Antiandrogenic activity and metabolism of the organophosphorus pesticide fenthion and related compounds

Environmental Health Perspectives

Volumn 111, Issue 4, 2003, Pages 503-508

  Kitamura, Shigeyuki ^a   Suzuki, Tomoharu ^a   Ohta, Shigeru ^a   Fujimoto, Nariaki ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Aldehyde oxidase; Antiandrogenic activity; Cytochrome P450; Endocrine disruption; Fenthion; Fenthion sulfoxide

Indexed keywords

ALDEHYDE OXIDASE; ANDROSTANOLONE; ANTIANDROGEN; CHEMICAL COMPOUND; CYTOCHROME P450; FENTHION; FLUTAMIDE; LUCIFERASE; ORGANOPHOSPHATE PESTICIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFONE; SULFOXIDE; UNSPECIFIC MONOOXYGENASE;

ANIMAL CELL; ANIMAL EXPERIMENT; BIOTRANSFORMATION; CASTRATION; CELL ASSAY; CELL STRAIN 3T3; CELL STRAIN MCF 7; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; ELECTRON; ENDOCRINE FUNCTION; ESTROGEN ACTIVITY; EXTRACTION; HORMONE RESPONSIVE ELEMENT; LIVER CYTOSOL; LIVER MICROSOME; MALE; METABOLITE; NONHUMAN; PRIORITY JOURNAL; RAT; REVIEW; SCREENING TEST;

ANIMALIA; MINK CELL FOCUS-FORMING VIRUS;

EID: 0038746812     PISSN: 00916765     EISSN: None     Source Type: Journal    
DOI: 10.1289/ehp.5917     Document Type: Review

References (59)

1. Andersen HR, Andersson A-M, Arnold SF, Autrup H, Barfoed M, Beresford NA et al. 1999. Comparison of short-term estrogenicity test for identification of hormone-disrupting chemicals. Environ Health Perspect 107(suppl 1):89-108.
2. Ashby J, Lefevre PA. 2000. The peripubertal male rat assay as an alternative to the Hershberger castrated male rat assay for the detection of anti-androgens, oestrogens and metabolic modulators. J Appl Toxicol 20:35-47.
3. Benoit E, Cresteil T, Riviere J-L, De La Tour P. 1992. Specific and enantioselective sulfoxidation of an aryl-trifluoromethyl sulfide by rat liver cytochromes P-450. Drug Metab Dispos 20:877-881.
4. Brady UE, Arthur BW. 1961. Metabolism of O,O-dimethyl O-[4-methylthio)-m-tolyl)phosphorothioate by white rats. J Econ Entomol 54:1232-1236.
5. Cabras P, Garau VL, Melis M, Pirisi FM, Spanedda L. 1993. Persistence and fate of fenthion in olives and olive products. J Agric Food Chem 41:2431-2433.
6. Cavanna S, Molinari GP. 1998. Residues of fenthion and trichloron in olives and olive oil after olive tree treatments. Food Addit Contam 15:518-527.
7. Charles GD, Bartels MJ, Zacharewski TR, Gollapudi BB, Freshour NL, Carney EW. 2000. Activity of benzo[a]pyrene and its hydroxylated metabolites in an estrogen receptor-α reporter gene assay. Toxicol Sci 55:320-326.
8. Chen CW, Hurd C, Vorojeikina DP, Arnold SF, Notides AC. 1997. Transcriptional activation of the human estrogen receptor by DDT isomers and metabolites in yeast and MCF-7 cells. Biochem Pharmacol 53:1161-1172.
9. Connor K, Ramamoorthy M, Moore M, Mustain M, Chen I, Safe S, et al. 1997. Hydroxylated polychlorinated biphenyls (PCBs) as estrogens and antiestrogens: structure-activity relationships. Toxicol Appl Pharmacol 145:111-123.
10. Cove D, Perego R, Nebuloni C, Fontana G, Molinari GP. 1995. In vitro cytotoxicity of fenthion and related metabolites in human neuroblastoma cell lines. Chemosphere 30:1709-1715.
11. Curtis LR. 2001. Organophosphate antagonism of the androgen receptor. Toxicol Sci 60:1-2.
12. DeBaun J, Menn JJ. 1976. Sulfoxide reduction in relation to organophosphorus insecticide detoxification. Science 191:187-188.
13. Esaac EG, Matsumura F. 1980. Metabolism of insecticides by reductive systems. Pharmacol Ther 53:1161-1172.
14. Fertuck KC, Matthews JB, Zacharewski TR. 2001. Hydroxylated benzo[a]pyrene metabolites are responsible for in vitro estrogen receptor-mediated gene expression induced by benzo[a]pyrene, but do not elicit uterotrophic effects in vivo. Toxicol Sci 59:231-240.
15. Fukuda H, Masuda T, Miyahara Y. 1962. Fate of O,O-dimethyl O-(3-methyl-4-methylmercaptophenyl)thiophosphate sprayed on rice plant. Jpn J Appl Entomol Zool 6:230-236.
16. Fukushima M. 1991. Fate and behavior of pesticide in aquatic environment. Case study of Yodo River Basin. Japan J Water Pollution Res 14:79-83.
17. Gaido KW, Leonard LS, Lovell S, Gould JC, Babai D, Portier CJ, et al. 1997. Evaluation of chemicals with endocrine modulating activity in yeast-based steroid hormone receptor gene transcription assay. Toxicol Appl Pharmacol 143:205-212.
18. Gaido KW, Leonard LS, Maness SC, Hall JM, Mcdonell DP, Saville B, et al. 1999. Differential interaction of the methoxychlor metabolite 2,2′-bis-(p-hydroxyphenyl)-1,1-trichloroethane with estrogen receptors alpha and beta. Endocrinology 140:5746-5753.
19. Garner CE, Jefferson WN, Burka LT, Matthews HB, Newbold RR. 1999. In vitro estrogenicity of the catechol metabolites of selected polychlorinated biphenyls. Toxicol Appl Pharmacol 154:188-197.
20. Gray LE Jr, Ostby J, Kelce WR. 1994. Developmental effects of an environmenal antiandrogen: the fungicide vinclozolin alters sex differentiation of the male rat. Toxicol Appl Pharmacol 129:46-52.
21. Gray LE Jr, Ostby J, Monosson E, Kelce WR. 1999a. Environmental antiandrogens: low doses of the fungicide vinclozolin alter sexual differentiation of the male rat. Toxicol Ind Health 15:48-64.
22. Gray LE Jr, Wolf C, Lambright C, Mann P, Price M, Cooper RL, Ostby J. 1999b. Administration of potentially antiandrogenic pesticides (procymidone, linuron, iprodion, chlozolinate, p,p′-DDE, and ketoconazole) and toxic substances (dibutyl-and diethylhexyl phthalate, PCB 169, and ethane dimethane sulphonate) during sexual differentiation produces diverse profiles of reproductive malformations in the male rat. Toxicol Ind Health 15:94-118.
23. Hershberger L, Shipley E, Meyer R. 1953. Myotrophic activity of 19-nortestosterone and other steroids determined by modified levator ani muscle method. Proc Soc Exp Biol Med 83:175-180.
24. Kelce WR, Monosson E, Gamcsik MP, Laws SC, Gray LE. 1994. Environmental hormone disruptors: evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolites. Toxicol Appl Pharmacol 126:276-285.
25. Kelce WR, Stone CR, Laws SC, Gray LE, Kemppainen JA, Wilson EM. 1995. Persistent DDT metabolite p,p′-DDE is a potent androgen receptor antagonist. Nature 375:581-585.
26. Kelce WR, Wilson EM. 1997. Environmental antiandrogens: developmental effects, molecular mechanisms, and clinical implications. J Mol Med 75:198-207.
27. Kitamura S, Kadota T, Yoshida M, Jinno N, Ohta S. 2000. Whole-body metabolism of the organophosphorus pesticide, fenthion, in goldfish, Carassius auratus. Comp Biochem Physiol [C] 126C:259-266.
28. Kitamura S, Shimizu Y, Shiraga Y, Yoshida M, Sugihara K, Ohta S, 2002. Reductive metabolism of p,p′-DDT and o,p′-DDT by rat liver cytochrome P450. Drug Metab Dispos 30:113-118.
29. Kitamura S, Yoshida M, Sugihara K, Ohta S, Hara A. 1999. Effect of fenthion on the level of vitellogenin in goldfish, Carassius auratus. J Health Sci 45:262-265.
30. Korach KS, Sarver P, Chae K, McLachlan JA, McKinney JD. 1988. Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: conformationally restricted structural probes. Mol Pharmacol 33:120-126.
31. Lacorte S, Jeanty G, Marty J-L, Barcelo D. 1997. Identification of fenthion and temephos and their transformation products in water by high-performance liquid chromatography with diode array detection and atmospheric pressure chemical ionization mass spectrometric detection. J Chromatogr A 777:99-114.
32. Lambright C, Ostby J, Bobseine K, Wilson V, Hotchkiss AK, Mann PC, et al. 2000. Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rats. Toxicol Sci 56:389-399.
33. McIntyre BS, Barlow NJ, Wallace DG, Maness SC, Gaido KW, Foster PM. 2000. Effects of in utero exposure to linuron on androgen-dependent reproductive development in the male Crl:CD(SD)BR rat. Toxicol Appl Pharmacol 167:87-99.
34. McLane KE, Fisher J, Ramakrishnan K. 1983. Reductive drug metabolism. Drug Metab Rev 14:741-799.
35. Meyer E, Borrey D, Lambert W, Van Peteghem C, Piette M, De Leenheer A. 1998. Analysis of fenthion in postmortem samples by HPLC with diode-array detection and GC-MS using solid-phase extraction. J Anal Toxicol 22:248-252.
36. Mitchell SC, Waring RH. 1986. The early history of xenobiotic sulfoxidation. Drug Metab Rev 16:255-284.
37. Mullie WC, Diallo AO, Gadji B, Ndiaye MD. 1999. Environmental hazards of mobile ground spraying with cyanophos and fenthion for quelea control in Senegal. Ecotoxicol Environ Saf 43:1-10.
38. Nakagawa Y, Suzuki T. 2002. Metabolism of 2-hydroxy-4-methoxybenzophenone in isolated rat hepatocytes and xenoestrogenic effects of its metabolites on MCF-7 human breast cancer cells. Chem-Biol Interact 139:115-128.
39. Ostby J, Kelce WR, Lambright C, Wolf C, Mann P, Gray LE Jr. 1999. The fungicide procymidone alters sexual differentiation in the male rat by acting as an androgen-receptor antagonist in vivo and in vitro. Toxicol Ind Health 15:80-93.
40. Peiris HT, Hemingway J. 1996. Effect of fenthion treatment on larval densities of insecticide-resistant Culex quinquefasciatus in an urban area of Sri Lanka. Med Vet Entomology 10:283-287.
41. Pereira WE. Hostettler FD. 1993. Nonpoint source contamination of the Mississippi River and its tributaries by herbicides. Environ Science Technol 27:1542-1552.
42. Prasad MP, Rajendran G, Sabesan S, Kalyanasundaram M. 1997. Field evaluation of biodegradable controlled release formulation of fenthion against Mansonia mosquitos. Southeast Asian J Trop Med Public Health 28:208-211.
43. Roberts T, Hutson D. 1999. Metabolic Pathways of Agrochemicals. 2. Insecticides and fungicides. Cambridge, UK:The Royal Society of Chemistry, 326-331.
44. Roux D, Jooste S, Truter E, Kempster P. 1995. An aquatic toxicological evaluation of fenthion in the context of finch control in South Africa. Ecotoxicol Environ Saf 31:164-172.
45. Schoor WP, Middaugh DP, Marcovich DT. 2000. Effects of aerially applied fenthion on survival and reproduction of the panacea sand fiddler, Uca panacea, in laboratory habitats. Arch Environ Contam Toxicol 38:327-333.
46. Sohoni P, Lefevre PA, Ashby J, Sumpter JP. 2001. Possible androgenic/anti-androgenic activity of the insecticide fenitrothion. J Appl Toxicol 21:173-178.
47. Soto AM, Chung KL, Sonnenschein C. 1994. The pesticides endosulfan, toxaphene and dieldrin have estrogenic effects on human estrogen-sensitive cells. Environ Health Perspect 102:380-383.
48. Sugihara K, Kitamura S, Sanoh S, Ohta S, Fujimoto N, Maruyama S, et al. 2000. Metabolic activation of the proestrogens trans-stilbene and trans-stilbene oxide by rat liver microsomes. Toxicol Appl Pharmacol 167:46-54.
49. Sugihara K, Kitamura S, Tatsumi K. 1995. Strain differences of liver aldehyde oxidase activity in rats. Biochem Mol Biol Inter 37:861-869.
50. Sunami O, Kunimatsu T, Yamada T, Yabushita S, Sukata T, Miyata K, et al. 2000. Evaluation of a 5-day Hershberger assay using young mature male rats: methyltestosterone and p,p′-DDE, but not fenitrothion, exhibited androgenic or antiandrogenic activity in vivo. J Toxicol Sci 25:403-415.
51. Tamura H, Maness SC, Reischmann K, Dorman DC, Gray LE, Gaido KW. 2001. Androgen receptor antagonism by the organophosphate insecticide fenitrothion. Toxicol Sci 60:56-62.
52. Tandon P, Padilla S, Barone S, Pope CN, Tilson HA. 1994. Fenthion produce a persistent decrease in muscarinic receptor function in the adult rat retina. Toxicol Appl Pharmacol 125:271-280.
53. Tatsumi K, Kitamura S, Yamada H. 1983. Sulfoxide reductase activity of liver aldehyde oxidase. Biochim Biophys Acta 747:86-92.
54. Tsuda T, Kojima M, Harada H, Nakajima A, Aoki S. 1996. Accumulation and excretion of fenthion, fenthion sulfoxide and fenthion sulfone by killifish (Oryzias latipes). Comp Biochem Physiol [C] 113C:45-49.
55. Tuler SM, Bowen JM. 1999. Chronic fenthion toxicity in laying hens. Vet Hum Toxicol 41:302-307.
56. Wong C, Kelce W, Sar M, Wilson EM. 1995. Androgen receptor antagonist versus agonist activities of the fungicide vinclozolin relative to hydroxyflutamide. J Biol Chem 270:19998-20003.
57. Yamaguchi Y, Fukushima M. 1994. Nouyaku Osen no Jyotai hyoka. Environ Conserv Engineer 23:70-73 [in Japanese].
58. You L, Brenneman KA, Heck H. 1999. In utero exposure to antiandrogens alters the responsiveness of the prostate to p,p′-DDE in adult rats and may induce prostatic inflammation. Toxicol Appl Pharmacol 161:258-266.
59. Zutshi B, Murthy PS. 2001. Ultrastructural changes in testis of gobiid fish Glossogobiuris (Ham) induced by fenthion. Indian J Exp Biol 39:170-173.