19F NMR spectroscopic investigation into the absorption and metabolism of 3-trifluoromethylaniline in Eisenia veneta

Ecotoxicology and Environmental Safety

Volumn 54, Issue 2, 2003, Pages 157-168

  Lenz, E M ^a,c   Lindon, J C ^a   Nicholson, J K ^a   Weeks, J M ^b,d   Osborn, D ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b CENTRE FOR ECOLOGY AND HYDROLOGY   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

^d WRC PLC   (United Kingdom)

Author keywords

3 trifluoromethylaniline; 19F nuclear magnetic resonance spectroscopy; Filter paper contact toxicity test; Metabolism

Indexed keywords

3 TRIFLUOROMETHYLANILINE; ANILINE DERIVATIVE; UNCLASSIFIED DRUG; 3 AMINOBENZOTRIFLUORIDE; 3-AMINOBENZOTRIFLUORIDE;

TOXICITY TEST;

ABSORPTION; ARTICLE; CROP; EARTHWORM; EISENIA VENETA; ENVIRONMENTAL EXPOSURE; FILTER; HEAD; INTESTINE; LETHALITY; METABOLISM; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OBSERVATION; ORGAN; PAPER; TESTIS; ANIMAL; ANNELID WORM; DOSE RESPONSE; LD 50; METHODOLOGY; SOIL POLLUTANT; TISSUE DISTRIBUTION;

PHERETIMA SIEBOLDI;

ABSORPTION; ANILINE COMPOUNDS; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; LETHAL DOSE 50; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOCHAETA; SOIL POLLUTANTS; TISSUE DISTRIBUTION;

EID: 0037330681     PISSN: 01476513     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0147-6513(02)00049-0     Document Type: Article

References (24)

1. Akitt, J.W. (1992) NMR and chemistry. In: An Introduction to Modern NMR Spectroscopy, 3rd Edition, Chapman & Hall, London, 17pp.
2. Belfroid A., Seinen W., van Gestel K., Hermens J. The acute toxicity of chlorobenzenes for earthworms (Eisenia andrei) in different exposure systems. Chemosphere. 26:1993;2265-2277.
3. Belfroid A., van den Berg M., Seinen W., Hermens J., van Gestel K. Uptake, bioavailability and elimination of hydrophobic compounds in earthworms (Eisenia andrei) in field-contaminated soil. Environ. Toxicol. Chem. 14:1995;605-612.
4. 19F-NMR spectroscopic studies on the metabolism and urinary excretion of mono- and disubtituted phenols in the rat. Xenobiotica. 26:1996;255-273.
5. Christensen, O.M., Mather, J.G., 1994. Earthworms as Ecotoxicological Test Organisms. Danish Environmental Protection Agency, Ministry of the Environment, No. 5.
6. Eadsforth C.V., Coveney P.C., Hutson D.H., Logan C.J., Samuel A.J. The metabolism of o-fluoroaniline by rats, rabbits and marmosets. Xenobiotica. 16:1986;555-566.
7. Ehlhardt W.J., Howbert J.J. Metabolism and disposition of p-chloroaniline in rat, mouse and monkey. Drug Metab. Disp. 19:1991;366-369.
8. Haimi J., Salminen J., Huhta V., Knuutinen J., Palm H. Bioaccumulation of organochlorine compounds in earthworms. Soil Biol. Biochem. 24:1992;1699-1703.
9. Kiese M., Lenk W. Metabolites of 4-chloroaniline and chloroacetanilides produced by rabbits and pigs. Biochem. Pharmacol. 20:1971;379-391.
10. Lindon, J.C. (1995) Fluorine nuclear magnetic resonance. In: Encyclopedia of Analytical Science, edited by A. Townshend, P.J. Worsfold, S.J. Haswell, R. Macrae, H.W. Werner, and I.D. Wilson. Academic Press, London, pp. 3408.
11. Malet-Martino M.C., Martino R. The application of NMR spectroscopy to drug metabolism studies. Xenobiotica. 19:1989;583-607.
12. Organization for Economic Cooperation and Development, OECD, 1984. OECD guideline for testing of chemicals, No. 207. Earthworm, acute toxicity test. Adopted April 4, 1984.
13. Radomski J.L. The primary aromatic amines. their biological properties and structure-activity relationships Annu. Rev. Pharmacol. Toxicol. 19:1979;129-157.
14. Rietjens I.M.C.M., Vervoort J. Microsomal metabolism of fluoroanilines. Xenobiotica. 19:1989;1297-1305.
15. Rietjens I.M.C.M., Tyrakowska B., Veeger C., Vervoort J. Reaction pathways for biodehalogenation of fluorinated anilines. Eur. J. Biochem. 194:1990;945-954.
16. Scarfe G.B., Wilson I.D., Spraul M., Hofmann M., Braumann U., Lindon J.C., Nicholson J.K. Application of directly coupled high-performance liquid chromatography-nuclear magnetic resonance-mass spectrometry to the detection and characterisation of the metabolites of 2-bromo-4-trifluoromethylaniline in rat urine. Anal. Commun. 34:1997;37-39.
17. 19F-NMR and directly coupled HPLC-NMR-MS investigations into the metabolism of 2-bromo-4-trifluoromethylaniline in rat. a urinary excretion balance study without the use of radiolabelling Xenobiotica. 28:1998;373-388.
18. Stenersen J., Brekke E., Engelstadt F. Earthworms for toxicity testing; species differences in response towards cholinesterase inhibiting insecticides. Soil Biol. Biochem. 24:1992;1761-1764.
19. Van Gestel C.A.M., Van Dis W.A. The influence of soil characteristics on the toxicity of four chemicals to the earthworm Eisenia andrei. Biol. Fert. Soils. 6:1988;262-265.
20. Van Gestel C.A.M., Dirven-Van Bremen E.M., Baerselman R., Emans H.J.B., Jannsen J.A.M., Postuma R., van Vliet P.J.M. Comparison of sublethal and lethal criteria for nine different chemicals in standardized toxicity tests using the earthworm Eisenia andrei. Ecotoxicol. Environ. Saf. 23:1992;206-220.
21. 19F-NMR method for studies on the in vivo and in vitro metabolism of 2-fluoroaniline. Xenobiotica. 20:1990;657-670.
22. 19F NMR. NMR Biomed. 4:1991;255-261.
23. 1H magnetic resonance strategies for metabolic studies on fluorinated xenobiotics. application to flurbiprofen [2-(2-fluoro-4-biphenylyl)propionic acid] J. Pharm. Biomed. Anal. 8:1990;401-410.
24. 14C-p-trifluoromethyl aniline. production of an oxanilic acid as the major metabolite by the rat Biochem. Pharmacol. 34:1985;2025-2028.