Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 28, 1998 - Issue 7
56
Views
27
CrossRef citations to date
0
Altmetric
Research Article

Changes in rat liver cytochrome P450 enzymes by atrazine and simazine treatment

, , , &
Pages 683-698 | Published online: 22 Sep 2008

References

  • ADAMS, N. H., LEVI, P. E. and HODGSON, E., 1990, In vitro studies of the metabolism of atrazine, simazine, and terbutryn in several vertebrate species, Journal of Agricultural and Food Chemistry, 38, 1411–1417.
  • AITIO, A., 1978, A simple and sensitive assay of 7-ethoxycoumarin deethylation, Analytical Biochemistry, 85, 488–491.
  • AOYAMA, T., KORZEKWA, K., NAGATA, K., GILLETTE, J., GELBOIN, H. V. and GONZALEZ, F. J., 1990, Estradiol metabolism by complementary deoxyribonucleic acid-expressed human cytochrome P450s, Endocrinology, 129, 3101–3106.
  • AOYAMA, T. and SATO, R., 1988, High pressure liquid chromatography methods for separation of co- and (co-H-hydroxy fatty acids: their applications to microsomal fatty acid co-oxidation, Analytical Biochemistry, 170, 73–82.
  • BAKKE, J. E., LARSON, J. D. and PRICE, C. E., 1972, Metabolism of atrazine and 2-hydroxyatrazine by the rat, Journal of Agricultural and Food Chemistry, 20, 602–607.
  • BALINOV A., 1993, Solid-phase extraction followed by high-performance liquid chromatographic analysis for monitoring herbicides in drinking water, Journal of Chromatography, 643, 203–207.
  • BRADWAY, D. E. and MOSEMAN, R. F., 1982, Determination of urinary residue levels of the N-dealkyl metabolites of triazine herbicides, Journal of Agricultural and Food Chemistry, 30, 244–247.
  • BULGER, W. H., NUCCITELLI, R. M. and KUPFER, D., 1978, Studies on the in vivo and in vitro estrogenic activities of methoxychlor and its metabolites role of hepatic mono-oxygenase in methoxychlor activation, Biochemical Pharmacology, 27, 2417–2423.
  • BURKE, M. D., THOMPSON, S., ELCOMBE, C. R., HALPERT, J., HAAPARANTA, T. and MAYER, R. T., 1985, Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450, Biochemical Pharmacology, 43, 3337–3345.
  • BURKE, M. D., THOMPSON, S., WEAVER, R. J., WOLF, C. R. and MAYER, R. T., 1994, Cytochrome P450 specificities of alkoxyresorufin 0-dealkylation in human and rat liver, Biochemical Pharmacology, 48, 923–936.
  • CHEN, W., PETER, R. M., MCARDLE, S., THUMMEL, K. E., STOLE, R. 0. and NELSON, S. D., 1996, Baculovirus expression and purification of human and rat cytochrome P450 2E1, Archives of Biochemistry and Biophysics, 335, 12–130.
  • CONNOR, K., HOWELL, J., CHEN, I., LIU, H., BERHANE, K., SCIARRETTA, C., SAFE, S. and ZACHAREWSKI T., 1996, Failure of chloro-s-triazine-derived compounds to induce estrogen receptor-mediated responses in vivo and in vitro, Fundamental and Applied Toxicology, 30, 93–101.
  • DANNAN, G. A., PORUBEK, D. J., NELSON, S. D., WAXMAN, D. J. and GUENGERICH, F. P., 1986, 17)3-Estradiol 2- and 4-hydroxylation catalyzed by rat hepatic cytochrome P-450: roles of individual forms, inductive effects, developmental patterns, and alterations by gonadectomy and hormone replacement, Endocrinology, 118, 1952–1960.
  • ELDRIDGE, J. C., TENNANT, M. K., WETZEL, L. T., BRECKENRIDGE, C. B. and STEVENS, J. T., 1994, Factors affecting mammary tumor incidence in chlorotriazine-treated female rats: hormonal properties, dosage, and animal strain, Environmental Health Perspectives, 102, 29–36.
  • FRANK, R., LOGAN, L. and CLEGG, B. S., 1991, Pesticide and polychlorinated biphenyl residues in waters at the mouth of the Grand, Saugeen, and Thames Rivers, Ontario, Canada, Archives of Environmental Contamination and Toxicology, 21, 585–595.
  • FUNAE, Y. and IMAOKA, S., 1987, Purification and characterization of liver microsomal cytochrome P-450 from untreated male rats, Biochimka et Biophysica Acta, 926, 349–358.
  • GlasoN, G. G., ORTON, T. C. and TAMBURINI, P. P., 1982, Cytochrome P450 induction by clofibrate: purification and properties of a hepatic cytochrome P450 relatively specific for the 12- and 11-hydroxylation of dodecanoic acid (lauric acid), Biochemical Journal, 203, 161–168.
  • GlERTHY, J. F., LINCOLN, D. W., ROTH, K. E., BOWSER, S. S., BENNETT, J. A., BRADLEY, L. and DICKERMAN, H. W., 1991, Estrogen-stimulation of postconfluent cell accumulation and foci formation of human MCF-7 breast cancer cells, Journal of Cellular Biochemistry, 45, 177–187.
  • GYSIN, H. and KNUESLI, E., 1960, Chemistry and herbicidal properties of triazine derivatives. In R. Metcalf (ed), Advances in Pest Control Research, vol. 3 (New York: Wiley), pp. 289–358.
  • HAYES, W. J. and LAWS, E. R., 1991, Herbicides, vol. 3 (New York: Academic).
  • JEAN, A., REISS, A., DESROCHERS, M., DUBOI S., TROTT1ER, E., TROTT1ER, Y., WIRTANEN, L., ADESNIK M., WAXMAN, D. J. and ANDERSON A., 1994, Rat liver cytochrome P450 2B3: structure of the CYP2B3 gene and immunological identification of a constitutive P450 2B3-likeprotein in rat liver, DNA and Cell Biology, 13, 781–792.
  • KNIEWALD, J., MILDNER, P. and KN1EWALD, Z., 1979, Effects of s-triazine herbicides on hormone—receptor complex formation, 5a-reductase and 3a-hydroxysteroid dehydrogenase activity at the anterior pituitary level, Journal of Steroid Biochemistry, 11, 833–838.
  • KNORBACH, T., 1991, Bufuralol, dextromethorphan, and debrisoquine as prototype substrates for human P450IID6. In M. R. Waterman and E. F. Johnson (eds), Methods in Enzymology, vol. 206 (New York: Academic), pp. 509–517.
  • KOGA, N., BEPPU, M. and YOSHIMURA, H., 1990, Metabolism in vivo of 3,4,5,3',4"-pentachlorobiphenyl and toxicological assessment of the metabolite in rats, Journal of Pharmacobio-Dynamics, 13, 479–506.
  • LAEMMLI U. K., 1970, Cleavage of structural proteins during the assembly of the head of bacteriophage T4, Nature (London), 227, 680–685.
  • LAKE, B. G., TREDGER, J. M., GRAY, T. J. B., STUBBERFIELD, C. R., HODDER, K. D., GANGOLLI, S. D. and WILLIAMS, R., 1984, The effect of peroxisome proliferators on the metabolism and spectral interaction of endogenous substrates of cytochrome P-450 in rat hepatic microsomes, Life Sciences, 35, 2621–2626.
  • LANG, D., CR1EGEE, D., GROTHUSEN, A., SAALFRANK, R. W. and BöcKER, R. H., 1996, In vitro metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in rats, pigs, and humans, Drug Metabolism and Disposition, 24, 859–865.
  • LOWRY, 0. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin phenol reagent, Journal of Biological Chemistry, 193, 265–275.
  • LUCAS, D., MENEZ, J. F. and BERTHOU, F., 1996, Chlorzoxazone: an in vitro and in vivo substrate probe for liver CYP2E1. In E. F. Johnson and M. R. Waterman (eds), Methods in Enzymology, vol. 272 (New York: Academic), pp. 115–123.
  • MASON, G., FARRELL, K., KEYS, B., PISKORSKA -PLISZCZYNSKA, J., SAFE, L. and SAFE, S., 1986, Polychlorinated dibenzo-p-dioxins : quantitative in vitro and in vivo structure—activity relation-ships, Toxicology, 41, 21–31.
  • MEANS, J. C., PLEWA, M. J. and GENTILE, J. M., 1988, Assessment of the mutagenicity of fractions from s-triazine-treated Zea mays, Mutation Research, 197, 325–336.
  • MIMURA M., YAMAZAKI, H., SUGAHARA, C., HIROI, T., FuNAE, Y. and SHIMADA, T., 1994, Differential roles of cytochromes P450 2D1, 2C11, and 1A1/2 in the hydroxylation of bufuralol by rat liver microsomes, Biochemical Pharmacology, 47, 1957–1963.
  • MOLINARI, G. P., FONTANA, G. and CARRARA, G., 1995, Evaluation of herbicide migration from water to gorgonzola and mozzarella cheeses in industrial processing, Food Additives and Contaminants, 12, 195–201.
  • MURNIK, M. R. and NASH, C. L., 1977, Mutagenicity of the triazine herbicides atrazine, cyanazine, and simazine in Drosophila melanogaster, Journal of Toxicology and Environmental Health, 3, 691–697.
  • NAGATA, K., GONZALEZ, F. J., YAMAZOE, Y. AND KATO, R., 1990, Purification and characterization of four catalytically active testosterone 6J3-hydroxylase P-450s from rat liver microsomes: comparison of a novel form with three structurally and functionally related forms, Journal of Biochemistry (Tokyo), 107, 718–725.
  • NERURKAR, P. V., PARK, S. S., THOMAS, P. E., Nims, R. W. and LUBET, R., 1993, Methoxyresorufin and benzyloxyresorufin: substrates preferentially metabolized by cytochromes P4501A2 and 2B respectively, in the rat and mouse, Biochemical Pharmacology, 46, 933–943.
  • OMURA, T. and SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes: I. Evidence for its hemoprotein nature, Journal of Biological Chemistry, 239, 2370–2378.
  • PHILLIPS, A. H. and LANGDON, R. G., 1962, Hepatic triphosphopyridine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies, Journal of Biological Chemistry, 237, 2652–2660.
  • POHL, R. J. and FOUTS, J. R., 1980, A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions, Analytical Biochemistry, 107, 150–155.
  • RITTER, W. F., 1990, Pesticide contamination of ground water in the United States, Journal of Environmental Science and Health B, 25, 1–29.
  • ROUTLEDGE, E. J. and SUMPTER, J. P., 1996, Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen, Environmental Toxicology and Chemistry, 15, 241–248.
  • RYAN, D. E. and LEVIN, W., 1990, Purification and characterization of hepatic microsomal cytochrome P450, Pharmacology and Therapeutics, 45, 153–239.
  • SIMMONS, V. F., POOLE, D. C., Ricci(), E. S., ROBINSON, D. E., MITCHELL, A. D. and WATERS, M. D., 1979, In vitro mutagenicity and genotoxicity assays of 38 pesticides, Environmental Mutagenesis, 1, 142–143.
  • TAKESUE, S. and OMURA, T., 1970, Purification and properties of NADH-cytochrome b5 reductase solubilized by lysosomes from rat liver microsomes, Journal of Biochemistry (Tokyo), 67, 267–276.
  • TENNANT, M. K., HILL, D. S., ELDRIDGE, J. C., WETZEL, L. T., BRECKENRIDGE, C. B. and STEVENS, J. T., 1994, Chloro-s-triazine antagonism of estrogen action: limited interaction with estrogen receptor binding, Journal of Toxicology and Environmental Health, 43, 197–211.
  • TowsiN, H., STAEHELIN, T. and GORDON, J., 1979, Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications, Proceedings of the National Academy of Sciences, USA, 76, 4350–4354.
  • US ENVIRONMENTAL PROTECTION AGENCY, 1991, Drinking Water Health Advisory: Pesticides (London: Lewis).
  • WAXMAN, D. J., 1984, Rat hepatic cytochrome P-450 isoenzyme 2c: identification as a male-specific, developmentally induced steroid 16a-hydroxylase and comparison to a female-specific cytochrome P-450 isoenzyme, Journal of Biological Chemistry, 259, 15481–15490.
  • WAXMAN, D. J., DANNAN, G. A. and GUENGERICH, F. P., 1985, Regulation of rat hepatic cytochrome P-450: age-dependent expression, hormonal imprinting, and xenobiotic inducibility of sex-specific isozymes, Biochemistry, 24, 4409–4417.
  • WETZEL, L. T., LUEMPERT III, L. G., BRECKENRIDGE, C. B., TISDEL, M. 0., STEVENS, J. T., THAKUR, A. K., EXTROM, P. J. and ELDRIDGE, J. C., 1994, Chronic effects of atrazine on estrus and mammary tumor formation in female Sprague-Dawley and Fischer 344 rats, Journal of Toxicology and Environmental Health, 43, 169–182.
  • YAMADA, H., MINEMATSU, Y., NAKAMURA, T., MISE M., FUJISAKI, H. and OGURI, K., 1996, Brucine as a potent inducer of CYP2B3, the third member of the CYP2B subfamily P450 in rats, Biological and Pharmaceutical Bulletin, 19, 291–293.
  • YOSHIHARA S., NAGATA, K., WADA, I., YOSHIMURA, H. and MASUDA, Y., 1982, A unique change in steroid metabolism in rat liver microsomes induced with highly toxic polychlorinated biphenyl (PCB) and polychlorinated dibenzofuran (PCDF), Journal of Pharmacobio-Dynamics, 5, 994–1004.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.