Rat α-fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities

Chemical Research in Toxicology

Volumn 25, Issue 11, 2012, Pages 2553-2566

  Hong, Huixiao ^a   Branham, William S ^a   Dial, Stacey L ^a   Moland, Carrie L ^a   Fang, Hong ^a   Shen, Jie ^a   Perkins, Roger ^a   Sheehan, Daniel ^a   Tong, Weida ^a  

^a NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYBENZOIC ACID ESTER; ALPHA FETOPROTEIN; BENZOPHENONE; BIBENZYL DERIVATIVE; CHALCONE; COUMARIN; ESTROGEN DERIVATIVE; ESTROGEN RECEPTOR; ETHYLENE DERIVATIVE; FLAVANONE; FLAVONE; ISOFLAVONE; PHENOL; PHTHALIC ACID; STEROID; STILBENE;

AMNION FLUID; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING ASSAY; BINDING SITE; CONCENTRATION RESPONSE; ESTROGEN BINDING; HYDROGEN BOND; HYDROPHOBICITY; NONHUMAN; PROTEIN ANALYSIS; PROTEIN BINDING; RAT; STRUCTURE ACTIVITY RELATION;

ALPHA-FETOPROTEINS; ANIMALS; BINDING, COMPETITIVE; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA; RATTUS; RODENTIA;

EID: 84869424357     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx3003406     Document Type: Article

References (60)

1. Wetherill, Y. B., Akingbemi, B. T., Kanno, J., McLachlan, J. A., Nadal, A., Sonnenschein, C., Watson, C. S., Zoeller, R. T., and Belcher, S. M. (2007) In vitro molecular mechanisms of bisphenol A action Reprod. Toxicol. 24, 178-198
2. vom Saal, F. S., Akingbemi, B. T., Belcher, S. M., Birnbaum, L. S., Crain, D. A., Eriksen, M., Farabollini, F., Guillette, L. J., Jr., Hauser, R., and Heindel, J. J. 2007, Chapel Hill bisphenol A expert panel consensus statement: integration of mechanisms, effects in animals and potential to impact human health at current levels of exposure Reprod. Toxicol. 24, 131-138
3. Kavlock, R. J., Daston, G. P., DeRosa, C., Fenner-Crisp, P., Gray, L. E., Kaattari, S., Lucier, G., Luster, M., Mac, M. J., Maczka, C., Miller, R., Moore, J., Rolland, R., Scott, G., Sheehan, D. M., Sinks, T., and Tilson, H. A. (1996) Research needs for the risk assessment of health and environmental effects of endocrine disruptors: a report of the U.S. EPA-sponsored workshop Environ. Health. Perspect. 104, 715-740
4. http://water.epa.gov/lawsregs/rulesregs/sdwa/index.cfm (accessed Nov 18, 2011).
5. http://www.fda.gov/RegulatoryInformation/Legislation/ FederalFoodDrugandCosmeticActFDCAct/SignificantAmendmentstotheFDCAct/ucm148008. htm (accessed Nov 18, 2011).
6. http://www.epa.gov/scipoly/oscpendo/ (accessed Nov 18, 2011).
7. Shanle, E. K. and Xu, W. (2011) Endocrine disrupting chemicals targeting estrogen receptor signaling: identification and mechanisms of action Chem. Res. Toxicol. 24, 6-19
8. Wormke, M., Stoner, M., Saville, B., Walker, K., Abdelrahim, M., Burghardt, R., and Safe, S. (2003) The aryl hydrocarbon receptor mediates degradation of estrogen receptor α through activation of proteasomes Mol. Cell. Biol. 6, 1843-1855
9. Safe, S. and Kim, K. (2008) Nonclassical genomic ER/Sp and ER/AP-1 signaling pathways J. Mol. Endocrinol. 41, 263-275
10. Pandey, D. P., Lappano, R., Albanito, L., Madeo, A., Maggiolini, M., and Picard, D. (2009) Estrogenic GPR30 signalling induces proliferation and migration of breast cancer cells through CTGF EMBO J. 28, 523-532
11. Albanito, L., Sisci, D., Aquila, S., Brunelli, E., Vivacqua, A., Madeo, A., Lappano, R., Pandey, D. P., Picard, D., Mauro, L., Andò, S., and Maggiolini, M. (2008) Epidermal growth factor induces G protein-coupled receptor 30 expression in estrogen receptor-negative breast cancer cells Endocrinology 149, 3799-3808
12. Revankar, C. M., Cimino, D. F., Sklar, L. A., Arterburn, J. B., and Prossnitz, E. R. (2005) A transmembrane intracellular estrogen receptor mediates rapid cell signaling Science 307, 1625-1630
13. Maggiolini, M. and Picard, D. (2010) The unfolding stories of GPR30, a new membrane-bound estrogen receptor J. Endocrinol. 204, 105-114
14. Filardo, E. J. and Thomas, P. (2005) GPR30: a seven-transmembrane- spanning estrogen receptor that triggers EGF release Trends Endocrinol. Metab. 16, 362-367
15. Blair, R., Fang, H., Branham, W. S., Hass, B., Dial, S. L., Moland, C. L., Tong, W., Shi, L., Perkins, R., and Sheehan, D. M. (2000) Estrogen receptor relative binding affinities of 188 natural and chemicals: Structural diversity of ligands Toxicol. Sci. 54, 138-153
16. Fang, H., Tong, W., Shi, L., Blair, R., Perkins, R., Branham, W. S., Dial, S. L., Moland, C. L., and Sheehan, D. M. (2001) Structure activity relationship for a large diverse set of natural, synthetic and environmental chemicals Chem. Res. Toxicol. 14, 280-294
17. Bergstrand, C. G. and Czar, B. (1956) Paper electrophoretic study of human fetal serum proteins with demonstration of a new protein fraction Scand. J. Clin. Lab. Invest. 9, 277-286
18. Mizejewski, G. J. and MacColl, R. (2003) Alpha-fetoprotein growth inhibitory peptides: potential leads for cancer therapeutics Mol. Cancer Ther. 2, 1243-55
19. Nishi, S., Matsue, H., Yoshida, H., Yamaoto, R., and Sakai, M. (1991) Localization of the estrogen-binding site of alpha-fetoprotein in the chimeric human-rat proteins Proc. Natl. Acad. Sci. U.S.A. 88, 3102-3105
20. Savu, L., Benassayag, C., Vallette, G., Christeff, N., and Nunez, E. (1981) Mouse alpha 1-fetoprotein and albumin. Comparison of their binding properties with estrogen and fatty acid ligands J. Biol. Chem. 256, 9414-9418
21. Savu, L., Benassayag, C., Vallette, G., Nunez, E., and Jayle, M. F. (1977) Purification and estrogen binding properties of mouse AFP and two forms of the protein with different affinities for Con-A Biochemistry 59, 323-328
22. Uriel, J., Bouillon, D., Aussel, C., and Dupiers, M. (1976) Alpha-fetoprotein: the major high-affinity estrogen binder in rat uterine cytosols Proc. Natl. Acad. Sci. U.S.A. 73, 1452-1456
23. Crandall, B. F. (1981) Alpha-fetoprotein: a review Crit. Rev. Clin. Lab. Sci. 15, 127-85
24. Deutsch, H. F. (1991) Chemistry and biology of alpha-fetoprotein Adv. Cancer Res. 56, 253-312
25. Nunez, E. A. (1994) Biological role of alpha-fetoprotein in the endocrinological field: data and hypotheses Tumour Biol. 15, 63-72
26. Gitlin, D. and Boesman, M. (1967) Sites of serum alpha-fetoprotein synthesis in the human and in the rat J. Clin. Invest. 46, 1010-1016
27. Uriel, J., de Nechaud, B., and Dupiers, M. (1972) Estrogen-binding properties of rat, mouse and man fetospecific serum proteins. Demonstration by immuno-autoradiographic methods Biochem. Biophys. Res. Commun. 46, 1175-80
28. Nunez, E. A, Bennassayag, C., Sava, L., Vallette, G., and Delorme, J. (1979) Oestrogen binding function of AFP J. Steroid Biochem. 11, 237-243
29. Vallette, G., Bennassayag, C., Savu, L., Delorme, J., Nunez, E. A., and Doumas, J. (1980) The serum competitor of estrogen-AFP interactions: a mixture of nonesterified fatty acids Biochem. J. 187, 851-856
30. Herve, F., Gentin, M., Rajkowski, K. M., Wong, L. T., Hsia, C. J., and Cittanova, N. (1990) Estrogen-binding properties of rat AFP and its isoforms: investigation of the apparent non-integrality of sites on the unfractionated protein J. Steroid Biochem. 36, 319-324
31. VanBrocklin, H. F., Brodack, J. W., Mathiss, C. J., Welch, M. J., Katzenellenbogen, J. A., Keenan, J. F., and Mizejewski, G. J. (1992) Binding of a 16 a-F18-fluoro-17B-estradiol to alpha-fetoprotein in Sprague-Dawley female rats affects blood levels Nucl. Med. Biol. 17, 769-773
32. Payne, D. W and Katzenellenbogen, J. A. (1979) Binding specificity of rat alpha-fetoprotein for a series of estrogen derivatives: studies using equilibrium and nonequilibrium binding techniques Endocrinology 105, 745-753
33. Garreau, B., Vallette, G., Adlercreutz, H., Wähälä, K., Mäkelä, T., Benassayag, C., and Nunez, E. A. (1991) Phytoestrogens: new ligands for rat and human alpha-fetoprotein Biochim. Biophys. Acta 1094, 339-345
34. Baker, M. E., Medlock, K. L., and Sheehan, D. M. (1998) Flavonoids inhibit estrogen binding to rat alpha-fetoprotein Proc. Soc. Exp. Biol. Med. 217, 317-721
35. Milligan, S. R., Khan, O., and Nash, M. (1998) Competitive binding of xenobiotic oestrogens to rat alpha-fetoprotein and to sex steroid binding proteins in human and rainbow trout (Oncorhynchus mykiss) plasma Gen. Comp. Endrocrinol. 112, 89-95
36. Petersona, J. J., Beecherb, G. R., Bhagwatc, S. A., Dwyera, J. T., Gebhardtc, S. E., Haytowitzc, D. B., and Holden, J. M. (2006) Flavanones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature J. Food Compost. Anal. 19, S74-S80
37. Go., M. L., Wu, X., and Liu, X. L. (2005) Chalcones: an update on cytotoxic and chemoprotective properties Curr. Med. Chem. 12, 481-499
38. Hallmark, N., Walker, M., McKinnell, C., Mahood, I. K., Scott, H., Bayne, R., Coutts, S., Anderson, R. A., Greig, I., Morris, K., and Sharpe, R. M. (2007) Effects of monobutyl and di(n-butyl) phthalate in vitro on steroidogenesis and leydig cell aggregation in fetal testis explants from the rat: comparison with effects in vivo in the fetal rat and neonatal marmoset and in vitro in the human Environ. Health Perspect. 115, 390-396
39. Byford, J. R., Shaw, L. E., Drew, M. G., Pope, G. S., Sauer, M. J., and Darbre, P. D. (2002) Oestrogenic activity of parabens in MCF7 human breast cancer cells J. Steroid Biochem. Mol. Biol. 80, 49-60
40. Beronius, A., Rudén, C., Håkansson, H., and Hanberg, A. (2010) Risk to all or none? A comparative analysis of controversies in the health risk assessment of Bisphenol A Reprod. Toxicol. 29, 132-146
41. Cohn, B. A., Cohn, B. A., Wolff, M. S., Cirillo, P. M., and Sholtz, R. I. (2007) DDT and breast cancer in young women: new data on the significance of age at exposure Environ. Health Perspect. 115, 1406-1414
42. Dodds, E. C., Goldberg, L., Lawson, W., and Robinson, R. (1938) Estrogenic activity of certain synthetic compounds Nature 141, 247-248
43. Hong, H., Tong, W., Fang, H., Shi, L., Xie, Q., Wu, J., Pekins, R., Walker, J. D., Branham, W., and Sheehan, D. M. (2002) Prediction of estrogen receptor binding for 58,000 chemicals using integrated system of a tree-based model with structure alerts Environ. Health Perspect. 110, 29-36
44. Raynaud, J. P., Mercier-Bodard, C., and Baulieu, E. E. (1971) Rat estradiol binding plasma protein (EBP) Steroids 18, 767-788
45. Savu, L., Nunez, E., and Jayle, M. F. (1975) Plasma diethylstilboestrol binding proteins of rat, mouse and man in the course of development: relations with the binding of estradiol Steroids 25, 717-728
46. Sheehan, D. M. and Young, M. (1979) Diethylstilbestrol and estradiol binding to serum albumin and pregnancy plasma of rat and human Endocrinology 104, 1442-1426
47. Hervé, F., Rajkowski, K., Martin, M. T., Dessen, P., and Cittanova, N. (1984) Drug-binding properties of rat alpha 1-foetoprotein. Binding of warfarin, phenylbutazone, azapropazone, diazepam, digitoxin and cholic acid Biochem. J. 221, 401-406
48. Hervé., F., Rajkowski, K., Martin, M. T., Dessen, P., and Cittanova, N. (1986) Drug-binding properties of rat alpha-foetoprotein. Specificities of the phenylbutazone-binding and warfarin-binding sites Biochem. J. 239, 451-458
49. Baker, M. E., Frecker, D. G., and Fanestil, D. D. (1982) Inhibition of estrogen binding to rat alpha-fetoprotein by tryptophan p-nitrophenyl esters J. Steroid Biochem. 16, 503-507
50. Mizejewski, G. J. (2004) Biological roles of alpha-fetoprotein during pregnancy and perinatal development Exp. Biol. Med. 229, 439-463
51. Mizejewski, G. J. (2001) Alpha-fetoprotein structure and function: relevance to isoforms, epitopes, and conformational variants Exp. Biol. Med. 226, 377-408
52. Morinaga, T., Sakai, M., Wegmann, T. G., and Tomoaki, T. (1983) Primary structures of human AFP and its mRNA Proc. Natl. Acad. Sci. U.S.A. 80, 4604-4608
53. Benassayag, C., Savu, L., Vallette, C., Delorme, J., and Nunez, E. A. (1979) Relations between fatty acids and estrogen binding properties of pure rat AFP Biochem. Biophys. Acta 587, 227-237
54. Mizejewski, G. J. (2011) Review of the putative cell-surface receptors for alpha-fetoprotein: identification of a candidate receptor protein family Tumour Biol. 32, 241-58
55. Mizejewski, G. J. (2002) Biological role of alpha-fetoprotein in cancer: prospects for anticancer therapy Expert Rev. Anticancer Ther. 2, 89-115
56. Laborda, J., Naval, J., Allouche, M., Calvo, M., Georgoulias, V., Mishal, Z., and Uriel, J. (1987) Specific uptake of alpha-fetoprotein by malignant human lymphoid cells Int. J. Cancer 40, 314-318
57. Alava, M. A., Sturralde, M., Lampreave, F., and Pineiro, A. (1999) Specific uptake of alpha-fetoprotein and albumin by rat Morris 777 hepatoma cells Tumour Biol. 20, 52-64
58. Uriel, J., Faivre-Bauman, A., Trojan, J., and Foiret, D. (1981) Immunocytochemical demonstration of alpha-fetoprotein uptake by primary cultures of fetal hemisphere cells from mouse brain Neurosci. Lett. 272, 171-175
59. Hajeri-Germond, M., Trojan, J., Uriel, J., and Hauw, J. J. (1983) In vitro uptake of exogenous AFP by chicken dorsal root ganglia Dev. Neurosci. 6, 11-15
60. Uriel, J., Trojan, J., Dubouch, P., and Pineiro, A. (1982) Intracellular alpha-fetoprotein and albumin in the developing nervous system of the baboon Pathol. Biol. 302, 79-83