Nephrotoxic potential of 2-amino-5-chlorophenol and 4-amino-3-chlorophenol in Fischer 344 rats: Comparisons with 2-and 4-chloroaniline and 2-and 4-aminophenol

Toxicology

Volumn 108, Issue 1-2, 1996, Pages 109-123

  Rankin, Gary O ^a   Beers, Kelly W ^a   Nicoll, Derek W ^a   Anestis, Dianne K ^a   Hong, Suk K ^a   Hubbard, John L ^a   Ball, John G ^a   Valentovic, Monica A ^a   Brown, Patrick I ^a  

^a MARSHALL UNIVERSITY   (United States)

Author keywords

Aminophenols; Aniline compounds; Halogenated hydrocarbons; Nephrotoxicity; Rats

Indexed keywords

2 AMINO 5 CHLOROPHENOL; 2 AMINOPHENOL; 2 CHLOROANILINE; 4 AMINO 3 CHLOROPHENOL; 4 AMINOPHENOL; 4 CHLOROANILINE; AMINOPHENOL DERIVATIVE; ANILINE DERIVATIVE; CHLOROPHENOL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; IN VITRO STUDY; IN VIVO STUDY; KIDNEY CORTEX SLICE; KIDNEY FUNCTION; MALE; METABOLITE; NEPHROTOXICITY; NONHUMAN; PRIORITY JOURNAL; RAT;

AMINOPHENOLS; ANILINE COMPOUNDS; ANIMALS; CHLOROPHENOLS; INJECTIONS, INTRAPERITONEAL; KIDNEY; KIDNEY FUNCTION TESTS; MALE; ORGAN SIZE; RATS; RATS, INBRED F344;

ANIMALIA;

EID: 0029886009     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0300-483X(95)03294-P     Document Type: Article

References (38)

1. Bing, R.J. (1944) The effect of hemoglobin and related pigments on renal functions of the normal and acidotic dog. Bull. Johns Hopkins Hosp. 74, 161-176.
2. Bradford, M.M. (1976) A rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Anal. Biochem. 72, 248-254.
3. Chhabra, R.S., Thompson, M., Elwell, M.R. and Gerken, D.K. (1990) Toxicity of p-chloroaniline in rats and mice. Food Chem. Toxicol. 28, 717-722.
4. Chow, A.Y.K. and Murphy, S.D. (1975) Propanil (3,4-dichloropropionanilide)-induced methemoglobin formation in relation to its metabolism in vitro. Toxicol. Appl. Pharmacol. 33, 14-20.
5. Cnubben, N.H.P., Peelen, S., Borst, J.-W., Vervoot, J., Veeger, C. and Rietjens, I.M.C.M. (1994) Molecular orbital-based quantitative structure-activity relationship for the cytochrome P450-catalyzed 4-hydroxylation of halogenated anilines. Chem. Res. Toxicol. 7, 590-598.
6. Davis, J.M., Emslie, K.R., Sweet, R.S., Walker, L.L., Naughton, R.J., Skinner, S.L. and Tange, J.D. (1983) Early functional and morphological changes in renal tubular necrosis due to p-aminophenol. Kidney Int. 24, 740-747.
7. Eadsforth, C.V., Coveney, P.C., Hutson, D.H., Logan, C.J. and Samuel, A.J. (1986) The metabolism of o-fluoroaniline by rats, rabbits and marmosets. Xenobiotica 16, 555-566.
8. Ehlhardt, W.J. and Howbert, J.J. (1991) Metabolism and disposition of p-chloroaniline in rat, mouse, and monkey. Drug Metab. Dispos. 19, 366-369.
9. Flamenbaum, W., Gehr, M., Gross, M., Kaufman, J. and Hamburger, R. (1983) Acute renal failure associated with myoglobinuria and hemoglobinuria. In: B.M. Brenner and J.M. Lazarus (Eds), Acute Renal Failure, W.B. Saunders, Philadelphia, pp. 269-282.
10. Fowler, L.M., Moore, R.B., Foster, J.R. and Lock, E.A. (1991) Nephrotoxicity of 4-aminophenol glutathione conjugate. Hum. Exp. Toxicol. 10, 451-459.
11. Fowler, L.M., Foster, J.R. and Lock, E.A. (1994) Nephrotoxicity of 4-amino-3-S-glutathionylphenol and its modulation by metabolism or transport inhibitors. Arch. Toxicol. 68, 15-23.
12. Gartland, K.P.R., Bonner, F.W., Trimbrell, J.A. and Nicholson, J.K. (1989) Biochemical characterisation of para-aminophenol-induced nephrotoxic lesions in the F344 rat. Arch. Toxicol. 63, 97-106.
13. Grossman, S.J. and Jollow, D.J. (1986) Use of the NIH shift to determine the relative contribution of competing pathways of aniline metabolism in the rat. Drug Metab. Dispos. 14, 689-691.
14. Harrison, H.E., Bunting, H., Ordway, N.K. and Albrink, W.S. (1947) The pathogenesis of the renal injury produced in the dog by hemoglobin or methemoglobin. J. Exp. Med. 86, 333-356.
15. Harrison, J.H., Jr. and Jollow, D.J. (1986) Role of aniline metabolites in aniline-induced hemolytic anemia. J. Pharmacol. Exp. Ther. 238, 1045-1054.
16. Harrison, J.H., Jr. and Jollow, D.J. (1987) Contribution of aniline metabolites to aniline-induced methemoglobinemia. Mol. Pharmacol. 32, 423-431.
17. Kiese, M. and Lenk, W. (1969) Oxidation of acetanilides to glycolanilides and oxanilic acids in rabbits. Biochem. Pharmacol. 18, 1325-1333.
18. Kimbrough, R.D. (1980) Human health effects of selected pesticides, chloroaniline derivatives. Environ. Health Sci. B15, 977-992.
19. Klos, C., Koob, M., Kramer, C. and Dekant, W. (1992) p-Aminophenol nephrotoxicity: biosynthesis of toxic glutathione conjugates. Toxicol. Appl. Pharmacol. 115, 98-106.
20. Linch, A.L. (1974) Biological monitoring for industrial exposure to cyanogenic aromatic nitro and amino compounds. Am. Ind. Hyg. Assoc. 35, 426-432.
21. Lo, H.H., Brown, P.I. and Rankin, G.O. (1990) Acute nephrotoxicity induced by isomeric dichloroanilines in Fischer 344 rats. Toxicology 63, 215-231.
22. Lo, H.H., Valentovic, M.A., Brown, P.I. and Rankin, G.O. (1994) Effect of chemical form, route of administration and vehicle on 3,5-dichloroaniline-induced nephrotoxicity in the Fischer 344 rat. J. Appl. Toxicol. 14, 417-422.
23. Lock, E.A., Cross, T.J. and Schnellmann, R.G. (1993) Studies on the mechanism of 4-aminophenol-induced toxicity to renal proximal tubules. Hum. Exp. Toxicol. 12, 383-388.
24. McCarthy, D.J., Waud, W.R., Struck, R.F. and Hill, D.L. (1985) Disposition and metabolism of aniline in Fischer 344 rats. Cancer Res. 45, 174-180.
25. McMillan, D.C., Bradshaw, T.P., Hinson, J.A. and Jollow, D.J. (1991) Role of metabolites in propanil-induced hemolytic anemia. Toxicol. Appl. Pharmacol. 110, 70-78.
26. National Cancer Institute (1979) Bioassay of p-chloroaniline for possible carcinogenicity. Carcinogenesis technical report series No. 189, DHHS Publication No. (NIH) 79-1745, US Govt. Print. Office, Washington, DC.
27. 36Cl] ring-substituted monochloroacetanilides. Biochem. Pharmacol. 5, 30-38.
28. Newton, J.F., Kuo, C-H., Gemborys, M.W., Mudge, G.H. and Hook, J.B. (1982), Nephrotoxicity of p-aminophenol, a metabolite of acetaminophen, in the Fischer 344 rat. Toxicol. Appl. Pharmacol. 65, 336-344.
29. Pritchard, J.B. and Miller, D.S. (1993) Mechanisms mediating renal secretion of organic anions and cations. Physiol. Rev. 73, 765-796.
30. Rankin, G.O., Yang, D.J., Cressey-Veneziano, K., Casto, S., Wang, R.T. and Brown, P.I. (1986) In vivo and in vitro nephrotoxicity of aniline and its monochloroaniline derivatives in the Fischer 344 rat. Toxicology 38, 269-283.
31. Rankin, G.O., Shih, H.C., Yang, D.J., Richmond, C.D., Teets, V.J. and Brown, P.I. (1988) Acute nephrotoxicity of N-(3,5-dichlorophenyl)succinimide metabolites in vivo and in vitro. Toxicol. Appl. Pharmacol. 96, 405-416.
32. Rankin, G.O., Valentovic, M.A., Beers, K.W., Nicoll, D.W., Ball, J.G., Anestis, D.K., Brown, P.I. and Hubbard, J.L. (1993) Renal and hepatic toxicity of monochloroacetanilides in the Fischer 344 rat. Toxicology 79, 181-193.
33. Rankin, G.O., Valentovic, M.A., Hong, S.K., Anestis, D.K., Ball, J.G., Dial, L.D. and Brown, P.I. (1995) In vitro and acute in vivo renal effects induced by 2-chloro-4-hydroxyacetanilide and 4-chloro-2-hydroxyacetanilide in the Fischer 344 rat. Toxic Subst. Mech. 14, 93-109.
34. Reichert, D. and Schutz, S. (1986) Mercapturic acid formation is an activation and intermediary step in the metabolism of hexachlorobutadiene. Biochem. Pharmacol. 35, 1271-1275.
35. Stijntjes, G.J., Commandeur, J.N.M., te Koppele, J.M., McGuiness, S., Gandolfi, A.J. and Vermeulen, N.P.E. (1993) Examination of the structure-toxicity relationships of L-cysteine-S-conjugates of halogenated alkenes and their corresponding mercapturic acids in rat renal tissue slices. Toxicology 79, 67-79.
36. Valentovic, M.A., Ball, J.G., Anestis, D.K., Beers, K.W., Madan, E., Hubbard, J.L. and Rankin, G.O. (1992) Acute renal and hepatic toxicity of 2-haloanilines in Fischer 344 rats. Toxicology 75, 121-131.
37. Worthing, C.R. (1987) The Pesticide Manual. A World Compendium. 8th ed., The Laverham Press, Laverham, Suffolk, UK.
38. Yang, D.J., Lo, H.H., Teets, V.J., Brown, P.I. and Rankin, G.O. (1987) Nephrotoxicity of N-(3,5-dihalophenyl)succinimides in Fischer 344 rats. J. Toxicol. Environ. Health 20, 333-346.