Biochemical and molecular changes at the cellular level in response to exposure to environmental estrogen-like chemicals

Journal of Toxicology and Environmental Health

Volumn 50, Issue 1, 1997, Pages 1-30

  Roy, Deodutta ^a   Palangat, Murali ^a   Chen, Chiao Wen ^a   Thomas, Ronald D ^a   Colerangle, John ^a   Atkinson, Alfonzo ^a   Yan, Zhi Jie ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; ALKYLPHENOL; CAMPHECLOR; CHLORDECONE; CHLOROFLUOROCARBON; CHLORPHENOTANE; DICOFOL; DIELDRIN; DIETHYLSTILBESTROL; DNA POLYMERASE; ENDOSULFAN; ENVIRONMENTAL CHEMICAL; ESTRADIOL; ESTROGEN; INDUSTRIAL CHEMICAL; METHOXYCHLOR; PARATHION; PESTICIDE; PHTHALIC ACID ESTER; POLYBROMINATED BIPHENYL; POLYCHLORINATED BIPHENYL; POLYCHLORINATED DIBENZODIOXIN; RNA POLYMERASE; SOMATOMEDIN C RECEPTOR; STYRENE; ZEARALENONE; ZERANOL;

ANIMAL EXPERIMENT; CARCINOGENICITY; DNA BINDING; DNA DAMAGE; DNA REPAIR; GENOTOXICITY; HUMAN; NONHUMAN; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; REPRODUCTIVE TOXICITY; REVIEW; SYRIAN HAMSTER; TERATOGENICITY;

ANIMALS; CELL CYCLE; CELL TRANSFORMATION, NEOPLASTIC; DIETHYLSTILBESTROL; DNA DAMAGE; DNA REPAIR; ENVIRONMENTAL POLLUTANTS; ESTROGENS; ESTROGENS, NON-STEROIDAL; HUMANS; NEOPLASMS; NUCLEAR PROTEINS; OXIDATION-REDUCTION; PHENOLS; REPRODUCTION;

ANIMALIA; CRICETINAE; MESOCRICETUS AURATUS;

EID: 0031056040     PISSN: 00984108     EISSN: None     Source Type: Journal    
DOI: 10.1080/009841097160573     Document Type: Article

References (180)

1. Adams, S. P., and Notides, A. G. 1986. Metabolism and irreversible binding of diethylstilbestrol in the kidney of the Syrian golden hamster. Biochem. Pharmacol. 35:2171-2178.
2. Aizu-Yokota, E., Ichinoeski, K., and Sato, Y. 1994. Microtubule disruption induced by estradiol in estrogen receptor-positive and -negative human breast cell lines. Carcinogenesis 15:1875-1879.
3. Ashby, J., and Tennant, R. W. 1988. Chemical structure, Salmonella mutagenicity and extent of carcinogenicity as indicators of genotoxic carcinogens. Mutat. Res. 204:17-115.
4. Atkinson, A. 1995. The genotoxicity and reproductive toxicity of bisphenol A. PhD thesis, University of Alabama at Birmingham.
5. Atkinson, A., and Roy, D. 1995a. In vivo genotoxicity of bisphenol A. Environ. Mutagen. 26:60-66.
6. Atkinson, A., and Roy, D. 1995b. In vitro conversion of estrogenic compound bisphenol A to DNA binding metabolites. Biochem. Biophys. Res. Commun. 210:424-433.
7. Banerjee, S. K., and Roy, D. 1996. Is exposure of cells to environmental estrogen-like chemicals able to induce telomeric associations? Proc. Am. Assoc. Cancer Res. 37:547.
8. Banerjee, S. H., Banerjee, S., Li, S. A., and Li, J. J. 1992. Cytogenetic changes in renal neoplasms and during estrogen-induced carcinogenesis. In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and S. A. Li, pp. 247-251. New York: Springer-Verlag.
9. Banerjee, S. K., Banerjee, S., Li, S. A., and Li, J. J. 1994. Induction of chromosome aberrations in Syrian hamster renal cortical cells by various estrogens. Mutat. Res. 311:191-197.
10. Beleh, M. A., Brueggemeier, R. W., Chang, G. C., and Lin, Y. C. 1993. Biosynthesis and secretion of growth factor proteins by kidney cells from DES-treated Syrian hamsters. Biochem. Biophys. Res. Commun. 190:1029-1036.
11. Bergeron, J. M., Crews, D., and McLachlan, J. A. 1994. PCBs as environmental estrogens: Turtle sex determination as a biomarker of environmental contamination. Environ. Health Perspect. 102:780-781.
12. Bern, H. A. 1992. Diethylstilbestrol (DES) syndrome: Present status of animal and human studies. In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and S. A. Li, pp. 1-8. New York: Springer-Verlag.
13. Birnbaum, L. S. 1994. Endocrine effects of prenatal exposure to PCBs, dioxins and other xenobi-otics: Implications for policy and future research. Environ. Health Perspect. 102:676-679.
14. Bond, G. P., McGinnin, P. M., Cheever, K. L., Harris, S. J., Plotnick, H. B., and Niemeier, R. W. 1980. Reproductive effects of bisphenol A. Proc. Soc. Toxicol. 19:A23.
15. Bornstein, J., Adam, E., Adler-Storthz, K., and Kaufman, R. H. 1988. Development of cervical and vaginal squamous cell neoplasia as a late consequence of in utero exposure to diethylstilbestrol. Obstet. Gynecol. Survey 43:15-21.
16. Brotons, J. A., Oleo-Serrano, M. F., Villalobos, M., Pedraza, V., and Olea, N. 1995. Xeno-estrogens released from lacquer coatings in food cans. Environ. Health Perspect. 103:608-612.
17. Brueggemeier, R. W., Kimball, J. G., and Kraft, F. 1984. Estrogen metabolism in rat liver microsomal and isolated hepatocyte preparations. I. Metabolic formation and irreversible binding to cellular macromolecules. Biochem. Pharmacol. 33:3853-3859.
18. Burroughs, C. D., Mills, K. T., and Bern, H. A. 1990a. Long term genital tract changes in female mice treated neonatally with coumestrol. Reprod. Toxicol. 4:127-135.
19. Burroughs, C. D., Mills, K. T., and Bern, H. A. 1990b. Reproductive abnormalities in female mice exposed neonatally to various doses of coumestrol. J. Toxicol. Environ. Health 30:105-122.
20. Carlsen, E., Giwercman, A., Keiding, N., and Skakkebaek, N. E. 1992. Evidence for decreasing quality of semen during past 50 years. Br. Med. J. 304:609-613.
21. Chen, C. W., and Roy, D. 1995. Activation of plasma membrane IGF-I receptor tyrosine phosphorylation by stilbene estrogen exposure. Carcinogenesis 16:1339-1344.
22. Chen, C. W., and Roy, D. 1996. Up-regulation of nuclear IGF-I receptor by short term exposure of stilbene estrogen, diethylstilbestrol. Mol. Cell. Endocrinol. 118:1-8.
23. Chen, C. W., Oberley, T. D., and Roy, D. 1996. Inhibition of stilbene estrogen-induced cell proliferation through the modulation of insulin-like growth factor-I receptor. Fund. Appl. Toxicol. 30:130.
24. Cody, P. 1991. Your research and our lives. In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and S. A. Li, pp. 268-271. New York: Springer-Verlag.
25. Coe, J. E., Ishak, K. G., and Ross, M. J. 1990. Estrogen induction of hepatocellular carcinomas in Armenian hamsters. Hepatology 11:570-577.
26. Cohn, W. J., Boylan, J. J., Blanke, R. V., Farris, M. W., Howell, J. R., and Guzellian, P. S. 1978. Treatment of chlordecone (Kepone) toxicity with cholestyramine: Results of a case controlled clinical trial. N. Engl. J. Med. 298:243-248.
27. Colborn, T., Vom Saal, F. S., and Soto, A. M. 1993. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ. Health Perspect. 101:378-384.
28. Colerangle, J., and Roy, D. 1995a. Perturbations of cell cycle kinetics in the mammary gland in response to exposure of stilbene estrogen, diethylstilbestrol. Cancer Lett. 94:55-63.
29. Colerangle, J., and Roy, D. 1995b. Exposure of rats to environmental estrogenic compound nonylphenol alters cell cycle kinetics in the mammary gland. Toxicologist 15:233.
30. Colerangle, J., and Roy, D. 1995c. The antiproliferative effect of luteolin against diethylstilbestrol-induced cell proliferation in the mammary gland of rat. Int. J. Oncol. 7:1361-1366.
31. Colerangle, J., and Roy, D. 1996a. Exposure of bisphenol A, an environmental estrogenic compound, produces adverse effects in the mammary gland. Fund. Appl. Toxicol. 30:133.
32. Colerangle, J., and Roy, D. 1996b. Alterations in telomere length in mammary tissue of Noble rats exposed to environmental estrogens. Proc. Am. Assoc. Cancer Res. 37:543.
33. Colerangle, J., and Roy, D. 1996c. Exposure of rats to environmental estrogenic compound nonylphenol to Noble rats alters cell cycle kinetics in the mammary gland. Endocrine 4:115-122.
34. Cortes-Vizcaino, V., and Llombart-Bosch, A. 1993. Estrogen and progesterone receptors in the diethylstilbestrol-induced kidney neoplasms of the Syrian golden hamster: Correlation with histopathology and tumoral stages. Carcinogenesis 14:1215-1219.
35. Cutts, J. H.1964. Estrone-induced mammary tumors in the rat. II. Effect of alterations in the hormonal environment on tumor induction, behavior, and growth. Cancer Res. 24:1124-1130.
36. Cutts, J. H., and Noble, R. L. 1964. Estrone-induced mammary tumors in the rat. I. Induction and behavior of tumors. Cancer Res. 24:1116-1123.
37. Danielian, P. S., White, R., Hoare, S. A., Fawell, S. A., and Parker, M. G. 1993. Identification of residues in estrogen receptor that confer differential sensitivity to estrogen and hydroxyta-moxifen. Mol. Endocrinol. 7:232-240.
38. Davis, D. L., Bradlow, H. L., Wolff, M., Woodruff, T., Hoel, D.G., and Anton-Cu lver, H. 1993. Medical hypothesis: Xenoestrogens as preventable causes of breast cancer. Environ. Health Perspect. 101:372-377.
39. De Sario, A., Vagnarelli, P., and DeCarli, L. 1990. Aneuploidy assay on diethylstilbestrol by means of in situ hybridization of radioactive and biotinylated probes on interphase nuclei. Mutat. Res. 243:127-131.
40. DiAugustine, R. P., Snedeker, S. M., and Jahnke, G. D. 1992. Functional aspects of EGF-like peptides in ovarian steroid responsive organs. In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and S. A. Li, pp. 172-181. New York: Springer-Verlag.
41. Dodds, E. C., and Lawson, W. 1938. Molecular structure in relation to oestrogenic activity. Compounds without a phenanthrene nucleus. Proc. R. Soc. Biol. 125:222-232.
42. Eastmond, D. A., and Pinkel, D. 1990. Detection of aneuploidy and aneuploidy-inducing agents in human lymphocytes using fluorescence in situ hybridization with chromosome-specific DNA probes. Mutat. Res. 234:303-318.
43. Ebert, R., Barrett, J. C., Wiseman, R. W., Pechan, R., Reiss, E., Rollich, G., and Schiffmann, D. 1990. Activation of cellular oncogenes by chemical carcinogens in Syrian hamster embryo fibroblasts. Environ. Health Perspect. 88:175-178.
44. Egle, J. L., Fernandez, S. B., Guzelian, P. S., and Borzelleca, J. F. 1978. Distribution and excretion of chlordecone (Kepone) in the rat. Drug. Metab. Dispos. 6:91-95.
45. Endo, S., Kodama, S., Newbold, R., McLachlan, J., and Barrett, J. C. 1994. Cytogenetic analysis of murine cells from diethylstilbestrol-induced uterine endometrial adenocarcinomas. Cancer Genet. Cytogenet. 74:99-103.
46. Feuer, E. G., and Wun, L.-M. 1992. How much of the recent rise in breast cancer can be explained in mammography utilization? A dynamic population model approach. Am. J. Epidemiol. 136:1423-1436.
47. Gilbert, J., Shepherd, M. K., Startin, J. R., and Wallwork, M. A. 1982. Identification by gas chromatography-mass spectrometry of vinylchloride oligomers and other low molecular weight components in poly (vinylchloride) resins for food package applications. J. Chromatogr. 237:249-261.
48. Giwercman, A., Carlsen, E., Keiding, N., and Skakkebaek, N. E. 1993. Evidence for increasing incidence of abnormalities of the human testis: A review. Environ. Health Perspect. (Suppl.) 102:65-71.
49. Gladeck, A., and Liehr, J. G. 1989. Mechanism of genotoxicity of diethylstilbestrol in vivo. J. Biol. Chem. 264:16847-16852.
50. Gray, K., Eitzman, B., Raszmann, K., Steed, T., Geboff, A., McLachlan, J., and Bidwell, M. 1995. Coordinate regulation by diethylstilbestrol of the platelet-derived growth factor-A (PDGF-A) and B-subunits and the PDGF-receptor a- and p-subunits in the mouse uterus and vagina: Potential mediators of estrogen action. Endocrinology 136:2325-2340.
51. Hammond, B., Katzenellenbogen, B. S., Krauthammer, N., and McConnell, J. 1979. Estrogenic activity of the insecticide chlordecone (Kepone) and interaction with uterine estrogen receptors. Proc. Natl. Acad. Sci. USA 76:6641-6645.
52. Hardin, B. D., Bond, G. P., Sikov, M. R., Andrew, F. D., Beililes, R. P., and Niemeier, R. W. 1981. Testing of selected workplace chemicals for teratogenic potential. Scand. J. Work Environ. Health (Suppl.) 7:66-75.
53. Henderson, B. E., Ross, R. R., and Pike, M. 1993. Hormonal chemoprevention of cancer in women. Science 259:633-638.
54. Hertz, R. 1985. The estrogen problem—Retrospect and prospect. In Estrogens in the environment. II. Influences on development, ed. J. A. McLachlan, pp. 1-11. New York: Elsevier.
55. Ho, S. M., and Roy, D. 1994. Sex hormone-induced increases in DNA strand breakage and lipid peroxidation in the dorsolateral prostate of Noble rats. Cancer Lett. 84:155-164.
56. Holland, M., and Roy, D. 1995. Estrone-induced cell proliferation and differentiation in the mammary gland of the female Noble rats. Carcinogenesis 16:1955-1961.
57. Holland, M., and Roy, D. 1996. Antiproliferative activity of naturally occurring edible plant flavone-induced cell proliferation in the mammary gland of Noble rats. In Hormonal carcinogenesis II, eds. J. J. Li, S. A. Li, J.-A. Gustafsson, S. Nandi, and L. I. Sekely, pp. 471-474. New York: Springer-Verlag.
58. Hunter, D. J., and Kelsey, K. T. 1993. Pesticide residues and breast cancer: The harvest of a silent spring. J. Natl. Cancer lnst. 85:598-599.
59. Hyder, S. M., Chiappetta, C., Kirkland, J. L., Lin, T. H., Loose-Mitchell, D. S., Murphy, L., Orengo, C. A., Tipins, U., and Stancel, G. M. 1992. Estrogen regulation of protooncogene expression. In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and S. A. Li, pp. 193-200. New York: Springer-Verlag.
60. IARC. 1979. Sex Hormones. IARCMonogr. Eval. Carcinogen. Risk Chem. Hum. 21:173-221.
61. Iguchi, T., Edery, M., Tasi, P. S., Ozawa, S., Sato, T., and Bern, H. A. 1993. Epidermal growth factor receptor levels in reproductive organs of female mice exposed neonatally to diethyl-stilbestrol. Proc. Soc. Exp. Biol. Med. 204:110-116.
62. Imagawa, I., Bandyopadhyay, G. K., and Nandi, S. 1991. Regulation of mammary epithelial cell growth in mice and rat. Endocrinol. Rev. 11:494-523.
63. Ivett, J. L., Brown, B. M., Anderson, B. C., Resnick, M. A., and Zeiger, E. 1989. Chromosomal aberration and sister chromatid exchange tests in Chinese hamster ovary cells in vitro results with 15 chemicals. Environ. Mol. Mutagen. 14:165-197.
64. Jensen, E. J. 1992. Current concepts of sex hormone action. In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and S. A. Li, pp. 43-50. New York: Springer-Verlag.
65. Jobling, S., Reynolds, T., White, R., Parker, M. G., and Sumpter, J. P. 1995. A variety of environmentally persistent chemicals, including some phthalate plasticizers, are weakly estrogenic. Environ. Health Perspect. 103:582-587.
66. Kelce, W. R., Stone, C. R., Laws, S. C., Gray, L. E., Kemppainen, J. A., and Wilson, E. M. 1995. Persistent DDT metabolite p, p'-DDE is a potent androgen receptor antagonist. Nature 375:581-585.
67. Kirkman, H., and Bacon, R. 1952. Estrogen-induced tumors of the kidney I. Incidence of renal tumors in intact and gonadectomized male golden hamsters treated with diethylstilbestrol. J. Natl. Cancer Inst. 13:745-755.
68. Knaak, J. B., and Sullivan, L. J. 1966. Metabolism of bisphenol A in the rat. Toxicol. Appl. Pharmacol. 8:175-184.
69. Kodama, M., Inoue, F., Kaneko, M., Oda, T., and Sato, Y. 1993. Formation of free radicals and active oxygen species from diethylstilbestrol and its derivatives. Anticancer Res. 13:1209-1213.
70. Korah, R. M., and Humayun, M. Z. 1993. Mutagenic and recombinagenic effects of diethylstilbestrol quinone. Mutat. Res. 289:205-214.
71. Krieger, N., Wolff, M. S., Hiatt, R. A., Rivera, M., Vogelman, J., Vogelman, J., and Orentreich, N. 1994. Breast cancer and serum organochlorine. A perspective study among white, black and Asian women. J. Natl. Cancer Inst. 86:589-599.
72. Krishnan, A. V., Stathis, P., Permuth, S. F., Tokes, L., and Feldman, D. 1993. Bisphenol-A: An estrogenic substance is released from polycarbonate flask during autoclaving. Endocrinology 132:2279-2286.
73. Kutz, F. W., Wood, W. H., and Bottimore, D. P. 1991. Organochlorine pesticides and polychlorinated biphenyls in human adipose tissue. Rev. Environ. Contam. Toxicol. 120:1-82.
74. Li, J. J., and Li, S. A. 1984. Estrogen-induced tumorigenesis in hamsters: role for hormonal and carcinogenic activities. Arch. Toxicol. 55:110-116.
75. Li, J. J., and Li, S. A. 1987. Estrogen carcinogenesis in hamster tissues: role of metabolism. Fed. Proc. 46:1858-1863.
76. Li, J. J., and Li, S. A. 1990. Estrogen carcinogenesis in hamster tissues: A critical review. Endocrine Rev. 11:524-531.
77. Li, J. J., Li, S. A., and Cuthbertson, T. L. 1979. Nuclear retention of steroid hormone receptor classes in the hamster renal carcinoma. Cancer Res. 39:2647-2651.
78. Li, J. J., Li, S. A., Klicka, J. K., and Heller, J. A. 1985. Some biological and toxicological studies of various estrogen mycotoxins and phytoestrogens. In Estrogens in the environment. II. Influences on development, ed. J. A. McLachlan, pp. 168-186. New York: Elsevier.
79. Li, J. J., Gonzalez, A., Banerjee, S., and Banerjee, S. K. 1993. Estrogen carcinogenesis in the hamster kidney: role of cytotoxicity and cell proliferation. Environ. Health Perspect. (Suppl.) 101:259-264.
80. Li, J. J., Li, S. A., Oberley, T. D., and Parsons, J. A. 1995. Carcinogenic activities of various steroidal and nonsteroidal estrogens in the hamster kidney: Relation to hormonal activity and cell proliferation. Cancer Res. 55:4347-4351.
81. Li, Y., and Trush, M. A. 1994. Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism. Cancer Res. (Suppl.) 54:1995-1998.
82. Liehr, J. G. 1983. 2-Fluoroestradiol: Separation of estrogenicity from carcinogenicity. Mol. Pharmacol. 23:278-282.
83. Liehr, J. G. 1990. Genotoxic effects of estrogens. Mutat. Res. 238:269-276.
84. Liehr, J. G., and Roy, D. 1990. Free radical generation by redox cycling of estrogen. Free Radical Biol. Med. 8:415-423.
85. Liehr, J. G., Ulubelen, A. A., and Strobel, H. W. 1986. Cytochrome P450-mediated redox cycling of estrogens. J. Biol. Chem. 261:16865-16870.
86. Liehr, J. G., Roy, D., Ari-Ulubelen, A., Bui, Q. D., Weisz, J., and Strobel, W. H. 1990. Target organ specific enhancement of microsomal mediated redox cycling preceding estrogen induced renal carcinogenesis. J. Steroid Biochem. 35:555-560.
87. Liehr, J. G., Chiappetta, C., Roy, D., and Stancel, G. M. 1992a. Elevation of protooncogene messenger RNAs in estrogen-induced kidney tumors in the hamster. Carcinogenesis 13:601-604.
88. Liehr, J. G., Han, W., and Roy, D. 1992b. Lack of inhibition of estrogen-induced renal carcinogenesis by antiestrogens. Cancer Lett. 64:23-29.
89. Lingham, R. B., Stancel, G. M., and Loose-Mitchell, D. S. 1988. Estrogen regulation of epidermal growth factor receptor messenger ribonucleic acid. Mol. Endocrinol. 2:230-235.
90. Malone, K. 1993. Diethylstilbestrol (DES) and breast cancer. Epidemiol. Rev. 15:108-109.
91. Markaverich, B. M., Webb, B., Densmore, C. L., and Gregory, R. R. 1995. Effects of coumestrol on estrogen receptor function and uterine growth in ovariectomized rats. Environ. Health Perspect. 103:574-581.
92. Marselos, M., and Tomatis, L. 1992a. Diethylstilbestrol I: Pharmacology, toxicology, and carcinogenicity in humans. Eur. J. Cancer 28:1182-1189.
93. Marselos, M., and Tomatis, L. 1992b. Diethylstilbestrol II: Pharmacology, toxicology, and carcinogenicity in experimental animals. Eur. J. Cancer 29:149-155.
94. Marshall, E. 1993. Search for a killer: Focus shifts from fat to hormones. Science 259:518-520.
95. McLachlan, J. A. 1993. Functional toxicology: A new approach to detect biologically active xenobiotics. Environ. Health Perspect. 101:386-387.
96. McLachlan, J. A., Newbold, R. R., and Lamb J. C. 1977. Genital tract abnormalities in mice following gestational exposure to DES. Environ. Health Perspect. 20:240-248.
97. McLachlan, J. A., Newbold, R. R., Nelson, K. G., and Korach, K. S. 1992. Control of uterine epithelial growth and differentiation: Implications for estrogen-associated neoplasm. In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and S. A. Li, pp. 43-50. New York: Springer-Verlag.
98. Metzler, M., 1984. Metabolism of stilbene estrogens and steroidal estrogens in relation to carcinogenicity. Arch. Toxicol. 55:104-109.
99. Metzler, M., and McLachlan, J. A. 1978. Oxidative metabolites of diethylstilbestrol in the fetal, neonatal, and adult mouse. Biochem. Pharmacol. 27:1087-1094.
100. Metzler, M., Pfeiffer, E., Kohl, W., and Schnitzler, R. 1992. Interactions of carcinogenic estrogens with microtubular proteins In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and J. J. Li, pp. 86-93. New York: Springer-Verlag.
101. Michnovicz, J. J., and Bradlow, H. L. 1991. Altered estrogen metabolism and excretion in humans following consumption of indole-3-carbinol. Nutr. Cancer 16:59-66.
102. Michnovicz, J. J., and Bradlow, H. L. 1992. Dietary and pharmacological control of estradiol metabolism in humans. Ann. NY Acad. Sci. 290:291-299.
103. Montandon, F., and Williams, G. M. 1994. Comparison of DNA reactivity of the polyphenyl-ethylene hormonal agents diethylstilbestrol, tamoxifen and toremifene in rat and hamster liver. Arch. Toxicol. 68:272-275.
104. Morrissey, R. E., George, J. D., Price, C. J., Tyl, R. W., Marr, M. C., and Kimmel, C. A. 1987. The developmental toxicity of bisphenol-A in rats and mice. Fundam. Appl. Toxicol. 8:571-582.
105. Mueller, G., and Kim, U. H. 1978. Displacement of estradiol from estrogen receptors by simple alkylphenols. Endocrinology 102:1429-1435.
106. Mulheron, G. W., and Schomberg, D. W. 1992. Effects of diethylstilbestrol on rat granulosa cell and the interstitial cell transforming growth factor-beta 2 mRNA expression in vivo: Analysis by reverse transcription polymerase chain reaction. Biol. Reprod. 46:546-550.
107. Nagel, S. C., Thayer, K. A., Boechler, M., Dhar, M., Morellini, F., Taylor, J. A., vom Saal, F. S., and Welshons, W. V. 1995. An in vitro assay to predict the in vivo activity of environmental estrogens. Proc. Soc. Reprod. 28:96.
108. Narayan, S., and Roy, D. 1992. Enhanced expression of protein tyrosine kinases in estrogen-induced kidney tumors in the hamster. Biochem. Biophys. Res. Commun. 186:228-236.
109. Narayan, S., and Roy, D. 1993. Characterization of insulin-like growth factor I receptors in normal and estrogen-induced neoplastic Syrian hamster kidney. Cancer Res. 53:2256-2259.
110. 1Mice. National Toxicology Program Tech. Rep. 215, pp. 1-21.
111. Nelson, K. G., Sakai, Y., Eitzman, B., Steed, T., and McLachlan, J. 1994. Exposure to diethylstilbestrol during a critical development period of the mouse reproductive tract leads to persistent induction of two estrogen-regulated genes. Cell Growth Differentiation 5:595-606.
112. Newbold, R. R., Bullock, B. C., and McLachlan, J. A. 1990. Uterine adenocarcinoma in mice following developmental treatment with estrogens: A model for hormonal carcinogenesis. Cancer Res. 50:7677-7681.
113. Ni, N., and Yager, J. D. 1994. The co-mitogenic effects of various estrogens for TGF-a-induced DNA synthesis in cultured female rat hepatocytes. Cancer Lett. 84:133-140.
114. NIOSH. 1985. 4,4'-Isopropylidenediphenol. NIOSH Registry of Toxic Effects of Chemical Substances 4:3263.
115. NIOSH. 1987. 4,4'-Isopropylidenediphenol. Registry of Toxic Effects of Chemical Substances 1985-1986. Data Sheet for Prioritized NIOSH/OSHA Substances Proposed for the National Toxicology Program. U.S. Department of Health Education and Welfare, Public Health Service, Center for Disease Control, Rockville, MD.
116. Oberley, T. D., Pugh, T. D., Gonzalez, A., Goldfarb, S., Li, S. A., and Li, J. J. 1989. Specific estrogen-induced cell proliferation of cultured Syrian hamster proximal renal tubular cells in serum free chemically defined media. Proc. Natl. Acad. Sci. USA 86:2107-2111.
117. Oberley, T. D., Schultz, J. L., and Oberley, L. W. 1994. In vitro modulation of antioxidant enzyme levels in normal hamster kidney and estrogen-induced hamster kidney tumor. Free Radical Biol. Med. 16:741-751.
118. Oda, T., Sato, Y., Kitajima, S., and Yasukochi, Y. 1991. Inhibition of transcription by mammalian ribonucleic acid polymerase II: Effects of diethylstilbestrol and its analogues. Chem. Pharm. Bull. 39:2627-2629.
119. Oda, T., Sato, Y., Kodama, M., and Kaneko, M. 1993. Inhibition of DNA polymerase I activity by diethylstilbestrol and its analogues. Biol. Pharm. Bull. 16:708-710.
120. Ofner, P., Bosland, M. C., and Vena, R. L. 1992, Differential effects of diethylstilbestrol and estradiol-17 beta in combination with testosterone on rat prostate lobes. Toxicol. Appl. Pharmacol. 112:300-309.
121. Ousterhout, J., Struck, R. F., and Nelson, J. A. 1981. Estrogenic activities of methoxychlor metabolites. Biochem. Parmacol. 30:2869-2871.
122. Palangat, M., and Roy, D. 1994. Diethylstilbestrol induced modulation of nuclear protein tyrosine phosphorylation in kidney, target organ of cancer: Transcriptional implications. Proc. Int. Cancer Congress 16:103-107.
123. Palangat, M., and Roy, D. 1995a. Organ specific inhibition of type I, II and III transcriptional activity by stilbene estrogen. Carcinogenesis 16:1017-1021.
124. Palangat, M., and Roy, D. 1995b. Phosphorylation of tyrosine residues of RNA polymerase II by active chromatin tyrosine kinases. Biochem. Biophys. Res. Commun. 209:356-364.
125. Palangat, M., and Roy, D. 1996. Stilbene estrogen-induced enhanced tyrosine phosphorylation of p53 by nuclear matrix tyrosine kinases. Int. Oncol. 8:1011-1016.
126. Perez-Comas, A. P. 1982. Precocious sexual development in Puerto Rico. Lancet 1:1299-1300.
127. Pike, M., and Spicer, D. 1992. Endogenous estrogen and progesterone as the major determinants of breast cancer risk: Prospects for control by natural and technological means. In Hormonal carcinogenesis, eds. J. J. Li, S. Nandi, and S. A. Li, pp. 209-216. New York: Springer-Verlag.
128. Poliner, F. 1993. A holistic approach to breast cancer research. Environ. Health Perspect. 101:116-120.
129. Preston-Martin, S., Pike, M. C., Ross, R. K., Jones, P. A., and Henderson, B. E. 1990. Increased cell division as a cause of human cancer. Cancer Res. 50:7415-7421.
130. Purewal, M., and Roy, D. 1994. Estrogen enhanced cell proliferation in the target organ of carcinogenesis. Proc. lnt. Cancer Congress 16:602-604.
131. Pylkkanen, L., Makela, S., Valve, E., Harkonen, P., Toikkanen, S., and Santti, R. 1993. Prostatic dysplasia associated with increased expression of c-myc in neonatally estrogenized mice. J. Urol. 149:1593-1601.
132. Reijnders, P. J. H. 1986. Reproductive failure in common seals feeding on fish from polluted coastal waters. Nature 33:456-457.
133. Risinger, J. I., Terry, L. A., and Boyd, J. 1994. Use of representational difference analysis for the identification of mdm2 oncogene amplification in diethylstilbestrol-induced murine uterine adenocarcinomas. Mol. Carcinogen. 11:13-18.
134. Rogan, W. J., Gladen, B. C., McKinney, J. D., Carreras, N., Hardy, P., Thullen, J., Tinglestad, J., and Tully, M. 1987. Polychlorinated biphenyls (PCBs) and dichlorodiphenyl dichloroethane (DDE) in human milk: Effects on growth, morbidity and duration of lactation. Am. J. Public Health 77:1294-1297.
135. Roy, D. 1990. Reactive potential of diethylstilbestrol reactive metabolites towards cellular nuclear proteins. In Biological reactive intermediates. IV, eds. C. M. Witmer, R. R. Snyder, D. J. Jollow, G. F. Kalf, J. J. Kocsis, and I. G. Sipes, pp. 809-812. New York: Plenum Press.
136. Roy, D., and Liehr, J. G. 1988a. Temporary decrease in quinone reductase activity induced by chronic administration of estradiol in male Syrian hamsters: Increased superoxide radical formation by redox cycling of estrogens. J. Biol. Chem. 263:3646-3651.
137. Roy, D., and Liehr, J. G. 1988b. Characterization of drug metabolizing enzymes in estrogen induced kidney tumors in male Syrian hamsters. Cancer Res. 48:5726-5729.
138. Roy, D., and Liehr, J. G. 1989a. Inhibition by vitamin C of in vivo conversion of diethylstilbestrol to diethylstilbestrol 4,4'-quinone in hamsters. Carcinogenesis 10:1241-1245.
139. Roy, D., and Liehr, J. G. 1989b. Changes in activities of free radical scavenging enzymes in kidney and liver of estradiol treated hamsters. Cancer Res. 49:1475-1480.
140. Roy, D., and Liehr, J. G. 1990. Inhibition of estrogen-induced renal carcinogenesis by modulators of estrogen metabolism. Carcinogenesis 11:567-570.
141. Roy, D., and Liehr, J. G. 1992. Target organ specific inactivation of drug metabolism enzymes in the kidney of hamsters treated with estradiol. Mol. Cell. Biochem. 110:31-39.
142. Roy, D., and Palangat, M. 1994. Active chromatin-associated protein tyrosine kinases: Their probable role in hormonal carcinogenesis. Proc. Int. Cancer Congress 16:633-637.
143. Roy, D., and Pathak, D. N. 1993. Modifications in the transcriptionally active chromatin low mobility group proteins by reactive metabolites of diethylstilbestrol. Biochem. Mol. Biol. Int. 31:923-934.
144. Roy, D., and Pathak, D. N. 1995. Covalent modifications in nuclear histone proteins by reactive metabolites of diethylstilbestrol. J. Toxicol. Environ. Health 44:447-457.
145. Roy, D., and Thomas, R. D. 1994. Catalysis of the redox cycling reactions of estrogens by nuclear enzymes. Arch. Biochem. Biophys. 315:310-316.
146. 5 mediated redox cycling of estrogen. Arch. Biochem. Biophys. 285:331-338.
147. Roy, D., Kalyanaraman, B., and Liehr, J. G. 1991b. Superoxide radical mediated reduction of estrogen quinones to estrogen semiquinones. Biochem. Pharmacol. 42:1627-1631.
148. Roy, D., Floyd, R., and Liehr, J. G. 1991c. Elevated 8-hydroxyguanosine levels in DNA of diethylstilbestrol-treated Syrian hamsters: Covalent DNA damage by free radicals generated by redox cycling of diethylstilbestrol. Cancer Res. 51:3882-3886.
149. Roy, D., Strobel, H. W., Coon, M. J., and Liehr, J. G. 1992. The oxidation of estrogens to estrogen quinones is catalyzed by beta-naphthoflavone-inducible cytochrome P 450 IA1. Arch. Biochem. Biophys. 296:450-456.
150. Roy, D., Chen, C. W., and Yan, Z. J. 1994. Attenuation in DNA repair system coupled with increased cell proliferation lead to genetic instability: A possible mechanism of estrogen-induced carcinogenesis. Can. J. Physiol. Pharmacol. 72:604.
151. Roy, D., Pathak, D. N., and Palangat, M. 1995. Higher covalent attack by reactive metabolites of diethylstilbestrol on nuclear proteins of the target organ than that of nontarget organ. Cancer Lett. 90:215-224.
152. Roy, D., Chen, C. W., and Yan, Z. J. 1996. Increased nuclear IGF-I receptor level coupled with attenuation in DNA repair system play an important role in the induction of estrogen-induced carcinogenesis. In Hormonal carcinogenesis II, eds. J. J. Li, S. A. Li, J.-A. Gustafsson, S. Nandi, and L. I. Sekely, pp. 463-466. New York Springer-Verlag.
153. Safe, S. H. 1995. Environmental and dietary estrogens and human health: Is there a problem? Environ. Health Perspect. 103:346-351.
154. Santti, R., Newbold, R. R., Makela, S., Pylkknen, L., and McLachlan, J. A. 1994. Developmental estrogenization and prostatic cancer. Prostate 24:67-68.
155. Sax, N. I. 1975. Toxicology of phenols. In Dangerous properties of industrial chemicals, pp. 458-1008. New York: Von Nostrand.
156. Segura-Aguilar, J., Cortes-Vizcaino, V., Llombart-Bosch, A., Ernster, L., Monsalve, E., and Romero, F. J. 1990. The levels of quinone reductases, superoxide dismutases and glutathione-related enzymatic activities in diethylstilbestrol-induced carcinogenesis in the kidney of male Syrian golden hamsters. Carcinogenesis 11:1727-1732.
157. Seychell, K. D. R. 1985. Naturally occurring nonsteroidal estrogens of dietary origin. In Estrogens in the environment. II. Influences on development, ed. J. A. McLachlan, pp. 69-85. New York: Elsevier.
158. Sharpe, R. M. 1995. Reproductive biology. Another DDT connection. Nature 375:538-539.
159. Sharpe, R. M., and Skakkeback, N. E. 1993. Are estrogens involved in falling sperm count and disorders of male reproductive tract? Lancet 341:1392-1395.
160. Shiraishi, H., Carter, D. S., and Hites, R. A. 1989. Identification and determination of tert-alkylphenols in carp from the Trenton channel of the Detroit River, Michigan, U.S.A. Biomed. Environ. Mass Spectrosc. 18:478-483.
161. Soto, M. A., Justicia, H., Wray, J. W., and Sonnenschein, C. 1991. p-Nonylphenol: An estrogenic xenobiotic released from "modified" polystyrene. Environ. Health Perspect. 92:167-173.
162. Soto, A. M., Lin, T.-M, Justicia, H., Silvia, R. M., and Sonnenschein, C. 1992. An "in culture" bioassay to assess the estrogenicity of xenobiotics. In Chemically induced alterations in sexual development: The wildlife/human connection, eds. T. Colborn, and C. Clement, pp. 295-309. Princeton, New Jersey: Princeton Scientific.
163. Soto, A. M., Chung, K. L., and Sonnenschein, C. 1994. The pesticides endosulfan, toxaphene, and dieldrin have estrogenic effects on human estrogen-sensitive cells. Environ. Health Perspect. 102:380-383.
164. Stone, R. 1993. DES surprises medical researcher again. Science 259:1815.
165. Stone, R. 1994. Environmental estrogen stir debate. Science 265:308-310.
166. Swaneck, G. E., and Fishman, J. 1988. Covalent binding of the endogenous 16a-hydroxy-esterone to estradiol receptor in human breast cancer cells: Characterization and intranuclear localization. Proc. Natl. Sci. Acad. USA 85:7831-7835.
167. Thomas, R. D., and Roy, D. 1994a. Mitochondrial DNA is a major target of attack by diethylstilbestrol metabolites in vivo. Proc. Am. Assoc. Cancer Res. 35:260.
168. Thomas, R. D., and Roy, D. 1994b. In vivo mitochondrial genotoxicity of diethylstilbestrol. Toxicologist 14:327.
169. Thomas, R. D., and Roy, D. 1995. Redox cycling of estrogens catalyzed by mitochondrial enzymes. Carcinogenesis 16:891-895.
170. Tsutsi, T., Maizumi, H., McLachlan, J. A., and Barret, J. C. 1983. Aneuploidy induction and cell transformation by DES: A possible chromosomal mechanism in carcinogenesis. Cancer Res. 43:3814-3818.
171. U.S. Environmental Protection Agency. 1995. Bisphenol A. IRIS (computer search engine).
172. Wang, M. Y., and Liehr, J. G. 1994. Identification of fatty acid hydroperoxide cofactors in the cytochrome P450-mediated oxidation of estrogens to quinone metabolites: Role and balance of lipid peroxides during estrogen-induced carcinogenesis. J. Biol. Chem. 269:284-291.
173. White, R., Jobling, S., Hoare, S. A., Sumpter, J. P., and Parker, M. G. 1994. Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135:175-182.
174. Williams, B. A., Mills, K. T., Burroughs, C. D., and Bern, H. A. 1989. Reproductive alterations in female C57BL/Crgl mice exposed neonatally to zearalonone, an estrogenic mycotoxin. Cancer Lett. 46:225-230.
175. Williams, G. W., latropoulos, M., Cheung, R., Radi, L., and Wang, C. X. 1993. Diethylstilbestrol liver carcinogenicity and modifications of DNA in rats. Cancer Lett. 68:193-198.
176. Wolff, M. S., Toniolo, P. G., Lee, E. W., Rivera, M., and Dubin, N. 1993. Blood levels of organochlorine residues and risk of breast cancer. J. Natl. Cancer Inst. 85:648-652.
177. Yan, Z. J., and Roy, D. 1994. Attenuation of DNA polymerase ß gene expression in estrogen-induced kidney tumor. Proc. Am. Assoc. Cancer Res. 35:260.
178. Yan, Z. J., and Roy, D. 1995. Mutations of DNA polymerase ß mRNA in stilbene estrogen-induced kidney tumors. Biochem. Mol. Biol. Int. 37:175-183.
179. Yu, S. C., and Fishman, J. 1985. Interaction of histones with estrogens: Covalent adduct formation with 16a-hydroxyesterone. Biochemistry 24:8017-8021.
180. Yunbo, L., Trush, M. A., and Yager, J. 1994. DNA damage caused by reactive oxygen species originating from a copper-dependent oxidation of the 2-hydroxy catechol of estradiol. Carcinogenesis 15:1421-1427.