Human cytochrome P450 3A4 is involved in the biotransformation of the herbicide 2,4-dichlorophenylacetic acid

Environmental Toxicology and Pharmacology

Volumn 2, Issue 4, 1996, Pages 397-401

  Mehmood, Zahid ^a   Williamson, Michael P ^a   Kelly, Diane E ^a   Kelly, Steven L ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

CYP3A4; Nuclear magnetic resonance; Pesticide biotransformation; Thin layer chromatography; Yeast P450 expression

Indexed keywords

2,4 DICHLOROPHENOXYACETIC ACID; CYTOCHROME P450; HERBICIDE; ISOENZYME;

ARTICLE; BIOTRANSFORMATION; ENZYME ACTIVITY; GENE EXPRESSION; HUMAN; INFRARED SPECTROPHOTOMETRY; LIVER METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; THIN LAYER CHROMATOGRAPHY;

EID: 0030596067     PISSN: 13826689     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1382-6689(96)00077-4     Document Type: Article

References (27)

1. Arkhipove, G.N. and I.N. Kozlova, 1974, Carcinogenic properties of the herbicide ammonium 2.4-D amine salt, Vopr. Pitan. 5, 83 [Russian].
2. Arrhenius, E., L. Renberg, L. Johansson and M.A. Zetterqvist, 1977, Disturbance of microsomal detoxification mechanisms in liver by chlorophenol pesticides, Chem. Biol. Interact. 18, 35.
3. Bauer, E., Z. Guo, Y-F. Ueng, C. Bell, D. Zeldin. and F.P. Guenguerich, 1995, Oxidation of benzo(a)pyrene by recombinant human cytochrome P450 enzymes, Chem. Res. Toxicol. 8, 136-142.
4. Bleiberg, J., M. Wallen, R. Brodkin and I.L. Applebaum, 1964, Industrially acquired porphyria, Arch. Dermatol. 89, 793.
5. Carlo, G.L., P. Cole, A.B. Miller, A.I.C. Munro, K.R. Solomon and R.A. Squire, 1992, Review of study reporting an association between 2,4-dichlorophenoxy-acetic acid and canine malignant lymphoma, Reg. Toxicol. Pharmacol. 16, 245.
6. Diels, L., R. Van, K. Somers, I. Willems, W. Doyen, M. Mergeny, D. Springael and R. Leysen, 1995, The use of bacteria immobilised in tubular memberane reactors for heavy metal recovery and degradation of chlorinated aromatics, J. Membr. Sci. 100, 249.
7. Gehring, P.J. and J.E. Besto, 1977, Phenoxy acids, effects and fate in mammals. Conference on Chlorinated phenoxy acids and their dioxins. Mode of action, health risks and environmental effects, Feb. 6 (The Royal Swedish Academy of Sciences, Stockholm).
8. Gonzalez, F.J., 1988, The molecular biology of cytochrome P450s, Pharmacol. Rev. 40, 243.
9. Guengerich, F.P., W.R. Brian, M.A. Sari and J.T. Ross, 1991. Expression of mammalian cytochrome P450 enzymes using yeast-based vectors, Methods Enzymol. 206, 130.
10. Hansen, W.H., M.L. Quaife, R.T. Haberman and O.G. Fitzhugh, 1971. Chronic toxicity of 2,4-dichlorophenoxyacetic acid in rats and dogs, Toxicol. Appl. Pharmacol. 20, 122.
11. Ibrahim, M.A., G.G. Bond, T.A. Burke, P. Cole, F.N. Dost, P.E. Enterline, M. Gough, R.S. Greenberg, W.E. Halperin, E. McConnel, I.C. Munro, J.A. Swenberg, S.H. Zahm and J.D. Graham, 1991, Weight of the evidence on the human carcinogenicity of 2,4-D, Env. Health Persp. 96, 213.
12. Innes, J.R.M., M.G. Ulland, I. Valerio, L. Petrucelli, F.R. Fishbein, A.J. Hart, R.R. Pallotta, H.L. Bates, J.J. Falk, M. Gast, I. Klein and J. Peters, 1969, Bioassay of pesticides and industrial chemicals for tumorigenicity in mice: a preliminary note, J. Natl. Cancer Inst. 42, 1101.
13. Jefcoate, C.R., 1979, Measurement of substrate and inhibitor binding to microsomal cytochrome P450 by optical difference spectroscopy, Methods Enzymol. 40, 258.
14. Jurek, A., 1974, Carcinogenicity of pesticides, Roczn. Panstw. Jakl. Hig. 25, 563 [Polish].
15. Ka, J.O., W.E. Holben and J.M. Tiedje, 1994, Analysis of competition in soil among 2,4-dichlorophenoxyacetic acid degrading bacteria, Appl. Environ. Microbiol. 60, 1121.
16. Kaufman, D.D. and P.C. Kearney, 1976, Microsomal transformation in the soil. In: Herbicides, Physiology, Biochemistry and Echology, ed. J. Audus (Academic Press, London) pp. 26.
17. Kosak, V.P., G.V. Simsiman, G. Chesters, D. Stensby and J. Harkin, 1979, Reviews on the environmental effect of pollutions, XI. Chlorophenols, ORNL/EIS-128, June (EPA/600/10) (Oak Ridge Natl. Lab., Oak Ridge).
18. Lowry, O.H., N.J. Rosebrough, L. Farr and R.J. Randall, 1951, Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265.
19. Matsumura, F., 1984, International encyclopedia of pharmacology and therapeutics, Sect. 113, Differential Toxicities of Insecticides and Halogenated Aromatics (Pergamon Press, Oxford) pp. 453.
20. Mehmood, Z., D.E. Kelly and S.L. Kelly, 1995a, Progesterone biotransformation by human cytochrome P450 3A4 in yeast, Biotechnol. Lett. 17, 83.
21. Mehmood, Z., D.E. Kelly and S.L. Kelly, 1995b, Metabolism of the herbicide chlortoluron by human cytochrome P450 3A4, Chemosphere, 31, 4515.
22. Mehmood, Z., D.E. Kelly and S.L. Kelly, 1996, Involvement of human cytochrome P450 3A4 in the metabolism of vamidothion, Pestic. Sci. 46, 287.
23. Omura, T. and R.J. Sato, 1964, The carbon-monoxide pigment of liver microsomes. I. Evidence for its haemoprotein nature, J. Biol. Chem. 239, 2370.
24. Paulino, C.A., G.H. Oliveria and J. Palermo Neto, 1994, Acute 2,4-dichlorophenoxy-acetic acid intoxication in cattle, Vet. Hum. Toxicol., 36, 433.
25. Topal, A., N. Adams, W.C. Dauterman, E. Hodgson and S.L. Kelly, 1993, Purification and herbicide metabolism studies on tulip cytochrome P450, Pestic. Sci. 38, 9.
26. Tripathy, N.K., P.K. Rooutray, G.P. Sahu and K.A. Anand, 1993, Geno-toxicity of 2,4-dichlorophenoxyacetic acid tested in somatic and germ line cells of Drosophila, Mutat. Res. 319, 237.
27. Waxman, D.J., D.P. Lapenson, T. Aoyama, H.V. Gelboin, F.J. Gonzalez and K. Korzekwa, 1991, Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s, Arch. Biochem. Biophys. 290, 160.