Stereoselective biotransformation of permethrin to estrogenic metabolites in fish

Chemical Research in Toxicology

Volumn 23, Issue 10, 2010, Pages 1568-1575

  Nillos, Mae Grace ^a,b   Chajkowski, Sarah ^c   Rimoldi, John M ^c   Gan, Jay ^a   Lavado, Ramon ^a   Schlenk, Daniel ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF THE PHILIPPINES   (Philippines)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETOCONAZOLE; MESSENGER RNA; PERMETHRIN; VITELLOGENIN;

ANIMAL CELL; ARTICLE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; FISH; HYDROXYLATION; IN VITRO STUDY; MALE; NONHUMAN; PROTEIN EXPRESSION; RAINBOW TROUT; STEREOCHEMISTRY; STEREOISOMERISM;

ANIMALS; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; ESTERASES; ESTROGENS; FISHES; HEPATOCYTES; HYDROXYLATION; INSECTICIDES; MALE; ONCORHYNCHUS MYKISS; ORYZIAS; PERMETHRIN; STEREOISOMERISM; VITELLOGENINS;

ONCORHYNCHUS MYKISS; ORYZIAS LATIPES;

EID: 77958103688     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100167x     Document Type: Article

References (41)

1. Spurlock, F. and Lee, M. (2008) Synthetic Pyrethroids Use Patterns, Properties and Environmental Effects, in Synthetic Pyrethroids: Occurrence and Behavior in Aquatic Environments (Gan, J., Spurlock, F., Hendley, P., and Weston, D., Eds.) ACS Symposium Series 991, pp 3 - 25, American Chemical Society, Washington, DC.
2. Laskowski, D. (2002) Physical and chemical properties of pyrethroids Rev. Environ. Contam. Toxicol. 174, 49-170
3. Gan, J., Lee, S. J., Liu, W. P., Haver, D. L., and Kabashima, J. N. (2005) Distribution and persistence of pyrethroids in runoff sediments J. Environ. Qual. 34, 836-841
4. Amweg, E., Weston, D., You, J., and Lydy, M. (2006) Pyrethroid insecticides and sediment toxicity in Urban creeks from California and Tennessee Environ. Sci. Technol. 40, 1700-1706
5. Coats, J. R. (2008) Toxicology of Synthetic Pyrethroid Insecticides in Fish, in Toxicology of Fishes (DiGiulio, R. T. and Hinton, D. E., Eds.) pp 805 - 817, Taylor and Francis, Boca Raton, FL.
6. Leahey, J. P. (1985) The Pyrethroid Insecticides, Taylor and Francis, London, U.K.
7. Glickman, A. H. and Lech, J. J. (1981) Hydrolysis of permethrin, a pyrethroid insecticide, by rainbow trout and mouse tissues In Vitro: A comparative study Toxicol. Appl. Pharmacol. 60, 186-192
8. Bradbury, S. and Coats, J. (1989) Toxicokinetics and toxicodynamics of pyrethroid insecticides in fish Environ. Toxicol. Chem. 8, 373-380
9. Elliot, M., Farnham, A., Janes, N., Needham, P., and Pulman, D. (1974) Insecticidally Active Confirmations of Pyrethroids, in Mechanism of Pesticide Action (Kohn, G., Ed.) pp 80 - 91, American Chemical Society, Washington DC.
10. Leicht, W., Fuchs, R., and Londershausen, M. (1996) Stability and biological activity of cyfluthrin isomers Pestic. Sci. 48, 325-332
11. Liu, W., Gan, J., Schlenk, D., and Jury, W. (2005a) Enantioselectivity in environmental safety of current chiral insecticides Proc. Natl. Acad. Sci. U.S.A. 102, 701-706
12. Qin, S., Budd, R., Bondarenko, S., Liu, W., and Gan, J. (2006) Enantioselective degradation and chiral stability of pyrethroids in soil and sediment J. Agric. Food Chem. 54, 5040-5045
13. Wang, L. M., Liu, W., Yang, C., Pan, Z., Gan, J., Xu, C., Zhao, M., and Schlenk, D. (2007) Enantioselectivity in estrogenic potential and uptake of bifenthrin Environ. Sci. Technol. 41, 6124-6128
14. Jin, Y., Wang, W., Xu, C., Fu, Z., and Liu, W. (2008) Induction of hepatic estrogen-responsive genes expression by permethrin enantiomers in adult male zebrafish Aquat. Toxicol. 88, 146-152
15. Tyler, C., Beresford, N., van der Woning, M., Sumpter, J., and Thorpe, K. (2000) Metabolism and environmental degradation of pyrethroid insecticides produce compounds with endocrine activities Environ. Toxicol. Chem. 19, 801-809
16. McCarthy, A., Thomson, B., Shaw, I., and Abell, A. (2006) Estrogenicity of pyrethroid insecticide metabolites J. Environ. Monit. 8, 197-202
17. Gaughan, L. C., Unai, T., and Casida, J. E. (1977) Permethrin metabolism in rats J. Agric. Food Chem. 25, 9-17
18. Glickman, A. H., Shono, J. E., Casida, J. E., and Lech, J. J. (1979) In vitro metabolism of permethrin isomers by carp and rainbow trout liver microsomes J. Agric. Food Chem. 27, 1038-1048
19. Negishi, E., Rand, C. L., and Jadhav, K. P. (1981) Selective carbon-carbon bond formation via transition metal catalysis. 23. Highly selective and convenient method for the synthesis of 1,5-enynes and 1,5-dienes by the reaction of 1,3-dilithiopropargyl phenyl sulfide with allylic halides J. Org. Chem. 46, 5041-5044
20. McCarthy, A. R., Thomson, B. M., Shaw, I. C., and Abell, A. D. (2006) Estrogenicity of pyrethroid insecticide metabolites J. Environ. Monit. 8, 197-202
21. Liu, W., Gan, J., and Qin, S. ((2005)) Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides Chirality 17 S127-S133
22. Carlson, D. B. and Williams, D. E. (1999) Sex-specific vitellogenin production in immature rainbow trout Environ. Toxicol. Chem. 18, 2361-2363
23. Lavado, R., Loyo-Rosales, J. E., Floyd, E., Kolodziej, E. P., Snyder, S. A., Sedlak, D. L., and Schlenk, D. (2009) Site-specific profiles of estrogenic activity in agricultural areas of California's inland waters Environ. Sci. Technol. 43, 9110-9116
24. Mosmann, T. (1983) Rapid colorimetric assay of cellular growth and survival: Application to proliferation and cytotoxicity assays J. Immunol. Methods 65, 55-63
25. U.S. Environmental Protection Agency (USEPA) (1994) Short-term Methods for Estimating the Chronic Toxicity of Effluents and Receiving Waters to Freshwater Organism, EPA-600-4-91-002.
26. Lavado, R., Rimoldi, J., and Schelenk, D. (2009) Mechanisms of fenthion activation in rainbow trout (Oncorhynchus mykiss) acclimated to hypersaline environments Toxicol. Appl. Pharmacol. 235, 143-152
27. Godin, S. J., Scollon, E. J., Hughes, M. F., Potter, P. M., DeVito, M. J., and Ross, M. K. (2006) Species differences in the in vitro metabolism of deltamethrin and esfenvalerate: differential oxidative and hydrolytic metabolism by humans and rats Drug Metab. Dispos. 34, 1764-1771
28. Choi, J., Rose, R. L., and Hodgson, E. (2002) In vitro human metabolism of permethrin: the role of human alcohol and aldehyde dehydrogenases Pestic. Biochem. Physiol. 74, 117-128
29. Hutchinson, T. H., Ankley, G. T., Segner, H., and Tyler, C. H. (2006) Screening and testing for endocrine disruption in fish: Biomarkers as "signposts," not "traffic lights," in risk assessment Environ. Health Perspect. 114, 106-114
30. Sumpter, J. P. and Johnson, A. C. (2005) Lessons from the endocrine disruption and their application to other issues concerning trace organic in the aquatic environment Environ. Sci. Technol. 39, 4321-4332
31. Fang, H., Tong, W., Shi, L. M., Blair, R., Perkins, R., Branham, W., Hass, B. S., Xie, Q., Dial, S. L., Moland, C. L., and Sheehan, D. M. (2001) Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens Chem. Res. Toxicol. 14, 280-294
32. Pesonen, M. and Andersson, T. (1991) Characterization and induction of xenobiotic metabolizing enzyme activities in a primary culture of rainbow trout hepatocytes Xenobiotica 21, 461-471
33. Parkinson, A. and Ogilvie, B. W. (2009) Biotransformation of Xenobiotics, in Casertt and Doull's Toxicology: The Basic Science of Poisons (Klaassen, C. D., Ed.) 7 th ed., pp 161 - 304, McGraw Hill, New York.
34. Scollon, E. J., Starr, J. M., Godin, S. J., DeVito, M. J., and Hughes, M. F. (2009) In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome P450 Isoforms Drug Metab. Dispos. 37, 221-228
35. Zhang, S. Y., Ueyama, J., Ito, Y., Yanagiba, Y., Okamura, A., Kamijima, M., and Nakajima, T. (2008) Permethrin may induce male mouse reproductive toxicity due to cis isomer not trans isomer Toxicology 248, 136-141
36. Gray, A. J. and Soderlund, D. M. (1985) Mammalian Toxicology of Pyrethroids, in Insecticides (Huston, D. H. and Roberts, T. R., Eds.) pp 193 - 248, John Wiley and Sons, New York.
37. Schulz, R. and Stehle, S. (2008) Synthetic Pyrethroids in Agricultural Surface Waters: Exposure, Effects and Risk Mitigation, in Synthetic Pyrethroids: Occurrence and Behavior in Aquatic Environments (Gan, J., Spurlock, F., Hendley, P., and Weston, D., Eds.) ACS Symposium Series 991, pp 171 - 202, American Chemical Society, Washington, DC.
38. Spehar, R. L., Danny, K., Tanner, D. K., and Nordling, B. R. (1983) Toxicity of the synthetic pyrethroids, permethrin and AC 222, 705 and their accumulation in early life stages of fathead minnows and snails Aquat. Toxicol. 3, 171-182
39. Saha, A. K., Rapoport, H., and Schultz, P. (1989) 1,1-Carbonylbis(3- methylimidazolium) triflate: an efficient reagent for aminoacylations J. Am. Chem. Soc. 111, 4856-4859
40. Unai, T. and Casida, J. E. (1977) Synthesis of isomeric 3-(2,2-dichlorovinyl)-2-hydroxymethyl-2 methylcyclopropanecarboxylic acids and other permethrin metabolites J. Agric. Food Chem. 25, 979-987
41. Nillos, M. G. (2009) Stereoselectivity in Modern-Use Chiral Pesticides: Enantiomer-Specific Ecotoxicological Assessment of Chiral Organophosprus, Fipronil and Pyrethroid Insecticides, Ph.D. Thesis, University of California, Riverside, Riverside, CA.