Laccase-mediated transformations of endocrine disrupting chemicals abolish binding affinities to estrogen receptors and their estrogenic activity in zebrafish

Applied Biochemistry and Biotechnology

Volumn 168, Issue 4, 2012, Pages 864-876

  Torres Duarte, Cristina ^a   Viana, María Teresa ^b   Vazquez Duhalt, Rafael ^a  

^a INSTITUTO DE BIOTECNOLOGÍA   (Mexico)

^b UNIVERSIDAD AUTÓNOMA DE BAJA CALIFORNIA   (Mexico)

Author keywords

Bisphenol A; Endocrine disruption; Estrogen receptor; Immobilized laccase; Laccase; Nonylphenol; Triclosan; Vitellogenin; Zebrafish

Indexed keywords

BISPHENOL A; ENDOCRINE DISRUPTION; ESTROGEN RECEPTOR; LACCASES; NONYLPHENOLS; TRICLOSAN; VITELLOGENIN; ZEBRAFISH;

AQUACULTURE; BINDING ENERGY; BIOLOGICAL WATER TREATMENT; CHEMICALS; PHENOLS;

ENDOCRINE DISRUPTERS;

COUMESTROL; ENDOCRINE DISRUPTOR; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; LACCASE; UNCLASSIFIED DRUG; VITELLOGENIN; VITELLOGENIN 1;

ANIMAL EXPERIMENT; ANISOTROPY; AQUACULTURE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DOWN REGULATION; ENDOCRINE FUNCTION; IC 50; IN VITRO STUDY; IN VIVO STUDY; INTERNALIZATION; LIGAND BINDING; MOLECULAR WEIGHT; MORTALITY; NONHUMAN; PROTEIN CONFORMATION; PROTEIN EXPRESSION; SOLUBILITY; ZEBRA FISH;

ANIMALS; BIOCATALYSIS; BIOTRANSFORMATION; ENDOCRINE DISRUPTORS; ENZYMES, IMMOBILIZED; ESTROGENS; GENE EXPRESSION REGULATION; HUMANS; LACCASE; POLYPORALES; PROTEIN BINDING; RECEPTORS, ESTROGEN; RNA, MESSENGER; VITELLOGENINS; ZEBRAFISH; ZEBRAFISH PROTEINS;

CORIOLOPSIS GALLICA; DANIO RERIO;

EID: 84869123784     PISSN: 02732289     EISSN: 15590291     Source Type: Journal    
DOI: 10.1007/s12010-012-9825-2     Document Type: Article

References (62)

1. Johnson, A., & Jürgens, M. (2003). Pure and Applied Chemistry, 75, 1895-1904.
2. Thomas, P., Alyea, R., Pang, Y., Peyton, C., Dong, J., & Berg, A. H. (2010). Steroids, 75, 595-602.
3. Milnes, M. R., Bermudez, D. S., Bryan, T. A., Edwards, T. M., Gunderson, M. P., Larkin, I. L. V., Moore, B. C., & Guillette, J. L. J. (2006). Environmental Research, 100, 3-17.
4. Sanderson, J.T. (2006) Toxicological Sciences, 94, 3-21.
5. Gutendorf, B., & Westendorf, J. (2001). Toxicology, 166, 79-89.
6. Pillon, A., Boussioux, A.-M., Escande, A., Aït-Aïssa, S., Gomez, E., Fenet, H., Ruff, M., Moras, D., Vignon, F., Duchesne, M.-J., Casellas, C., Nicolas, J.-C., & Balaguer, P. (2005). Environmental Health Perspectives, 113, 278-284.
7. Kausch, U., Alberti, M., Haindl, S., Budczies, J., & Hock, B. (2008). Environmental Toxicology, 23, 15-24.
8. Vandenberg, L. N., Maffini, M. V., Sonnenschein, C., Rubin, B. S., & Soto, A. M. (2009). Endocrine Reviews, 30, 75-95.
9. Soares, A., Guieysse, B., Jefferson, B., Cartmell, E., & Lester, J. N. (2008). Environment International, 34, 1033-1049.
10. Vazquez-Duhalt, R., Marquez-Rocha, F., Ponce, E., Licea, A. F., & Viana, M. T. (2006). Applied Ecology and Environmental Research, 4, 1-25.
11. Dann, A. B., & Hontela, A. (2011). Journal of Applied Toxicology, 31, 285-311.
12. Oberdörster, E., & Cheek, A. O. (2001). Environmental Toxicology and Chemistry, 20, 23-36.
13. Schultz, T. W., Sinks, G. D., & Cronin, M. T. D. (2002). Environmental Toxicology, 17, 14-23.
14. Giesy, J. P., & Snyder, E. M. (1998). In R. J. Kendall, R. L. Dickerson, J. P. Giesy, & W. A. Suk (Eds.), Principles and processes for evaluating endocrine disruption in wildlife (pp. 155-237). Pensacola: SETAC.
15. Imai, S., Shiraishi, A., Gamo, K., Watanabe, I., Okuhata, H., Miyasaka, H., Ikeda, K., Bamba, T., & Hirata, K. (2007). Journal of Biosciences and Bioengineering, 103, 420-426.
16. Lee, B.-C., Kamata, M., Akatsuka, Y., Takeda, M., Ohno, K., Kamei, T., & Magara, Y. (2004). Water Research, 38, 733-739.
17. Liu, Z.-H., Kanjo, Y., & Mizutani, S. (2009). Science of the Total Environment, 407, 731-748.
18. Vidal, G., Becerra, J., Hernández, V., Decap, J., & Xavier, C. R. (2007). Journal of Biosciences and Bioengineering, 104, 476-480.
19. Cabana, H., Jones, J. P., & Agathos, S. N. (2007). Engineering in Life Sciences, 7, 429-456.
20. Tsutsumi, Y., Haneda, T., & Nishida, T. (2001). Chemosphere, 42, 271-276.
21. Pointing, S. B. (2001). Applied Microbiology and Biotechnology, 57, 20-33.
22. Tinoco, R., Pickard, M. A., & Vazquez-Duhalt, R. (2001). Letters in Applied Microbiology, 32, 331-335.
23. Vandertol-Vanier, H. A., Vazquez-Duhalt, R., Tinoco, R., & Pickard, M. A. (2002). Journal of Industrial Microbiology and Biotechnology, 29, 214-220.
24. Chefetz, B., Chen, Y., & Hadar, Y. (1998). Applied and Environmental Microbiology, 64, 3175-3179.
25. Gurer-Orhan, H., Kool, J., Vermeulen, N. P. E., & Meerman, J. H. N. (2005). International Journal of Environmental Analytical Chemistry, 85, 149-161.
26. Bakker, M., van de Velde, F., van Rantwijk, F., & Sheldon, R. A. (2000). Biotechnology and Bioengineering, 70, 342-348.
27. Camarero, S., Ibarra, D., Martinez, M. J., & Martinez, A. T. (2005). Applied and Environmental Microbiology, 71, 1775-1784.
28. Menuet, A., Pellegrini, E., Anglade, I., Blaise, O., Laudet, V., Kah, O., & Pakdel, F. (2002). Biology of Reproduction, 66, 1881-1892.
29. Eiler, S.,Gangloff, M.,Duclaud, S.,Moras,D.,&Ruff, M. (2001). Protein Expression and Purification, 22, 165-173.
30. De la Mora, E., Lovett, J. E., Blanford, C. F., Garman, E. F., Valderrama, B., & Rudino-Pinera, E. (2012). Acta Crystallographica Section D, 68, 564-577.
31. Pickard, M. A., Roman, R., Tinoco, R., & Vazquez-Duhalt, R. (1999). Applied and Environmental Microbiology, 65, 3805-3809.
32. Reyes, P., Pickard, M. A., & Vazquez-Duhalt, R. (1999). Biotechnology Letters, 21, 875-880.
33. Torres-Duarte, C., Roman, R., Tinoco, R., & Vazquez-Duhalt, R. (2009). Chemosphere, 77, 687-692.
34. Auriol, M., Filali-Meknassi, Y., Adams, C. D., Tyagi, R. D., Noguerol, T.-N., & Piňa, B. (2008). Chemosphere, 70, 445-452.
35. Fukuda, T., Uchida, H., Suzuki, M., Miyamoto, H., Morinaga, H., Nawata, H., & Uwajima, T. (2004). Journal of Chemical Technology and Biotechnology, 79, 1212-1218.
36. Cabana, H., Jones, J. P., & Agathos, S. N. (2007). Journal of Biotechnology, 132, 23-31.
37. Levin, R. D., & Lias, S. G. (1982). Ionization potential and appearance potential measurements, 1971- 1981. Washington, D. C.: U.S. Dept. of Commerce, National Bureau of Standards.
38. Gianfreda, L., Xu, F., & Bollag, J.-M. (1999). Bioremediation Journal, 3, 1-26.
39. Nicotra, S., Intra, A., Ottolina, G., Riva, S., & Danieli, B. (2004). Tetrahedron-Asymmetry, 15, 2927- 2931.
40. Uchida, H., Fukuda, T., Miyamoto, H., Kawabata, T., Suzuki, M., & Uwajima, T. (2001). Biochemical and Biophysical Research Communications, 287, 355-358.
41. Matthews, J., Celius, T., Halgren, R., & Zacharewski, T. (2000). The Journal of Steroid Biochemistry and Molecular Biology, 74, 223-234.
42. Nakai, M. (2003). MEDAKA: development of test methods and suitability of medaka as test organism for detection of endocrine disrupting chemicals. Ministry of the Environment, Japan and Chemicals Evaluation and Research Institute, Japan, pp. 21-26.
43. Olsen, C. M., Meussen-Elholm, E. T. M., Hongslo, J. K., Stenersen, J., & Tollefsen, K.-E. (2005). Comparative Biochemistry and Physiology. Part C: Toxicology and Pharmacology, 141, 267-274.
44. Parker, G. J., Law, T. L., Lenoch, F. J., & Bolger, R. E. (2000). Journal of Biomolecular Screening, 5, 77-88.
45. Gale, W. L., Patiňo, R., & Maule, A. G. (2004). General and Comparative Endocrinology, 136, 338-345.
46. Kloas,W., Schrag, B., Ehnes, C.,& Segner, H. (2000). General and Comparative Endocrinology, 119, 287-299.
47. Passos, A. L. S., Pinto, P. I. S., Power, D. M., & Canario, A. V. M. (2009). Ecotoxicology and Environmental Safety, 72, 1529-1537.
48. Rider, C. V., Hartig, P. C., Cardon, M. C., & Wilson, V. S. (2009). Environmental Toxicology and Chemistry, 28, 2175-2181.
49. Costache, A. D., Pullela, P. K., Kasha, P., Tomasiewicz, H., & Sem, D. S. (2005). Molecular Endocrinology, 19, 2979-2990.
50. Katagi, T. (2010). Reviews of Environmental Contamination and Toxicology, 204, 1-132.
51. von Hofsten, J., & Olsson, P.-E. (2005). Reproductive Biology and Endocrinology, 3, 63-73.
52. Kidd, K. A., Blanchfield, P. J., Mills, K. H., Palace, V. P., Evans, R. E., Lazorchak, J. M., & Flick, R. W. (2007). Proceedings of the National Academy of Sciences, 104, 8897-8901.
53. Tamagawa, Y., Hirai, H., Kawai, S., & Nishida, T. (2005). FEMS Microbiology Letters, 244, 93-98.
54. Tamagawa, Y., Yamaki, R., Hirai, H., Kawai, S., & Nishida, T. (2006). Chemosphere, 65, 97-101.
55. Ishibashi, H., Matsumura, N., Hirano, M., Matsuoka, M., Shiratsuchi, H., Ishibashi, Y., Takao, Y., & Arizono, K. (2004). Aquatic Toxicology, 67, 167-179.
56. Sun, L., Wen, L., Shao, X., Qian, H., Jin, Y., Liu, W., & Fu, Z. (2010). Chemosphere, 78, 793-799.
57. Palumbo, A. J., Denison, M. S., Doroshov, S. I., & Tjeerdema, R. S. (2009). Environmental Toxicology and Chemistry, 28, 1749-1755.
58. Shanle, E. K., & Xu, W. (2011). Chemical Research in Toxicology, 24, 6-19.
59. Diano, N., Grano, V., Fraconte, L., Caputo, P., Ricupito, A., Attanasio, A., Bianco, M., Bencivenga, U., Rossi, S., Manco, I., Mita, L., Del Pozzo, G., & Mita, D. G. (2007). Applied Catalysis B: Environmental, 69, 252-261.
60. Cabana, H., Alexandre, C., Agathos, S. N., & Jones, J. P. (2009). Bioresource Technology, 100, 3447-3458.
61. Nicolucci, C., Rossi, S., Menale, C., Godjevargova, T., Ivanov, Y., Bianco, M., Mita, L., Bencivenga, U., Mita, D., & Diano, N. (2011). Biodegradation, 22, 673-683.
62. Li, X., Ying, G.-G., Su, H.-C., Yang, X.-B., & Wang, L. (2010). Environment International, 36, 557-562.