Involvement of molybdenum hydroxylases in reductive metabolism of nitro polycyclic aromatic hydrocarbons in mammalian skin

Drug Metabolism and Disposition

Volumn 33, Issue 9, 2005, Pages 1312-1318

  Ueda, Osamu ^a   Sugihara, Kazumi ^a   Ohta, Shigeru ^a   Kitamura, Shigeyuki ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 NITROPYRENE; 2 DIETHYLAMINOETHANOL; 2 FLUORENYLAMINE; 2 HYDROXYPYRIMIDINE; 2 NITROFLUORENE; 4 HYDROXYPYRIMIDINE; 4 NITROBIPHENYL; ALDEHYDE OXIDASE; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; BENZALDEHYDE OXIDASE; BENZENE DERIVATIVE; ENZYME; HYPOXANTHINE; MARKER; N METHYLNICOTINAMIDE; NITROREDUCTASE; OXIDOREDUCTASE INHIBITOR; OXIPURINOL; OXYGENASE; POLYCYCLIC AROMATIC HYDROCARBON; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; XANTHINE; XANTHINE OXIDASE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CATALYSIS; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CYTOSOL; ENZYME ACTIVITY; ENZYME INHIBITION; GUINEA PIG; HAMSTER; INHIBITION KINETICS; MALE; MAMMAL; METABOLISM; MOUSE; NONHUMAN; POLLUTANT; PRIORITY JOURNAL; RABBIT; RAT; REDUCTION; SKIN; SKIN CELL; SPECIES; SPECIES COMPARISON;

ALDEHYDE OXIDASE; ANIMALS; CELLS, CULTURED; CRICETINAE; CYTOSOL; ENVIRONMENTAL POLLUTANTS; GUINEA PIGS; MALE; MESOCRICETUS; MICE; MICE, INBRED STRAINS; MICROSOMES; NITROREDUCTASES; OXIDATION-REDUCTION; POLYCYCLIC HYDROCARBONS, AROMATIC; RABBITS; RATS; RATS, SPRAGUE-DAWLEY; SKIN; XANTHINE OXIDASE;

ANIMALIA; CAVIA; CRICETINAE; MAMMALIA; ORYCTOLAGUS CUNICULUS;

EID: 23944454203     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.105.005306     Document Type: Article

References (40)

1. Bauer SL and Howard PC (1990) The kinetics of 1-nitropyrene and 3-nitrofluoranthene metabolism using bovine liver xanthine oxidase. Cancer Lett 54:37-42.
2. Beedham C (1985) Molybdenum hydroxylases as drug-metabolizing enzyme. Drug Metab Rev 16:119-156.
3. Beedham C, Peet CF, Panoutsopoulos GI, Carter H, and Smith A (1995) Role of aldehyde oxidase in biogenic amine metabolism. Prog Brain Res 106:345-353.
4. Beije B and Möller L (1988) 2-Nitrofluorene and related compounds: prevalence and biological effects. Mutat Res 196:177-209.
5. Clarke SE, Harrell AW, and Chenery RJ (1995) Role of aldehyde oxidase in the in vitro conversion of famciclovir to penciclovir in human liver. Drug Metab Dispos 23:251-254.
6. El-Bayoumy K, Hecht SS, and Hoffmann D (1982) Comparative tumor initiating activity on mouse skin of 6-nitrobenzo[a]pyrene, 6-nitrochrysene, 3-nitroperylene, 1-nitropyrene and their parent hydrocarbons. Cancer Lett 16:333-337.
7. Fowles SE, Pratt SK, Laroche J, and Prince WT (1994) Lack of a pharmacokinetic interaction between oral famciclovir and allopurinol in healthy volunteers. Eur J Clin Pharmacol 46:355-359.
8. Fu PP (1990) Metabolism of nitro-polycyclic aromatic hydrocarbons. Drug Metab Rev 22:209 268.
9. Garattini E, Mendel R, Romão MJ, Wright R, and Terao M (2003) Mammalian molybdoflavoenzymes, an expanding family of proteins: structure, genetics, regulation, function and pathophysiology. Biochem J 372:15-32.
10. Hille R (2005) Molybdenum-containing hydroxylases. Arch Biochem Biophys 433:107-116.
11. Hirao Y, Kitamura S, and Tatsumi K (1994) Epoxide reductase activity of mammalian liver cytosols and aldehyde oxidase. Carcinogenesis 15:739-743.
12. Jones DB, Rustgi VK, Kornhauser DM, Woods A, Quinn R, Hoofnagle JH, and Jones EA (1987) The distribution of 6-deoxyacyclovir, a xanthine oxidase-activated prodrug of acyclovir, in the isolated perfused rat liver. Hepatology 7:345-348.
13. Jordan CGM, Rashidi MR, Laljee H, Clarke SE, Brown JE, and Beedham C (1999) Aldehyde oxidase-catalyzed oxidation of methotrexate in the liver of guinea-pig, rabbit and man. J Pharm Pharmacol 51:411-418.
14. Kishore GS and Boutwell (1980) Enzymatic oxidation and reduction of retinal by mouse epidermis. Biochem Biophys Res Commun 94:1381-1386.
15. Kitamura S, Nakatani K, Sugihara K, and Ohta S (1999a) Strain differences of the ability to hydroxylate methotrexate in rats. Comp Biochem Physiol 122C:331-336.
16. Kitamura S, Sugihara K, Nakatani K, Ohta S, Oh-hara T, Ninomiya S, Green CE, and Tyson CA (1999b) Variation of hepatic methotrexate 7-hydroxylase activity in animals and humans. IUBMB Life 48:607-611.
17. Kitamura S and Tatsumi K (1984) Involvement of liver aldehyde oxidase in the reduction of nicotinamide N-oxide. Biochem Biophys Res Commun 120:602-606.
18. Kooij A, Bosch KS, Frederiks WM, and Van Noorden CJ (1992) High levels of xanthine oxidoreductase in rat endothelial, epithelial and connective tissue cells. A relation between localization and function? Virchows Arch B Cell Pathol Incl Mol Pathol 62:43-150.
19. Krenitsky TA, Hall WW, Miranda PD, Beauchamp LM, Schaeffer HJ, and Whiteman PD (1984) 6-Deoxyacyclovir: a xanthine oxidase-activated prodrug of acyclovir. Proc Natl Acad Sci USA 81:3209-3213.
20. Krenitsky TA, Neil SM, Elion GB, and Hitchings GH (1972) A comparison of the specificities of xanthine oxidase and aldehyde oxidase. Arch Biochem Biophys 150:585-599.
21. Krenitsky TA, Tuttle JV, Cattau EL, and Wang P (1974) A comparison of the distribution and electron acceptor specificities of xanthine oxidase and aldehyde oxidase. Comp Biochem Physiol B 49:687-703.
22. Kurosaki M, Demontis S, Barzago MM, Garanttini E, and Terao M (1999) Molecular cloning of the cDNA coding for mouse aldehyde oxidase: tissue distribution and regulation in vivo by testosterone. Biochem J 341:71-80.
23. Möller L, Rafter J, and Gustafsson J-Å (1987) Metabolism of the carcinogenic air pollutant 2-nitrofluorene in the rat. Carcinogenesis 8:637-645.
24. Moriwaki Y, Yamamoto T, Yamaguchi K, Takahashi S, and Higashino K (1996) Immunohistochemical localization of aldehyde and xanthine oxidase in rat tissues using polyclonal antibodies. Histochem Cell Biol 105:71-79.
25. Purohit V and Basu AK (2000) Mutagenicity of nitroaromatic compounds. Chem Res Toxicol 13:673-692.
26. Rashidi MR, Smith JA, Clarke SE, and Beedham C (1997) In vitro oxidation of famciclovir and 6-deoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit and rat liver. Drug Metab Dispos 25:805-813.
27. Relling MV, Lin J-S, Ayers GD, and Evans WE (1992) Racial and gender differences in N-acetyltransferase, xanthine oxidase and CYP1A2 activities. Clin Pharmacol Ther 52:643-658.
28. Rodrigues AD (1994) Comparison of levels of aldehyde oxidase with cytochrome P450 activities in human liver in vitro. Biochem Pharm 48:197-200.
29. Saito K, Kamataki T, and Kato R (1984) Participation of cytochrome P-450 in reductive metabolism of 1-nitropyrene by rat liver microsomes. Cancer Res 44:3169-3173.
30. Siegenthaler G, Gumowski-Sunek D, and Saurat JH (1990) Metabolism of natural retinoids in psoriatic epidermis. J Investig Dermatol 95:47S-48S.
31. Sugihara K, Kitamura S, and Tatsumi K (1995) Strain differences of liver aldehyde oxidase activity in rats. Biochem Mol Int 37:861-869.
32. Sugihara K, Kitamura S, and Tatsumi K (1996) Involvement of mammalian liver cytosols and aldehyde oxidase in reductive metabolism of zonisamide. Drug Metab Dispos 24:199-202.
33. Sugihara K, Kitamura S, Tatsumi K, Asahara T, and Dohi K (1997) Differences in aldehyde oxidase activity in cytosolic preparations of human and monkey liver. Biochem Mol Biol Int 41:1153-1160.
34. Tatsumi K, Kitamura S, and Narai N (1986) Reductive metabolism of aromatic nitro compounds including carcinogens by rabbit liver preparations. Cancer Res 46:1089-1093.
35. Terao M, Kurosaki M, Saltini G, Demontis S, Marini M, Salmona M, and Garattini E (2000) Cloning of the cDNAs coding for two novel molybdo-flavoproteins showing high similarity with aldehyde oxidase and xanthine oxidoreductase. J Biol Chem 39:30690-30700.
36. Turner NA, Doyle WA, Ventom AM, and Bray RC (1995) Properties of rabbit liver aldehyde oxidase and the relationship of the enzyme to xanthine oxidase and dehydrogenase. Eur J Biochem 232:646-657.
37. Ueda O, Kitamura S, Kubo R, Yano Y, Kanzaki Y, Fujimoto T, Tatsumi K, and Ohta S (2001) Metabolism of 2-nitrofluorene, 2-aminofluorene and 2-acetylaminofluorene in rat and dog and the role of intestinal bacteria. Xenobiotica 31:33-49.
38. Ueda O, Kitamura S, Ohashi K, Sugihara K, and Ohta S (2003) Xanthine oxidase-catalyzed metabolism of 2-nitrofluoren, a carcinogenic air pollutant, in rat skin. Drug Metab Dispos 31:367-372.
39. Ueda O, Kitamura S, and Ohta S (2002) Metabolism of 2-nitrofluorene, an environmental pollutant, by liver preparations of sea bream, Pagrus major. Xenobiotica 32:667-682.
40. Van Duuren BL (1980) Carcinogenicity of hair dye components. J Environ Pathol Toxicol 3:237-251.