Metabolism and metabolites of polychlorinated biphenyls

Critical Reviews in Toxicology

Volumn 45, Issue 3, 2015, Pages 245-272

  Grimm, Fabian A ^a   Hu, Dingfei ^b   Kania Korwel, Izabela ^a   Lehmler, Hans Joachim ^a   Ludewig, Gabriele ^a   Hornbuckle, Keri C ^b   Duffel, Michael W ^a   Bergman, Åke ^c   Robertson, Larry W ^a  

^a UNIVERSITY OF IOWA   (United States)

^b University of Iowa   (United States)

^c Swedish Toxicology Sciences Research Center   (Sweden)

Author keywords

Human exposure; Hydroxylated PCBs; PCB methyl sulfones; PCB sulfates; Polychlorobiphenylols; Reactive intermediates

Indexed keywords

2,2',4,4',5,5' HEXACHLOROBIPHENYL; BIPHENYL DERIVATIVE; CHLORINE DERIVATIVE; ENDOCRINE DISRUPTOR; EPOXIDE; HYDROXYL GROUP; POLYCHLORINATED BIPHENYL; POLYCHLORINATED BIPHENYL DERIVATIVE; POLYCHLORINATED BIPHENYL METHYL SULFONE; POLYCHLORINATED BIPHENYL SULFATE; SEMIQUINONE; UNCLASSIFIED DRUG; POLLUTANT;

BIOLOGICAL ACTIVITY; BLOOD; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DETOXIFICATION; DRUG HALF LIFE; DRUG HYDROXYLATION; DRUG MANUFACTURE; DRUG METABOLISM; ENVIRONMENT; HEALTH HAZARD; HUMAN; LIVER MICROSOME; MAMMAL; METABOLITE; MOLECULE; NOMENCLATURE; NONHUMAN; PLASMA; REVIEW; RISK ASSESSMENT; SULFATION; TOXICITY TESTING; VOLATILIZATION; XENOBIOTIC METABOLISM; ADVERSE EFFECTS; ANALYSIS; ANIMAL; ENVIRONMENTAL EXPOSURE; METABOLISM; PHARMACOKINETICS; POLLUTANT; TOXICITY;

MAMMALIA;

ANIMALS; ENVIRONMENTAL EXPOSURE; ENVIRONMENTAL POLLUTANTS; HUMANS; POLYCHLORINATED BIPHENYLS;

EID: 84924062858     PISSN: 10408444     EISSN: 15476898     Source Type: Journal    
DOI: 10.3109/10408444.2014.999365     Document Type: Review

References (284)

1. Achman, DR, Hornbuckle, KC, Eisenreich, SJ. (1993) Volatilization of Polychlorinated-Biphenyls from Green Bay, Lake Michigan. Environ Sci Technol, 27, 75-87.
2. Alvares AP, Fischbein A, Anderson KE, Kappas A. (1977). Alterations in drug metabolism in workers exposed to polychlorinated biphenyls. Clin Pharmacol Ther, 22, 140-6.
3. Amaro AR, Oakley GG, Bauer U, Spielmann HP, Robertson LW. (1996). Metabolic activation of PCBs to quinones: reactivity toward nitrogen and sulfur nucleophiles and infl uence of superoxide dismutase. Chem Res Toxicol, 9, 623-9.
4. Asvold BO, Vatten LJ, Nilsen TI, Bjoro T. (2007). The association between TSH within the reference range and serum lipid concentrations in a population-based study. The HUNT Study. Eur J Endocrinol, 156, 181-6.
5. ATSDR. (2000). Toxicological Profile for Polychlorinated Biphenyls (PCBs), U.S. Dept. Health Services, Public Health Service.
6. Bakke JE, Bergman AL, Larsen GL. (1982). Metabolism of 2,4 ',5-trichlorobiphenyl by the mercapturic acid pathway. Science, 217, 645-7.
7. Bakke JE, Feil VJ, Bergman A. (1983). Metabolites of 2,4',5-trichlorobiphenyl in rats. Xenobiotica, 13, 555-64.
8. Ballschmiter K, Mennel A, Buyten J. (1993). Long chain alkylpolysiloxanes as non-polar stationary phases in capillary gas chromatography. Fresenius J Anal Chem, 346, 396-402.
9. Ballschmiter K, Zell M. (1980). Analysis of polychlorinated-biphenyls (PCB) by glass-capillary gas-chromatography-composition of technical Aroclor-PCB and Clophen-PCB mixtures. Fresenius J Anal Chem, 302, 20-31.
10. Barron MG, Yurk JJ, Crothers DB. (1994). Assessment of potential cancer risk from consumption of PCBs bioaccumulated in fish and shellfish. Environ Health Perspect, 102, 562-7.
11. Basu I, Arnold KA, Venier M, Hites RA. (2009). Partial pressures of PCB-11 in air from several Great Lakes sites. Environ Sci Technol, 43, 6488-92.
12. Bender RP, Lehmler HJ, Robertson LW, Ludewig G, OsheroffN. (2006). Polychlorinated biphenyl quinone metabolites poison human topoisomerase IIalpha: altering enzyme function by blocking the N-terminal protein gate. Biochemistry, 45, 10140-52.
13. Bender RP, OsheroffN. (2007). Mutation of cysteine residue 455 to alanine in human topoisomerase IIalpha confers hypersensitivity to quinones: enhancing DNA scission by closing the N-terminal protein gate. Chem Res Toxicol, 20, 975-81.
14. Bergman A, Brandt I, Jansson B. (1979). Accumulation of methylsulfonyl derivatives of some bronchial-seeking polychlorinated biphenyls in the respiratory tract of mice. Toxicol Appl Pharmacol, 48, 213-20.
15. Bergman A, Klasson-Wehler E, Kuroki H. (1994a). Selective retention of hydroxylated PCB metabolites in blood. Environ Health Perspect, 102, 464-9.
16. Bergman A, Norstrom RJ, Haraguchi K, Kuroki H, Beland P. (1994b). PCB and DDE methyl sulfones in mammals from Canada and Sweden. Environ Toxicol Chem, 13, 121-8.
17. Birnbaum LS. (1983). Distribution and excretion of 2,3,6,2 ',3 ',6 '-and 2,4,5,2 ',4 ',5 '-hexachlorobiphenyl in senescent rats. Toxicol Appl Pharmacol, 70, 262-72.
18. Bitman J, Cecil HC. (1970). Estrogenic activity of DDT analogs and polychlorinated biphenyls. J Agric Food Chem, 18, 1108-12.
19. Bloom MS, Vena JE, Olson JR, Kostyniak PJ. (2009). Assessment of polychlorinated biphenyl congeners, thyroid stimulating hormone, and free thyroxine among New York state anglers. Int J Hyg Environ Health, 212, 599-611.
20. Boucher O, Muckle G, Bastien CH. (2009). Prenatal exposure to polychlorinated biphenyls: a neuropsychologic analysis. Environ Health Perspect, 117, 7-16.
21. Bradbury S, Mekenyan O, Ankley G. (1996). Quantitative structureactivity relationships for polychlorinated hydroxybiphenyl estrogen receptor binding affinity-an assessment of conformer fl exibility. Environ Toxicol Chem, 15, 1945-54.
22. Breivik K, Sweetman A, Pacyna JM, Jones KC. (2007). Towards a global historical emission inventory for selected PCB congeners-a mass balance approach 3. An update. Sci Total Environ, 377, 296-307.
23. Brouwer A, Longnecker MP, Birnbaum LS, Cogliano J, Kostyniak P, Moore J, et al. (1999). Characterization of potential endocrine-related health Effects at low-dose levels ofexposure to PCBs. Environ Health Perspect, 107, 639-49.
24. Brouwer A, Morse DC, Lans MC, Schuur AG, Murk AJ, Klasson-Wehler E, Bergman A, Visser TJ. (1998). Interactions of persistent environmental organohalogens with the thyroid hormone system: mechanisms and possible consequences for animal and human health. Toxicol Ind Health, 14, 59-84.
25. Chauhan KR, Kodavanti PR, Mckinney JD. (2000). Assessing the role of ortho-substitution on polychlorinated biphenyl binding to transthyretin, a thyroxine transport protein. Toxicol Appl Pharmacol, 162, 10-21.
26. Choi SD, Baek SY, Chang YS, Wania F, Ikonomou MG, Yoon YJ, et al. (2008). Passive air sampling of polychlorinated biphenyls and organochlorine pesticides at the Korean Arctic and Antarctic research stations: implications for long-range transport and local pollution. Environ Sci Technol, 42, 7125-31.
27. Christensen H, Heggberget TM, Gutleb AC. (2010). Polychlorinated biphenyls and reproductive performance in otters from the Norwegian coast. Arch Environ Contam Toxicol, 59, 652-60.
28. Chu S, Covaci A, Haraguchi K, Voorspoels S, Van De Vijver K, Das K, et al. (2003a). Levels and enantiomeric signatures of methyl sulfonyl PCB and DDE metabolites in livers of harbor porpoises (Phocoena phocoena) from the Southern North Sea. Environ Sci Technol, 37, 4573-8.
29. Chu S, Covaci A, Jacobs W, Haraguchi K, Schepens P. (2003b). Distribution of methyl sulfone metabolites of polychlorinated biphenyls and p,p '-DDE in human tissues. Environ Health Perspect, 111, 1222-7.
30. Connor K, Ramamoorthy K, Moore M, Mustain M, Chen I, Safe S, et al. (1997). Hydroxylated polychlorinated biphenyls (PCBs) as estrogens and antiestrogens: structure-activity relationships. Toxicol Appl Pharmacol, 145, 111-23.
31. Cuadra SN, Linderholm L, Athanasiadou M, Jakobsson K. (2006). Persistent organic pollutants in children working in a waste disposal site and in female high fish consumers in Managua, Nicaragua. Ambio, 35, 109-16.
32. Custer TW, Custer CM, Gray BR. (2010). Polychlorinated biphenyls, dioxins, furans, and organochlorine pesticides in belted kingfisher eggs from the upper Hudson River basin, New York, USA. Environ Toxicol Chem, 29, 99-110.
33. Daidoji T, Gozu K, Iwano H, Inoue H, Yokota H. (2005). UDPglucuronosyltransferase isoforms catalyzing glucuronidation of hydroxy-polychlorinated biphenyls in rat. Drug Metab Dispos, 33, 1466-76.
34. Dallaire R, Muckle G, Dewailly E, Jacobson SW, Jacobson JL, Sandanger TM, et al. (2009). Thyroid hormone levels of pregnant inuit women and their infants exposed to environmental contaminants. Environ Health Perspect, 117, 1014-20.
35. Darnerud PO, Morse D, Klasson-Wehler E, Brouwer A. (1996). Binding of a 3,3 ', 4,4 '-tetrachlorobiphenyl (CB-77) metabolite to fetal transthyretin and Effects on fetal thyroid hormone levels in mice. Toxicology, 106, 105-14.
36. Darras VM. (2008). Endocrine disrupting polyhalogenated organic pollutants interfere with thyroid hormone signalling in the developing brain. Cerebellum, 7, 26-37.
37. Daubeze M, Narbonne JF. (1984). Incorporation of labeled 2,4,5,2 ',4 ',5 '-hexachlorobiphenyl into the nuclear fraction of rat hepatocytes in vivo. Toxicology, 31, 315-8.
38. DeCastro BR, Korrick SA, Spengler JD, Soto AM. (2006). Estrogenic activity of polychlorinated biphenyls present in human tissue and the environment. Environ Sci Technol, 40, 2819-25.
39. Dhakal K, Adamcakova-Dodd A, Lehmler HJ, Thorne PS, Robertson LW. (2013). Sulfate conjugates are urinary markers of inhalation exposure to 4-chlorobiphenyl (PCB3). Chem Res Toxicol, 26, 853-5.
40. Dhakal K, He X, Lehmler HJ, Teesch LM, Duffel MW, Robertson LW. (2012). Identification of sulfated metabolites of 4-chlorobiphenyl (PCB3) in the serum and urine of male rats. Chem Res Toxicol, 25, 2796-804.
41. Dhakal K, Uwimana E, Adamcakova-Dodd A, Thorne PS, Lehmler HJ, Robertson LW. (2014). Disposition of phenolic and sulfated metabolites after inhalation exposure to 4-chlorobiphenyl (PCB3) in female rats. Chem Res Toxicol.
42. Dirtu AC, Covaci A. (2010). Estimation of daily intake of organohalogenated contaminants from food consumption and indoor dust ingestion in Romania. Environ Sci Technol, 44, 6297-304.
43. Domingo JL, Bocio A. (2007). Levels of PCDD/PCDFs and PCBs in edible marine species and human intake: a literature review. Environ Int, 33, 397-405.
44. Du S, Wall SI, Cacia D, Rodenburg LA. (2009). Passive air sampling for polychlorinated biphenyls in the Philadelphia metropolitan area. Environ Sci Technol, 43, 1287-92.
45. Ekuase EJ, Liu Y, Lehmler HJ, Robertson LW, Duffel MW. (2011). Structure-activity relationships for hydroxylated polychlorinated biphenyls as inhibitors of the sulfation of dehydroepiandrosterone catalyzed by human hydroxysteroid sulfotransferase SULT2A1. Chem Res Toxicol, 24, 1720-8.
46. El Majidi N., Bouchard M, Carrier G. (2014). Systematic analysis of the relationship between standardized biological levels of polychlorinated biphenyls and thyroid function in pregnant women and newborns. Chemosphere, 98, 1-17.
47. Ellerichmann T, Bergmann A, Franke S, Huehnerfuss H, Jakobsson E, Koenig WA, Larsson C. (1998). Gas chromatographic enantiomer separations of chiral PCB methyl sulfons and identification of selectively retained enantiomers in human liver. Fresenius Environ Bull, 7, 244-57.
48. Erickson MD. (1997). Analytical Chemistry of PCBs Boca, Raton: CRC Lewis Publishers.
49. Erickson MD. (2001). Introduction: PCB properties, uses, occurrence, and regulatory history. In: Robertson LW, Hansen LG, Eds. PCBs:Recent Advances in Environmental Toxicology and Health Effects. Lexington, Kentucky: The University Press of Kentucky xi-xxx.
50. Erickson MD, Kaley RG II. (2011). Applications of polychlorinated biphenyls. Environ Sci Pollut Res Int, 18, 135-51.
51. Espandiari P, Glauert HP, Lehmler HJ, Lee EY, Srinivasan C, Robertson LW. (2003). Polychlorinated biphenyls as initiators in liver carcinogenesis: resistant hepatocyte model. Toxicol Appl Pharmacol, 186, 55-62.
52. Espandiari P, Glauert HP, Lehmler HJ, Lee EY, Srinivasan C, Robertson LW. (2004). Initiating activity of 4-chlorobiphenyl metabolites in the resistant hepatocyte model. Toxicol Sci, 79, 41-6
53. Fgstr B, Athanasiadou M, Athanassiadis I, Weihe P, Bergman A. (2005a). Hydroxylated PCB metabolites in nonhatched fulmar eggs from the Faroe Islands. Ambio, 34, 184-7.
54. Fangstrom B, Athanasiadou M, Grandjean P, Weihe P, Bergman A. (2002). Hydroxylated PCB metabolites and PCBs in serum from pregnant Faroese women. Environ Health Perspect, 110, 895-9
55. Fgstr B, Hovander L, Bignert A, Athanassiadis I, Linderholm L, Grandjean P, et al. (2005b). Concentrations of PBDE, PCB and OHPCBs in serum from pregnant Faroese women and their children seven years later. Environ Sci Technol, 39, 9457-63.
56. Fangstrom B, Strid A, Grandjean P, Weihe P, Bergman A. (2005). A retrospective study of PBDEs and PCBs in human milk from the Faroe Islands. Environ Health, 4, 12.
57. Feinberg M, Soler L, Contenot S, Verger P. (2011). Assessment of seasonality in exposure to dioxins, furans and dioxin-like PCBs by using long-term food-consumption data. Food Addit Contam Part A Chem Anal Control Expo Risk Assess, 28, 502-12.
58. Fitzgerald EF, Belanger EE, Gomez MI, Cayo M, Mccaffrey RJ, Seegal RF, et al. (2008). Polychlorinated biphenyl exposure and neuropsychological status among older residents of upper Hudson River communities. Environ Health Perspect, 116, 209-15.
59. Fitzgerald EF, Shrestha S, Palmer PM, Wilson LR, Belanger EE, Gomez MI, et al. (2011). Polychlorinated biphenyls (PCBs) in indoor air and in serum among older residents of upper Hudson River communities. Chemosphere, 85, 225-31.
60. Flor S, Ludewig G. (2010). Polyploidy-induction by dihydroxylated monochlorobiphenyls: structure-activity-relationships. Environ Int, 36, 962-9.
61. Gabrio T, Piechotowski I, Wallenhorst T, Klett M, Cott L, Friebel P, et al. (2000). PCB-blood levels in teachers, working in PCB-contaminated schools. Chemosphere, 40, 1055-62.
62. Gallenberg LA, Ring BJ, Vodicnik MJ. (1990). The infl uence of time of maternal exposure to 2,4,5,2',4',5'-hexachlorobiphenyl on its accumulation in their nursing offspring. Toxicol Appl Pharmacol, 104, 1-8.
63. Giera S, Bansal R, Ortiz-Toro TM, Taub DG, Zoeller RT. (2011). Individual polychlorinated biphenyl (PCB) congeners produce tissue-and gene-specific Effects on thyroid hormone signaling during development. Endocrinology, 152, 2909-19.
64. Goncharov A, Bloom M, Pavuk M, Birman I, Carpenter DO. (2010). Blood pressure and hypertension in relation to levels of serum polychlorinated biphenyls in residents of Anniston, Alabama. J Hypertens, 28, 2053-60.
65. Goncharov A, Pavuk M, Foushee HR, Carpenter DO. (2011). Blood pressure in relation to concentrations of PCB congeners and chlorinated pesticides. Environ Health Perspect, 119, 319-25.
66. Grimm FA, Lehmler HJ, He X, Robertson LW, Duffel MW. (2013). Sulfated metabolites of polychlorinated biphenyls are high-affinity ligands for the thyroid hormone transport protein transthyretin. Environ Health Perspect, 121, 657-62.
67. Grossman E. (2013). Nonlegacy PCBs: pigment manufacturing by-products get a second look. Environ Health Perspect, 121, A86-93.
68. Guengerich FP. (2001). Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol, 14, 611-50.
69. Guroff G, Daly JW, Jerina DM, Renson J, Witkop B, Udenfriend S. (1967). Hydroxylation-induced migration: the NIH shift. Recent experiments reveal an unexpected and general result ofenzymatic hydroxylation of aromatic compounds. Science, 157, 1524-30.
70. Gutleb AC, Cenijn P, Velzen M, Lie E, Ropstad E, Skaare JU, et al. (2010). In vitro assay shows that PCB metabolites completely saturate thyroid hormone transport capacity in blood of wild polar bears (Ursus maritimus). Environ Sci Technol, 44, 3149-54.
71. Guvenius DM, Aronsson A, Ekman-Ordeberg G, Bergman A, Noren K. (2003). Human prenatal and postnatal exposure to polybrominated diphenyl ethers, polychlorinated biphenyls, polychlorobiphenylols, and pentachlorophenol. Environ Health Perspect, 111, 1235-41.
72. Guvenius DM, Hassanzadeh P, Bergman A, Noren K. (2002). Metabolites of polychlorinated biphenyls in human liver and adipose tissue. Environ Toxicol Chem, 21, 2264-9.
73. Haglund P. (1996). Isolation and characterization of polychlorinated biphenyl (PCB) atropisomers. Chemosphere, 32, 8.
74. Hagmar L, Rylander L, Dyremark E, Klasson-Wehler E, Erfurth EM. (2001). Plasma concentrations of persistent organochlorines in relation to thyrotropin and thyroid hormone levels in women. Int Arch Occup Environ Health, 74, 184-8.
75. Hansen LG. (1998). Stepping backward to improve assessment of PCB congener toxicities. Environ Health Perspect, 106, 171-89.
76. Hansen LG. (1999). The Ortho Side of PCBs: Occurrence and Disposition Boston : Kluwer Academic Publishers Boston.
77. Hansen LG. (2001). Identification of steady state and episodic PCB congeners from mulitple pathway exposures. In: Robertson LW & Hansen LG, Eds. PCBs: Recent Advances in Environmental Toxicology and Health Effects. Lexington, Kentucky, The University Press of Kentucky, 47-56.
78. Harrad S, Goosey E, Desborough J, Abdallah MA, Roosens L, Covaci A. (2010). Dust from U.K. primary school classrooms and daycare centers: the significance of dust as a pathway ofexposure of young U.K. children to brominated fl ame retardants and polychlorinated biphenyls. Environ Sci Technol, 44, 4198-202.
79. Harrad S, Ibarra C, Robson M, Melymuk L, Zhang X, Diamond M, Douwes J. (2009). Polychlorinated biphenyls in domestic dust from Canada, New Zealand, United Kingdom and United States: implications for human exposure. Chemosphere, 76, 232-8.
80. Herrick RF. (2010). PCBs in school-persistent chemicals, persistent problems. New Solut, 20, 115-26.
81. Herrick RF, Mcclean MD, Meeker JD, Baxter LK, Weymouth GA. (2004). An unrecognized source of PCB contamination in schools and other buildings. Environ Health Perspect, 112, 1051-3.
82. Hisada A, Shimodaira K, Okai T, Watanabe K, Takemori H, Takasuga T, et al. (2013). Serum levels of hydroxylated PCBs, PCBs and thyroid hormone measures of Japanese pregnant women. Environ Health Prev Med, 18, 205-14.
83. Hofvander L. (2006). Polychlorinated Biphenyls and Their Metabolites in Human Blood: Method Development, Identification and Quantification. Ph.D. Thesis, Department ofenvironmental Chemistry, University of Stockholm.
84. Hovander L, Athanasiadou M, Asplund L, Jensen S, Wehler EK. (2000). Extraction and cleanup methods for analysis of phenolic and neutral organohalogens in plasma. J Anal Toxicol, 24, 696-703.
85. Hovander L, Linderholm L, Athanasiadou M, Athanassiadis I, Bignert A, Fngstrm B, et al. (2006). Levels of PCBs and their metabolites in the serum of residents of a highly contaminated area in eastern Slovakia. Environ Sci Technol, 40, 3696-703.
86. Hovander L, Linderholm L, Athanasiadou M, Athanassiadis I, Trnovec T, Kocan A, et al. (2004). Analysis of PCB and PCB metabolites in humans from eastern Slovakia. Organohalogen Compd, 66, 3525-31.
87. Hrycay EG, Bandiera SM. (2003). Spectral interactions of tetrachlorobiphenyls with hepatic microsomal cytochrome P450 enzymes. Chem Biol Interact, 146, 285-96.
88. Hsu, YK, Holsen, TM, Hopke, PK. (2003) Locating and quantifying PCB sources in Chicago: Receptor modeling and field sampling. Environ Sci Technol, 37, 681-690.
89. Hu D, Hornbuckle KC. (2010). Inadvertent polychlorinated biphenyls in commercial paint pigments. Environ Sci Technol, 44, 2822-7.
90. Hu D, Lehmler HJ, Martinez A, Wang K, Hornbuckle KC. (2010a). Atmospheric PCB congeners across Chicago. Atmos Environ 44, 1550-7.
91. Hu D, Martinez A, Hornbuckle KC. (2008). Discovery of non-aroclor PCB (3,3 '-dichlorobiphenyl) in Chicago air. Environ Sci Technol, 42, 7873-7.
92. Hu D, Martinez A, Hornbuckle KC. (2011). Sedimentary records of nonaroclor and aroclor PCB mixtures in the Great Lakes. J Great Lakes Res, 37, 359-64.
93. Hu X, Adamcakova-Dodd A, Lehmler HJ, Hu D, Hornbuckle K, Thorne PS. (2012). Subchronic inhalation exposure study of an airborne polychlorinated biphenyl mixture resembling the Chicago ambient air congener profile. Environ Sci Technol, 46, 9653-62.
94. Hu X, Adamcakova-Dodd A, Lehmler HJ, Hu D, Kania-Korwel I, Hornbuckle KC, Thorne PS. (2010b). Time course of congener uptake and elimination in rats after short-term inhalation exposure to an airborne polychlorinated biphenyl (PCB) mixture. Environ Sci Technol, 44, 6893-900.
95. Hu X, Adamcakova-Dodd A, Thorne PS. (2014). The fate of inhaled (14)C-labeled PCB11 and its metabolites in vivo. Environ Int, 63, 92-100.
96. Hu X, Lehmler HJ, Adamcakova-Dodd A, Thorne PS. (2013). Elimination of inhaled 3,3 '-dichlorobiphenyl and the formation of the 4-hydroxylated metabolite. Environ Sci Technol, 47, 4743-51.
97. Jacobson JL, Jacobson SW, Humphrey HE. (1990). Effects of in utero exposure to polychlorinated biphenyls and related contaminants on cognitive functioning in young children. J Pediatr, 116, 38-45.
98. Jacobus JA, Flor S, Klingelhutz A, Robertson LW, Ludewig G. (2008). 2-(4 '-Chlorophenyl)-1,4-Benzoquinone Increases the Frequency of Micronuclei and Shortens Telomeres. Environ Toxicol Pharmacol, 25, 267-72.
99. James MO. (2001). Polychlorinated Biphenyls: Metabolism and Metabolites. In: Robertson L & Hansen LG, Eds. PCBs, Recent Advances in Environmental Toxicology and Health Effects. Lexington, Kentucky: The University Press of Kentucky, 35-46.
100. Jamshidi A, Hunter S, Hazrati S, Harrad S. (2007). Concentrations and chiral signatures of polychlorinated biphenyls in outdoor and indoor air and soil in a major U.K. conurbation. Environ Sci Technol, 41, 2153-8.
101. Jerina DM, Daly JW. (1974). Arene oxides: a new aspect of drug metabolism. Science, 185, 573-82.
102. Johansson M, Larsson C, Bergman A, Lund BO. (1998). Structure-activity relationship for inhibition of CYP11B1-dependent glucocorticoid synthesis in Y1 cells by aryl methyl sulfones. Pharmacol Toxicol, 83, 225-30
103. Jrundsdottir H, Norstrom K, Olsson M, Pham-Tuan H, Hhnerfuss H, Bignert A, Bergman A. (2006). Temporal trend of bis(4-chlorophenyl) sulfone, methylsulfonyl-DDE and-PCBs in Baltic guillemot (Uria aalge) egg 1971-2001-A comparison to 4,4 '-DDE and PCB trends. Environ Pollut, 141, 226-37.
104. Jugan ML, Levi Y, Blondeau JP. (2010). Endocrine disruptors and thyroid hormone physiology. Biochem Pharmacol, 79, 939-47.
105. Kaiser K. (1974). On the optical activity of polychlorinated biphenyls. Environ Poll, 7, 93-101.
106. Kallenborn, R, Huhnerfuss, H (eds.). (2001). Chiral Environmental Pollutants-Trace Analysis and Ecotoxicology. Berlin, Heidelberg: Springer Verlag.
107. Kaminsky LS, Kennedy MW, Adams SM, Guengerich FP. (1981). Metabolism of dichlorobiphenyls by highly purified isozymes of rat liver cytochrome P-450. Biochemistry, 20, 7379-84.
108. Kania-Korwel I, Barnhart CD, Stamou M, Truong KM, El-Komy MH, Lein PJ, et al. (2012). 2, 2,3,5,6-Pentachlorobiphenyl (PCB 95) and its hydroxylated metabolites are enantiomerically enriched in female mice. Environ Sci Technol, 46, 11393-401.
109. Kania-Korwel I, Duffel MW, Lehmler HJ. (2011). Gas chromatographic analysis with chiral cyclodextrin phases reveals the enantioselective formation of hydroxylated polychlorinated biphenyls by rat liver microsomes. Environ Sci Technol, 45, 9590-6.
110. Kania-Korwel I, Hrycay EG, Bandiera S, Lehmler H-J. (2008a). 2,2,3,3,6,6-Hexachlorobiphenyl (PCB 136) atropisomers interact enantioselectively with hepatic microsomal cytochrome P450 enzymes. Chem Res Toxicol, 21, 1295-303.
111. Kania-Korwel I, Vyas S, Song Y, Lehmler HJ. (2008b). Gas chromatographic separation of methoxylated polychlorinated biphenyl atropisomer. J Chromatogr A, 1207, 146-54.
112. Kato S, Mckinney JD, Matthews HB. (1980). Metabolism of symmetrical hexachlorobiphenyl isomers in the rat. Toxicol Appl Pharma, 53, 389-98.
113. Kato Y, Haraguchi K, Kawashima M, Yamada S, Masuda Y, Kimura R. (1995). Induction of hepatic microsomal drug-metabolizing enzymes by methylsulphonyl metabolites of polychlorinated biphenyl congeners in rats. Chem Biol Interact, 95, 257-68.
114. Kato Y, Haraguchi K, Shibahara T, Masuda Y, Kimura R. (1998). Reduction of thyroid hormone levels by methylsulfonyl metabolites of polychlorinated biphenyl congeners in rats. Arch Toxicol, 72, 541-4.
115. Kato Y, Haraguchi K, Shibahara T, Shinmura Y, Masuda Y, Kimura R. (2000). The induction of hepatic microsomal UDPglucuronosyltransferase by the methylsulfonyl metabolites of polychlorinated biphenyl congeners in rats. Chem Biol Interact, 125, 107-15.
116. Kato Y, Haraguchi K, Shibahara T, Yumoto S, Masuda Y, Kimura R. (1999). Reduction of thyroid hormone levels by methylsulfonyl metabolites of tetra-and pentachlorinated biphenyls in male Sprague-Dawley rats. Toxicol Sci, 48, 51-4.
117. Kato Y, Haraguchi K, Tomiyasu K, Hiroyuki S, Isogai M, Masuda Y, Kimura R. (1997). Structure-dependent induction of CYP2B1/2 by 3-methylsulfonyl metabolites of polychlorinated biphenyl congeners in rats. Environ Toxicol Pharmacol, 3, 137-44.
118. Kato Y, Ikushiro S, Haraguchi K, Yamazaki T, Ito Y, Suzuki H, et al. (2004). A possible mechanism for decrease in serum thyroxine level by polychlorinated biphenyls in Wistar and Gunn rats. Toxicol Sci, 81, 309-15.
119. Kester MH, Bulduk S, Tibboel D, Meinl W, Glatt H, Falany CN, et al. (2000). Potent inhibition ofestrogen sulfotransferase by hydroxylated PCB metabolites: a novel pathway explaining the estrogenic activity of PCBs. Endocrinology, 141, 1897-900.
120. Kester MH, Bulduk S, Van Toor H., Tibboel D, Meinl W, Glatt H, et al. (2002). Potent inhibition ofestrogen sulfotransferase by hydroxylated metabolites of polyhalogenated aromatic hydrocarbons reveals alternative mechanism for estrogenic activity ofendocrine disrupters. J Clin Endocrinol Metab, 87, 1142-50.
121. Kimbrough, RD, Jensen, AA (Eds.). (1989). Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products. Amsterdam, New York, Oxford: Elsevier, 2nd Ed.
122. Klasson Wehler E., Jonsson J, Bergman A, Brandt I, Darnerud PO. (1989). 3,3,4,4-Tetrachlorobiphenyl and 3,3,4,4,5-pentachlorobiphenyl: tissue localization and metabolic fate in the mourse. Chemosphere, 19, 809-12.
123. Klasson Wehler E., Lindberg L, Joensson CJ, Bergman A. (1993). Tissue retention and metabolism of 2,3,4,3,4-pentachlorobiphenyl in mink and mouse. Chemosphere, 27, 2397-412.
124. Knerr S, Schrenk D. (2006). Carcinogenicity of "non-dioxinlike" polychlorinated biphenyls. Crit Rev Toxicol, 36, 663-94.
125. Kodavanti PR, Curras-Collazo MC. (2010). Neuroendocrine actions of organohalogens: thyroid hormones, arginine vasopressin, and neuroplasticity. Front Neuroendocrinol, 31, 479-96.
126. Krishnan V, Safe S. (1993). Polychlorinated biphenyls (PCBs), dibenzop-dioxins (PCDDs), and dibenzofurans (PCDFs) as antiestrogens in MCF-7 human breast cancer cells: quantitative structure-activity relationships. Toxicol Appl Pharmacol, 120, 55-61.
127. Kutz FW, Wood PH, Bottimore DP. (1991). Organochlorine pesticides and polychlorinated biphenyls in human adipose tissue. Rev Environ Contam Toxicol, 120, 1-82.
128. Langer P, Kocan A, Tajtakova M, Koska J, Radikova Z, Ksinantova L, et al. (2008). Increased thyroid volume, prevalence of thyroid antibodies and impaired fasting glucose in young adults from organochlorine cocktail polluted area: outcome of transgenerational transmission Chemosphere, 73, 1145-50.
129. Lans MC, Klasson-Wehler E, Willemsen M, Meussen E, Safe S, Brouwer A. (1993). Structure-dependent, competitive interaction of hydroxy-polychlorobiphenyls-dibenzo-p-dioxins and-dibenzofurans with human transthyretin. Chem Biol Interact, 88, 7-21.
130. Larsdotter M, Darnerud P, Aune M, Glynn A, Bjerselius R. (2005). Serum concentrations of pentachlorophenol (PCP), polychlorinated biphenyls (PCBs), and hydroxylated metabolites of PCB during pregnancy and lactation (in Swedish). Swedish EPA Report on Contract 2190104, 2005,/http://www.naturvardsverket.se/dokument/mo/modok/export/klorfenoler.pdf/(Available Jan. 16, 2006).
131. Larsson C, Bergman A. (1998). Synthesis of radiolabelled methylsulphonyl CBs with specific retention in the rat liver. Organohalogen Compd, 35, 127-30.
132. Larsson C, Ellerichmann T, Huhnerfuss H, Bergman A. (2002). Chiral PCB methyl sulfones in rat tissues after exposure to technical PCBs. Environ Sci Technol, 36, 2833-8.
133. Larsson C, Norstrom K, Athanansiadis I, Bignert A, Konig WA, Bergman A. (2004). Enantiomeric specificity of methylsulfonyl-PCBs and distribution of bis(4-chlorophenyl) sulfone, PCB, and DDE methyl sulfones in grey seal tissues. Environ Sci Technol, 38, 4950-5.
134. Lauby-Secretan B, Loomis D, Grosse Y, EL Ghissassi F., Bouvard V, Benbrahim-Tallaa L, et al. (2013). Carcinogenicity of polychlorinated biphenyls and polybrominated biphenyls. Lancet Oncol, 14, 287-8.
135. Lehmann L, Esch HL, Kirby PA, Robertson LW, Ludewig G. (2007). 4-monochlorobiphenyl (PCB3) induces mutations in the livers of transgenic Fisher 344 rats. Carcinogenesis, 28, 471-8.
136. Lehmler HJ, Harrad SJ, Huhnerfuss H, Kania-Korwel I, Lee CM, Lu Z, Wong CS. (2010). Chiral polychlorinated biphenyl transport, metabolism, and distribution: a review. Environ Sci Technol, 44, 2757-66.
137. Lehmler HJ, Robertson LW, Garrison AW, Kodavanti PR. (2005). Effects of PCB 84 enantiomers on [3H]-phorbol ester binding in rat cerebellar granule cells and 45Ca2-uptake in rat cerebellum. Toxicol Lett, 156, 391-400.
138. Letcher RJ, Klasson-Wehler E, Bergman A. (2000). Methyl sulfone and hydroxylated metabolites of polychlorinated biphenyls. In: Paasivirta J., Ed. New Types of Persistent Halogenated Compounds. Berlin: Springer-Verlag, 317-57.
139. Li X, Parkin S, Duffel MW, Robertson LW, Lehmler HJ. (2010). An efficient approach to sulfate metabolites of polychlorinated biphenyls. Environ Int, 36, 843-8.
140. Liebl B, Schettgen T, Kerscher G, Broding HC, Otto A, Angerer J, Drexler H. (2004). Evidence for increased internal exposure to lower chlorinated polychlorinated biphenyls (PCB) in pupils attending a contaminated school. Int J Hyg Environ Health, 207, 315-24.
141. Lin PH, Sangaiah R, Ranasinghe A, Upton PB, La DK, Gold A, Swenberg JA. (2000). Formation of quinonoid-derived protein adducts in the liver and brain of Sprague-Dawley rats treated with 2,2,5, 5-tetrachlorobiphenyl. Chem Res Toxicol, 13, 710-8.
142. Litten S, Fowler B, Luszniak D. (2002). Identification of a novel PCB source through analysis of 209 PCB congeners by US EPA modified method 1668. Chemosphere, 46, 1457-9.
143. Liu Y, Apak TI, Lehmler HJ, Robertson LW, Duffel MW. (2006). Hydroxylated polychlorinated biphenyls are substrates and inhibitors of human hydroxysteroid sulfotransferase SULT2A1. Chem Res Toxicol, 19, 1420-5.
144. Liu Y, Lehmler HJ, Robertson LW, Duffel MW. (2011). Physicochemical properties of hydroxylated polychlorinated biphenyls aid in predicting their interactions with rat sulfotransferase 1A1 (rSULT1A1). Chem Biol Interact, 189, 153-60.
145. Liu Y, Smart JT, Song Y, Lehmler HJ, Robertson LW, Duffel MW. (2009). Structure-activity relationships for hydroxylated polychlorinated biphenyls as substrates and inhibitors of rat sulfotransferases and modification of these relationships by changes in thiol status. Drug Metab Dispos, 37, 1065-72.
146. Londono M, Shimokawa N, Miyazaki W, Iwasaki T, Koibuchi N. (2010). Hydroxylated PCB induces Ca2-oscillations and alterations of membrane potential in cultured cortical cells. J Appl Toxicol, 30, 334-42.
147. Lu Z, Kania-Korwel I, Lehmler HJ, Wong CS. (2013). Stereoselective formation of mono-and dihydroxylated polychlorinated biphenyls by rat cytochrome P450 2B1. Environ Sci Technol, 47, 12184-92.
148. Lu Z, Wong CS. (2011). Factors affecting phase I stereoselective biotransformation of chiral polychlorinated biphenyls by rat cytochrome P-450 2B1 isozyme. Environ Sci Technol, 45, 8298-305.
149. Lucier GW, Mcdaniel OS, Schiller CM, Matthews HB. (1978). Structural requirements for the accumulation of chlorinated biphenyl metabolites in the fetal rat intestine. Drug Metab Dispos, 6, 584-90.
150. Ludewig G. (2001). Cancer initiation by PCBs. In: Robertson LW & Hansen LG, Eds. PCBs, Recent Advances in Environmental Toxicology and Health Effects. The University Press of Kentucky, Lexington, Kentucky: 337-54.
151. Ludewig G, Esch H, Robertson L. (2007). Polyhalogenierte Bi-und Terphenyle. In: Dunkelberg H., Gebel T, Hartwig A., Eds. Handbuch der Lebensmitteltoxikologie: Belastungen, Wirkungen, Lebensmittelsicherheit, Hygiene. Weinheim: Wiley-VCH, 1031-1094.
152. Ludewig G, Lehmann L, Esch H, Robertson LW. (2008). Metabolic activation of PCBs to carcinogens in vivo-a review. Environ Toxicol Pharmacol, 25, 241-6.
153. Lund B-O, Rberg J, Bergman J, Larsson C, Bergman A, Bklin B-M, et al. (1999). Chronic and reproductive toxicity of a mixture of 15 methylsulfonyl-polychlorinated biphenyls and 3-methylsulfonyl-2,2-bis-(4-chlorophenyl)-1,1-dichloroethene in mink (Mustela vison). Environ Toxicol Chem, 18, 292-98.
154. Lund J, Brandt I, Poellinger L, Bergman A, Klasson-Wehler E, Gustafsson JA. (1985). Target cells for the polychlorinated biphenyl metabolite 4,4-bis(methylsulfonyl)-2,2,5,5-tetrachlorobiphenyl. Characterization of high affinity binding in rat and mouse lung cytosol. Mol Pharmacol, 27, 314-23.
155. Lund J, Nordlund L, Devereux T, Glaumann H, Gustafsson JA. (1987). Physicochemical and immunological characterization of binding protein for PCB methyl sulfones. Chemosphere, 16, 1677-80.
156. Luthe G, Jacobus JA, Robertson LW. (2008). Receptor interactions by polybrominated diphenyl ethers versus polychlorinated biphenyls: a theoretical Structure-activity assessment. Environ Toxicol Pharmacol, 25, 202-10.
157. Ma R, Sassoon DA. (2006). PCBs exert an estrogenic effect through repression of the Wnt7a signaling pathway in the female reproductive tract. Environ Health Perspect, 114, 898-904.
158. Macdonal RW, Barrie LA, Bidleman TF, Diamond ML, Gregor DJ, Semkin RG, et al. (2000). Contaminants in the Canadian Arctic: 5 years of progress in understanding sources, occurrence and pathways. Sci Total Environ, 254, 93-234.
159. Machala M, Blaha L, Lehmler HJ, Pliskova M, Majkova Z, Kapplova P, et al. (2004). Toxicity of hydroxylated and quinoid PCB metabolites: inhibition of gap junctional intercellular communication and activation of aryl hydrocarbon and estrogen receptors in hepatic and mammary cells. Chem Res Toxicol, 17, 340-7.
160. MacIntosh DL, Minegishi T, Fragala MA, Allen JG, Coghlan KM, Stewart JH, Mccarthy JF. (2012). Mitigation of building-related polychlorinated biphenyls in indoor air of a school. Environ Health, 11, 24.
161. Maervoet J, Covaci A, Schepens P, Sandau CD, Letcher RJ. (2004). A reassessment of the nomenclature of polychlorinated biphenyl (PCB) metabolites. Environ Health Perspect, 112, 291-4.
162. Malmberg T, Hoogstraate J, Bergman A, Klasson Wehler E. (2004). Pharmacokinetics of two major hydroxylated polychlorinated biphenyl metabolites with specific retention in rat blood. Xenobiotica, 34, 581-9.
163. Mannschreck A, Pustet N, Robertson L, Oesch F, Ptmann M. (1985). Enantiomers of polychlorinated biphenyls: Semi-preparative enrichment by liquid chromatography. Liebigs Ann Chem, 2101-2103.
164. Marek RF, Martinez A, Hornbuckle KC. (2013a). Discovery of hydroxylated polychlorinated biphenyls (OH-PCBs) in sediment from a lake Michigan waterway and original commercial aroclors. Environ Sci Technol, 47, 8204-10.
165. Marek RF, Thorne PS, DeWall J, Hornbuckle KC. (2015). Variability in PCB and OH-PCB serum levels in children and their mothers in urban and rural U.S. communities. Environ Sci Technol. 10.1021/es5048039.
166. Marek RF, Thorne PS, Wang K, Dewall J, Hornbuckle KC. (2013b). PCBs and OH-PCBs in serum from children and mothers in urban and rural U.S. communities. Environ Sci Technol, 47, 3353-61.
167. Matthews HB, Anderson MW. (1975). Effect of chlorination on the distribution and excretion of polychlorinated biphenyls. Drug Metab Disp, 3, 371-80.
168. Matthews HB, Kato S. (1979). The metabolism and disposition of halogenated aromatics. Ann N Y Acad Sci, 320, 131-7.
169. Mayes BA, Mcconnell EE, Neal BH, Brunner MJ, Hamilton SB, Sullivan TM, et al. (1998). Comparative carcinogenicity in Sprague-Dawley rats of the polychlorinated biphenyl mixtures Aroclors 1016, 1242, 1254, and 1260. Toxicol Sci, 41, 62-76.
170. McFarland VA, Clarke JU. (1989). Environmental occurrence, abundance, and potential toxicity of polychlorinated biphenyl congeners: considerations for a congener-specific analysis. Environ Health Perspect, 81, 225-39.
171. McGraw JE Jr, Waller DP. (2006). Specific human CYP 450 isoform metabolism of a pentachlorobiphenyl (PCB-IUPAC# 101). Biochem Biophys Res Commun, 344, 129-33.
172. McLean MR, Bauer U, Amaro AR, Robertson LW. (1996a). Identification of catechol and hydroquinone metabolites of 4-monochlorobiphenyl. Chem Res Toxicol, 9, 158-64.
173. McLean MR, Robertson LW, Gupta RC. (1996b). Detection of PCB adducts by the 32P-postlabeling technique. Chem Res Toxicol, 9, 165-71.
174. Meerts IA, Assink Y, Cenijn PH, Van Den Berg JH, Weijers BM, Bergman A, et al. (2002). Placental transfer of a hydroxylated polychlorinated biphenyl and Effects on fetal and maternal thyroid hormone homeostasis in the rat. Toxicol Sci, 68, 361-71.
175. Meerts IA, Hoving S, Van Den Berg JH, Weijers BM, Swarts HJ, Van Der Beek EM, et al. (2004). Effects of in utero exposure to 4-hydroxy-2,3,3,4,5-pentachlorobiphenyl (4-OH-CB107) on developmental landmarks, steroid hormone levels, and female estrous cyclicity in rats. Toxicol Sci, 82, 259-67.
176. Meijer L, Weiss J, Van Velzen M., Brouwer A, Bergman A, Sauer P. (2004). Flame retardants, polychlorinated biphenyls and insecticides in pregnant women in the northern part of The Netherlands. Organohalogen Comd, 66, 3552-6.
177. Melymuk L, Robson M, Helm PA, Diamond ML. (2012). PCBs, PBDEs, and PAHs in Toronto air: spatial and seasonal trends and implications for contaminant transport. Sci Total Environ, 429, 272-80.
178. Menichini E, Iacovella N, Monfredini F, Turrio-Baldassarri L. (2007). Atmospheric pollution by PAHs, PCDD/Fs and PCBs simultaneously collected at a regional background site in central Italy and at an urban site in Rome. Chemosphere, 69, 422-34.
179. Mills RA, Millis CD, Dannan GA, Guengerich FP, Aust SD. (1985). Studies on the structure-activity relationships for the metabolism of polybrominated biphenyls by rat liver microsomes. Toxicol Appl Pharmacol, 78, 96-104.
180. Mills SA, iii Thal DI, Barney J. (2007). A summary of the 209 PCB congener nomenclature. Chemosphere, 68, 1603-12.
181. Morales NM, Matthews HB. (1979). In vivo binding of 2,3,6,2 ,3,6 '-hexachlorobiphenyl and 2,4,5,2 ',4 ',5 '-hexachlorobiphenyl to mouse liver macromolecules. Chem Biol Interact, 27, 99-110.
182. Morck A, Larsen G, Wehler EK. (2002). Covalent binding of PCB metabolites to lipids: route of formation and characterization. Xenobiotica, 32, 625-40.
183. Morse DC, Groen D, Veerman M, Van Amerongen C. J., Koeter HB, Smits Van Prooije AE, et al. (1993). Interference of polychlorinated biphenyls in hepatic and brain thyroid hormone metabolism in fetal and neonatal rats. Toxicol Appl Pharmacol, 122, 27-33.
184. Morse DC, Wehler EK, Van De Pas M, De Bie A. T., Van Bladeren P. J, Brouwer A. (1995). Metabolism and biochemical effects of 3,3,4,4-tetrachlorobiphenyl in pregnant and fetal rats. Chem Biol Interact, 95, 41-56.
185. Morse DC, Wehler EK, Wesseling W, Koeman JH, Brouwer A. (1996). Alterations in rat brain thyroid hormone status following pre-and postnatal exposure to polychlorinated biphenyls (Aroclor 1254). Toxicol Appl Pharmacol, 136, 269-79.
186. Mortimer RH, Landers KA, Balakrishnan B, Li H, Mitchell MD, Patel J, Richard K. (2012). Secretion and transfer of the thyroid hormone binding protein transthyretin by human placenta. Placenta, 33, 252-6.
187. Newsome WH, Davies D. (1996). Determination of PCB metabolites in Canadian human milk. Chemosphere, 33, 559-65.
188. Nezel T, Mller-Plathe F, Mller MD, Buser H-R. (1997). Theoretical considerations about chiral PCBs and their methylthio and methylsulfonyl metabolites being possibly present as stable enantiomers. Chemosphere, 35, 1895-906.
189. Niknam Y, Feng W, Cherednichenko G, Dong Y, Joshi SN, Vyas SM, et al. (2013). Structure-activity relationship of selected meta-and parahydroxylated non-dioxin like polychlorinated biphenyls: from single RyR1 channels to muscle dysfunction. Toxicol Sci, 136, 500-13.
190. Nomiyama K, Murata S, Kunisue T, Yamada TK, Mizukawa H, Takahashi S, Tanabe S. (2010). Polychlorinated biphenyls and their hydroxylated metabolites (OH-PCBs) in the blood of toothed and baleen whales stranded along Japanese coastal waters. Environ Sci Technol, 44, 3732-8.
191. Noren K, Lunden A, Pettersson E, Bergman A. (1996). Methylsulfonyl metabolites of PCBs and DDE in human milk in Sweden, 1972-1992. Environ Health Perspect, 104, 766-72.
192. Norstrom K, Eriksson J, Haglund J, Silvari V, Bergman A. (2006). Enantioselective formation of methyl sulfone metabolites of 2,2 ',3,3 ',4,6 '-hexachlorobiphenyl in rat. Environ Sci Technol, 40, 7649-55.
193. Oakley GG, Robertson LW, Gupta RC. (1996). Analysis of polychlorinated biphenyl-DNA adducts by 32P-postlabeling. Carcinogenesis, 17, 109-14.
194. Oberg M, Sjodin A, Casabona H, Nordgren I, Klasson-Wehler E, Hakansson H. (2002). Tissue distribution and half-lives of individual polychlorinated biphenyls and serum levels of 4-hydroxy-2,3,3 ',4 ',5-pentachlorobiphenyl in the rat. Toxicol Sci, 70, 171-82.
195. Ockenden WA, Lohmann R, Shears JR, Jones KC. (2001). The significance of PCBs in the atmosphere of the southern hemisphere. Environ Sci Pollut Res Int, 8, 189-94.
196. Ohta S, Haraguchi K, Kato Y, Endo T, Kimura O, Koga N. (2015). Distribution and excretion of 2,2 ,3,4 ,5,5 ,6-heptachlorobiphenyl (CB187) and its metabolites in rats and guinea pigs. Chemosphere, 118, 5-11.
197. Onozuka D, Yoshimura T, Kaneko S, Furue M. (2009). Mortality after exposure to polychlorinated biphenyls and polychlorinated dibenzofurans: a 40-year follow-up study of Yusho patients. Am J Epidemiol, 169, 86-95.
198. Otake T, Yoshinaga J, Enomoto T, Matsuda M, Wakimoto T, Ikegami M, et al. (2007). Thyroid hormone status of newborns in relation to in utero exposure to PCBs and hydroxylated PCB metabolites. Environ Res, 105, 240-6.
199. Park JS, Bergman A, Linderholm L, Athanasiadou M, Kocan A, Petrik J, et al. (2008). Placental transfer of polychlorinated biphenyls, their hydroxylated metabolites and pentachlorophenol in pregnant women from eastern Slovakia. Chemosphere, 70, 1676-84.
200. Park JS, Linderholm L, Charles MJ, Athanasiadou M, Petrik J, Kocan A, et al. (2007). Polychlorinated biphenyls and their hydroxylated metabolites (OH-PCBS) in pregnant women from eastern Slovakia. Environ Health Perspect, 115, 20-7.
201. Park JS, Petreas M, Cohn BA, Cirillo PM, Factor-Litvak P. (2009). Hydroxylated PCB metabolites (OH-PCBs) in archived serum from 1950-60s California mothers: a pilot study. Environ Int, 35, 937-42.
202. Parkinson A, Safe SH, Robertson LW, Thomas PE, Ryan DE, Reik LM, Levin W. (1983). Immunochemical quantitation of cytochrome P-450 isozymes and epoxide hydrolase in liver microsomes from polychlorinated or polybrominated biphenyl-treated rats. A study of structure-activity relationships. J Biol Chem, 258, 5967-76.
203. Patrick L. (2009). Thyroid disruption: mechanism and clinical implications in human health. Altern Med Rev, 14, 326-46.
204. Pearce EN, Braverman LE. (2009). Environmental pollutants and the thyroid. Best Pract Res Clin Endocrinol Metab, 23, 801-13.
205. Pereg D, Robertson LW, Gupta RC. (2002). DNA adduction by polychlorinated biphenyls: adducts derived from hepatic microsomal activation and from synthetic metabolites. Chem Biol Interact, 139, 129-44.
206. Pereg D, Tampal N, Espandiari P, Robertson LW. (2001). Distribution and macromolecular binding of benzo[a]pyrene and two polychlorinated biphenyl congeners in female mice. Chem Biol Interact, 137, 243-58.
207. Persoon C, Peters TM, Kumar N, Hornbuckle KC. (2010). Spatial distribution of airborne polychlorinated biphenyls in Cleveland, Ohio and Chicago, Illinois. Environ Sci Technol, 44, 2797-802.
208. Pessah IN, Hansen LG, Albertson TE, Garner CE, Ta TA, Do Z, et al. (2006). Structure-activity relationship for noncoplanar polychlorinated biphenyl congeners toward the ryanodine receptor-Ca2 channel complex type 1 (RyR1). Chem Res Toxicol, 19, 92-101.
209. Pessah IN, Lehmler HJ, Robertson LW, Perez CF, Cabrales E, Bose DD, Feng W. (2009). Enantiomeric specificity of (-)-2,2 ',3,3 ',6,6 '-hexachlorobiphenyl toward ryanodine receptor types 1 and 2. Chem Res Toxicol, 22, 201-7.
210. Pliskova M, Vondracek J, Canton RF, Nera J, Kocan A, Petrik J, et al. (2005). Impact of polychlorinated biphenyls contamination on estrogenic activity in human male serum. Environ Health Perspect, 113, 1277-84.
211. Preston BD, Miller JA, Miller EC. (1983). Non-arene oxide aromatic ring hydroxylation of 2,2,5,5-tetrachlorobiphenyl as the major metabolic pathway catalyzed by phenobarbital-induced rat liver microsomes. J Biol Chem, 258, 8304-11.
212. Ptak A, Ludewig G, Lehmler HJ, Wojtowicz AK, Robertson LW, Gregoraszczuk EL. (2005). Comparison of the actions of 4-chlorobiphenyl and its hydroxylated metabolites on estradiol secretion by ovarian follicles in primary cells in culture. Reprod Toxicol, 20, 57-64.
213. Ptak A, Ludewig G, Robertson L, Lehmler HJ, Gregoraszczuk EL. (2006). In vitro exposure of porcine prepubertal follicles to 4-chlorobiphenyl (PCB3) and its hydroxylated metabolites: Effects on sex hormone levels and aromatase activity. Toxicol Lett, 164, 113-22.
214. Purkey HE, Palaninathan SK, Kent KC, Smith C, Safe SH, Sacchettini JC, Kelly JW. (2004). Hydroxylated polychlorinated biphenyls selectively bind transthyretin in blood and inhibit amyloidogenesis: rationalizing rodent PCB toxicity. Chem Biol, 11, 1719-28.
215. Ptmann M, Mannschreck A, Oesch F, Robertson L. (1989). Chiral Effects in the induction of drug-metabolizing enzymes using synthetic atropisomers of polychlorinated biphenyls (PCBs). Biochem Pharmacol, 38, 1345-52
216. Ptmann M, Oesch F, Robertson L, Mannschreck A. (1986). Characteristics of polychlorinated biphenyl (PCB) atropisomers. Chemosphere, 15, 2061-4.
217. Qin X, Lehmler HJ, Teesch LM, Robertson LW, Duffel MW. (2013). Chlorinated biphenyl quinones and phenyl-2,5-benzoquinone differentially modify the catalytic activity of human hydroxysteroid sulfotransferase hSULT2A1. Chem Res Toxicol, 26,1474-85.
218. Quinete N, Schettgen T, Bertram J, Kraus T. (2014). Occurrence and distribution of PCB metabolites in blood and their potential health Effects in humans: a review. Environ Sci Pollut Res Int.
219. Rayne S, Forest K. (2010). pK(a) values of the monohydroxylated polychlorinated biphenyls (OH-PCBs), polybrominated biphenyls (OH-PBBs), polychlorinated diphenyl ethers (OH-PCDEs), and polybrominated diphenyl ethers (OH-PBDEs). J Environ Sci Health A Tox Hazard Subst Environ Eng, 45, 1322-46.
220. Razvi S, Shakoor A, Vanderpump M, Weaver JU, Pearce SH. (2008). The infl uence of age on the relationship between subclinical hypothyroidism and ischemic heart disease: a metaanalysis. J Clin Endocrinol Metab, 93, 2998-3007.
221. Rickenbacher U, Mckinney JD, Oatley SJ, Blake CC. (1986). Structurally specific binding of halogenated biphenyls to thyroxine transport protein. J Med Chem, 29, 641-8.
222. Ring BJ, Seitz KR, Vodicnik MJ. (1988). Transfer of 2,4,5,2 ',4 ',5 '-hexachlorobiphenyl across the in situ perfused guinea pig placenta. Toxicol Appl Pharmacol, 96, 7-13.
223. Robertson LW, Gupta R. (2000). Metabolism of polychlorinated biphenyls (PCBs) generates eletrophiles and reactive oxygen species that damage DNA. In: Williams GM, Aruoma OI, Eds. Molecular Drug Metabolism and Toxicology. OICA International, 16-32.
224. Robertson LW, Ludewig G. (2011). Polychlorinated Biphenyl (PCB) carcinogenicity with special emphasis on airborne PCBs. Gefahrst Reinhalt Luft, 71, 25-32.
225. Rodenburg LA, Du S, Fennell DE, Cavallo GJ. (2010a). Evidence for widespread dechlorination of polychlorinated biphenyls in groundwater, landfills, and wastewater collection systems. Environ Sci Technol, 44, 7534-40.
226. Rodenburg LA, Guo J, Du S, Cavallo GJ. (2010b). Evidence for unique and ubiquitous environmental sources of 3,3 '-dichlorobiphenyl (PCB 11). Environ Sci Technol, 44, 2816-21.
227. Rudel RA, Perovich LJ. (2009). Endocrine disrupting chemicals in indoor and outdoor air. Atmos Environ 43, 170-81.
228. Safe S. (2001). Hydroxylated polychlorinated biphenyls (PCBs) and organochlorine pesticides as potential endocrine disruptors. Handbook Environ Chem, 3, 155-67.
229. Safe S, Bandiera S, Sawyer T, Robertson L, Safe L, Parkinson A, et al. (1985). PCBs: structure-function relationships and mechanism of action. Environ Health Perspect, 60, 47-56.
230. Sandanger TM, Dumas P, Berger U, Burkow IC. (2004). Analysis of HO-PCBs and PCP in blood plasma from individuals with high PCB exposure living on the Chukotka Peninsula in the Russian Arctic. J Environ Monit, 6, 758-65.
231. Sandau CD, Ayotte P, Dewailly E, Duffe J, Norstrom RJ. (2002). Pentachlorophenol and hydroxylated polychlorinated biphenyl metabolites in umbilical cord plasma of neonates from coastal populations in Quebec. Environ Health Perspect, 110, 411-7.
232. Schecter A, Colacino J, Haffner D, Patel K, Opel M, Papke O, Birnbaum L. (2010). Perfl uorinated compounds, polychlorinated biphenyl, and organochlorine pesticide contamination in composite food samples from Dallas, Texas. Environ Health Perspect, 118, 796-802.
233. Schnellmann RG, Vickers AEM, Sipes IG. (1985). Metabolism and disposition of polychlorinated biphenyls. In: Hodgson E., Bend J. R., Philpot R.M., Eds. Reviews in Biochemical Toxicology. New York, Amsterdam, Oxford: Elsevier, 247-282.
234. Schuur AG, Brouwer A, Bergman A, Coughtrie MW, Visser TJ. (1998a). Inhibition of thyroid hormone sulfation by hydroxylated metabolites of polychlorinated biphenyls. Chem Biol Interact, 109, 293-7.
235. Schuur AG, Legger FF, Van Meeteren ME, Moonen MJ, Van Leeuwen-Bol I., Bergman A, et al. (1998b). In vitro inhibition of thyroid hormone sulfation by hydroxylated metabolites of halogenated aromatic hydrocarbons. Chem Res Toxicol, 11, 1075-81.
236. Senthilkumar PK, Klingelhutz AJ, Jacobus JA, Lehmler H, Robertson LW, Ludewig G. (2011). Airborne polychlorinated biphenyls (PCBs) reduce telomerase activity and shorten telomere length in immortal human skin keratinocytes (HaCat). Toxicol Lett, 204, 64-70.
237. Shang H, Li Y, Wang T, Wang P, Zhang H, Zhang Q, Jiang G. (2014). The presence of polychlorinated biphenyls in yellow pigment products in China with emphasis on 3,3 '-dichlorobiphenyl (PCB 11). Chemosphere, 98, 44-50.
238. Sharma R, Kodavanti PR. (2002). In vitro Effects of polychlorinated biphenyls and hydroxy metabolites on nitric oxide synthases in rat brain. Toxicol Appl Pharmacol, 178, 127-36.
239. Silberhorn EM, Glauert HP, Robertson LW. (1990). Carcinogenicity of polyhalogenated biphenyls: PCBs and PBBs. Crit Rev Toxicol, 20, 440-96.
240. Silverstone AE, Rosenbaum PF, Weinstock RS, Bartell SM, Foushee HR, Shelton C, Pavuk M. (2012). Polychlorinated biphenyl (PCB) exposure and diabetes: results from the Anniston Community Health Survey. Environ Health Perspect, 120, 727-32.
241. Simcik MF, Basu I, Sweet CW, Hites RA. (1999) Temperature dependence and temporal trends of polychlorinated biphenyl congeners in the Great Lakes atmosphere. Environ Sci Technol, 33, 1991-1995.
242. Sjodin A, Hagmar L, Klasson-Wehler E, Bjork J, Bergman A. (2000). Infl uence of the consumption of fatty Baltic Sea fish on plasma levels of halogenated environmental contaminants in Latvian and Swedish men. Environ Health Perspect, 108, 1035-41
243. Sjin A, Tullsten AK, Klasson-Wehler E. (1998). Identification of the parent compounds to selectively retained hydroxylated PCB metabolites in rat blood plasma. Organohalogen Compd, 37, 365-8.
244. Sleight S. (1985). Effects of PCBs and related compounds on hepatocarcinogenesis in rats and mice. Environ Health Perspect, 60, 35-9.
245. Soechitram SD, Athanasiadou M, Hovander L, Bergman A, Sauer PJ. (2004). Fetal exposure to PCBs and their hydroxylated metabolites in a Dutch cohort. Environ Health Perspect, 112, 1208-12.
246. Song Y, Buettner GR, Parkin S, Wagner BA, Robertson LW, Lehmler HJ. (2008a). Chlorination increases the persistence of semiquinone free radicals derived from polychlorinated biphenyl hydroquinones and quinones. J Org Chem, 73, 8296-304.
247. Song Y, Wagner BA, Lehmler HJ, Buettner GR. (2008b). Semiquinone radicals from oxygenated polychlorinated biphenyls: electron paramagnetic resonance studies. Chem Res Toxicol, 21, 1359-67.
248. Song Y, Wagner BA, Witmer JR, Lehmler HJ, Buettner GR. (2009). Nonenzymatic displacement of chlorine and formation of free radicals upon the reaction of glutathione with PCB quinones. Proc Natl Acad Sci USA, 106, 9725-30.
249. Srinivasan A, Lehmler HJ, Robertson LW, Ludewig G. (2001). Production of DNA strand breaks in vitro and reactive oxygen species in vitro and in HL-60 cells by PCB metabolites. Toxicol Sci, 60, 92-102.
250. Srinivasan A, Robertson LW, Ludewig G. (2002). Sulfhydryl binding and topoisomerase inhibition by PCB metabolites. Chem Res Toxicol, 15, 497-505.
251. Sun P, Basu I, Hites RA. (2006). Temporal trends of polychlorinated biphenyls in precipitation and air at chicago. Environ Sci Technol, 40, 1178-83.
252. Tampal N, Lehmler HJ, Espandiari P, Malmberg T, Robertson LW. (2002). Glucuronidation of hydroxylated polychlorinated biphenyls (PCBs). Chem Res Toxicol, 15, 1259-66.
253. Tampal N, Myers S, Robertson LW. (2003). Binding of polychlorinated biphenyls/metabolites to hemoglobin. Toxicol Lett, 142, 53-60.
254. Tanabe S. (1988). PCB problems in the future: foresight from current knowledge. Environ Pollut, 50, 5-28.
255. Tilson HA, Kodavanti PR. (1998). The neurotoxicity of polychlorinated biphenyls. Neurotoxicology, 19, 517-25.
256. Todaka T, Hori T, Hirakawa H, Kajiwara J, Yasutake D, Onozuka D, et al. (2009). Concentrations of polychlorinated biphenyls in blood of Yusho patients over 35 years after the incident. Chemosphere, 74, 902-9.
257. Troisi GM, Haraguchi K, Kaydoo DS, Nyman M, Aguilar A, Borrell A, et al. (2001). Bioaccumulation of polychlorinated biphenyls (PCBs) and dichlorodiphenylethane (DDE) methyl sulfones in tissues of seal and dolphin morbillivirus epizootic victims. J Toxicol Environ Health A, 62, 1-8.
258. Van Den Berg KJ, Zurcher C, Brouwer A. (1988). Effects of 3,4,3,4 '-tetrachlorobiphenyl on thyroid function and histology in marmoset monkeys. Toxicol Lett, 41, 77-86.
259. Van Den Hurk P, Kubiczak GA, Lehmler HJ, James MO. (2002). Hydroxylated polychlorinated biphenyls as inhibitors of the sulfation and glucuronidation of 3-hydroxy-benzo[a]pyrene. Environ Health Perspect, 110, 343-8.
260. Vansell NR, Muppidi JR, Habeebu SM, Klaassen CD. (2004). Promotion of thyroid tumors in rats by pregnenolone-16alpha-carbonitrile (PCN) and polychlorinated biphenyl (PCB). Toxicol Sci, 81, 50-9.
261. Vermiglio F, Lo Presti V. P., Moleti M, Sidoti M, Tortorella G, Scaffidi G, et al. (2004). Attention deficit and hyperactivity disorders in the offspring of mothers exposed to mild-moderate iodine deficiency: a possible novel iodine deficiency disorder in developed countries. J Clin Endocrinol Metab, 89, 6054-60.
262. Waller SC, He YA, Harlow GR, He YQ, Mash EA, Halpert JR. (1999). 2,2 ',3,3 ',6,6 '-hexachlorobiphenyl hydroxylation by active site mutants of cytochrome P450 2B1 and 2B11. Chem Res Toxicol, 12, 690-9.
263. Wang LQ, Lehmler HJ, Robertson LW, James MO. (2006). Polychlorobiphenylols are selective inhibitors of human phenol sulfotransferase 1A1 with 4-nitrophenol as a substrate. Chem Biol Interact, 159, 235-46.
264. Wangpradit O, Mariappan SV, Teesch LM, Duffel MW, Norstrom K, Robertson LW, Luthe G. (2009). Oxidation of 4-chlorobiphenyl metabolites to electrophilic species by prostaglandin H synthase. Chem Res Toxicol, 22, 64-71.
265. Warner NA, Martin JW, Wong CS. (2009). Chiral polychlorinated biphenyls are biotransformed enantioselectively by mammalian cytochrome P-450 isozymes to form hydroxylated metabolites. Environ Sci Technol, 43, 114-21.
266. Weintraub M, Birnbaum LS. (2008). Catfish consumption as a contributor to elevated PCB levels in a non-Hispanic black subpopulation. Environ Res, 107, 412-7.
267. Weistrand C, Noren K. (1997). Methylsulfonyl metabolites of PCBs and DDE in human tissues. Environ Health Perspect, 105, 644-9.
268. Weistrand C, Noren K, Nilsson A. (1997). Occupational exposure. Organochlorine compounds in blood plasma from potentially exposed workers. PCB, PCN, PCDD/F, HCB and methylsulfonyl metabolites of PCB. Environ Sci Pollut Res Int, 4, 2-9.
269. Wethington DM III, Hornbuckle KC. (2005). Milwaukee, WI, as a source of atmospheric PCBs to Lake Michigan. Environ Sci Technol, 39, 57-63.
270. Wu X, Duffel M, Lehmler HJ. (2013a). Oxidation of polychlorinated biphenyls by liver tissue slices from phenobarbital-pretreated mice is congener-specific and atropselective. Chem Res Toxicol, 26, 1642-51.
271. Wu X, Kammerer A, Lehmler HJ. (2014). Microsomal oxidation of 2,2 ',3,3 ',6,6 '-hexachlorobiphenyl (PCB 136) results in speciesdependent chiral signatures of the hydroxylated metabolites. Environ Sci Technol, 48, 2436-44.
272. Wu X, Kania-Korwel I, Chen H, Stamou M, Dammanahalli KJ, Duffel M, et al. (2013b). Metabolism of 2,2',3,3',6,6'-hexachlorobiphenyl (PCB 136) atropisomers in tissue slices from phenobarbital or dexamethasoneinduced rats is sex-dependent. Xenobiotica, 43, 933-47.
273. Wu X, Pramanik A, Duffel MW, Hrycay EG, Bandiera SM, Lehmler HJ, Kania-Korwel I. (2011). 2,2',3,3',6,6'-Hexachlorobiphenyl (PCB 136) is enantioselectively oxidized to hydroxylated metabolites by rat liver microsomes. Chem Res Toxicol, 24, 2249-57.
274. Xie W, Wang K, Robertson LW, Ludewig G. (2010). Investigation of mechanism(s) of DNA damage induced by 4-monochlorobiphenyl (PCB3) metabolites. Environ Int, 36, 950-61.
275. Yang D, Kania-Korwel I, Ghogha A, Chen H, Stamou M, Bose DD, et al. (2014). PCB 136 atropselectively alters morphometric and functional parameters of neuronal connectivity in cultured rat hippocampal neurons via ryanodine receptor-dependent mechanisms. Toxicol Sci, 138, 379-92.
276. Zettner MA, Flor S, Ludewig G, Wagner J, Robertson LW, Lehmann L. (2007). Quinoid metabolites of 4-monochlorobiphenyl induce gene mutations in cultured Chinese hamster v79 cells. Toxicol Sci, 100, 88-98.
277. Zhai G, Hu D, Lehmler HJ, Schnoor JL. (2011). Enantioselective biotransformation of chiral PCBs in whole poplar plants. Environ Sci Technol, 45, 2308-16.
278. Zhai G, Lehmler HJ, Schnoor JL. (2013a). Sulfate metabolites of 4-monochlorobiphenyl in whole poplar plants. Environ Sci Technol, 47, 557-62.
279. Zhai G, Wu X, Lehmler HJ, Schnoor JL. (2013b). Atropisomeric determination of chiral hydroxylated metabolites of polychlorinated biphenyls using HPLC-MS. Chem Cent J, 7, 183.
280. Zhang X, Diamond ML, Robson M, Harrad S. (2011). Sources, emissions, and fate of polybrominated diphenyl ethers and polychlorinated biphenyls indoors in Toronto, Canada. Environ Sci Technol, 45, 3268-74.
281. Zhao HX, Adamcakova-Dodd A, Hu D, Hornbuckle KC, Just CL, Robertson LW, et al. (2010). Devlelopment of a synthetic PCB mixture resembling the average polychlorinated biphenyl profile in Chicago air. Environ Int, 36, 819-27.
282. Zhao S, Narang A, Ding X, Eadon G. (2004). Characterization and quantitative analysis of DNA adducts formed from lower chlorinated PCB-derived quinones. Chem Res Toxicol, 17, 502-11.
283. Zhu Y, Mapuskar KA, Marek RF, Xu W, Lehmler HJ, Robertson LW, et al. (2013). A new player in environmentally induced oxidative stress: polychlorinated biphenyl congener, 3,3 '-dichlorobiphenyl (PCB11). Toxicol Sci, 136, 39-50.
284. Zoeller RT, Rovet J. (2004). Timing of thyroid hormone action in the developing brain: clinical observations and experimental findings. J Neuroendocrinol, 16, 809-18.