Characterization of diuron N-demethylation by mammalian hepatic microsomes and cDNA-expressed human cytochrome P450 enzymes

Drug Metabolism and Disposition

Volumn 35, Issue 9, 2007, Pages 1634-1641

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

^a UNIVERSITY OF OULU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEMENTARY DNA; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 2C19; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; DIURON; NITROGEN;

ANIMAL CELL; ARTICLE; ATOM; BIOTRANSFORMATION; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DEMETHYLATION; DOG; EMBRYO DISPOSITION; ENZYME ACTIVITY; ENZYME MECHANISM; HUMAN; HUMAN CELL; HUMAN VERSUS ANIMAL COMPARISON; LIQUID CHROMATOGRAPHY; LIVER HOMOGENATE; LIVER MICROSOME; MAMMAL; MASS SPECTROMETRY; METABOLISM; METABOLITE; MINIPIG; MONKEY; MOUSE; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RABBIT; RAT; RISK ASSESSMENT; SAFETY; SPECIES DIFFERENCE; TOXICOKINETICS; UNCERTAINTY;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; DEALKYLATION; DIURON; DNA, COMPLEMENTARY; DOGS; ENZYME INHIBITORS; HUMANS; KINETICS; MACACA FASCICULARIS; MASS SPECTROMETRY; MICE; MICE, INBRED DBA; MICROSOMES, LIVER; RABBITS; RATS; RATS, SPRAGUE-DAWLEY; SWINE; SWINE, MINIATURE;

ANIMALIA; CANIS FAMILIARIS; MAMMALIA; ORYCTOLAGUS CUNICULUS; RATTUS;

EID: 34548088206     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.016295     Document Type: Article

References (40)

1. Abass K, Reponen P, Jalonen J, and Pelkonen O (2007a) In vitro metabolism and interaction of profenofos by human, mouse and rat liver preparations. Pestic Biochem Physiol 87:238-247.
2. Abass K, Reponen P, Jalonen J, and Pelkonen O (2007b) In vitro metabolism and interactions of the fungicide metalaxyl in human liver preparations. Environ Toxicol Pharmacol 23:39-47.
3. Ábelö A, Andersson TB, Antonsson M, Naudot AK, Skanberg I, and Weidolf L. (2000) Stereoselective metabolism of omeprazole by human cytochrome P450 enzymes. Drug Metab Dispos 28:966-972.
4. Agrawal RC, Kumar S, and Mehrotra NK (1996) Micronucleus induction by diuron in mouse bone marrow. Toxicol Lett 89:1-4.
5. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
6. Burke MD, Prough RA, and Mayer RT (1977) Characteristics of a microsomal cytochrome P-448-mediated reaction. ethoxyresorufin O-de-ethylation. Drug Metab Dispos 5:1-8.
7. European Commission (2001) Decision no. 2455/2001/EC, establishing the list of priority substances in the field of water policy and amending directive 2000/60/EC. OJ L (Official Journal of the European Communities L Series) 331:1-5.
8. Falk-Filipsson A, Warholm M, Victorin K, Wallén M, and Hanberg A (2007) Assessment factors - applications in health risk assessment of chemicals. Environ Res 104:108-127.
9. Giacomazzi S and Cochet N (2004) Environmental impact of diuron transformation: a review. Chemosphere 56:1021-1032.
10. Greenlee WF and Poland A (1978) An improved assay of 7-ethoxycoumarin O-deethylase activity: induction of hepatic enzyme activity in C57BL/6J and DBA/2J mice by phenobarbital, 3-methylcholanthrene and 2,3,7,8- tetrachlorodibenzo-p-dioxin. J Pharmacol Exp Ther 205:596-605.
11. Hodge HC, Downs WL, Panner BS, Smith DW, and Maynard EA (1967) Oral toxicity and metabolism of diuron (N-(3,4-dichlorophenyl)-N′,N′- dimethylurea) in rats and dogs. Food Cosmet Toxicol 5:513-531.
12. Kronbach T, Mathys D, Umeno M, Gonzalez FJ, and Meyer UA (1989) Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol Pharmacol 36:89-96.
13. Kronbach T, Mathys D, Gut J, Catin T, and Meyer UA (1987) High-performance liquid chromatographic assays for bufuralol 1′-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P-450 isozymes of human liver. Anal Biochem 162:24-32.
14. Lamoree MH, Swart CP, van der Horst A, and van Hattum B (2002) Determination of diuron and the antifouling paint biocide irgarol 1051 in dutch marinas and coastal waters. J Chromatogr A 970:183-190.
15. Lang D, Criegee D, Grothusen A, Saalfrank RW, and Bocker RH (1996) In vitro metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in rats, pigs, and humans. Drug Metab Dispos 24:859-865.
16. Li X, Bjorkman A, Andersson TB, Ridderstrom M, and Masimirembwa CM (2002) Amodiaquine clearance and its metabolism to N-desethylamodiaquine is mediated by CYP2C8: A new high affinity and turnover enzyme-specific probe substrate. J Pharmacol Exp Ther 300:399-407.
17. Madhum YA and Freed VH (1987) Degradation of the herbicides bromacil, diuron and chlortoluron in soil. Chemosphere 16:1003-1011.
18. Mutch E and Williams FM (2006) Diazinon, chlorpyrifos and parathion are metabolised by multiple cytochromes P450 in human liver. Toxicology 224:22-32.
19. Okamura H, Aoyama I, Ono Y, and Nishida T (2003) Antifouling herbicides in the coastal waters of western Japan. Mar Pollut Bull 47:59-67.
20. Pelkonen O, Kaltiala EH, Larmi TKI, and Karki NT (1974) Cytochrome P 450-linked monooxygenase system and drug-induced spectral interactions in human liver microsomes. Chem Biol Interact 9:205-216.
21. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, and Raunio H (1998) Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica 28:1203-1253.
22. Peter R, Bocker R, Beaune PH, Iwasaki M, Guengerich FP, and Yang CS (1990) Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem Res Toxicol 3:566-573.
23. Raunio H, Valtonen J, Honkakoski P, Lang MA, Stahlberg M, Kairaluoma MA, Rautio A, Pasanen M, and Pelkonen O (1990) Immunochemical detection of human liver cytochrome P450 forms related to phenobarbital-inducible forms in the mouse. Biochem Pharmacol 40:2503-2509.
24. Rendic S and Di Carlo FJ (1997) Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab Rev 29:413-580.
25. Renwick AG and Lazarus NR (1998) Human variability and noncancer risk assessment - an analysis of the default uncertainty factor. Regul Toxicol Pharmacol 27:3-20.
26. Rostami-Hodjegan A, Rostami-Hodjegan A, and Tucker GT (2007) Simulation and prediction of in vivo drug metabolism in human populations from in vitro data. Nat Rev Drug Discov 6:140-148.
27. Sullivan-Klose TH, Ghanayem BI, Bell DA, Zhang ZY, Kaminsky LS, Shenfield GM, Miners JO, Birkett DJ, and Goldstein JA (1996) The role of the CYP2C9-Leu359 allelic variant in the tolbutamide polymorphism. Pharmacogenetics 6:341-349.
28. Suzuki T and Casida JE (1981) Metabolites of diuron, linuron, and methazole formed by liver microsomal enzymes and spinach plants. J Agric Food Chem 29:1027-1033.
29. Tang J, Cao Y, Rose RL, Brimfield AA, Dai D, Goldstein JA, and Hodgson E (2001) Metabolism of chlorpyrifos by human cytochrome P450 isoforms and human, mouse, and rat liver microsomes. Drug Metab Dispos 29:1201-1204.
30. Thomas KV, Hurst MR, Matthiessen P, Sheahan D, and Williams RJ (2001) Toxicity characterisation of organic contaminants in stormwaters from an agricultural headwater stream in south east England. Water Res 35:2411-2416.
31. Tixier C, Bogaerts P, Sancelme M, Bonnemoy F, Twagilimana L, Cuer A, Bohatier J, and Veschambre H (2000) Fungal biodegradation of a phenylurea herbicide, diuron: structure and toxicity of metabolites. Pest Manage Sci 56:455-462.
32. Turpeinen M, Nieminen R, Juntunen T, Taavitsainen P, Raunio H, and Pelkonen O (2004) Selective inhibition of CYP2B6-catalyzed bupropion hydroxylation in human liver microsomes in vitro. Drug Metab Dispos 32:626-631.
33. U.S. Environmental Protection Agency (2005) Fact Sheet: The Drinking Water Contaminant Candidate List - The Source of Priority Contaminants for the Drinking Water Program, U.S. Environmental Protection Agency, Washington DC.
34. U.S. Environmental Protection Agency (2004) Chemicals Evaluated for Carcinogenic Potential, p 22, U.S. Environmental Protection Agency, Washington, DC.
35. Usmani KA, Usmani KA, Hodgson E, and Rose RL (2004) In vitro metabolism of carbofuran by human, mouse, and rat cytochrome P450 and interactions with chlorpyrifos, testosterone, and estradiol. Chem Biol Interact 150:221-332.
36. Van Boven M, Laruelle L, and Daenens P (1990) HPLC analysis of diuron and metabolites in blood and urine. J Anal Toxicol 14:231-234.
37. Verheij ER, van der Greef J, La Vos GF, van der Pol W, and Niessen WM (1989) Identification of diuron and four of its metabolites in human postmortem plasma and urine by LC/MS with a moving-belt interface. J Anal Toxicol 13:8-12.
38. Vinggaard AM, Larsen JC, Hnida C, and Breinholt V (2000) Screening of selected pesticides for inhibition of CYP19 aromatase activity in vitro. Toxicol in Vitro 14:227-234.
39. Walton K, Dorne JL, and Renwick AG (2001) Uncertainty factors for chemical risk assessment: interspecies differences in glucuronidation. Food Chem Toxicol 39:1175-1190.
40. World Health Organization/International Programme on Chemical Safety (2005) Chemical-specific adjustment factors for interspecies differences and human variability: Guidance document for use of data in dose/concentration- response assessment. World Health Organization, Geneva.