Identification of aldehyde oxidase as the neonicotinoid nitroreductase

Chemical Research in Toxicology

Volumn 18, Issue 2, 2005, Pages 317-323

  Dick, Ryan A ^a   Kanne, David B ^a   Casida, John E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE OXIDASE; ALLOPURINOL; AMINOGUANIDINE; BENZALDEHYDE; CHLORPROMAZINE; CIMETIDINE; CYTOCHROME P450 2D6; DIQUAT; FLAVOPROTEIN; IMIDACLOPRID; INSECTICIDE; MENADIONE; N METHYLNICOTINAMIDE; NITROREDUCTASE; NITROSOGUANIDINE; POTASSIUM CYANIDE; PROMETHAZINE; PYRIMIDINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; XANTHINE;

ANIMAL CELL; ARTICLE; CAT; CHICKEN; CONTROLLED STUDY; CROP PROTECTION; DOG; ENZYME ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; INSECT CONTROL; LIVER CYTOSOL; METABOLITE; MONKEY; NONHUMAN; RABBIT; REDUCTION; SPECIES DIFFERENCE; TANDEM MASS SPECTROMETRY; XENOBIOTIC METABOLISM;

ALDEHYDE OXIDASE; ANABASINE; ANIMALS; CYTOSOL; ENZYME INHIBITORS; GUANIDINES; HUMANS; IMIDAZOLES; LIVER; MOLECULAR CONFORMATION; NITROREDUCTASES; NITROSOGUANIDINES; TIME FACTORS;

EID: 13844294285     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049737i     Document Type: Article

References (33)

1. Tomizawa, M., and Casida, J. E. (2005) Neonicotinoid insecticide toxicology: mechanisms of selective action. Annu. Rev. Pharmacol. Toxicol 45, 247-268.
2. Kagabu, S. (1999) Discovery of chloronicotinyl insecticides. In Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor (Yamamoto, I., and Casida, J. E., Eds.) pp 91-106, Springer-Verlag: Tokyo.
3. Schenker, R., Tinembart, O., Humbert-Droz, E., Cavaliero, T., and Yerly, B. (2003) Comparative speed of kill between nitenpyram, fipronil, imidacloprid, selamectin and cythioate against adult Ctenocephalides felis (Bouche) on cats and dogs. Vet. Parasitol. 112, 249-254.
4. Tomizawa, M., and Casida, J. E. (2003) Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors. Annu. Rev. Entomol. 48, 339-364.
5. Solecki, R. (2001) Toxicological evaluations. Imidacloprid. www.inchem.org/documents/jmpr/jmpmono/2001pr07.htm.
6. Environmental Protection Agency (2003) Imidacloprid; Pesticide Tolerances. Fed. Regist. 68, 35303-35315.
7. Klein, O. (1994) The metabolism of imidacloprid in animals. In Eighth IUPAC International Congress of Pesticide Chemistry; Abstract 367, Washington, DC.
8. Schulz-Jander, D. A., and Casida, J. E. (2002) Imidacloprid insecticide metabolism: human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction. Toxicol. Lett. 132, 65-70.
9. Schulz-Jander, D. A., Leimkuehler, W. M., and Casida, J. E. (2002) Neonicotinoid insecticides: reduction and cleavage of imidacloprid nitroimine substituent by liver microsomal and cytosolic enzymes. Chem. Res. Toxicol. 15, 1158-1165.
10. Rajagopalan, K. V. (1980) Xanthine oxidase and aldehyde oxidase. In Enzymatic Basis of Detoxication (Jakoby, W. B., Ed.) Vol. 1, pp 295-309, Academic Press: Orlando, FL.
11. Wolpert, M. K., Althaus, J. R., and Johns, D. G. (1973) Nitroreductase activity of mammalian liver aldehyde oxidase. J. Pharmacol. Exp. Ther. 185, 202-213.
12. Garattini, E., Mendel, R., Romao, M. J., Wright, R., and Terao, M. (2003) Mammalian molybdo-flavoenzymes, an expanding family of proteins: structure, genetics, regulation, function and pathophysiology. Biochem. J. 372, 15-32.
13. Johns, D. G. (1967) Human liver aldehyde oxidase: differential inhibition of oxidation of charged and uncharged substrates. J. Clin. Invest. 46, 1492-1505.
14. Beedham, C., Critchley, D. J., and Ranee, D. J. (1995) Substrate specificity of human liver aldehyde oxidase toward substituted quinazolines and phthalazines: a comparison with hepatic enzyme from guinea pig, rabbit, and baboon. Arch. Biochem. Biophys. 319, 481-490.
15. Patai, S. (1970) The Chemistry of the Carbon-Nitrogen Double Bond, Interscience: New York.
16. Dick, R. A., Kanne, D. B., and Casida, J. E. (2004) Aldehyde oxidase catalyzes the reduction of the nitroimine moiety of the neonicotinoid insecticide imidacloprid. 7th International ISSX meeting. Drug Metab. Rev. 36 (Suppl 1), 270.
17. Maia, L., and Mira, L. (2002) Xanthine oxidase and aldehyde oxidase: a simple procedure for the simultaneous purification from rat liver. Arch. Biochem. Biophys. 400, 48-53.
18. Frostling, H., Hoff, A., Jacobsson, S., Pfaffli, P., Vainiotalo, S., and Zitting, A. (1984) Analytical, occupational and toxicologic aspects of the degradation products of polypropylene plastics. Scand. J. Work Environ. Health 10, 163-169.
19. Bryant, C., and McElroy, W. D. (1991) Nitroreductases. In Chemistry and Biochemistry of Flavoenzymes (Muller, F., Ed.) Vol. 2, pp 291-304, CRC Press: Boca Raton, FL.
20. Maskos, Z., and Winston, G. W. (1994) Mechanism of p-nitrosophenol reduction catalyzed by horse liver and human p-alcohol dehydrogenase (ADH). Human p-ADH as a quinone reductase. J. Biol. Chem. 269, 31579-31584.
21. Guengerich, F. P. (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 14, 611-650.
22. Kitamura, S., Ohashi, K., Nakatani, K., Sugihara, K., Hosokawa, R., Akagawa, Y., and Ohta, S. (2001) Extremely high drug-reductase activity based on aldehyde oxidase in monkey liver. Biol. Pharm. Bull. 24, 856-859.
23. Massey, V., Komai, H., Palmer, G., and Elion, G. B. (1970) On the mechanism of inactivation of xanthine oxidase by allopurinol and other pyrazolo[3,4-d]pyrimidines. J. Biol. Chem. 245, 2837-2844.
24. Berkman, C. E., Park, S. B., Wrighton, S. A., and Cashman, J. R. (1995) In vitro-in vivo correlations of human (S)-nicotine metabolism. Biochem. Pharmacol. 50, 565-570.
25. Yoshihara, S., Harada, K., and Ohta, S. (2000) Metabolism of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in perfused rat liver: involvement of hepatic aldehyde oxidase as a detoxification enzyme. Drug Metab. Dispos. 28, 538-543.
26. Calderbank, A., and Slade, P. (1976) Diquat and paraquat. In Herbicides: Chemistry, Degradation, and Mode of Action (Kearney, P. C., and Kaufman, D. D., Eds.) Vol. 2, pp 501-533, Marcel Dekker: New York.
27. Massey, V., and Edmondson, D. (1970) On the mechanism of inactivation of xanthine oxidase by cyanide. J. Biol. Chem. 245, 6595-6598.
28. Beedham, C., Bruce, S. E., Critchley, D. J., al-Tayib, Y., and Ranee, D. J. (1987) Species variation in hepatic aldehyde oxidase activity. Eur. J. Drug. Metab. Pharmacokinet. 12, 307-310.
29. Le Goff, G., Boundy, S., Daborn, P. J., Yen, J. L., Sofer, L., Lind, R., Sabourault, C., Madi-Ravazzi, L., and ffrench-Constant, R. H. (2003) Microarray analysis of cytochrome P450 mediated insecticide resistance in Drosophila. Insect Biochem. Mol. Biol. 33, 701-708.
30. Daborn, P., Boundy, S., Yen, J., Pittendrigh, B., and ffrench-Constant, R. (2001) DDT resistance in Drosophila correlates with Cyp6 g1 overexpression and confers cross-resistance to the neonicotinoid imidacloprid. Mol. Genet. Genomics 266, 556-563.
31. Nishiwaki, H., Sato, K., Nakagawa, Y., Miyashita, M., and Miyagawa, H. (2004) Metabolism of imidacloprid in houseflies. J. Pestic. Sci. 29, 110-116.
32. Hemingway, J., Coleman, M., Paton, M., McCarroll, L., Vaughan, A., and DeSilva, D. (2000) Aldehyde oxidase is coamplified with the World's most common Culex mosquito insecticide resistance-associated esterases. Insect Mol. Biol. 9, 93-99.
33. Coleman, M., Vontas, J. G., and Hemingway, J. (2002) Molecular characterization of the amplified aldehyde oxidase from insecticide resistant Culex quinquefasciatus. Eur. J. Biochem. 269, 768-779.