New biological reactive intermediates: Metabolic activation of thiophene derivatives

Advances in Experimental Medicine and Biology

Volumn 387, Issue , 1996, Pages 1-6

  Mansuy, Daniel ^a   Dansette, Patrick M ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 ISOENZYME; SULFOXIDE; THIOPHENE DERIVATIVE; TIENILIC ACID;

ALKYLATION; ANIMAL CELL; CONFERENCE PAPER; DRUG METABOLISM; DRUG OXIDATION; HUMAN; HUMAN CELL; LIVER MICROSOME; LIVER TOXICITY; METABOLIC ACTIVATION; NONHUMAN; PRIORITY JOURNAL; RAT;

EID: 0029760474     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4757-9480-9_1     Document Type: Conference Paper

References (16)

1. Beaune, P., Pessayre, D., Dansette, P., Mansuy, D. and Manns, M., 1994, Autoantibodies against cytochrome P450: Role in human diseases, Advances in Pharmacology. 30:199-245.
2. Bray, H.G., Carpanini F.M.B. and Waters, B.D., 1971, The metabolism of thiophene in the rabbit and in the rat, Xenobiotica 1:157-168.
3. Dansette, P.M., Amar, C., Valadon, P., Pons, C., Beaune, P.H. and Mansuy, D., 1991, Hydroxylation and formation of electropholic metabolites of tienilic acid and its isomer by human liver microsomes: Catalysis by a P450 IIC different from that responsible for mephenytoin hydroxylation, Biochem. Pharmacol. 41:553-560.
4. Dansette, P.M., Thang, D.C., El Amri, H. and Mansuy, D., 1992, Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: Formation of a dihydrothiophene sulfoxide mercapturic acid, Biochem. Biophys. Res. Commun. 186:1624-1630.
5. Lecoeur, S., Bonierbale, E., Challine, D., Gautier, J.C., Valadon, P., Dansette, P.M., Catinot, R., Ballet, F., Mansuy D. and Beaune, P.H., 1994, Specificity of in vitro covalent binding of tienilic acid metabolites to human liver microsomes in relationship to the type of hepatotoxicity: Comparison with two directly hepatotoxic drugs, Chem. Res. Toxicol. 7:434-442.
6. Lopez-Garcia, M.P., Dansette, P.M., Valadon, P., Amar, C., Beaune, P.H., Guengerich, F.P. and Mansuy, D., 1993, Human liver P450s expressed in yeast as tools for reactive metabolite formation studies: Oxidative activation of tienilic acid by P450 2C9 and P450 2C10, Eur. J. Biochem. 213:223-232.
7. Lopez-Garcia, M.P., Dansette, P.M. and Mansuy, D., 1994, Thiophene derivatives as new mechanism-based inhibitors of cytochromes P450: Inactivation of yeast expressed human liver cytochrome P450 2C9 by ticnilic acid, Biochemistry 33:166-175.
8. Mansuy, D., Dansette, P., Foures, C., Jaouen, M., Moinet, G. and Bayer, N., 1984, Metabolic hydroxylation of the thiophene ring: Isolation of 5-hydroxytienilic acid as the major urinary metabolite in rat and man, Biochem. Pharmacol. 33:1429-1435.
9. Mansuy, D., 1990, Formation of reactive metabolites and appearance of anti-organelle antibodies in man, Advances in Exp. Med. and Biol. 283:133-137.
10. Mansuy, D., Valadon, P., Erdelmeier, I., Lopez-Garcia, M.P., Amar, C., Girault, J.P. and Dansette, P.M., 1991, Thiophene-S-oxides as new reactive metabolites: Formation by cytochrome P450-dependent oxidation and reaction with nucleophiles, J. Am. Chem. Soc. 113:7825-7826.
11. Neau, E., Dansette, P.M., Andronik, V. and Mansuy, D., 1990, Evidence for 5-hydroxylation of 2-aroyl-thiophenes as a general metabolic pathway using a simple UV-visible assay. Biochem. Pharmacol. 39, 1101-1107.
12. Poupon, R., Homberg, J.C., Abuaf, N., Petit, J., Bodin, F. and Darnis, F., 1980, Atteintes hépatiques dues à l'acide ténilique. Six observations avec présence d'anticorps antireticulum endoplasmique, Nouv. Presse Med. 9:1881-1884.
13. Pouzet, P., Erdelmeier, I., Ginderow, D., Mornon, J.P., Dansette, P. and Mansuy, D., 1995, Thiophene-S-oxides: Convenient preparation, first complete structural characterization and unexpected dimerization of one of them, 2,5-diphenyl-1-oxide, JCS Chem. Comm. in press.
14. Raasch, M.S., 1985, Chemistry of heterocyclic compounds, thiophene and its derivatives, (Gronowitz S., edit.) Wiley, New-York, 44:871.
15. Rance, D.J., 1989, Sulfur-containing drugs and related organic compounds, chemistry, biochemistry and toxicology: Metabolism of sulfur functional groups (Damani L.A. Edit.) 1 part B, Ellis Norwood Ldt, Chichester, 217-268.
16. Zimmerman, H.J., Lewis, J.H., Ishak, K.G. and Maddrey, W., 1984, Ticrynafen-associated hepatic injury: Analysis of 340 cases, Hepatology 4:315-323.