Prediction of the health effects of polychlorinated biphenyls (PCBS) and their: Metabolites using quantitative structure-activity relationship (QSAR)

Toxicology Letters

Volumn 181, Issue 1, 2008, Pages 53-65

  Ruiz, P ^a   Faroon, O ^a   Moudgal, C J ^b   Hansen, H ^a   De Rosa, C T ^a   Mumtaz, M ^a  

^a AGENCY FOR TOXIC SUBSTANCES AND DISEASE REGISTRY   (United States)

^b U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

Computational toxicology; PCBs; Polychlorinated biphenyls; QSAR; SAR

Indexed keywords

POLYCHLORINATED BIPHENYL;

ANIMAL; ARTICLE; FEMALE; METABOLISM; MOUSE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT;

ANIMALS; FEMALE; MICE; POLYCHLORINATED BIPHENYLS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS;

EID: 56149095273     PISSN: 03784274     EISSN: 18793169     Source Type: Journal    
DOI: 10.1016/j.toxlet.2008.06.870     Document Type: Article

References (74)

1. Accelrys, 2006. TOPKAT User Guide 6.2. Accelrys, Inc., Burlington, MA.
2. Anderson, L.M., Beebe, L.E., Fox, S.D., 1991. Promotion of mouse lung tumors by bioaccumulated polychlorinated aromatic hydrocarbons. Exp. Lung Res. 17, 455-471.
3. Anderson, L.M., Logsdon, D., Ruskie, S., 1994. Promotion by polychlorinated biphenyls of lung and liver tumors in mice. Carcinogenesis 15 (10), 2245-2248.
4. Anderson, L.M.,Ward, J.M., Fox, S.D., 1986. Effects of a single dose of polychlorinated biphenyls to infant mice on N-nitrosodimethylamine-initiated lung and liver tumors. Int. J. Cancer 38, 109-116.
5. Aoki, Y., 2001. Polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins, and polychlorinated dibenzofurans as endocrine disrupters-what we have learned from Yusho disease. Environ. Res. 86, 2-11.
6. Arif, J.M., Hans-Joachim, J.M., Lehmler, H.J., Robertson, L.W., Gupta, R.C., 2003. Interaction of benzoquinone- and hydroquinone-derivatives of lower chlorinated biphenyls with DNA and nucleotides in vitro. Chem.-Biol. Interact. 142 (3), 307-316.
7. Ashby, J., Paton, D., 1993. The influence of chemical structure on the extent and sites of carcinogenesis for 522 rodent carcinogens and 55 different human carcinogens exposures. Mutat. Res. 286, 3-74.
8. ATSDR, 2000. Toxicological Profile for Polychlorinated Biphenyls. Agency for Toxic Substances and DiseaseRegistry,U. S. Department of Health andhumanServices, Public Health Service, Atlanta, GA.
9. ATSDR, 2007. CERCLA, 2005. Priority List of Hazardous Substances. http://www.atsdr.cdc.gov/cercla/07list.html.
10. Bager, Y., Kato, Y., Kenne, K., Wärngard, L., 1997. The ability to alter the gap junction protein expression outside GST-P positive foci in liver of rats was associated to the tumor promotion potency of different polychlorinated biphenyls. Chem. Biol. Interact. 103, 199-212.
11. Barratt, M.D., Rodford, R.A., 2001. The computational prediction of toxicity. Curr. Opin. Chem. Biol. 5, 383-388.
12. Beebe, L.E., Kim, Y.E., Amin, S., 1993. Comparison of transplacental and neonatal initiation of mouse lung and liver tumors by N-nitrosodimethylamine (NDMA) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and promotability by a polychlorinated biphenyls mixture (Aroclor 1254). Carcinogenesis 14 (8), 1545-1548.
13. Benigni, R., Passerini, L., 2002. Carcinogenicity of the aromatic amines: from structure-activity relationships to mechanisms of action and risk assessment. Mutat. Res. 511, 191-206.
14. Bro-Rasmussen, F., 1996. Contamination by persistent chemicals in food chain and human health. Sci. Total Environ. 188, 45-60.
15. Brouwer, A., Longnecker, M.P., Birnbaum, L.S., Cogliano, J., Kostyniak, P., Moore, J., Schantz, S., Winneke, G., 1999. Characterization of potential endocrine-related health effects at low-dose levels of exposure to PCBs. Environ. Health Perspect. 107, 639-649.
16. Buchmann, A., Ziegler, S., Wolf, A., 1991. Effects of polychlorinated biphenyls in rat liver: correlation between primary subcellular effects and promoting activity. Toxicol. Appl. Pharmacol. 111, 454-468.
17. Carpenter, D.O., 1998. Polychlorinated biphenyls and human health. Int. J. Occup. Med. Environ. Health 11, 291-303.
18. CDC, 2005. Third National Report on Human Exposure to Environmental Chemicals. US Department of Health and Human Services, Centers for Disease Control and Prevention, National Center for Environmental Health, Division of Laboratory Sciences, Atlanta, GA. http://elib2.cdc.gov:2087/exposurereport (online).
19. Cogliano, V.J., 1998. Assessing the cancer risk from environmental PCBs. Environ. Health Perspect. 106, 317-323.
20. Combes, R.D., Judson, P., 1995. The use of artificial intelligence systems for predicting toxicity. Pestic. Sci. 45, 179-194.
21. Crettaz, P., 2003. SAR and QSAR used in aweight of evidence approach for evaluating the effects on human health of pesticides. Toxicol. Lett. 144 (Suppl. 1, 28, and 52).
22. Cronin, M.T., Jaworska, J.S.,Walker, J.D., Comber,M.H.,Watts, C.D.,Worth, A.P., 2003. Use of QSARs in international decision-making frameworks to predict health effects of chemical substances. Environ. Health Perspect. 111, 1391-1401.
23. Dearden, J.C., 1990. Physico-chemical descriptors. In: Karcher,W., Devillers, J. (Eds.), Practical Applications of Quantitative Structure-Activity Relationships (QSAR) in Environmental Chemistry and Toxicology. Kluwer, Dordrecht, pp. 25-29.
24. Deml, E., Oesterle, D., 1982. Sex-dependent promoting effect of polychlorinated biphenyls on enzymealtered islands induced by diethylnitrosamine in rat liver. Carcinogenesis 3, 1449-1453.
25. Enslein, K., Gombar, V.K., Blake, B.W., 1994. Use of SAR in computer-assisted prediction of carcinogenicity and mutagenicity of chemicals by the TOPKAT program. Mutat. Res. 305, 47-61.
26. Espandiari, P., Glauert, H.P., Lehmler, H.J., Lee, E.Y., Srinivasan, C., Robertson, L.W., 2003. Polychlorinated biphenyls as initiators in liver carcinogenesis: resistant hepatocyte model. Toxicol. Appl. Pharmacol. 186, 55-62.
27. Gombar, V.K., Enslein, K., Blake, B.W., 1993. Carcinogenicity of azathioprine: an S-AR investigation. Mutat. Res. 302, 7-12.
28. Greene, N., 2002. Computer systems for the prediction of toxicity: an update. Adv. Drug Del. Rev. 54, 417-431.
29. Haag-Grönlund, M., Johansson, N., Fransson-Stehen, R., Hakanson, H., Scheu, G., Wärngard, L., 1998. Interactive effects of three structurally different polychlorinated biphenyls in a rat liver tumor promotion bioassay. Toxicol. Appl. Pharmacol. 152, 153-165.
30. Hansen, L.G., 1998. Stepping backward to improve assessment of PCB congener toxicities. Environ. Health Perspect. 106, 171-187.
31. Hemming, H., Flodstrom, S., Warngard, L., 1993. Relative tumor promoting activity of three polychlorinated biphenyls in rat liver. Eur. J. Pharmacol. 248 (2), 163-174.
32. Hirose, M., Shirai, T., Tsuda, H., et al., 1981. Effect of Phenobarbital, polychlorinated biphenyl and sodium saccharin on hepatic and renal carcinogenesis in unilaterally nephrectomized rats given N-ethyl-Nhydroxyethylnitrosamine orally. Carcinogenesis 2, 1299-1302.
33. Hsia, M.T.S., Lin, F.S.D., Allen, J.R., 1978. Comparative mutagenicity and toxic effects of 2,5,2',5'-tetrachlorobiphenyl and itsmetabolites in bacterial and mammalian test systems. Res. Commun. Chem. Pathol. Pharmacol. 21, 485-496.
34. IARC, 1997. Working Group on the Evaluation of Carcinogenic Risks to Humans, polychlorinated dibenzo-para-dioxins and polychlorinated dibenzofurans. IARC Monogr. Eval. Carcinog. Risks Hum. 69, 1-631.
35. IRIS, 2000. Integrated Risk Information System. Polychlorinated Biphenyls (PCBs). U.S. Environmental Protection Agency, http://www.epa.goc/ngispgm3/iris/subst/0294.htm.
36. Ito, N., Nagasaki, H., Arai, M., 1973. Histopathologic studies on liver tumorigenesis in mice by technical polychlorinated biphenyls and its promoting effect on liver tumors induced by benzene hexachloride. J. Natl. Cancer Inst. 51, 1637-1646.
37. Jaworska, J.S., Comber, M., Auer, C., Van Leeuwen, C.J., 2003. Summary of a workshop on regulatory acceptance of (Q)SARs for human health and environmental endpoints. Environ. Health Perspect. 111, 1358-1360.
38. Kang, K.S., Wilson, M., Hayashi, T., Chang, C.C., Trosko, J.E., 1996. Inhibition of gap junctional intercellular communication in normal human breast epithelial cells after treatment with pesticides, PCBs, and PBBs, alone or in mixture. Environ. Health Perspect. 104, 192-200.
39. Kimbrough, R.D., 1995. Polychlorinated biphenyls (PCBs) and human health: an update. Crit. Rev. Toxicol. 25, 133-163.
40. Kimbrough, R.D., Linder, R.E., 1974. Induction of adenofibrosis and hepatomas in the liver of Balb/cJ mice by polychlorinated biphenyls (Aroclor 1254). J. Natl. Cancer Inst. 53, 547-552.
41. Kimura, N.T., Kanematsu, T., Baba, T., 1976. Polychlorinated biphenyl(s) as a promotor in experimental hepatocarcinogenesis in rats. Z Krebsforsch. 87, 257-266.
42. Kunz, S., Schwarz, M., Schilling, B., Päpke, O., Lehmler, H.-J., Robertson, L.W., Schrenk, D., Schmitz, H.J., 2006. Tumor promoting potency of PCBs 28 and 101 in rat liver. Toxicol. Lett. 164 (2), 133-143.
43. Kutz, F.W., Wood, P.H., Bottimore, D.P., 1991. Organochlorine pesticides and polychlorinated biphenyls in human adipose tissue. Rev. Environ. Contam. Toxicol. 60, 115-120.
44. Laib, R.J., Rose, J., Brunn, H., 1991. Hepatocarcinogenicity of PCB congeners: I. Initiation and promotion of enzyme-altered rat liver foci by 2,2',4,5'-tetra- and 2,2',4,4',5,5'-hexachlorobiphenyl. Toxicol. Environ. Chem. 34, 19-22.
45. Lehmann, L.L., Esch, H.A., Kirby, P.W., Robertson, L., Ludewig, G., 2007. 4-Monochlorobiphenyl (PCB3) induces mutations in the livers of transgenic Fisher 344 rats. Carcinogenesis 28 (2), 471-478.
46. Ludewig, G., 2001. Cancer initiation by PCBs. In: Robertson, L.W., Hansen, L.G. (Eds.), PCBs Recent Advances in Environmental Toxicology and Health Effects. University Press of Kentucky, Lexington, pp. 337-354.
47. Ludewig, G., Lehmann, L., Esch, H., Robertson, L.W., 2008. Metabolic activation of PCBs to carcinogens in vivo-a review. Environ. Toxicol. Pharmacol. 25 (2), 241-246.
48. Machala, M., Bláha, L., Vondrácek, J., Trosko, J.E., Scott, J.,Upham, B.L., 2003. Inhibition of gap junctional intercellular communication by noncoplanar polychlorinated biphenyls: inhibitory potencies and screening for potential mode(s) of action. Toxicol. Sci. 76, 102-111.
49. McLean, M.R., Robertson, L.W., Gupta, R.C., 1996. Detection of PCB adducts by the 32P-postlabeling technique. Chem. Res. Toxicol. 9 (1), 165-171.
50. Mayes, B.A., McConnell, E.E., Neal, B.H., 1998. Comparative carcinogenicity in Sprague-Dawley rats of the polychlorinated biphenyl mixtures Aroclors 1016, 1242, 1254, and 1260. Toxicol. Sci. 41, 62-76.
51. Moudgal, C.J., Lipscomb, J.C., Bruce, R.M., 2000. Potential health effects of drinking water disinfection by-products using quantitative structure toxicity relationship. Toxicology 147, 109-131.
52. Mumtaz, M.M., Knauf, L.A., Reisman, D.J., Peirano, W.B., DeRosa, C.T., Gombar, V.K., Enslein, K., Carter, J.R., Blake, B.W., Huque, K.I., Ramanujam, V.M.S., 1995. Assessment of effect levels of chemicals from quantitative structure-activity relationship (QSAR) models. I. Chronic lowest-observed-adverse-effect level (LOAEL). Toxicol. Lett. 79, 131-143.
53. NTP, 2007. National Toxicology Program. 11th Annual Report on Carcinogens. http://ehis.niehs.nih.gov/roc/toc9.html.
54. Oakley, G.G., Devanaboyina, U., Robertson, L.W., Gupta, R.C., 1996. Oxidative DNA damage induced by activation of polychlorinated biphenyls (PCBs): implications for PCB-induced oxidative stress in breast cancer. Chem. Res. Toxicol. 9, 1285-1292.
55. Oesterle, D., Deml, E., 1983. Promoting effect of polychlorinated biphenyls on development of enzyme-altered islands in livers of weanling and adult rats. J. Cancer Res. Clin. Oncol. 105, 141-147.
56. Preston, B.D., Miller, E.C., Miller, J.A., 1985. The activities of 2,2',5,5'-tetrachlorobiphenyl, its 3,4-oxide metabolite, and 2,2',4,4'-tetrachlorobiphenyl in tumor induction and promotion assays. Carcinogenesis 6 (3), 451-453.
57. Rogan, W.J., Gladen, B.C., McKinney, J.D., Carreras, N., Hardy, P., Thullen, J., Tigelstad, J., Tully, M., 1987. Polychlorinated biphenyls (PCBs) and dichlorodiphenyl dichloroethane (DDE) in human milk: effects on growth, morbidity and duration of lactation. Am. J. Publ. Health 77, 1294-1297.
58. Rose, N., Laib, R.J., Brunn, H., 1985. Biotransformation and toxicity of polychlorinated biphenyls (PCB's): investigation of initiating and promoting activities of 2,2',4,5'-tetra- and 2,2',4,4',5,5'- hexachlorobiphenyl. Naunyn-Schmiedebergs Arch. Pharmacology 330 (Suppl.), R21.
59. Safe, S.H., 1994. Polychlorinated biphenyls (PCBs): environment impact, biochemical and toxic responses, and implications for risk assessment. Crit. Rev. Toxicol. 24, 87-149.
60. Safe, S., 1989. Polychlorinated biphenyls (PCBs): mutagenicity and carcinogenicity. Mutat. Res. 220, 31-47.
61. Sargent, L., Dragan, Y.P., Erickson, C., et al., 1991. Study of the separate and combined effects of the nonplanar 2,5,2',5'- and the planar 3,4,3',4'-tetrachlorobiphenyl in liver and lymphocytes in vivo. Carcinogenesis 12, 793-800.
62. Schoeny, R., 1982. Mutagenicity testing of chlorinated biphenyl and chlorinated dibenzofurans. Mutat. Res. 101, 45-56.
63. Schoeny, R.S., Smith, C.C., Loper, J.C., 1979. Non-mutagenicity for Salmonella of the chlorinated hydrocarbons Arochlor 1254, 1,2,4,-trichlorbenzene, mirex and kepone. Mutat. Res. 68, 125-132
64. Silberhorn, E.M., Glauert, H.P., Robertson, L.W., 1990. Carcinogenicity of polyhalogenated biphenyls: PCBs and PBBs. Crit. Rev. Toxicol. 20, 440-496.
65. Sipes, I.G., Schnellmann, R.G., 1987. Biotransformation of PCBs: metabolic pathways and mechanisms. In: Safe, S., Hutzinger, O. (Eds.), Polychlorinated Biphenyls (PCBs):Mammalianand Environmental Toxicology. Springer-Verlag, Heidelberg, pp. 97-110.
66. Stevens, Y.W., Cibulas, W., De Rosa, C.T., 1998. Voluntary research program of the Agency for Toxic Substances and Disease Registry. Environ. Law Pract. 6 (2), 28-32.
67. Swierenga, S.H.H., Yamasaki, H., Piccoli, C., Robertson, L., Bourgon, L., Marceau, N., Fitzgerald, D.J., 1990. Effects on intercellular communication in human keratinocytes and liver-derived cells of polychlorinated biphenyl congeners with differing in vivo promotion activities. Carcinogenesis 11, 921-926.
68. Van der Plas, S.A., Sundberg, H., van den Berg, H., Scheu, G., Wester, P., Jensen, S., Bergman, A., Boer, J., Koeman, J., Brouwer, A. 2000. Contribution of planar (0-1 ortho) and nonplanar (2-4 ortho) fractions of Aroclor 1260 to the induction of altered hepatic foci in female Sprague-Dawley rats. Toxcol. Appl. Pharmacol. 169, 255-268.
69. Walker, J.D., Carlsen, L., Jaworska, J., 2003. Improving opportunities for regulatory acceptance of QSARs: the importance of model domain, uncertainty, validity and predictability. QSAR Comb. Sci. 22 (3), 346-350.
70. WHO, 1993. Polychlorinated Biphenyls and Terphenyls (Environmental Health Criteria 140), second ed. United Nations Environment Programme, International Labor Organization, World Health Organization, Geneva.
71. Winneke, G.J.,Walkowiak, J., Lilienthal, H., 2002. PCB-induced neurodevelopmental toxicity in human infants and its potential mediation by endocrine dysfunction. Toxicology 181-182, 161-165.
72. Wong, A., Basrur, P.K., Safe, S., 1979. The metabolically mediated DNA damage and subsequence repair by 4-chlorobiphenyl in Chinese hamster ovary cells. Res. Commun. Chem. Pathol. Pharmacol. 24, 543-570.
73. Wyndham, C., Devenish, J., Safe, S., 1976. The in vitro metabolism, macromolecular binding and bacterial mutagenicity of 4-chlorobiphenyl, a model PCB substrate. Res. Commun. Chem. Pathol. Pharmacol. 15, 563-570.
74. Zeiger, E., Ashby, J., Bakale, G., Enslein, K., Klopman, G., Rosenkranz, H.S., 1996. Prediction of salmonella mutagenicity. Mutagenesis 11 (5), 471-484.