Examination of the in vitro and in vivo estrogenic activities of eight commercial phthalate esters

Toxicological Sciences

Volumn 46, Issue 2, 1998, Pages 282-293

  Zacharewski, T R ^a   Meek, M D ^a   Clemons, J H ^a   Wu, Z F ^a   Fielden, M R ^a   Matthews, J B ^a  

^a Michigan State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTRADIOL; ESTROGEN RECEPTOR; PHTHALIC ACID BIS(2 ETHYLHEXYL) ESTER; PHTHALIC ACID ESTER;

ANIMAL TISSUE; ARTICLE; ESTROGEN ACTIVITY; FEMALE; GENE EXPRESSION; HUMAN; HUMAN CELL; NONHUMAN; RAT; RECEPTOR BINDING; REPRODUCTIVE TOXICITY; UTERUS WEIGHT; VAGINA EPITHELIUM;

ANIMALIA; MAMMALIA; MINK CELL FOCUS-FORMING VIRUS;

EID: 0032418291     PISSN: 10966080     EISSN: None     Source Type: Journal    
DOI: 10.1006/toxs.1998.2505     Document Type: Article

References (102)

1. F. Adams C.J. Newton H. Braunsberg N. Shaikh M. Ghilchik V.H.T. James Effects of human breast fibroblasts on growth and 17β-estradiol dehydrogenase activity of MCF-7 cells in culture Breast Cancer Res. Treat. 11 1988 165 172
2. J.B. Adams N.S. Phillips R. Hall Metabolic fate of estradiol in human mammary cancer cells in culture: Estrogen sulfate formation and cooperativity exhibited by estrogen sulfotransferase Mol. Cell. Endocrinol. 58 1986 231 242
3. J. Alam J.L. Cook Reporter genes: Application to the study of mammalian gene transcription Anal. Biochem. 188 1990 245 254
4. S.F. Arnold M.K. Robinson A.C. Notides L.J. Guillette Jr. J.A. McLachlan A yeast estrogen screen for examining the relative exposure of cells to natural and xenoestrogens Environ. Health Perspect. 104 1996 544 548
5. J. Ashby H. Tinwell P.A. Lefevre J. Odum D. Paton S.W. Millward S. Tittensor A.N. Brooks Normal sexual development of rats exposed to butylbenzyl phthalate from conception to weaning Regul. Toxicol. Pharmacol. 56 1997 102 118
6. P. Balaguer A. Joyeux M. Denison R. Vincent B. Gillesby T. Zacharewski Assessing the estrogenic and dioxin-like activities of chemicals and complex mixtures using in vitro Can. J. Physiol. Pharmacol. 74 1996 216 222
7. P. Balaguer B.E. Gillesby Z.F. Wu M.D. Meek J. Annick T. Zacharewski Assessment of chemicals alleged to possess estrogen receptor-mediated activities using in vitro Toxicol. Appl. Pharmacol. 30 1996 143
8. M. Berry D. Metzger P. Chambon Role of the two activating domains of the oestrogen receptor in the cell-type and promoter-context dependent agonist activity of the anti-oestrogen 4-hydroxytamoxifen EMBO J. 9 1990 2811 2818
9. G. Blom Statistical Estimates and Transformation Beta Variables 1958 Wiley New York
10. K.L. Bondy T.R. Zacharewski ICI 164,384: A control for estrogen responsive genes Nucleic Acids Res. 21 1993 5277 5278
11. J. Botella E. Duranti V. Viader I. Duc R. Delansorne J. Paris Lack of estrogenic potential of progesterone- or 19-nor-progesterone-derived progestins as opposed to testosterone or 19-nor-testosterone derivatives on endometrial Ishikawa cells J. Steroid Biochem. Mol. Biol. 55 1995 77 84
12. Brady, A. M. Moffat, G. J. Hall, M. G. Martens, F. Martens, M. Nair, R. 1998, An assessment if in vivo
13. A.R. Brasier J.E. Tate J.F. Habener Optimized use of the firefly luciferase assay as a reporter gene in mammalian cell lines Biotechniques 7 1989 1116 1122
14. L. Castagnetta O.M. Granata M.L. Casto V. Miserendo M. Colo G. Carruba Estrone conversion rates by human endometrial cancer cell lines J. Steroid Biochem. 25 1986 231 242
15. J.H. Clark C. Watson S. Upchurch S. McCormack H. Padykula B. Markaverich J.W. Hardin Estrogen action in normal and abnormal cell growth Estrogens in the Environment 1980 Elsevier New York p. 53–67
16. J.H. Clemons C.R. Marvin Z.F. Wu B.E. McCarry L. Allan D.W. Bryant T.R. Zacharewski Identification of estrogen- and dioxin-like activities in urban air particulate matter using recombinant receptor/reporter gene bioassays Environ. Sci. Technol. 32 1998 1853 1860
17. T. Colborn F.S. vom Saal A.M. Soto Developmental effects of endocrine-disrupting chemicals in wildlife and humans Environ. Health Perspect. 101 1993 378 384
18. N.G. Coldham M. Dave S. Sivapthasundaram D.P. McDonnell C. Connor M. Sauer Evaluation of a recombinant yeast cell estrogen screening assay Environ. Health Perspect. 105 1997 734 742
19. K. Connor J. Howell I. Chen H. Liu K. Berhane C. Sciarretta S. Safe T. Zacharewski Failure of chloro-S-triazine-derived compounds to induce estrogen receptor-mediated responses in vivo in vitro Fundam. Appl. Toxicol. 30 1995 93 101
20. K. Connor Hydroxylated polychlorinated biphenyls (PCBs) as estrogens and antiestrogens: Structure–activity relationships Toxicol. Appl. Pharmacol. 145 1997 111 123
21. D.L. Davis H.L. Bradlow M. Wolff T. Woodruff D.G. Hoel H. Anton-Culver Medical hypothesis: Xenoestrogens as preventable causes of breast cancer Environ. Health Perspect. 101 1993 372 377
22. G.L. DeGeorge J.M. Mitchell T. Newcomb G. Newcomb L. Kieffer D.R. Cerven Development of a uterotrophic response assay for assessment of estrogenic activity and reproductive system toxicity of dermally applied industrial chemicals and environmental pollutants Fundam. Appl. Toxicol. (Suppl. Toxicol.) 36 1997 59
23. D. Dexter W.S. Moye-Rowley A.-L. Wu J. Golin Mutations in the yeast PDR3, PDR4, PDR7 and PDR9 pleiotropic (multiple) drug resistant loci affect the transcript level of an ATP binding cassette transporter encoding gene Genetics 186 1994 505 515
24. R.I. Dorfman A.S. Dorfman Estrogen assays using the rat uterus Endocrinology 55 1954 65 69
25. Drill, V. A. 1966, Biological properties, Oral Contraceptives, 16, 43, McGraw-Hill, New York
26. V.A. Drill Endocrine properties and long-term safety of oral contraceptives Metabolism 14 1965 295 301
27. C. Dunnett New tables for multiple comparisons with a control Biometrics 20 1964 482 491
28. D.A. Eigenberg H.P. Bozigian D.E. Carter I.G. Sipes Distribution, excretion and metabolism of butylbenzyl phthalate in the rat J. Toxicol. Environ. Health 17 1986 445 456
29. C.W. Emmens L. Martin Methods in Hormone Research 1964 Academic Press New York p. 1–80
30. M.W. Eubanks Hormones and health Environ. Health Perspect. 105 1997 482 487
31. D. Feldman D. Yung A. Burshell P. Stathis D.S. Loose An estrogen-binding protein in Saccharomyces cerevisiae Science 218 1982 297 298
32. M. Fielden Z.F. Wu I. Chen B. Chittim S. Safe T. Zacharewski Examination of the estrogenicity of 2,2′,4,6,6′-pentachlorobiphenyl (PCB104), its hydroxylated and chlorinated derivatives, 2,2′,4,6,6′-pentachloro-4-biphenylol (HO-PCB104) and a further chlorinated derivative 2,2′,4,4′,6,6′-hexachlorobiphenyl (PCB155) Environ. Health Perspect. 105 1997 1238 1248
33. M.J. Garabedian K.R. Yamamoto Genetic dissection of the signalling domain of a mammalian steroid receptor in yeast Mol. Biol. Cell. 3 1992 1245 1257
34. J.F. Gierthy D.W. Lincoln S.J. Kampick D.W. Dickerman H.L. Bradlow T. Niwa G.E. Swanek Enhancement of 2- and 16α-estradiol hydroxylation in MCF-7 human breast cancer cells by 2,3,7,8-tetrachlorodibenzo- p Biochem. Biophys. Res. Commun. 157 1988 515 520
35. L.E. Gray Endocrine screening methods workshop report: Detection of estrogenic and androgenic hormonal and antihormonal activity for chemicals that act via receptor or steroidogenic enzyme mechanisms Reprod. Toxicol. 11 1997 719 750
36. C.A. Harris P. Henttu M.G. Parker J.P. Sumpter The estrogenic activity of phthalate esters in vivo Environ. Health Perspect. 105 1997 802 811
37. M. Harris C. Kamps S. Safe Role of 4-5S binding protein in the induction of aryl hydrocarbon hydroxylase in the rat Carcinogenesis 9 1988 1475 1479
38. D.M. Heery T. Zacharewski B. Pierrat H. Gronemeyer P. Chambon Efficient transactivation by retinoic acid receptors in yeast requires retinoid X receptors Proc. Natl. Acad. Sci. USA 90 1993 4281 4285
39. F.L. Hisaw Comparative effectiveness of estrogens on fluid imbibition and growth of the rat's uterus Endocrinology 54 1959 276 289
40. K.B. Horwitz A.W. Pike C. Gonzalez-Aller P.V. Fennessey Progesterone metabolism in T47Dco human breast cancer cells. II. Intacellular metabolic path of progesterone and synthetic progestins J. Steroid Biochem. 25 1986 911 916
41. S. Jobling T. Reynolds R. White M.G. Parker J.P. Sumpter A variety of environmentally persistent chemicals, including some plasticizers, are weakly estrogenic Environ. Health Perspect. 103 1995 582 587
42. R.C. Jones R.A. Edgren The effects of various steroids on the vaginal histology in the rat Fertil. Steril. 24 1973 284 291
43. B.S. Katzenellenbogen Estrogen receptors: Bioactivities and interactions with cell signalling pathways Biol. Reprod. 54 1996 287 293
44. J.A. Katzenellenbogen B.W. O'Malley B.S. Katzenellenbogen Tripartite steroid hormone receptor pharmacology: interaction with multiple effector sites as a basis for the cell- and promoter-specific action of these hormones Mol. Endocrinol. 10 1996 119 131
45. W.M. Kluwe Overview of phthalate ester pharmacokinetics in mammalian species Environ. Health Perspect. 45 1982 3 9
46. H. Kohno O. Gandini S.W. Curtis K.S. Korach Antiestrogen activity in the yeast transcription system: estrogen receptor mediated agonist response Steroids 59 1994 572 578
47. K.S. Korach J.A. McLachlan Techniques for detection of estrogenicity Environ. Health Perspect. 103 1995 5 8
48. V. Kumar S. Green G. Stack M. Berry J.R. Jin P. Chambon Functional domains of the human estrogen receptor Cell 51 1987 941 951
49. H.D. Lauson C.G. Heller J.B. Golden E.L. Sevringhaus The immature rat uterus in the assay of estrogenic substances and a comparison of estradiol, estrone and estriol Endocrinology 24 1939 35 44
50. S.C. Laws S.A. Carey W.R. Kelce R.L. Cooper L.E. Gray Vinclozolin does not alter progesterone receptor (PR) function in vivo in vitro Toxicology 110 1996 1 11
51. J. Lindzey K.S. Korach Development and physiological effects of estrogen receptor gene disruption in mice Trends Endocrinol. Metab. 8 1997 137 145
52. B.A. Littlefield E. Gurpide L. Markiewicz B. McKinley R.B. Hochberg A simple and sensitive microtiter plate estrogen bioassay based on stimulation of alkaline phosphatase in Ishikawa cells: Estrogen action of adrenal steroids Endocrinology 127 1990 2757 2762
53. C.R. Lyttle P. Damian-Matsumura H. Juul T.R. Butt Human estrogen receptor regulation in a yeast model and studies on receptor agonists and antagonists J. Steroid Biochem. Mol. Biol. 42 1992 677 685
54. L. Martin P.J. Claringbold The mitogenic action of oestrogens in the vaginal epithelium of the ovariectomized mouse J. Endocrinol. 20 1960 173 186
55. D.P. McDonnell W. Pike D.J. Drutz T.R. Butt B.W. O'Malley Reconstitution of the vitamin D-responsive osteocalcin transcription unit in Saccharomyces cerevisiae Mol. Cell. Biol. 9 1989 3517 3523
56. D.P. McDonnell E. Vegeto B.W. O'Malley Identification of a negative regulatory function for steroid receptors Proc. Natl. Acad. Sci. USA 89 1992 10563 10567
57. J.A. McLachlan Functional toxicology: A new approach to detect biologically active xenobiotics Environ. Health Perspect. 101 1993 386 387
58. D. Metzger S. Ali J.-M. Bornert P. Chambon Characterization of the amino-terminal transcriptional activation function of the human estrogen receptor in animal and yeast cells J. Biol. Chem. 270 1995 9535 9542
59. D. Metzger M. Berry S. Ali P. Chambon Effect of antagonists on DNA binding properties of the human estrogen receptor in vitro in vivo Mol. Endocrinol. 9 1995 579 591
60. D. Metzger R. Losson J.-M. Bornert Y. Lemoine P. Chambon Promoter specificity of the two transcriptional activation functions of the human estrogen receptor in yeast Nucleic Acids Res. 20 1992 2813 2817
61. D. Metzger J. White P. Chambon The human estrogen receptor functions in yeast Nature 334 1988 31 35
62. W.R. Miller J.S. O'Neil Significance of steroid metabolism in human cancer J. Steroid Biochem. Mol. Biol. 37 1990 317 325
63. M. Moore M. Mustain K. Daniel I. Chen S. Safe T. Zacharewski B. Gillesby A. Joyeux P. Balaguer Antiestrogenic activity of hydroxylated polychlorinated biphenyl congeners identified in human serum Toxicol. Appl. Pharmacol. 142 1997 160 168
64. S.R. Mulligan A.V. Balasubramanian J.C. Kalita Relative potency of xenobiotic estrogens in an acute in vivo Environ. Health Perspect. 106 1998 23 26
65. A. Najid Comparison of DHEA metabolism by MCF-7 cells in culture and their extracts Cancer J. 4 1991 45 48
66. J.A. Nelson R.F. Struck R. James Estrogenic activities of chlorinated hydrocarbons J. Toxicol. Environ. Health 4 1978 325 339
67. T. Niwa H.L. Bradlow J. Fishman G.E. Swaneck Determination of estradiol 2- and 16α-hydroxylase activities in MCF-7 human breast cancer cells using radiometric analysis J. Steroid Biochem. 33 1989 311 314
68. T. Niwa H.L. Bradlow J. Fishman G.E. Swaneck Induction and inhibition of estradiol hydroxylase activities in MCF-7 human breast cancer cells in culture Steroids 55 1990 297 302
69. K. Oerter Klein J. Baron M.J. Colli D.P. McDonnell G.B. Cutler Estrogen levels in childhood determined by an ultrasensitive recombinant cell bioassay J. Clin. Invest. 1994 2475 2480
70. H. Ohashi Y.-F. Yang P.G. Walfish Rat liver c-erb A b1 thyroid receptor is a constitutive activator in yeast ( Saccharomyces cerevisiae Biochem. Biophys. Res. Commun. 178 1991 1167 1175
71. F. Pakdel C. Le Guellec C. Vailliant M.G. Le Roux Y. Valotaire Identification and estrogen induction of two estrogen receptor (ER) messenger ribonucleic acids in the rainbow trout liver: Sequence homology with other ERs Mol. Endocrinol. 3 1989 44 51
72. J.R. Pasqualini C. Gelly Effect of tamoxifen and tamoxifen derivatives on the conversion of estrone sulfate to estradiol in the MCF-7 mammary cancer cell line Cancer Lett. 40 1988 115 119
73. J.R. Pasqualini C. Gelly F. Lecerf Estrogen sulfates: biological and ultrastructural responses and metabolism in MCF-7 human breast cancer cells Breast Cancer Res. Treat. 8 1986 233 237
74. C. Pelissero G. Flouriot J.L. Foucher B. Bennetau J. Dunogues F. Le Gac J.P. Sumpter Vitellogenin synthesis in cultured hepatocytes: An in vitro J. Steroid Biochem. Mol. Biol. 44 1993 263 272
75. E. Perel D. Daniilescu L. Kharlip M.E. Blackenstein D.W. Killinger The relationship between growth and androstenedione metabolism in four cell lines of human breast carcinoma cells in culture Mol. Cell. Endocrinol. 41 1985 197 203
76. B. Pierrat D. Heery Y. Lemoine R. Losson Functional analysis of the human estrogen receptor using a phenotypic transactivation assay in yeast Gene 119 1992 237 245
77. M.L. Privalsky M. Sharif K.R. Yamamoto The viral erbA oncogene protein, a constitutive repressor in animal cells, is a hormone regulated activator in yeast Cell 63 1990 1277 1286
78. I.J. Purvis D. Chotai C.W. Dykes D.B. Lubahn F.S. French E.M. Wilson A.N. Hobden An androgen-inducible expression system for Saccharomyces cerevisiae Gene 106 1991 35 42
79. J.R. Reel J.C. Lamb B.H. Neal Survey and assessment of mammalian estrogen biological assays for hazard characterization Fundam. Appl. Toxicol. 34 1996 288 305
80. M.D. Rose F. Winston P. Hieter Methods in Yeast Genetics: A Laboratory Course Manual 1990 Cold Spring Harbor Laboratory Press Cold Spring Harbor
81. B.L. Rubin A.S. Dorfman L. Black R.I. Dorfman Bioassay of estrogens using the mouse uterine response Endocrinology 49 1951 429 439
82. M.F. Ruh T. Zacharewski K. Connor J. Howell I. Chen S. Safe Naringenin: A weak estrogenic bioflavonoid that exhibits antiestrogenic activity Biochem. Pharmacol. 50 1995 1485 1493
83. S.H. Safe Environmental and dietary estrogens and human health: Is there a problem? Environ. Health Perspect. 103 1995 346 351
84. J. Sambrook E.F. Fritsch T. Maniatis Molecular Cloning: A Laboratory Manual 1989 Cold Spring Harbor Laboratory Press Cold Spring Harbor
85. J. Scheider M.M. Huh H.L. Bradlow J. Fishman Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells J. Biol. Chem. 259 1984 4840 4845
86. N. Schutze G. Vollmer I. Tiemann M. Geiger R. Knuppen Catecholestrogens are MCF-7 cell estrogen receptor agonists J. Steroid Biochem. Mol. Biol. 46 1993 781 789
87. S.S. Shapiro M.B. Wilk Statistical Methods 1989 Iowa State Univ. Press Ames
88. R.M. Sharpe J.S. Fisher M.M. Millar S. Jobling J.P. Sumpter Gestational and lactational exposure of rats to xenoestrogens results in reduced testicular size and sperm production Environ. Health Perspect. 103 1995 1136 1143
89. A.M. Soto C. Sonnenschein L.K. Chung M.F. Fernandez N. Olea M.F. Olea-Serrano The E-SCREEN assay as a tool to identify estrogens: an update on estrogenic environmental pollutants Environ. Health Perspect. 103 1995 113 122
90. D.C. Spink H.P. Eugster D.W. Lincoln J.D. Schuetz E.G. Schuetz J.A. Johnson L.S. Kaminsky J.F. Gierthy 17β-Estradiol hydroxylation catalyzed by human cytochrome P4501A1: A comparison of the activities induced by 2,3,7,8-tetrachlorodibenzo- p Arch. Biochem. Biophys. 293 1992 342 348
91. D.C. Spink J.A. Johnson S.P. Connor K.M. Aldous J.F. Gierthy Stimulation of 17β-estradiol metabolism in MCF-7 cells by bromochloro- and chloromethyl-substituted dibenzo- p J. Toxicol. Environ. Health 41 1994 451 466
92. D.C. Spink D.W. Lincoln H.W. Dickerman J.F. Gierthy 2,3,7,8-Tetrachlorodibenzo- p Proc. Natl. Acad. Sci. USA 87 1990 6917 6921
93. T. Takahashi A. Tanaka Biochemical studies on phthalic esters. V. Comparative studies on in vitro n Arch. Toxicol. 63 1989 72 74
94. L. Terenius The Allen-Doisy test for estrogens reinvestigated Steroids 17 1971 653 661
95. L. Tora J. White C. Brou D. Tasset N. Webster E. Scheer P. Chambon The human estrogen receptor has two independent nonacidic transcriptional activation functions Cell 59 1989 477 487
96. N.J.G. Webster S. Green D. Tasset M. Ponglikitmongkol P. Chambon The transcriptional activation function located in the hormone-binding domain of the human oestrogen receptor is not encoded in a single exon EMBO J. 8 1989 1441 1446
97. R. Wine L.-H. Li L.H. Barnes D.K. Gulati R.E. Chapin Reproductive toxicity of di- n Environ. Health Perspect. 105 1997 102 107
98. C.K. Wrenn B.S. Katzenellenbogen Structural–function analysis of the hormone binding domain of human estrogen receptor by region-specific mutagenesis and phenotypic screening in yeast J. Biol. Chem. 268 1993 24089 24098
99. T. Zacharewski In vitro Environ. Sci. Technol. 31 1997 613 623
100. T. Zacharewski K. Berhane B. Gillesby K. Burnison Detection of estrogen- and dioxin-like activity in pulp and paper mill black liquor effluent using in vitro Environ. Sci. Technol. 29 1995 2140 2146
101. T. Zacharewski P. Campbell E. Routledge M.-C. Huet R. Cooper D. Kime A. Wenzel Current approaches for the use of in vitro SETAC-Europe/OECD/EC Expert Workshop on Endocrine Modulators and Wildlife: Assessment and Testing (EMWAT) 1997 SETAC-Europe Brussels p. 41–58
102. J.R. Zysk B. Johnson B.A. Ozenberger B. Bingham J. Gorski Selective uptake of estrogenic compounds by Saccharomyces cerevisiae Endocrinology 136 1995 1323 1326