In vitro metabolism of three major isomers of retinoic acid in rats: Intersex and interstrain comparison

Drug Metabolism and Disposition

Volumn 25, Issue 5, 1997, Pages 637-646

  Marchetti, Marie Noelle ^b   Sampol, Emmanuelle ^b   Bun, Hot ^b   Scoma, Huguette ^b   Lacarelle, Bruno ^b   Durand, Alain ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

4 OXO 9 CIS RETINOIC ACID; 4 OXO ALL TRANS RETINOIC ACID; 4 OXOISOTRETINOIN; ALITRETINOIN; CYTOCHROME P450; DRUG METABOLITE; ISOTRETINOIN; RETINOIC ACID; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG METABOLISM; FEMALE; ISOMERISM; LIVER METABOLISM; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; SEX DIFFERENCE; STRAIN DIFFERENCE; TOPICAL DRUG ADMINISTRATION;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; CYTOCHROMES B5; FEMALE; ISOENZYMES; ISOTRETINOIN; MALE; MICROSOMES, LIVER; RATS; RATS, SPRAGUE-DAWLEY; SEX FACTORS; SPECIES SPECIFICITY; STEREOISOMERISM; TRETINOIN;

ANIMALIA;

EID: 0030983505     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. L. Favennec and M.-J. Cals: The biological effects of retinoids on cell differentiation and proliferation. J. Clin. Chem. Clin. Biochem. 26, 479-489 (1988).
2. A. B. Roberts and M. B. Sporn: Cellular biology and biochemistry of the retinoids. In "The Retinoids" (M. B. Sporn, A. B. Roberts, and D. W. Goodman, eds.), vol. 2, pp. 209-286. Academic Press, Orlando, FL, 1984.
3. J. B. Williams and J. L. Napoli: Metabolism of retinoic acid and retinol during differentiation of F9 embryonal carcinoma cells. Proc. Natl. Acad. Sci. U.S.A. 82, 4658-4662 (1985).
4. J. L. Napoli and A. M. McCormick: Tissue dependence of retinoic acid metabolism in vivo. Biochim. Biophys. Acta 660, 165-175 (1981).
5. B. N. Swanson, C. A. Frolik, D. W. Zaharevitz, P. P. Roller, and M. B. Sporn: Dose-dependent kinetics of all-trans-retinoic acid in rats. Biochem. Pharmacol. 30, 107-113 (1981).
6. N. L. Rockley, B. A. Halley, and E. C. Nelson: Identification of a decarboxylation product of retinoic acid. Biochim. Biophys. Acta 627, 270-275 (1980).
7. A. B. Roberts, M. D. Nichols, D. L. Newton, and M. B. Sporn: In vitro metabolism of retinoic acid in hamster intestine and liver. J. Biol. Chem. 254, 6296-6302 (1979).
8. A. B. Roberts, L. C. Lamb, and M. B. Sporn: Metabolism of all-trans-retinoic acid in hamster liver microsomes: oxidation of 4-hydroxy-to 4-keto-retinoic acid. Arch. Biochem. Biophys. 199, 374-383 (1980).
9. C. A. Frolik, P. P. Roller, A. B. Roberts, and M. B. Sporn: In vitro and in vivo metabolism of all-trans-and 13-cis-retinoic acid in hamsters. J. Biol. Chem. 255, 8057-8062 (1980).
10. M. A. Leo, I. Shinji, and C. S. Lieber: Retinoic acid metabolism by a system reconstituted with cytochrome P450. Arch. Biochem. Biophys. 234, 305-312 (1984).
11. J. O. Sass, A. Forster, K. W. Bock, and H. Nau: Glucuronidation and isomerization of all-trans-and 13-cis-retinoic acid by liver microsomes of phenobarbital or 3-methylcholanthrene-treated rats. Biochem. Pharmacol. 47, 485-492 (1994).
12. T. W. Shih, Y. F. Shealy, D. L. Strother, and D. L. Hill: Nonenzymatic isomerization of all-trans-and 13-cis-retinoids catalyzed by sulfhydryl groups. Drug Metab. Dispos. 14, 698-702 (1986).
13. J. Urbach and R. R. Rando: Thiol dependent isomerization of all-trans-retinoic acid to 9-cis-retinoic acid. FEBS Lett. 351, 429-432 (1994).
14. J. Urbach and R. R. Rando: Isomerization of all-trans-retinoic acid to 9-cis-retinoic acid. Biochem. J. 299, 459-465 (1994).
15. R. Martini and M. Murray: Retinal dehydrogenation and retinoic acid 4-hydroxylation in rat hepatic microsomes: developmental studies and effect of foreign compounds on the activities. Biochem. Pharmacol. 47, 905-909 (1994).
16. M. A. Shirley, Y. L. Bennani, M. F. Boehm, A. P. Breau, C. Pathirana, and E. H. Ulm: Oxidative and reductive metabolism of 9-cis-retinoic acid in the rat. Identification of 13,14-dihydro-9-cis-retinoic acid and its taurine conjugate. Drug Metab. Dispos. 24, 293-302 (1996).
17. W. S. Blaner and J. A. Olson: Retinol and retinoic acid metabolism. In "The Retinoids: Biology, Chemistry, and Medicine" (M. B. Sporn, A. B. Roberts, and D. S. Goodman, eds.), 2nd ed., pp. 229-255. Raven Press, New York, 1994.
18. C. A. Frolik: Metabolism of retinoids. In "The Retinoids" (M. B. Sporn, A. B. Roberts, and D. S. Goodman, eds.), vol. 2. Academic Press, San Diego, 1984.
19. H. Vanden Bossche and G. Willemsens: Retinoic acid and cytochrome P-450. In "Retinoids: 10 Years On" (J. H. Saurat, ed.), pp. 2-11. Basel, Karger, 1985.
20. M. A. Leo, J. M. Lasker, J. L. Raucy, C.-I. Kim, M. Black, and C. S. Lieber: Metabolism of retinol and retinoic acid by human liver cytochrome P450IIC8. Arch. Biochem. Biophys. 269, 305-312 (1989).
21. E. S. Roberts, A. D. N. Vaz, and M. J. Coon: Role of isozymes of rabbit microsomal cytochrome P-450 in the metabolism of retinoic acid, retinol, and retinal. Mol. Pharmacol. 41, 427-433 (1992).
22. R. Martini and M. Murray: Participation of P450 3A enzymes in rat hepatic microsomal retinoic acid 4-hydroxylation. Arch. Biochem. Biophys. 303, 57-66 (1993).
23. E. Cheriathundam, R. Almirez, and A. P. Alvares: Comparisons of hepatic and renal cytochromes P450-dependent monooxygenases from Fuzzy and Sprague-Dawley rats. Drug Metab. Dispos. 20, 19-22 (1992).
24. T. A. Van Der Hooven and M. J. Coon: Preparation and properties of partially purified cytochrome P-450 and reduced nicotinamide adenine dinucleotide phosphate cytochrome P-450 reduced from rabbit liver microsomes. J. Biol. Chem. 249, 6302-6310 (1974).
25. F. P. Guengerich: Microsomal enzymes involved in toxicology: analysis and separation. In "Principles and Methods in Toxicology" (A. W. Hayes, ed.), pp. 609-634. Raven Press, New York, 1982.
26. B. Disdier, H. Bun, J. Catalin, and A. Durand: Simultaneous determination of all-trans-, 13-cis-, 9-cis-retinoic acid and their 4-oxo-metabolites in plasma by high-performance liquid chromatography. J. Chromatogr. B. 683, 143-154 (1996).
27. M. Bradford: A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254 (1976).
28. T. Omura and R. Sato: The carbon-monooxide binding pigment of liver microsomes. J. Biol. Chem. 239, 2370-2378 (1964).
29. M. D. Burke and R. T. Mayer: Ethoxyresorufin: direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene. Drug Metab. Dispos. 2, 583-588 (1974).
30. M. D. Burke, S. Thompson, C. R. Elcombe, J. Halpert, T. Haaparanta, and R. T. Mayer: Ethoxy-, pentoxy-and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450. Biochem. Pharmacol. 34, 3337-3345 (1985).
31. L. A. Reinke and M. J. Moyer: p-Nitrophenol hydroxylation. A microsomal oxidation which is highly inducible by ethanol. Drug Metab. Dispos. 13, 548-552 (1985).
32. W. Tassaneeyakul, M. E. Veronese, D. J. Birkett, F. J. Gonzalez, and J. O. Miners: Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem. Pharmacol. 46, 1975-1981 (1993).
33. C. D. Robeson and J. G. Baxter: Neovitamin A. J. Am. Chem. Soc. 69, 136-141 (1947).
34. R. R. Rando: The chemistry of vitamin A and vision. Angew. Chem. Int. Ed. Engl. 29, 461-480 (1990).
35. M. Negishi, K. Aida and H. Yoshioka: Sexually dimorphic expression of P-450 genes. In "Cytochrome P-450" (T. Omura, Y. Ishimura, and Y. Fujii-Kuriyama, eds.), 2nd. ed., pp. 230-242. Kodansha Ltd., Tokyo, and VCH Publishers, New York (1993).
36. R. Kato: Sex-related differences in drug metabolism. Drug Metab. Rev. 3, 1-32 (1974).
37. R. Kato and T. Kamataki: Cytochrome P-450 as a determinant of sex difference of drug metabolism in the rat. Xenobiotica 12, 787-800 (1982).
38. D. J. Waxman, N. A. Pampori, P. A. Ram, et al. Interpulse interval in circulating growth hormone patterns regulates sexually dimorphic expression of hepatic cytochrome P450. Biochemistry 88, 6868-6872 (1991).
39. R. Kato and Y. Yamazoe: Hormonal regulation of cytochrome P450 in rat liver. In "Handbook of Experimental Pharmacology, Volume 105: Cytochrome P450" (J. Schenkman and H. Greim, eds.), pp. 447-549. Springer-Verlag, Berlin, 1993.
40. G. M. Raner, A. D. N. Vaz, and M. J. Coon: Metabolism of all-trans, 9-cis, and 13-cis isomers of retinal by purified isozymes of microsomal cytochrome P450 and mechanism-based inhibition of retinoid oxidation by citral. Mol. Pharmacol. 49, 515-522 (1996).