In vitro metabolism and interactions of the fungicide metalaxyl in human liver preparations

Environmental Toxicology and Pharmacology

Volumn 23, Issue 1, 2007, Pages 39-47

  Abass, Khaled ^a   Reponen, Petri ^a   Jalonen, Jorma ^a   Pelkonen, Olavi ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

Fungicide; Human metabolism; LC MS; Metalaxyl; Toxicology

Indexed keywords

AMFEBUTAMONE; CYTOCHROME P450; CYTOCHROME P450 2B; CYTOCHROME P450 2B6; CYTOCHROME P450 3A4; FUNGICIDE; LACTONE; METALAXYL;

ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; DEMETHYLATION; DRUG METABOLISM; ENZYME METABOLISM; HUMAN; HUMAN TISSUE; HYDROXYLATION; IN VITRO STUDY; LIVER CELL; MICROSOME; PRIORITY JOURNAL;

EID: 33845191144     PISSN: 13826689     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.etap.2006.06.004     Document Type: Article

References (42)

1. Äbelö A., Andersson T.B., Antonsson M., Naudot A.K., Skanberg I., and Weidolf L. Stereoselective metabolism of omeprazole by human cytochrome P450 enzymes. Drug Metab. Dispos. 28 (2000) 966-972
2. Aitio A. A simple and sensitive assay of 7-ethoxycoumarin demethylation. Anal. Biochem. 85 (1978) 488-491
3. Bhaskara R.M.V., Shetty H.S., and Reddy S. Mobility, distribution and persistence of metalaxyl residues in Pearl Millet (Pennisetum americanum (L.) Leeke.). Bull. Environ. Contam. Toxicol. 45 (1990) 250-257
4. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 722 (1976) 248-254
5. Brian D.R. Gas chromatography-mass spectrometry of acylalanine fungicides. J. Agric. Food Chem. 33 (1985) 560-563
6. Buratti F.M., Volpe M.T., Meneguz A., Vittozzi L., and Testai E. CYP-specific bioactivation of four organophosphorothioate pesticides by human liver microsomes. Toxicol. Appl. Pharmacol. 186 (2003) 143-154
7. Burke M.D., Prough R.A., and Mayer R.T. Characteristics of a microsomal cytochrome P-448-mediated reaction ethoxy-resorufin O-deethylation. Drug Metab. Dispos. 5 (1977) 1-8
8. David L.S., Schlenk D., and Chambers J.E. Hepatic microsomal desulfuration and dearylation of chlorpyrifos and parathion in fingerling channel catfish: lack of effect from Aroclor 1254. Aquat. Toxicol. 50 (2000) 141-149
9. Greenlee W.F., and Poland A. An improved assay of 7-ethoxy-deethylase activity in C57BLy6J and DBAy2J mice by phen-3-methylcholanthrene and 2,3,7,8-tetrachlorodibenzo-p-diol. J. Pharmacol. Exp. Ther. 205 (1978) 596-605
10. Hamboeck, H., 1981. Metabolic pathways of CGA 48988 in the rat. Unpublished Report No. 31/81, dated 7 October 1981 from Ciba-Geigy Ltd., Basel, Switzerland. In: W.H.O., submitted to WHO by Syngenta Crop Protection AG, Basel, Switzerland, 2003.
11. Hassall K.A. The Biochemistry and Uses of Pesticides: Structure Metabolism, Mode of Action and Uses in Crop Protection (1990), VCH, Cambridge pp. 350-354
12. Hodgson E., and Goldstein J.A. Metabolism of toxicants: phase I reactions and pharmacogenetics. In: Hodgson E., and Smart R.C. (Eds). Introduction to Biochemical Toxicology (2001), Wiley, New York 67-113 (cf. Tang et al. (2006)).
13. 14C]-metalaxyl metabolites in rats. Unpublished Report No. ABR-90079, dated 19 October 1990, from Ciba-Geigy Corp., Greensboro, USA. In: WHO, 2003, submitted to WHO by Syngenta Crop Protection AG, Basel, Switzerland.
14. Knodell R., Hall S., Wilkinson G., and Guengerich F. Hepatic metabolism of tolbutamide: characterization of the form of cytochrome P-450 involved in methyl hydroxylation and relationship to in vivo disposition. J. Pharmacol. Exp. Ther. 241 (1987) 1112-1119
15. Kornreich, M., Montgomery, C.A., 1990. Toxicology and Carcinogenesis Studies of 2,6-xylidine (2,6-dimethylaniline) in Charles River CD Rats, National Toxicology Program (NTP). NTP TR 278, NIH Publication No. 90-2534, pp. 1-138.
16. Kronbach T., Mathys D., Gut J., Catin T., and Meyer U. High-performance liquid chromatographic assay for bufuralol 19-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P-450 isozymes of human liver. Anal. Biochem. 162 (1987) 24-32
17. Kronbach T., Mathys D., Umeno M., Gonzalez F., and Meyer U. Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol. Pharmacol. 38 (1989) 89-96
18. Langcake P., Kuhn J., and Wade M. Mode of action of systemyc fungicides. Prog. Pest. Biochem. Toxicol. 3 (1983) 1-109
19. Naidu K.A. Inhibition of monoamine oxidase by the fungicide metalaxyl. J. Toxicol. Environ. Health 27 (1989) 395-398
20. Naidu K.A., and Radhakrishnamurty R. Metalaxyl-induced bradycardia in rats mediated by alpha-adrenoreceptors. J. Toxicol. Environ. Health 23 (1988) 495-498
21. Naidu K.A., and Radhakrishnamurty R. Effect of metalaxyl on heart rate in rats: role of alpha 1-adrenoreceptors. J. Toxicol. Environ. Health 26 (1989) 203-207
22. Nuninger C., Watson G., Leadbitter N., and Ellgehausen H. CGA 329351: introduction of the enantiomeric form of the fungicide metalaxyl. Brighton Crop Protect Conf-Pests Diseases 2A-4 (1996) 41-46
23. Paolini M., Mesirca R., Pozzetti L., Sapone A., and Cantelli-Forti G. Biomarkers of effect in evaluating metalaxyl cocarcinogenesis, Selective induction of murine CYP 3A isoform. Mutat. Res. 361 (1996) 157-164
24. Park Y., Kullberg M., and Hinsvark O. Quantitative determination of dextromethorphan and three metabolites in urine by reverse-phase high-performance liquid chromatography. J. Pharmacol. Sci. 73 (1984) 24-29
25. Parkinson A. Biotransformation of xenobiotics. In: Klaassen C.D. (Ed). Casarett and Doull's Toxicology (2001), McGraw-Hill, New York 133-224 (in: Tang, et al. (2006))
26. Pelkonen O., Kaltiala E., Larmi T., and Kärki N. Cytochrome P-450-linked monooxygenase system and drug-induced spectral interactions in human liver microsomes. Chem. Biol. Interact. 9 (1974) 205-216
27. Pelkonen O., Mäenpää J., Taavitsainen P., Rautio A., and Raunio H. Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica 28 (1998) 1203-1253
28. Peter R., Böcker R., Beaune P., Iwasaki M., Guengerich F., and Yang C. Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem. Res. Toxicol. 3 (1990) 566-573
29. Raunio H., Syngelmä T., Pasanen M., Juvonen R., Honkakoski P., Kairaluoma M., Sotaniemi E., Lang M., and Pelkonen O. Immunochemical and catalytical studies on hepatic coumarin 7-hydroxylase in man, rat and mouse. Biochem. Pharmacol. 37 (1988) 3889-3895
30. Raunio H., Valtonen J., Honkakoski P., Lang M., Stahlberg M., Kairaluoma M., Rautio A., Pasanen M., and Pelkonen O. Immunochemical detection of human liver cytochrome P450 forms related to phenobarbital-inducible forms in the mouse. Biochem. Pharmacol. 40 (1990) 2503-2509
31. Sams C., Mason H.J., and Rawbone R. Evidence for the activation of organophosphate pesticides by cytochromes P450 3A4 and 2D6 in human liver microsomes. Toxicol. Lett. 116 (2000) 217-221
32. Smyser B., Sabourin P., and Hodgson E. Oxidation of pesticides by purified microsomal FAD-containing monooxygenase from mouse and pig liver. Pestic. Biochem. Physiol. 24 (1985) 368-374
33. Sullivan-Klose T., Ghanayem B., Bell D., Zhang A., Kaminsky L., Shenfield G., Miners J., Birkett D., and Goldstein J. The role of the CYP2C9-Leu359 allelic variant in the tolbutamide polymorphism. Pharmacogenetics 6 (1996) 341-349
34. Taavitsainen P., Juvonen R., and Pelkonen O. In vitro inhibition of cytochrome p450 enzymes in human liver microsomes by a potent cyp2a6 inhibitor, Trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. Drug Metab. Dispos. 29 (2001) 217-222
35. Tang J., Amin U.K., Hodgson E.A., and Rose R.L. In vitro metabolism of fipronil by human and rat cytochrome P450 and its interactions with testosterone and diazepam. Chem. Biol. Interact. 147 (2004) 319-329
36. Tang J., Cao Y., Rose R.L., Brimfield L.L., 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 (2001) 1201-1204
37. Tang J., Rose R.L., and Chambers J.E. In: Ramesh C.G. (Ed). Toxicology of Organophosphate and Carbamate Compounds: Metabolism of Organophosphorus and Carbamate Pesticides (2006), Academic Press 127-143
38. Turpeinen M., Nieminen R., Juntunen T., Taavitsainen P., Raunio H., and Pelkonen O. Inhibition of CYP2B6-catalyzed bupropion hydroxylation in human liver microsomes in vitro. Drug Metab. Dispos. 32 (2004) 626-631
39. Tydén E., Hans T., and Pia L. Metabolic activation of 2,6-xylidine in the nasal olfactory mucosa and the mucosa of the upper alimentary and respiratory tracts in rats. Toxicol. Sci. 81 (2004) 263-272
40. Tynes R., and Hodgson E. Magnitude of involvement of the mammalian flavin-containing monooxygenase in the microsomal oxidation of pesticides. J. Agric. Food Chem. 33 (1985) 471-479
41. Usmani K.A., Hodgson E., and Rose R.L. In vitro metabolism of carbofuran by human, mouse, and rat cytochrome P450 and interactions with chlorpyrifos, testosterone, and estradiol. Chem. Biol. Interact. 150 (2004) 221-232
42. Pesticide residues in food-2002 evaluations. Part II. Toxicological. World Health Organization, WHO/PCS/03.1, 2003.