Some nonylphenol isomers show antiestrogenic potency in the MVLN cell assay

Toxicology in Vitro

Volumn 24, Issue 1, 2010, Pages 129-134

  Preuss, Thomas G ^a   Gurer Orhan, Hande ^b   Meerman, John ^c   Ratte, Hans Toni ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b EGE UNIVERSITY   (Turkey)

^c LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Antagonists; Branched isomer; Nonylphenol; Receptor binding; Reporter gene assay; Xeno hormone

Indexed keywords

4 NONYLPHENOL; ENDOCRINE DISRUPTOR; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; NONYLPHENOL;

ARTICLE; BINDING AFFINITY; CELL STRAIN MCF 7; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENVIRONMENTAL EXPOSURE; ESTROGEN ACTIVITY; HUMAN; HUMAN CELL; ISOMERISM; RECEPTOR AFFINITY;

BINDING SITES; CELL LINE; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; ENDOCRINE DISRUPTORS; ESTRADIOL; ESTROGEN ANTAGONISTS; ESTROGEN RECEPTOR ALPHA; FEMALE; GENES, REPORTER; HUMANS; ISOMERISM; LIGANDS; PHENOLS;

EID: 72049093744     PISSN: 08872333     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tiv.2009.08.017     Document Type: Article

References (31)

1. Andersen H.R., Andersson A.M., Arnold S.F., Autrup H., Barfoed M., Beresford N.A., Bjerregaard P., Christiansen L.B., Gissel B., Hummel R., Jorgensen E.B., Korsgaard B., Le Guevel R., Leffers H., McLachlan J., Moller A., Nielsen J.B., Olea N., Oles-Karasko A., Pakdel F., Pedersen K.L., Perez P., Skakkeboek N.E., Sonnenschein C., Soto A.M., et al. Comparison of short-term estrogenicity tests for identification of hormone-disrupting chemicals. Environ. Health Perspect. 107 Suppl. 1 (1999) 89-108
2. Balaguer P., Francois F., Comunale F., Fenet H., Boussioux A.M., Pons M., Nicolas J.C., and Casellas C. Reporter cell lines to study the estrogenic effects of xenoestrogens. Sci. Total Environ. 233 (1999) 47-56
3. Coors A., Jones P.D., Giesy J.P., and Ratte H.T. Removal of estrogenic activity from municipal waste landfill leachate assessed with a bioassay based on reporter gene expression. Environ. Sci. Technol. 37 (2003) 3430-3434
4. Eiler S., Gangloff M., Duclaud S., Moras D., and Ruff M. Overexpression, purification, and crystal structure of native ER alpha LBD. Protein Expr. Purif. 22 2 (2001) 165-173
5. Folmar L.C., Hemmer M.J., Denslow N.D., Kroll K., Chen J., Cheek A., Richman H., Meredith H., and Grau E.G. A comparison of the estrogenic potencies of estradiol, ethynylestradiol, diethylstilbestrol, nonylphenol and methoxychlor in vivo and in vitro. Aquat. Toxicol. 60 (2002) 101-110
6. Gabriel F.L.P., Routledge E.J., Heidlberger A., Rentsch D., Guenther K., Giger W., Sumpter J.P., and Kohler H.P.E. Isomer-specific degradation and endocrine disrupting activity of nonylphenols. Environ. Sci. Technol. 42 (2008) 6399-6408
7. Guenther K., Kleist E., and Thiele B. Estrogen-active nonylphenols from an isomer-specific viewpoint: A systematic numbering system and future trends. Anal. Bioanal. Chem. 384 (2006) 542-546
8. Gurer-Orhan H., Kool J., Vermeulen N.P.E., and Meerman J.H.N. A novel microplate reader-based high-throughput assay for estrogen receptor binding. Int. J. Environ. Anal. Chem. 85 (2005) 149-161
9. Gutendorf B., and Westendorf J. Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. Toxicology 166 (2001) 79-89
10. Ieda T., Horii Y., Petrick G., Yamashita N., Ochiai N., and Kannan K. Analysis of nonylphenol isomers in a technical mixture and in water by comprehensive two-dimensional gas chromatography-mass spectrometry. Environ. Sci. Technol. 39 (2005) 7202-7207
11. Jordan V.C. Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 1. Receptor interactions. J. Med. Chem. 46 (2003) 883-908
12. Kim Y.S., Katase T., Sekine S., Inoue T., Makino M., Uchiyama T., Fujimoto Y., and Yamashita N. Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography. Chemosphere 54 (2004) 1127-1134
13. Kool J., Ramautar R., van Liempd S.M., Beckman J., de Kanter F.J.J., Meerman J.H.N., Schenk T., Irth H., Commandeur J.N.M., and Vermeulen N.P.E. Rapid on-line profiling of estrogen receptor binding metabolites of tamoxifen. J. Med. Chem. 49 11 (2006) 3287-3292
14. Kuiper G.G., Lemmen J.G., Carlsson B., Corton J.C., Safe S.H., van der Saag P.T., van der Burg B., and Gustafsson J.A. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 139 (1998) 4252-4263
15. Maguire R.J. Review of the persistence of nonylphenol and nonylphenol ethoxylates in aquatic environments. Water Qual. Res. J. Canada 34 (1999) 37-78
16. Murk A.J., Legler J., van Lipzig M.M., Meerman J.H., Belfroid A.C., Spenkelink A., van der Burg B., Rijs G.B., and Vethaak D. Detection of estrogenic potency in wastewater and surface water with three in vitro bioassays. Environ. Toxicol. Chem. 21 (2002) 16-23
17. Odum J., Lefevre P.A., Tittensor S., Paton D., Routledge E.J., Beresford N.A., Sumpter J.P., and Ashby J. The rodent uterotrophic assay: Critical protocol features, studies with nonyl phenols, and comparison with a yeast estrogenicity assay. Regulat. Toxicol. Pharmacol. 25 (1997) 176-188
18. Owens W., and Koeter H.B.W.M. The oecd program to validate the rat uterotrophic bioassay: An overview. Environ. Health Perspect. 111 (2003) 1527-1529
19. Pedersen S.N., and Lindholst C. Quantification of the xenoestrogens 4-tert.-octylphenol and bisphenol a in water and in fish tissue based on microwave assisted extraction, solid-phase extraction and liquid chromatography-mass spectrometry. J. Chromatogr. A 864 (1999) 17-24
20. Pons M., Gagne D., Nicolas J.C., and Mehtali M. A new cellular-model of response to estrogens - a bioluminescent test to characterize (anti)estrogen molecules. Biotechniques 9 (1990) 450
21. Preuss T.G., Gehrhardt J., Schirmer K., Coors A., Rubach M., Russ A., Jones P.D., Giesy J.P., and Ratte H.T. Nonylphenol isomers differ in estrogenic activity. Environ. Sci. Technol. 40 (2006) 5147-5153
22. Russ A.S., Vinken R., Schuphan I., and Schmidt B. Synthesis of branched para-nonylphenol isomers: occurrence and quantification in two commercial mixtures. Chemosphere 60 (2005) 1624-1635
23. Scippo M.L., Argiris C., Van De Weerdt C., Muller M., Willemsen P., Martial J., and Maghuin-Rogister G. Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors. Anal. Bioanal. Chem. 378 (2004) 664-669
24. Snyder S.A., Villeneuve D.L., Snyder E.M., and Giesy J.P. Identification and quantification of estrogen receptor agonists in wastewater effluents. Environ. Sci. Technol. 35 (2001) 3620-3625
25. Tabira Y., Nakai M., Asai D., Yakabe Y., Tahara Y., Shinmyozu T., Noguchi M., Takatsuki M., and Shimohigashi Y. Structural requirements of para-alkylphenols to bind to estrogen receptor. Eur. J. Biochem. 262 (1999) 240-245
26. Thiele B., Heinke V., Kleist E., and Guenther K. Contribution to the structural elucidation of 10 isomers of technical p-nonylphenol. Environ. Sci. Technol. 38 (2004) 3405-3411
27. Udenfriend S., Stein S., Bohlen P., Dairman W., Leimgruber W., and Weigele M. Fluorescamine: a reagent for assay of amino acids, peptides, proteins, and primary amines in the picomole range. Science 178 (1972) 871-872
28. Vinken R., Schmidt B., and Schaffer A. Synthesis of tertiary c-14-labelled nonylphenol isomers. J. Label. Compd. Radiopharm. 45 (2002) 1253-1263
29. Watanabe T., Inoue S., Ogawa S., Ishii Y., Hiroi H., Ikeda K., Orimo A., and Muramatsu M. Agonistic effect of tamoxifen is dependent on cell type, ere-promoter context, and estrogen receptor subtype: Functional difference between estrogen receptors alpha and beta. Biochem. Biophys. Res. Commun. 236 (1997) 140-145
30. Wheeler T.F., Heim J.R., LaTorre M.R., and Janes A.B. Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GC-MS. J. Chromatogr. Sci. 35 (1997) 19-30
31. White R., Jobling S., Hoare S.A., Sumpter J.P., and Parker M.G. Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135 (1994) 175-182