. Toxicol Appl Pharmacol 143:205

    Article  CAS  Google Scholar 

  • Gavis J, Ferguson JF (1972) The cycling of mercury through the environment. Water Res 6:989–1008

    Article  CAS  Google Scholar 

  • Gennadiyev AN, Pikovsky YI, Kozin IS (1996) Polycyclic aromatic hydrocarbons in soils: environmental and behavioral issues. Polycyclic Aromatic Compounds 9(1–4):169–176

    Article  CAS  Google Scholar 

  • Gennari A, Viviani B, Galli CL, Marinovich M, Pieters R, Corsini E (2000) Organotins induce apoptosis by disturbance of [Ca2+]i and mitochondrial activity, causing oxidative stress and activation of caspases in rat thymocytes. Toxicol Appl Pharmacol 169:185–190

    Article  CAS  Google Scholar 

  • Gibbs PE, Bryan GW (1986) Reproductive failure in populations of the dog-whelk, Nucella lapillus, caused by imposex induced by tributyltin from antifouling paints. J Mar Biol Assoc UK 66:767–777

    Article  CAS  Google Scholar 

  • Gilmartin WG, DeLong RL, Smith AW, Sweeney JC, de Lappe BW, Risebrough RW, Griner LA, Dailey MD, Peakall DB (1976) Premature parturition in the Californian sea lion. J Wild Dis 12:104–115

    Article  CAS  Google Scholar 

  • Gimeno S, Komen H, Venderbosch PWM, Bowmer T (1997) Disruption of sexual differentiation in genetic male common carp (Cyprinus carpio) exposed to an alkylphenol during different life stages. Environ Sci Technol 31:2884

    Article  CAS  Google Scholar 

  • Grassman JA, Masten SA, Walker NJ, Lucier GW (1998) Animal models of human response to dioxins. Environ Health Perspect 106(suppl 2):761–775

    Article  CAS  Google Scholar 

  • Gray LE, Wolf C, Lambright C, Mann P, Price M, Cooper RL, Ostby J (1999a) Administration of potentially antiandrogenic pesticides (procymidone, linuron, iprodione, chlozolinate, p, p’-DDE, and ketonazole) and toxic substances (dibutyl- and diethylhexyl phthalate, PCB 169, and ethane dimethane sulphonate) during sexual differentiation produces diverse profiles of reproductive malformations in the male rat. Toxicol Ind Health 15:94–118

    Article  Google Scholar 

  • Gray M, Teather K, Metcalfe C (1999b) Reproductive success and behavior of Japanese Medaka (Oryzias Latipes) exposed to 4-tert-octylphenol. Environ Toxicol Chem 18:2587

    CAS  Google Scholar 

  • Gross TS, Guillette LJ, Percival HF, Masson GR, Matter JM, Woodward AR (1995) Contaminant induced reproductive anomalies in Florida alligators. Comp Pathol Bull 4:2

    Google Scholar 

  • Gross, ST, Arnold BS, Sepulveda MS, McDonald K (2001) Endocrine disrupting chemicals and endocrine active agents, research work order no 193. Relations of environmental contaminants, algal toxins, and diet with the reproductive success of American alligators on Florida lakes

    Google Scholar 

  • Group EF (1986) Environmental fate and aquatic toxicology studies on phthalate esters. Environ Health Perspect 65:337–340

    CAS  Google Scholar 

  • Guillette LJ, Gross TS, Masson GR, Matter JM, Percival HF, Woodward AR (1994) Developmental abnormalities of the gonad and abnormal sex hormone concentrations in juvenile alligators from contaminated and control lakes in Florida. Environ Health Perspect 102:680

    Article  CAS  Google Scholar 

  • Hagger JA, Depledge MH, Oehlmann J, Jobling S, Galloway TS (2006) Is there a causal association between genotoxicity and the imposex effect? Environ Health Perspect 114(suppl 1):20–26

    Google Scholar 

  • Hagmar L (2003) Polychlorinated biphenyls and thyroid status in humans: a review. Thyroid 13:1021–1028

    Article  CAS  Google Scholar 

  • Hall AJ, McConnell BJ, Rowles TK, Aguilar A, Borrell A, Schwacke L (2006) Individual-based model framework to assess population consequences of polychlorinated biphenyl exposure in bottlenose dolphins. Environ Health Perspect 114(suppl 1):60–64

    Google Scholar 

  • Hamelink JL, Waybrant RC, Ball RC (1971) A proposal: exchange equillibria control the degree chlorinated hydrocarbons are biologically magnified in lentic environments. Trans Am Fisheries Soc 100:207

    Article  CAS  Google Scholar 

  • Harvey PW, Johnson I (2002) Approaches to the assessment of toxicity data with endpoints related to endocrine disruption. J Appl Toxicol 22:241–247

    Article  CAS  Google Scholar 

  • Hayes TB, Case P, Chui S, Chung D, Haeffele C, Haston K (2006) Pesticide mixtures, endocrine disruption, and amphibian declines: are we underestimating the impact? Environ Health Perspect 114(suppl 1):40–50

    Article  Google Scholar 

  • Heinz GH, Percival HF, Jennings ML (1991) Contaminants in American alligator eggs from lake Apopka, lake Griffin, and lake Okeechobee, Florida. Environ Monit Assess 16:277

    Article  CAS  Google Scholar 

  • Heitkamp MA, Franklin W, Cerniglia CE (1988) Microbial metabolism of polycyclic aromatic hydrocarbons: isolation and characterization of a pyrene-degrading bacterium. Appl Environ Microbiol 54(10):2549–2555

    CAS  Google Scholar 

  • Helander B, Olsson M, Bignert A, Litzén K, Asplund L, Bergman Å (1998) Abnormal dehydration in eggs of the whitetailed sea eagle (Haliaeetus albicilla) in Sweden—a persisting effect from high exposure to organochlorines? Organohalogen Compounds 39:423–426

    CAS  Google Scholar 

  • Helle E, Ollsson M, Jensen S (1976a) DDT and PCB levels and reproduction in ringed seals from the Bothnian Bay. Ambio 5:188–189

    CAS  Google Scholar 

  • Helle E, Ollsson M, Jensen S (1976b) High frequencies of pathological changes in seal uteri correlated with PCB levels. Ambio 5:261–263

    CAS  Google Scholar 

  • Hoffmann GR (1991) Genetic toxicology. In: Casarett and Doull’s Toxicology, The basic science of poisons, fourth edition, Amdur MO, Doull J, Klaassen CD, eds., McGraw-Hill, Inc., New York

    Google Scholar 

  • Hoffman D, Rice C, Kubiak T (1996) PCBs and dioxins in birds. In: Beyer W, Heinz G, Redmon-Norwood A (eds) Environmental contaminants in wildlife. Interpreting tissue concentrations. CRC Lewis Publishers, Boca Raton, 165

    Google Scholar 

  • Horiguchi T, Shiraishi H, Schimuzu M, Morita M (1994) Imposex and organotin compounds in Thais clavigera and T. bronni in Japan. J Mar Biol Assoc UK 74:651–669

    Article  CAS  Google Scholar 

  • Horiguchi T, Kojima M, Hamada F, Kajikawa A, Shiraishi H, Morita M (2006) Impact of tributyltin and triphenyltin on ivory shell (Babylonia japonica) populations. Environ Health Perspect 114(suppl 1):13–19

    Google Scholar 

  • Howdeshell KL, Hotchkiss AK, Thayer KA, Vandenbergh JG, vom Saal FS (1999) Exposure to bisphenol a advances puberty. Nature 401:763–764

    Article  CAS  Google Scholar 

  • Huwe JK, Feil VJ, Larsen GL, Wiener C (1996) Metabolism and disposition of 1,4,7,8-tetrachlorodibenzo p-dioxin in rats. Chemosphere 37(9–12):1885–1893

    Google Scholar 

  • IEH (1995) Environmental oestrogens: consequences to human health and wildlife. Institute for Environment and Health, University of Leicester, Leicester

    Google Scholar 

  • IPCS (International Programme on Chemical Safety) (1989) Polychlorinated dibenzo-p-dioxins and dibenzofurans. Environmental health criteria 88. WHO, Geneva

    Google Scholar 

  • IPCS (International programme on chemical safety) (1990) Environmental health criteria for methyl mercury; EHC 101. WHO, Geneva

    Google Scholar 

  • Ishihara A, Nishiyama N, Sugiyama S, Yamauchi K (2003) The effect of endocrine disrupting chemicals on thyroid hormone binding to Japanese quail transthyretin and thyroid hormone receptor. Gen Comp Endocrinol 134:36–43

    Article  CAS  Google Scholar 

  • Jahnke GD, Choksi NY, Moore JA, Shelby MD (2004) Thyroid toxicants: assessing reproductive health effects. Environ Health Perspect 112:363–368

    Article  CAS  Google Scholar 

  • Jobling S, Sumpter JP (1993) Detergent components in sewage effluent are weakly oestrogenic to fish: an in vitro study using rainbow trout (Oncorhynchus Mykiss) Hepatocytes. Aquat Toxicol 27:361

    Article  CAS  Google Scholar 

  • Jobling S, Reynolds T, White R, Parker MG, Sumpter JP (1995) A variety of environmentally persistent chemicals, including some phthalate plasticizers, are weakly estrogenic. Environ Health Perspect 103(suppl 7):582–587

    Article  CAS  Google Scholar 

  • Jobling S, Sheahan D, Osborne J, Matthiessen P, Sumpter J (1996) Inhibition of testicular growth in rainbow trout (Oncorynchus mykiss) exposed to environmental estrogens. Environ Toxicol Chem 15:194

    Article  CAS  Google Scholar 

  • Jobling S, Williams R, Johnson A, Taylor A, Gross-Sorokin M, Nolan M (2006) Predicted exposures to steroid estrogens in U.K. rivers correlate with widespread sexual disruption in wild fish populations. Environ Health Perspect 114(suppl 1):32–39

    Google Scholar 

  • Johansson N, Ahlborg UG (1994) PCDD/PCDF, PCB and related compounds: the Scandinavian situation. Dioxin ’94. Organohalogen Compounds 44:587–590

    Google Scholar 

  • Johnson DE, Seidler FJ, Slotkin TA (1998) Early biochemical detection of delayed neurotoxicity resulting from developmental exposure to chlorpyrifos. Brain Res Bull 45:143–147

    Article  CAS  Google Scholar 

  • Kanaly R, Harayama S (2000) Biodegradation of High-Molecular-Weight Polycyclic Aromatic Hydrocarbons by Bacteria. J Bacteriol 182 (8):2059–2067

    Article  CAS  Google Scholar 

  • Keith LH, Telliard WA (1979) Priority pollutants I–a perspective view. Environ Sci Technol 13:416–423

    Article  Google Scholar 

  • Kelce WR, Stone CR, Laws SC, Gray LE Jr, Kemppainen JA, Wilson EM (1995) Persistent DDT metabolite p, p-DDE is a potent androgen receptor antagonist. Nature Lond 375:581–585

    Article  CAS  Google Scholar 

  • Kelce WR, Lambright CR, Gray LE Jr, Roberts KP (1997) Vinclozolin and p, p-DDE alter androgen-dependent gene expression: in vivo confirmation of an androgen receptor-mediated mechanism. Toxicol Appl Pharmacol 142:192–200

    Article  CAS  Google Scholar 

  • Kelley I, Cerniglia CE (1991) The metabolism of fluoranthene by a species of Mycobacterium. J Ind Microbiol 7:19–26

    Article  CAS  Google Scholar 

  • Kelly SA, Di Giulio RT (2000) Developmental toxicity of estrogenic alkylphenols in Killifish (Fundulus Heteroclitus). Environ Toxicol Chem 19:2564

    Article  CAS  Google Scholar 

  • Kloas W, Lutz I, Einspanier R (1999) Amphibians as a model to study endocrine disruptors: II estrogenic activity of environmental chemicals in vitro and in vivo. Sci Total Environ 225:59–68

    Article  CAS  Google Scholar 

  • Knack JB (1971) Biological and nonbiological modifications of carbamates. Bull World Health Organ 44:121–131

    Google Scholar 

  • Krishnan AV, Starhis P, Permuth SF, Tokes L, Feldman D (1993) Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrin 132:2279–2286

    Article  CAS  Google Scholar 

  • Le Bail JC, Laroche T, Marre-Fournier F, Habrioux G (1998) Aromatase and 17β-hydroxysteroid dehydrogenase inhibition by flavonoids. Cancer Lett 133(1):101–106

    Article  Google Scholar 

  • Le HH, Emily MC, Chua JP, Belcher SM (2008) Bisphenol A is released from polycarbonate drinking bottles and mimics the neurotoxic actions of estrogen in developing cerebellar neurons. Toxicol Lett 176:149–156

    Article  CAS  Google Scholar 

  • LeBlanc GA (1995) Are environmental sentinels signalling? Environ Health Perspect 103:888–890

    Article  CAS  Google Scholar 

  • Lech JJ, Lewis SK, Ren L (1996) In Vivo estrogenic activity of nonylphenol in rainbow trout. Fundam Appl Toxicol 30:229

    Article  CAS  Google Scholar 

  • Lee Ferguson P, Iden CR, Brownawell BJ (2001) Distribution and fate of neutral alkylphenol ethoxylate metabolites in a sewage-impacted urban estuary. Environ Sci Technol 35:2428–2435

    Article  CAS  Google Scholar 

  • Lee HJ, Chattopadhyay S, Gong EY, Ahn RS, Lee K (2003) Antiandrogenic effects of bisphenol A and nonylphenol on the function of androgen receptor. Toxicol Sci 75(1):40–46

    Article  CAS  Google Scholar 

  • Leung KMY, Rita PY, Kwong WC, Horiguchi T, Qiu JW, Yang R, Song M, Jiang G, Zheng GJ, Lam PKS (2006) Ecological risk assessments of endocrine disrupting organotin compounds using marine neogastropods in Hong Kong. Chemosphere 65:922–938

    Article  CAS  Google Scholar 

  • Lim J, Miller MG (1997) The role of the benomyl metabolite carbendazim in benomyl-induced testicular toxicity. Toxicol Appl Pharmacol 142:401–410

    Article  CAS  Google Scholar 

  • Litovitz TL, Klein-Schwartz W, Dyer KS, Shannon M, Lee S Powers M (1998) 1997 Annual report of the American Association of Poison Control Centers Toxic Exposure Surveillance System. Am J Emerg Med 16: 443–497

    Article  CAS  Google Scholar 

  • Lundholm CE (1997) DDE-induced eggshell thinning in birds: effects of P,P’-DDE on the Calcium and prostaglandin metabolism of the eggshell gland. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol 118(2):113–128

    Article  CAS  Google Scholar 

  • Lyman WR, Lacoste RJ (1975) New developments in the chemistry and fate of ethylenebisdithiocarbamate fungicides. In Environ Qual Saf (Frederick Coulston et al. eds.), Stuttgart, West Germany: Georg Thieme Publishers 3:67–74

    Google Scholar 

  • Lyons G (for WWF) (1999) Chemicals trespass: a toxic legacy. WWF press release

    Google Scholar 

  • MacLatchy DL, Der Kraak V, Flen J (1995) The phytoestrogen beta-sitosterol alters the reproductive endocrine status of goldfish. Toxicol Appl Pharmacol 134:305–312

    Article  CAS  Google Scholar 

  • Madsen S, Mathiesen A, Korsgaard B (1997) Effects of 17 beta-estradiol and 4-nonylphenol on smoltification and vitellogenesis in Atlantic Salmon (Salmo Salar). Fish Physiol Biochem 17:303

    Article  CAS  Google Scholar 

  • Maiti PK, Kar A (1997) Dimethoate inhibits extrathyroidal 5’-monodeiodination of thyroxine to 3,3’,5-triiodothyronine in mice: the possible involvement of the lipid peroxidative process. Toxicol Lett 91:1–6

    Article  CAS  Google Scholar 

  • Matthiessen P, Gibbs P (1998) Critical appraisal of the evidence for tributyltin-mediated endocrine disruption in mollusks. Environ Toxicol Chem 17:37–43

    Article  CAS  Google Scholar 

  • Matthiessen P, Reynoldson T, Billinghurst Z, Brassard DW, Cameron P, Chandler GT, Davis IM, Horiguchi T, Mount DR, Oehlmann J, Pottinger TG, Sibley PK, Thompsom HM, Vethaak AD (1999) In: de Fur PL, Crane M, Ingersoll C, Tattersfield L (eds) Endocrine disruption in invertebrates: endocrinology testing and assessment. SETAC Press, Pensacola, pp 199–270

    Google Scholar 

  • McAllister BG, Kime DE (2003) Early life exposure to environmental levels of the aromatase inhibitor tributyltin causes masculinisation and irreversible sperm damage in zebrafish (Danio rerio). Aquat Toxicol 65:309–316

    Article  CAS  Google Scholar 

  • McGregor DB, Partensky C, Wilbourn J, Rice JM (1998) An IARC evaluation of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans as risk factors in human carcinogenesis. Environ Health Perspect 106(suppl 2):755–760

    Article  CAS  Google Scholar 

  • McLeese DW, Zitko V, Sergeant DB, Burridge L, Metcalfe CD (1981) Lethality and accumulation of alkylphenols in aquatic fauna. Chemosphere 10:723–730

    Article  CAS  Google Scholar 

  • Mehmood Z, Williamson MP, Kelly DE, Kelly SL (1996) Metabolism of organochlorine pesticides: the role of human cytochrome P450 3A4. Chemosphere 33(4):759–769

    Article  CAS  Google Scholar 

  • Mense Sarah M, Hei Tom K, Ganju Ramesh K, Bhat Hari K (2008) Phytoestrogens and breast cancer prevention: possible mechanisms of action. Environ Health Perspect 116:426–433

    Article  CAS  Google Scholar 

  • Messina M, McCaskill-Stevens W, Lampe JW (2006) Addressing the soy and breast cancer relationship: review, commentary, and workshop proceedings. J Natl Cancer Inst 98(18):1275–1284

    Article  Google Scholar 

  • Metcalf RL (1971) Structure-activity relationships for insecticidal carbamates. Bull World Health Organ 44:43–78

    CAS  Google Scholar 

  • Ministry of Agriculture, Fisheries and Food, UK (1992). Dioxins in food. Food surveillance paper no 31, Her Majesty’s Stationery Office, London

    Google Scholar 

  • Moon YJ, Wang X, Morris ME (2006) Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. Toxicol In Vitro 20(2):187–210

    Article  CAS  Google Scholar 

  • Moutsatsou P (2007) The spectrum of phytoestrogens in nature: our knowledge is expanding. Hormones 6(3):173–193

    Google Scholar 

  • Mueller SO, Simon S, Chae K, Metzler M, Korach KS (2004) Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ER alpha) and ER beta in human cells. Toxicol Sci 80(1):14–25

    Article  CAS  Google Scholar 

  • Mylchreest E, Sar M, Cattley RC, Foster PMD (1999) Disruption of androgen-related male reproductive revelopment by di(n-butyl) phthalate during late gestation in rats is different from Flutamide. Toxicol Appl Pharmacol 156:81–95

    Article  CAS  Google Scholar 

  • Nimrod AC, Benson WH (1996) Estrogenic Responses to Xenobiotics in Channel Catfish (Ictalurus Punctatus). Mar Environ Res 42:155

    Article  CAS  Google Scholar 

  • Norris DO (1996) Vertebrate endocrinology. Academic, San Diego

    Google Scholar 

  • Norseth T, Clarkson TW (1971) Intestinal transport of 203Hg-labeled methyl mercury chloride. Role of biotransformation in rats. Arch Environ Health 22:668–577

    Article  Google Scholar 

  • NTP (2011) Report on Carcinogens, Twelfth Edition. Research Triangle Park, NC: U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, 499 pp

    Google Scholar 

  • Odsjö T, Bignert A, Olsson M, Asplund L, Eriksson U, Häggberg L, Litzén K, de Wit C, Rappe C, Åslund K (1997) The Swedish environmental specimen bank—application in trend monitoring of mercury and some organohalogenated compounds. Chemosphere 34:2059–2066

    Article  Google Scholar 

  • Ogata R, Omura M, Shimasaki Y, Kubo K, Oshima Y, Aou S, Inoue N (2001) Two-generation reproductive toxicity study of tributyltin chloride in female rats. J Toxicol Environ Health A 63:127–144

    Article  CAS  Google Scholar 

  • Ohsawa M, Magos L (1974) The chemical form of methylmercury complex in rat bile. Biochem Pharmacol 23:1903–1906

    Article  CAS  Google Scholar 

  • Olea N, Pulgar R, Perez P, Olea-Serrano F, Rivas A, Novillo-Fertrell A, Pedraza V, Soto A, Sonnenschein C (1996) Estrogenicity of resin-based composites and sealants used in dentistry. Environ Health Perspect 104:298

    Article  CAS  Google Scholar 

  • Peters JM, Taubeneck MW, Keen CL, Gonzalez FJ (1997) Di(2-ethylhexyl)phthalate induces a functional zinc deficiency during pregnancy and teratogenesis that is independent of peroxisome proliferator-activated receptor-alpha. Teratology 56:311–316

    Article  CAS  Google Scholar 

  • Peterson RE, Theoblad HM, Kimmel GL (1993) Developmental and Reproductive Toxicity of Dioxins and Related Compounds: Cross-Species Comparisons. Crit Rev Toxicol 23(3):283–335

    Article  CAS  Google Scholar 

  • Philbert MA, Billingsley ML, Reuhl KR (2000) Mechanisms of injury in the central nervous system. Toxicol Pathol 28:43–53

    Article  CAS  Google Scholar 

  • IPEN International POPs Elimination Network (2009) A survey of mercury content. (www.ipen.org/hgfree)

  • Ragnarsdottir V (2000) Environmental fate and toxicology of organophosphate pesticides. J Geol Soc 157(4):859–876

    Article  CAS  Google Scholar 

  • Ramamoorthy K, Wang F, Chen I-C, Norris JD, McDonnell DP, Leonard LS, Gaido KW, Bocchinfuso WP, Korach KS, Safe S (1997) Estrogenic activity of a dieldrin/toxaphene mixture in the mouse uterus, MCF-7 human breast cancer cells, and yeast-based estrogen receptor assays: no apparent synergism. Endocrinology 138:1520–1527

    Article  CAS  Google Scholar 

  • Rawlings NC, Cook SJ, Waldbillig D (1998) Effects of the pesticides carbofuran, chlorpyrifos, dimethoate, lindane, triallate, trifluralin, 2,4-D, and pentachlorophenol on the metabolic endocrine and reproductive endocrine system in ewes. J Toxicol Environ Health 54:21–36

    Article  CAS  Google Scholar 

  • Raychoudhury S, Blake C, Millette C (1999) Toxic Effects ofOctylphenol on Cultured Spermatogenic Cells and Sertoli Cells. Toxicol Appl Pharmacol 157:192

    Article  CAS  Google Scholar 

  • Refsvik T, Norseth T (1975) Methylmercuric compounds in rat bile. Acta Pharmacol Toxicol 36:67–78

    Article  CAS  Google Scholar 

  • Rehnberg GL, Cooper RL, Goldman JM, Gray LE, Hein JF, McElroy WK (1989) Serum and testicular testosterone and androgen binding protein profiles following subchronic treatment with carbendazim. Toxicol Appl Pharmacol 101:55–61

    Article  CAS  Google Scholar 

  • Reijnders PJH (1980) Organochlorine and heavy metal residues in harbour seals from the Wadden Sea and their possible effects on reproduction. Neth J Sea Res 14:30–65

    Article  CAS  Google Scholar 

  • Reijnders PJH (1986) Reproductive failure in common seals feeding on fish from polluted coastal waters. Nature 324:456–457

    Article  CAS  Google Scholar 

  • Reijnders PJH (1990) Progesterone and oestradiol-17 concentration profiles throughout the reproductive cycle in harbour seals (Phoca vitulina). J Reprod Fert 90:403–409

    Article  CAS  Google Scholar 

  • Ren L, Lewis S, Lech J (1996) Effects of estrogen and nonylphenol on the post-transcriptional regulation of vitellogenin gene expression. Chem Biol Interact 100:67

    Article  CAS  Google Scholar 

  • Roos A, Bergman A, Greyerz E, Olsson M (1998) Time trend studies on DDT and PCB in juvenile grey seals (Halichoerus grypus), fish and guillemot eggs from the Baltic Sea. Organochlorine Compounds 39:109–112

    CAS  Google Scholar 

  • Rowland IR, Davies MJ, Evans JG (1980) Tissue content of mercury in rats given methylmercuric chloride orally: influence of intestinal flora. Arch Environ Health 35:155–160

    Article  CAS  Google Scholar 

  • Roy TS, Andrews JE, Seidler FJ, Slotkin TA (1998) Chlorpyrifos elicits mitotic abnormalities and apoptosis in neuroepithelium of cultured rat embryos. Teratology 58:62–68

    Article  CAS  Google Scholar 

  • Santti R, Mäkelä S, Strauss L, Korkman J, Kostian ML (1998) Phytoestrogens: potential endocrine disruptors in males. Toxicol Ind Health 14(1–2):223–237

    Article  CAS  Google Scholar 

  • Scott AP, Katsiadaki I, Kirby MF, Thain J (2006) Relationship between sex steroid and vitellogenin concentrations in flounder (Platichthys flesus) sampled from an estuary contaminated with estrogenic endocrine-disrupting compounds. Environ Health Perspect 114(suppl 1):27–31

    Google Scholar 

  • Shekhar PVM, Werdell J, Basrur VS (1997) Environmental estrogen stimulation of growth and estrogen receptor function in preneoplastic and cancerous human breast cell lines. J Natl Cancer Inst 89:1774–1782

    Article  CAS  Google Scholar 

  • Shelnutt SR, Cimino CO, Wiggins PA, Ronis MJ, Badger TM (2002) Pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein in men and women after consumption of a soy beverage. Am J Clin Nutr 76:588–594

    Article  CAS  Google Scholar 

  • Shilling A, Williams D (2000) Determining relative estrogenicity by quantifying vitellogenin induction in rainbow trout liver slices. Toxicol Appl Pharmacol 164:330

    Article  CAS  Google Scholar 

  • Shinkyo R, Sakaki T, Ohta M, Inouye K (2003) Metabolic pathways of dioxin by CYP1A1: species difference between rat and human CYP1A subfamily in the metabolism of dioxins. Arch Biochem Biophys 409(1):180–187

    Article  CAS  Google Scholar 

  • Shioda T, Wakabayashi M (2000) Effect of certain chemicals on the reproduction of Medaka (Oryzias Latipes). Chemosphere 40:239

    Article  CAS  Google Scholar 

  • Short JW, Thrower FP (1986) Accumulation of butyltins in muscle tissue of Chinook Salmon Reared in sea pens treated with Tri n butyltin. Northwest and Alaska Fisheries Center, National Marine Fisheries Service, U.S. National Oceanic and Atmospheric Administration, Auke Bay, pp 10–202

    Google Scholar 

  • Shuttleworth KL, Cerniglia CE (1995) Environmental aspects of PAH biodegradation. Appl Biochem Biotechnol 54:291–302

    Article  CAS  Google Scholar 

  • Silvestroni L, Palleschi S (1999) Effects of organochlorine xenobiotics on human spermatozoa. Chemosphere 39:1249–1252

    Article  CAS  Google Scholar 

  • Simms W, Ross PS (2001) Vitamin A physiology and its application as a biomarker of contaminant-related toxicity in marine mammals: a review. Toxicol Ind Health 16(7–8):291–302

    Google Scholar 

  • Sirtori CR, Arnoldi A, Johnson SK (2005) Phytoestrogens: end of a tale? Ann Med 37(6):423–438

    Article  CAS  Google Scholar 

  • Smeets J, Rankouhi T, Nichols K, Komen H, Kaminski N, Giesy J, Van den Berg M (1999) In vitro vitellogenin production by carp (Cyprinus Carpio) hepatocytes as a screening method for determining (Anti) estrogenic activity of xenobiotics. Toxicol Appl Pharmacol 157:68

    Article  CAS  Google Scholar 

  • Smith JR, Nakles DV, Sherman DF, Neuhauser EF, Loehr RC (1989) Environmental fate mechanisms influencing biological degradation of coal-tar derived polynuclear aromatic hydrocarbons in soil systems, p 397–405. In: The third international conference on new frontiers for hazardous waste management, U.S. Environmental Protection Agency, Washington, DC

    Google Scholar 

  • Sohoni P, Sumpter JP (1998) Several environmental oestrogens are also anti-androgens. J Endocrinol 158:327–339

    Article  CAS  Google Scholar 

  • Sonnenschein C, Soto A (1998) An updated review of environmental estrogen and androgen mimics and antagonists. J Steroid Biochem 65:143

    Article  CAS  Google Scholar 

  • Soto A, Justicia H, Wray J, Sonnenschein C (1991) P-nonyl-phenol: an estrogenic xenobiotic released from “modified” polystyrene. Environ Health Perspect 92:167

    Article  CAS  Google Scholar 

  • Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Olea Serrano F (1995) The E-SCREEN assay as a tool to Identify estrogens: an update on estrogenic environmental pollutants. Environ Health Perspect 103:113–122

    Article  CAS  Google Scholar 

  • Staples CA, Dorn PB, Klecka GM, Branson DR, O’Block ST, Harris LR (1998) A review of the environmental fate, effects and exposures of bisphenol A. Chemosphere 36:2149–2173

    Article  CAS  Google Scholar 

  • Startin JR (1994) Dioxins in food. In: Schecter A (ed) Dioxins and health. Plenum Press, New York, pp 115–137

    Chapter  Google Scholar 

  • Steiner I, Kubesch K, Wildhack A, Fiala F (1999) Migration of phthlates from PVC- consumption goods. Lebensmittelchemie 53:147–148

    CAS  Google Scholar 

  • Steinmetz R, Mitchner NA, Grant A, Allen DL, Bigsby RM, Ben-Jonathan N (1998) The xenoestrogen bisphenol A induces growth, differentiation, and c-fos gene expression in the female reproductive tract. Endocrin 139:2741–2747

    Article  CAS  Google Scholar 

  • Stjernberg T, Koivusaari J, Nuuja I (1990) Suomen merikotkakannan kehitys ja pesintätulos 1970–89, population trends and nesting success of the white-tailed eagle in Finland in 1970–89. Lintumies 25:65–75

    Google Scholar 

  • Suda I, Takahashi H (1986) Enhanced and inhibited bio-transformation of methylmercury in the rat spleen. Toxicol Appl Pharmacol 82:45–52

    Article  CAS  Google Scholar 

  • Sun H, Xu LC, Chen JF, Song L, Wang XR (2006) Effect of bisphenol A, tetrachlorobisphenol A and pentachlorophenol on the transcriptional activities of androgen receptor-mediated reporter gene. Food Chem Toxicol 44(11):1916–1921

    Article  CAS  Google Scholar 

  • Sutherland JB, Rafii F, Khan AA, Cerniglia CE (1995) Mechanisms of polycyclic aromatic hydrocarbon degradation. In: Young LY, Cerniglia CE (eds) Microbial transformation and degradation of toxic organic chemicals. Wiley-Liss, New York, pp 269–306

    Google Scholar 

  • Suzuki T, Yoshio Nakagawa, Ichiro Takano, Kumiko Yaguchi, Kazuo Yasuda (2004) Environmental fate of bisphenol A and Its biological metabolites in river water and their xeno-estrogenic activity. Environ Sci Technol 38(8):2389–2396

    Article  CAS  Google Scholar 

  • Tan SW, Meiller JC, Mahaffey KR (2009) The endocrine effects of mercury in humans and wildlife. Crit Rev Toxicol 39(3):228–269

    Article  CAS  Google Scholar 

  • Theelen RMC (1991) Modeling of human exposure to TCDD and I-TEQ in the Netherlands: background and occupational. In: Gallo MA, Scheuplein RJ, van der Heijden KA (eds) Banbury report 35: biological basis for risk assessment of dioxins and related compounds. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, pp 277–290

    Google Scholar 

  • Timothy JS, Cooke GM (2000) Examination of selected food additives and organochlorine food contaminants for androgenic activity in vitro. Toxicol Sci 53:278–288

    Article  Google Scholar 

  • Turner KJ, Sharpe RM (1997) Environmental oestrogens – present understanding. Rev Reprod 2:69–73

    Article  CAS  Google Scholar 

  • UNEP/FAO/RC/CRC (2005) Inclusion of chemicals in annex III of the Rotterdam convention: review of notifications of final regulatory actions to ban or severely restrict a chemical: tributyltin compounds

    Google Scholar 

  • USEPA (1997) Special report on environmental endocrine distruption: an effects assessment and analysis, Office of Research and Development, Washington, DC, EPA/630/R-96/012

    Google Scholar 

  • USEPA (United States Environmental Protection Agency) (1985) Technical support document: tributyltin. Office of Pesticide Programs, Washington, DC, pp 10–201

    Google Scholar 

  • USEPA (1994) Health Assessment Document for 2, 3, 7, 8-Tetrachlorodibenzo-P-Dioxin (TCDD) and Related Compounds. Volume I of III. U.S. Environmental Protection Agency, Washington, D.C., EPA/600/BP-92/001a (NTIS PB94205465)

    Google Scholar 

  • USGS (United States geological survey) (2000) Mercury in the environment: fact sheet 146–00. U.S. Dept. of the Interior/U.S. Geological Survey, Reston

    Google Scholar 

  • Van der Meer JR, de Vos WM, Harayama S, Zehnder AJB (1992) Molecular mechanisms of genetic adaptation to xenobiotic compounds. Microbiol Rev 56:677–694

    Google Scholar 

  • Van Leeuwen FXR, Younes MM (2000) Assessment of the health risk of dioxins: re-evaluation of the tolerable daily intake (TDI). Food Addit Contam 17:223–369

    Article  Google Scholar 

  • Veeramachaneni DNR, Amann RP, Jacobson JP (2006) Testis and antler dysgenesis in Sitka black-tailed deer on Kodiak Island, Alaska: sequela of environmental endocrine disruption? Environ Health Perspect 114(suppl 1):51–59

    Google Scholar 

  • Ventura F, Figueras A, Caixach J, Espadaler I, Romeru J, Guardiola J, Rivera J (1988) Characterization of polyethoxylated surfactants and their brominated derivatives formed at the water treatment plant of Barcelona by GC/MS and FAB mass spectrometry. Water Res 22:1211–1217

    Article  CAS  Google Scholar 

  • Vettorazzi G (1976) Carbamate and organophosphorus pesticides used in agriculture and public health. Residue Rev 63:1–76

    Article  CAS  Google Scholar 

  • Voccia I, Blakley B, Brousseau P, Fournier M (1999) Immunotoxicity of pesticides: a review. Toxicol Ind Health 15:119–132

    Article  CAS  Google Scholar 

  • VomSaal F, Cooke P, Buchanan D, Palanza P, Thayer K, Nagel S, Parmigiani S, Welsbons W (1998) A physiologically based approach to the study of bisphenol A and other estrogenic chemicals on the size of reproductive organs, daily sperm production, and behavior. Toxicol Ind Health 14:239

    Article  CAS  Google Scholar 

  • Voutsa D, Hartmann P, Schaffer C, Giger W (2006) Benzotriazols, alkylphenols and bisphenol A in municipal wastewaters and in the Glatt River, Switzerland. Environ Sci Pollut Res 13:333–341

    Article  CAS  Google Scholar 

  • Vreugdenhil HJ, Van Zanten GA, Brocaar MP, Mulder PG, Weisglas- Kuperus N (2004) Prenatal exposure to PCBs and breastfeeding: opposing effects on auditory P300 latencies in 9 year old Dutch children. Dev Med Child Neurol 46:398–405

    Article  CAS  Google Scholar 

  • Waring RH, Harris RM (2005) Endocrine disruptors: Human risk? – Review. Mol Cell Endocrinol 244:2–9

    Article  CAS  Google Scholar 

  • Weissenfels WD, Beyer M, Klein J, Rehm HJ (1991) Microbial metabolism of fluoranthene: isolation and identification of ring fission products. Appl Microbiol Biotechnol 34:528–535

    Article  CAS  Google Scholar 

  • Wetherill YB, Akingbemi BT, Kanno J, McLachlan JA, Nadal A, Sonnenschein C, Watson CS, Thomas Zoeller R, Belcher SM (2007) In vitro molecular mechanisms of bisphenol A action. Reprod Toxicol 24:178–198

    Article  CAS  Google Scholar 

  • White R, Jobling S, Hoare SA, Sumpter JP, Parker MG (1994) Environmentally persistent alkylphenolic compounds are estrogenic. Endocrin 135:175–182

    Article  CAS  Google Scholar 

  • WHO (1976) Environmental health criteria 1: mercury. World Health Organization, Geneva, 132

    Google Scholar 

  • WHO (1989) Mercury, environmental aspects. Environmental health criteria, vol 86. World Health Organization/WHO, Geneva

    Google Scholar 

  • Winneke G, Walkowiak J, Lilienthal H (2002) PCB-induced neurodevelopmental toxicity in human infants and its potential mediation by endocrine dysfunction. Toxicology 181–182:161–165

    Article  Google Scholar 

  • Woodward AR, Jennings ML, Percival HF, Moore JF (1993) Low clutch viability of American alligators on lake Apopka. Fla Sci 56:52

    Google Scholar 

  • Wunder T, Kremer S, Sterner O, Anke H (1994) Metabolism of the polycyclic aromatic hydrocarbon pyrene by Aspergillus niger SK 9317. Appl Microbiol Biotechnol 42:636–641

    Article  CAS  Google Scholar 

  • WWF (Germany) (1998) Evaluation of pesticides disrupting the hormone and reproductive system: a report by Andrea Dankwardt

    Google Scholar 

  • Xu LC, Sun H, Chen JF, Bian Q, Qian J, Song L (2005) Evaluation of androgen receptor transcriptional activities of bisphenol A, octylphenol and nonylphenol in vitro. Toxicology 216(2/3):197–203

    Article  CAS  Google Scholar 

  • Ying GG, Kookana RS (2003) Degradation of five selected endocrine-disrupting chemicals in seawater and marine sediment. Environ Sci Technol 37(7):1256–1260

    Article  CAS  Google Scholar 

  • Ying GG, William B, Kookana R (2002a) Environmental fate of alkylphenols and alkylphenol ethoxylates—A review. Environ Int 28(3):215–226

    Article  CAS  Google Scholar 

  • Ying G-G, Williams B, Kookana R (2002b) Environmental fate of alkylphenols and alkylphenol ethoxylates e a review. Environ Int 28:215–226

    Article  CAS  Google Scholar 

  • Zhang Y, Hendrich S, Murphy PA (2003) Glucuronides are the main isoflavone metabolites in women. J Nutr 133:399–404

    Article  CAS  Google Scholar 

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Nair, P.R.A., Sujatha, C.H. (2012). Organic Pollutants as Endocrine Disruptors: Organometallics, PAHs, Organochlorine, Organophosphate and Carbamate Insecticides, Phthalates, Dioxins, Phytoestrogens, Alkyl Phenols and Bisphenol A. In: Lichtfouse, E., Schwarzbauer, J., Robert, D. (eds) Environmental Chemistry for a Sustainable World. Environmental Chemistry for a Sustainable World. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-2442-6_8

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