Metabolism of xenobiotics in the incubated hen's egg: Investigations with ethyl 4-hydroxybenzoate

Altex

Volumn 22, Issue 3, 2005, Pages 135-141

  Kiep, Lutz ^a  

^a NONE   (Germany)

Author keywords

3R; Chick embryo; Ethyl 4 hydroxybenzoate; Hen's egg; Xenobiotic metabolism

Indexed keywords

4 HYDROXYBENZOIC ACID; AMINO ACID; ETHYL PARABEN; GLUCURONIDE; SULFATE; XENOBIOTIC AGENT;

AMNION FLUID; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEVELOPMENTAL STAGE; EGG; EMBRYO; HEN; IN VITRO STUDY; INOCULATION; MASS SPECTROMETRY; METABOLISM; METABOLITE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; YOLK SAC;

ANIMAL TESTING ALTERNATIVES; ANIMALS; CHICKENS; EGGS; FEMALE; HYDROXYBENZOIC ACIDS; OVUM; XENOBIOTICS;

EID: 27144508135     PISSN: 09467785     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (52)

1. Baldwin, B. C., Robinson, D. and Williams, R. T. (1960). Studies in detoxication - 82. The fate of benzoic acid in some domestic and other birds. Biochem. J. 76, 595-600.
2. 35-sulfobromophthalein: vascular factors, biliary secretion, and conjugation. Ann. New York Acad. Sci. 111, 136-156.
3. Bray, H. G., Thorpe, W. V. and White, K. (1950). The fate of certain organic acids and amides in the rabbit - 10. The application of paper chromatography to metabolic studies of hydroxybenzoic acids and amides. Biochem. J. 46, 271-275.
4. Bridges, J. W., French, M. R., Smith, R. L. and Williams, R. T. (1970). The fate of benzoic acid in various species. Biochem. J. 118, 47-51.
5. Brodie, B. B. and Maickel, R. P. (1962). Comparative biochemistry of drug metabolism. In B. B. Brodie and E. G. Erdös (Eds.), Proceedings of the First International Pharmacological Meeting (299-324). Oxford, London, New York, Paris: Pergamon Press.
6. Brunström, B. (1986). Activities in chick embryos of 7-ethoxycoumarin O-deethylase and aryl hydrocarbon (benzo[a]pyrene) hydroxylase and their induction by 3,3′,4,4′-tetrachlorobiphenyl in early embryos. Xenobiotica 16, 865-872.
7. Clement, B. und Mladek, C. (1995). Biotransformationsuntersuchungen im Hühnerei - Teil 1: Metabolische Umwandlung von 7-Ethoxycumarin. Pharmazie 50, 207-210.
8. Clement, B. und Mladek, C. (1996). Biotransformationsuntersuchungen im Hühnerei - Teil 2: Metabolische Umwandlung von p-Nitrophenol. Pharmazie 51, 882-885.
9. Collett, R. A. and Ungkitchanukit, A. (1979). Phenol sulphotransferase in developing chick embryo. Biochem. Soc. Trans. 7, 132-134.
10. DeEds, F., Booth, A. N. and Jones, F. T. (1957). Methylation and dehydroxylation of phenolic compounds by rats and rabbits. J. Biol. Chem. 225, 615-622.
11. Derache, R. and Gourdon, J. (1963). Metabolism of a food preservative: parahydroxybenzoic acid and its esters. Food Cosmet. Toxicol. 14, 189-195.
12. Dong, Q. G., Gu, J. K., Zhong, D. F. et al. (2003). Metabolism of SFZ-47 in chicken embryo by liquid chromatography-electrospray ion trap mass spectrometry. Acta Pharmacol. Sin. 24, 576-580.
13. Drel, K. O. (1965). Deamination of some amino acids in embryo livers during transition from ureotelism to uricotelism. Fed. Proc. Transl. Suppl. 24, 39-42.
14. Dutton, G. J. and Ko, V. (1966). The synthesis of o-aminophenyl glucuronide in several tissues of the domestic fowl, Gallus gallus, during development. Biochem. J. 99, 550-556.
15. Emmanuel, B. and Gilanpour, H. (1978). Studies on enzymes of nitrogen metabolism, and nitrogen end products in the developing chick (Gallus domesticus) embryo. Comp. Biochem. Physiol. B 61, 287-289.
16. Gruber, F. P. and Hartung, T. (2004). Alternatives to animal experimentation in basic research. ALTEX 21, Suppl. 1, 3-31.
17. Hamilton, J. W., Denison, M. S. and Bloom, S. E. (1983). Development of basal and induced aryl hydrocarbon (benzo[a]pyrene) hydroxylase activity in the chicken embryo in ovo. Proc. Natl. Acad. Sci. USA 80, 3372-3376.
18. Heim, F., Leuschner, F. und Wunderlich, G. (1957). Über das intermediäre Verhalten des p-Oxybenzoesäure-äthylesters. Klin. Wochenschr 35, 823-825.
19. Heinrich-Hirsch, B., Hofmann, D., Webb, J. and Neubert, D. (1990). Activity of aldrinepoxidase, 7-ethoxycoumarin-O-deethylase and 7-ethoxyresorufin-O-deethylase during the development of chick embryos in ovo. Arch. Toxicol. 64, 128-134.
20. Hillaert, U., Baert, K., Rozenski, J. et al. (2003). 2,5-Bis-(2-hydroxybenzoylamino)pentanoic acid, a salicylic acid-metabolite isolated from chicken: characterization and independent synthesis. Bioorg. Med. Chem. Lett. 13, 335-337.
21. Igarashi, K., Suzuki, R., Kasuya, F. and Fukui, M. (1992). Determination of ornithine conjugates of some carboxylic acids in birds by high-performance liquid chromatography. Chem. Pharm. Bull. 40, 2196-2198.
22. Ignarro, L. J. and Shideman, F. E. (1968). Catechol-O-methyltransferase and monoamine oxidase activities in the heart and liver of the embryonic and developing chick. J. Pharmacol. Exp. Ther. 159, 29-37.
23. Jaffé, M. (1877). Über das Verhalten der Benzoesäure im Organismus der Vögel. Ber Dtsch. Chem. Ges. 10, 1925-1930.
24. Jondorf, W. R. (1981). Drug metabolism and drug toxicity: some evolutionary considerations. In P. Jenner and B. Testa (Eds.), Concepts in Drug Metabolism, Part B (307-376). New York, Basel: Marcel Dekker.
25. Jones, P. S., Thigpen, D., Morrison, J. L. and Richardson, A. P. (1956). p-Hydroxybenzoic acid esters as preservatives - III. The physiological disposition of p-hydroxybenzoic acid and its esters. J. Am. Pharm. Assoc. Sci. Ed. 45, 268-273.
26. Kiep, L. (1997). Eignung früher Entwicklungsstadien des bebrüteten Hühnereies für eine Ersatz- und Ergänzungsmethode zur Untersuchung der Biotransformation von Xenobiotica. In H. Schöffl, H. Spielmann und H. A. Tritthart (Hrsg.), Ersatz- und Ergänzungsmethoden zu Tierversuchen, Band IV (428-429). Wien, New York: Springer-Verlag.
27. Kiep, L. und Bekemeier, H. (1986). Biotransformation und Toxizität von Xenobiotica im Kükenembryo. Pharmazie 41, 868-872.
28. Kiep, L., Maderner, S. and Seifert, K. (2002). Metabolism of metamizol in early stages of the incubated hen's egg. Pharmazie 57, 829-833.
29. Kiwada, H., Awazu, S. and Hanano, M. (1979). The study on the biological fate of paraben at the dose of practical usage in rat - I. The metabolism and excretion of ethyl p-hydroxybenzoate (ethyl paraben) and p-hydroxybenzoic acid. J. Pharmacobiodyn. 2, 356-364.
30. Marshall, F. D. and Koeppe, O. J. (1964). Enzymatic synthesis of benzoylornithines. Biochemistry 20, 1692-1695.
31. McGilvery, R. W. and Cohen, P. P. (1950). Enzymatic synthesis of ornithuric acids. J. Biol. Chem. 183, 179-189.
32. Neugebauer, M. (1995). Biotransformation von (+)-Metamfetamin im bebrüteten Hühnerei. Pharmazie 50, 201-206.
33. Peters, J. J., Vonderahe, A. R. and Powers, T. H. (1956). The functional chronology in developing chick nervous system. J. Exp. Zool. 133, 505-518.
34. Phillips, J. C., Topp, C. S. and Gangolli, S. D. (1978). The metabolism of ethyl and n-propyl-p-hydroxybenzoate ("parabens") in male cats. Toxicol. Lett. 2, 237-242.
35. Poland, A. and Kappas, A. (1971). The metabolism of aminopyrine in chick embryo hepatic cell culture: effects of competitive substrates and carbon monoxide. Mol. Pharmacol. 7, 697-705.
36. Powis, G., Drummond, A. H., MacIntyre, D. E. and Jondorf, W. R. (1976). Development of liver microsomal oxidations in the chick. Xenobiotica 6, 69-81.
37. Quick, A. J. (1932). The relationship between chemical structure and physiological response - II. The conjugation of hydroxy- and methoxybenzoic acids. J. Biol. Chem. 97, 403-419.
38. Rifkind, A. B., Troeger, M. and Muschick, H. (1982). Kinetic evidence for heterogeneous responsiveness of mixed function oxidase isozymes to inhibition and induction by allylisopropylacetamide in chick embryo liver. J. Biol. Chem. 257, 11717-11727.
39. Rosenbruch, M. (1997). Zur Sensitivität des Embryos im bebrüteten Hühnerei. ALTEX 14, 111-113.
40. Russel, W. M. S. and Burch, R. L. (1959). The principles of Humane Experimental Technique. London: Methuen.
41. Sabalitschka, T. und Neufeld-Crzellitzer, R. (1954). Zum Verhalten der p-Oxybenzoesäureester im menschlichen Körper. Arzneim. Forsch. 4, 575-579.
42. Smith, J. N. (1958). Comparative detoxication - 5. Conjugation of aromatic acids in reptiles: formation of ornithuric acid, hippuric acid and glucuronides. Biochem. J. 69, 509-516.
43. Steventon, G. B. and Hutt, A. J. (2002). The amino acid conjugations. In C. Ioannides (Ed.), Enzyme Systems that Metabolise Drugs and Other Xenobiotics (501-520). Chichester: John Wiley & Sons.
44. Strittmatter, C. F. and Umberger, F. T. (1969). Oxidative enzyme components of avian liver microsomes: changes during embryonic development and the effects of phenobarbital administration. Biochim. Biophys. Acta 180, 18-27.
45. Takahashi, M. (1928). Über den Entgiftungsvorgang im Fötalorganismus - Synthese der Ornithursäure im bebrüteten Hühnerei bei Einspritzung von Benzoesäure. Z. Physiol. Chem. 6, 291-297.
46. Topp, R. J. and van Bladeren, P. J. (1986). Oxidative biotransformation in primary cultures of chick embryo hepatocytes: induction of cytochrome P-450 and the metabolism of benzo(a)pyrene. Arch. Toxicol. 59, 150-155.
47. Tsukamoto, H. and Terada, S. (1964). Metabolism of drugs - XLVII. Metabolic fate of p-hydroxybenzoic acid and its derivatives in rabbit. Chem. Pharm. Bull. 12, 765-769.
48. Tyman, J. H. P. (1996). Phenols, aromatic carboxylic acids, and indoles. In J. Sherma and B. Fried (Eds.), Handbook of Thin-Layer Chromatography (877-920). New York, Basel, Hong Kong: Marcel Dekker.
49. Williams, R. T. (1967). Comparative patterns of drug metabolism. Fed. Proc. 26, 1029-1039.
50. Wiltshire, H. (2000). Thin-layer chromatography. In R. F. Venn (Ed.), Principles and Practice of Bioanalysis (149-159). London, New York: Taylor & Francis.
51. Wolfe, H. J. and Huang, K. C. (1959). The conjugation of the aminobenzoic acid isomers in the adult and embryonic Gallus domesticus. J. Cell. Comparat. Physiol. 54, 243-249.
52. Worth, A. R and Balls, M. (2002). Alternative (non-animal) methods for chemical testing: current status and future prospects. ATLA 30, Suppl. 1, 1-125.