Evidences for CYP3A4 autoactivation in the desulfuration of dimethoate by the human liver

Toxicology

Volumn 241, Issue 1-2, 2007, Pages 33-46

  Buratti, Franca M ^a   Testai, Emanuela ^a  

^a ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

Atypical kinetics; Autoactivation; CYP1A2; CYP3A4; Dimethoate; Omethoate; Organophosphorothionate pesticides

Indexed keywords

ACETYLCHOLINESTERASE; CYTOCHROME P450 1A2; CYTOCHROME P450 3A4; DIMETHOATE; OMETHOATE;

ANIMAL EXPERIMENT; ARTICLE; CATALYSIS; CONTROLLED STUDY; DESULFURIZATION; ENZYME INHIBITION; GENE EXPRESSION; HUMAN; HUMAN TISSUE; INTOXICATION; NONHUMAN; PRIORITY JOURNAL; RAT; TOXICOKINETICS;

ACETYLCHOLINESTERASE; ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; DATA INTERPRETATION, STATISTICAL; DIMETHOATE; DNA, COMPLEMENTARY; ENZYME ACTIVATION; ENZYME INHIBITORS; HUMANS; INSECTICIDES; KINETICS; LIVER; MALE; MICROSOMES, LIVER; OXIDATION-REDUCTION; RATS; RATS, SPRAGUE-DAWLEY; RECOMBINANT PROTEINS; SULFUR;

MAMMALIA;

EID: 35349005308     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2007.08.081     Document Type: Article

References (46)

1. Abass K., Reponen P., Jalonen J., and Pelkonen O. In vitro metabolism and interaction of profenofos by human, mouse and rat liver preparations. Pest. Biochem. Physiol. 87 (2007) 238-247
2. Abass K., Reponen P., Jalonen J., and Pelkonen O. In vitro metabolism and interactions of the fungicide metalaxyl in human liver preparations. Environ. Toxicol. Pharmacol. 23 (2007) 39-47
3. Adgate J.L., Barr D.B., Clayton C.A., Eberly L.E., Freeman N.C.G., Lioy P.J., Needham L.L., Pellizzari E.D., Quackenboss J.J., Roy A., and Sexton K. Measurement of children's exposure to pesticides: analysis of urinary metabolite levels in a probability-based sample. Environ. Health Perspect. 109 6 (2001) 583-589
4. Al-Jaghbir M.T., Salhab A.S., and Harmarsheh F.A. Dermal and inhalation exposure to dimethoate. Arch. Environ. Contam. Toxicol. 22 (1992) 358-361
5. Aprea C., Sciarra G., and Sartorelli P. Environmental and biological monitoring of exposure to mancozeb, ethylenethiourea, and dimethoate during industrial formulation. J. Toxicol. Environ. Health 53 (1998) 263-281
6. Aprea C., Terenzoni B., De Angelis V., Sciarra G., Lunghini L., Borzacchi G., Vasconi D., Fani D., Quercia A., Salvan A., and Settimi L. Evaluation of skin and respiratory doses and urinary excretion of alkylphosphates in workers exposed to dimethoate during treatment of olive trees. Arch. Environ. Contam. Toxicol. 48 (2004) 127-134
7. Buratti F.M., Volpe M.T., Fabrizi L., Meneguz A., Vittozzi L., and Testai E. Kinetic parameters of OPT pesticide desulfuration by c-DNA expressed human CYPs. Environ. Toxicol. Pharmacol. 11 3-4 (2002) 181-190
8. Buratti F.M., Volpe M.T., Meneguz A., Vittozzi L., and Testai E. CYP-specific bioactivation of four organophosphorothionate pesticides by human liver microsomes. Toxicol. Appl. Pharmacol. 186 (2003) 143-154
9. Buratti F.M., D'Aniello A., Volpe M.T., Meneguz A., and Testai E. Malathion bioactivation in the human liver: the contribution of different cytochrome P450 isoforms. Drug Metab. Dispos. 33 (2005) 295-302
10. Butler A.M., and Murray M. Biotransformation of parathion in human liver: participation of CYP3A4 and its inactivation during microsomal parathion oxidation. J. Pharmacol. Exp. Ther. 280 (1997) 966-973
11. Carrier G., and Brunet R.C. A toxicokinetic model to assess the risk of azinphosmethyl exposure in humans through measures of urinary elimination of alkylphosphates. Toxicol. Sci. 47 1 (1999) 23-32
12. Eddleston M., and Phillips M.R. Self-poisoning with pesticides. Br. Med. J. 328 (2004) 42-44
13. Eddleston M., Eyer P., Worek F., Mohamed F., Senarathna L., von Meyer L., Juszczak E., Hittarage A., Azhar S., Dissanayake W., Rezvi Sheriff M.H., Szinicz L., Dawson A.H., and Buckley N.A. Differences between organophosphorus insecticides in human self-poisoning: a prospective cohort study. Lancet 366 (2005) 1452-1459
14. EFSA. Conclusion regarding the peer review of the pesticide risk assessment of active substance: dimethoate. EFSA Sci. Rep. 84 (2006) 1-102
15. Ekins S., Ring B.J., Binkley S.N., Hall S.D., and Wrighton S.A. Autoctivation and activation of cytochrome P450s. Int. J. Clin. Pharmcol. Ther. 36 12 (1998) 642-651
16. Ellman G.L., Courtney D.K., Andres Jr. V., and Featherstone R.M. A new rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7 (1961) 88-95
17. EPA, 1999. Memorandum, Updated, revised dimethoate. The updated, revised HED Chapter of the re-registration, eligibility decision document (RED). PC code: 035001, case#0088. United States Environmental Protection Agency, Washington, DC.
18. EPA, 2006. Interim reregistration eligibility decision for dimethoate. United States Environmental Protection Agency, Washington, DC. Available at: http://www.epa.gov/oppsrrd1/reregistration/REDs/dimethoate_ired.pdf.
19. Fabrizi L., Gemma S., Testai E., and Vittozzi L. Identification of the cytochrome P450 isoenzymes involved in the metabolism of diazinon in the rat liver. J. Biochem. Mol. Toxicol. 13 (1999) 53-61
20. Ha-Duong N.-T., Dijols S., Macherey A.-C., Goldestein J.A., Dansette P.M., and Mansuy D. Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 40 (2001) 12112-12122
21. Halpert J.A., Hammond D., and Neal R.A. Inactivation of purified rat liver cytochrome P-450 during the metabolism of parathion (diethyl-p-nitrophenyl-phosphorothionate). J. Biol. Chem. 255 (1980) 1080-1089
22. Hosea N.A., Miller G.P., and Guengerich F.P. Elucidation of distinct ligand binding sites for cytochrome P450 3A4. Biochemistry 39 (2000) 5929-5939
23. Houston J.B., and Galetin A. Progress towards prediction of human pharmacokinetic parameters from in vitro technologies. Drug Metab. Rev. 35 4 (2003) 393-415
24. Houston J.B., and Galetin A. Modelling atypical CYP3A4 kinetics, principles and pragmatism. Arch. Biochem. Biophys. 433 (2005) 351-360
25. Houston J.B., and Kenworthy K.E. In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab. Dispos. 28 3 (2000) 246-254
26. Hutzler J.M., and Tracy T.S. Atypical kinetic profiles in drug metabolism reactions. Drug Metab. Dispos. 30 4 (2002) 355-362
27. Inoue S., Howgate E.M., Rowland-Yeo K., Shimada T., Yamazaki H., Tucker G.T., and Rostami-Hodjegan A. Prediction of in vivo drug clearence from in vitro data. II: Potenzial inter-ethnic differences. Xenobiotica 36 6 (2006) 499-513
28. Jamal G.A., Hansen S., and Julu P.O.O. Low level exposures to organophosphorus esters may cause neurotoxicity. Toxicology 181-182 (2002) 23-33
29. Kappers W.A., Edwards R.J., Murray S., and Boobis A.R. Diazinon is activated by CYP2C19 in human liver. Toxicol. Appl. Pharmacol. 177 (2001) 68-76
30. Korzekwa K.R., Krishnamachary N., Shou M., Ogai A., Parise R.A., Rettie A.E., Gonzalez F.J., and Tracy T.S. Evaluation of atypical cytochrome P450 kinetics with two-substrate models, evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites. Biochemistry 37 (1998) 4137-4147
31. Krieger R.I., and Dinoff T.M. Malathion deposition, metabolite clearance, and cholinesterase status of date dusters and harvesters in California. Arch. Environ. Contam. Toxicol. 38 (1999) 546-553
32. Krieger R.I., and Thongsinthusak T. Metabolism and excretion of dimethoate following ingestion of overtolerance peas and a bolus dose. Food Chem. Toxicol. 31 3 (1993) 177-182
33. Meneguz A., Bisso G.M., and Michalek H. Alterations in the distribution of cholinesterase molecular forms in maternal and fetal brain following diisopropyl fluorophosphate treatment of pregnant rats. Neurochem. Res. 14 3 (1989) 285-291
34. Nolan R.J., Rick D.L., Freshour N.L., and Saunders J.H. Chlorpyrifos, pharmacokinetics in human volunteers. Toxicol. Appl. Pharmacol. 73 1 (1984) 8-15
35. Norman B.J., Poore R.F., and Neal R.A. Studies of the binding of sulfur released in the mixed-function oxidase-catalysed metabolism of diethyl p-nitrophenyl phosphorothioate (parathion) to diethyl p-nitrophenyl phosphate (paraoxon). Biochem. Pharmacol. 23 (1974) 1733-1744
36. Reiss R., and Gaylor D. Use of benchmark dose and meta-analysis to determine the most sensitive endpoint for risk assessment for dimethoate. Regul. Toxicol. Pharmacol. 43 (2005) 55-65
37. Reuber M.D. Carcinogenicity of dimethoate. Environ. Res. 34 (1984) 193-211
38. Richter T., Mürdter T.E., Heinkele G., Pleiss J., Tatzel S., Schwab M., Eichelbaum M., and Zanger U.M. Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J. Pharmacol. Exp. Ther. 308 (2004) 189-197
39. Rigas M.L., Okino M.S., and Quackenboss J.J. Use of pharmacokinetic model to assess chlorpyrifos exposure and dose in children, based on urinary biomarker measurment. Toxicol. Sci. 61 2 (2001) 374-381
40. Schurdut B.A., Barraj L., and Francis M. Aggregate exposures under the food quality protection act, an approach using chlorpyrifos. Regul. Toxicol. Pharmacol. 28 (1998) 165-177
41. Sharma Y., Bashir S., Irshad M., Datta Gupta S., and Dogra T.D. Effects of acute dimethoate administration on antioxidant status of liver and brain of experimental rats. Toxicology 206 (2005) 49-57
42. Tang J., Cao Y., Rose R.L., Brimfield A.A., Dai D., Goldstein J.A., and Hodgson E. Metabolism of chlorpyrifos by human cytochrome P450 isoforms and human, mouse, and rat liver microsomes. Drug Metab. Dispos. 29 9 (2001) 1201-1204
43. Walsky B.L., Astuccio A.V., and Obach R.S. Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J. Clin. Pharmacol. 46 (2006) 1426-1438
44. WHO IPCS, 2005. WHO recommended classification of pesticides by hazard and guidelines to classification 2004.
45. Witherow L.E., and Houston J.B. Sigmoidal kinetics of CYP3A substrates, an approach for scaling dextromethorphan metabolism in hepatic microsomes and isolated hepatocytes to predict in vivo clearance in rat. J. Pharmacol. Exp. Ther. 290 (1999) 58-65
46. Yasmashita M., Tanaka J., and Ando Y. Human mortality in organophosphate poisoning. Vet. Human Toxicol. 39 (1997) 84-85