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 Metabolism and Disposition

Volumn 24, Issue 3, 1996, Pages 293-302

  Shirley, Michael A ^a   Bennani, Youssef L ^a   Boehm, Marcus F ^a   Breau, Alan P ^b,c   Pathirana, Charles ^a   Ulm, Edgar H ^a  

^a LIGAND PHARMACEUTICALS INC   (United States)

^b ALLERGAN INC   (United States)

^c PERKINELMER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

13,14 DIHYDRO 9 CIS RETINOIC ACID; ALITRETINOIN; ISOETRETIN; RECEPTOR SUBTYPE; RETINOIC ACID RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; DRUG BLOOD LEVEL; DRUG HYDROXYLATION; DRUG OXIDATION; DRUG RECEPTOR BINDING; FEMALE; INTRAVENOUS DRUG ADMINISTRATION; MALE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RAT; RECEPTOR AFFINITY; STRUCTURE ANALYSIS;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; HUMANS; KERATOLYTIC AGENTS; LIVER; MALE; OXIDATION-REDUCTION; RATS; RATS, SPRAGUE-DAWLEY; TRETINOIN;

EID: 0029981972     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (49)

1. R. A. Heyman, D. J. Mangelsdorf, J. A. Dyck, R. B. Stein, G. Eichele, R. M. Evans, and C Thaller: 9-Cis retinoic acid is a high affinity ligand for the rennoid X receptor. Cell 68, 397-406 (1992).
2. A. A. Levin, L. J. Sturzenbecker, S. Kazmer, T. Bosakowski, C. Huselton, G. Allenby, J. Speck, C I. Kratzeisen, M. Rosenberger, A. Lovey, and J. F. Grippo: 9-cis retinoic acid stereoisomer binds and activates the nuclear receptor RXRα. Nature 355, 359-361 (1992).
3. G. Allenby, M.-T. Bocquel, M. Saunders, S. Kazmer, J. Speck, M. Rosenberger, A. Lovey, P. Kastner, J. F. Grippo, P. Chambon, and A. A. Levin: Retinoic acid receptors and retinoid X receptors: interactions with endogenous retinoic acids. Proc. Natl. Acad. Sci. U.S.A. 90, 30-34 (1993).
4. E. A. Allegretto, M. R. McClurg, S. B. Lazarchik, D. L. Clemm, S. A. Kerner, M. G. Elgort, M. F. Boehm, S. K. White, J. W. Pike, and R. A. Heyman: Transactivation properties of retinoic acid and retinoid X receptors in mammalian cells and yeast. J. Biol. Chem. 268, 26625-26633 (1993).
5. G. Allenby, R. Janocha, S. Kazmer, J. Speck, J. F. Grippo, and A. A. Levin: Binding of 9-cis-retinoic acid and all-trans-retinoic acid to retinoic acid receptors α. β. and γ. J. Biol. Chem. 269, 16689-16695 (1994).
6. L. J. Gudas, M. B. Sporn, and A. B. Roberts: Cellular biology and biochemistry of the retinoids. In "The Retinoids. Biology, Chemistry, and Medicine" (M. B. Sporn, A. B. Roberts and D. S. Goodman, eds.), 2nd ed. pp. 443-520. Raven Press, New York, 1994.
7. A. J. Durston, J. P. M. Timmermans, W. J. Hage, H. F. J. Hendriks, N. J. de Vries, M. Heideveld, and P. D. Nieuwkoop: Retinoic acid causes an anteroposterior transformation in the developing central nervous system. Nature 340, 140-144 (1989).
8. C. Thaller and G. Eichele: Identification and spatial distribution of retinoids in the developing chick limb bud. Nature 327, 625-628 (1987).
9. C. E. Orfanos, R. Ehlert, and H. Gollnick: The retinoids. A review of their clinical pharmacology and therapeutic use. Drugs 34, 459-503 (1987).
10. M. A. Smith, D. R. Parkinson, B. D. Cheson, and M. A. Friedman: Retinoids in cancer therapy. J. Clin. Oncol. 10, 839-864 (1992).
11. E. E. Yokes, R R. Weichselbaum, S. M. Lippman, and W. K. Hong: Head and neck cancer. N. Engl J. Med. 328, 184-194 (1993).
12. J. J. DiGiovanna, L. A. Zech, M. E. Ruddel, G. Gantt, and G. L. Peck: Etretinate: persistent serum levels after long-term therapy. Arch. Dermatol. 125, 246-251 (1989).
13. W. W. M. Pijnappel, H. F. J. Hendriks, G. E. Folkers, C. E. van den Brink, E. J. Dekker, C. Edelenbosch, P. T. van der Saag, and A. J. Durston: The retinoid ligand 4-oxo-retinoic acid is a highly active modulator of positional specification. Nature 366, 340-344 (1993).
14. J. Muindi, S. R. Frankel, W. H. Miller, Jr., A. Jakubowski, D. A. Scheinberg, C. W. Young, E. Dmitrovsky, and R. P. Warrell, Jr.: Continuous treatment with all-trans retinoic acid causes a progressive reduction in plasma drug concentrations: implications for relapse and retinoid resistance in patients with acute promyelocytic leukemia. Blood 79, 299-303 (1992).
15. 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.
16. J. A. Olson: Vitamin A. In "Handbook of Vitamins" (L. J. Machlin, ed.), pp. 1-43. Marcel Dekker, New York, 1984.
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. R. Hanni and F. Bigler: Isolation and identification of three major metabolites of retinoic acid from rat feces. Helv. Chim. Acta 60, 881-887 (1977).
19. A. M. McCormick, J. L. Napoli, H. K. Schnoes, and H. F. DeLuca: Isolation and identification of 5,6-epoxyretinoic acid: a biologically active metabolite of retinoic acid. Biochemistry 17, 4085-4090 (1978).
20. 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).
21. 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).
22. M. A. Leo, S. Iida, and C. S. Lieber: Retinoic acid metabolism by a system reconstituted with cytochrome P-450. Arch. Biochem. Biophys 234, 305-312 (1984).
23. R. Kojima, T. Fujimori, N. Kiyota, Y. Tonya, T. Fukuda, T. Ohashi, T. Sato, Y. Yoshizawa, K. Takeyama, H. Mano, S. Masishige. and S. Kato: In vivo isomerization of retinoic acids: rapid isomer exchange and gene expression. J. Biol. Chem. 269, 32700-32707 (1994).
24. G. Tzimas, J. O. Sass, W. Wittfoht, M. M. A. Elmazar, K. Ehlers, and H. Nau: Identification of 9.13-dicis-retinoic acid as a major plasma metabolite of 9-cis-retinoic acid and Limited transfer of 9-cis-retinoic acid and 9,13-dicis-retinoic acid to the mouse and rat embryos. Drug Metab. Dispos. 22, 928-936 (1994).
25. R. L. Horst, T. A. Reinhardt J. P. Goff, B. J. Nonnecke, V. K. Gambhir, P. D. Fiorella, and J. L. Napoli: Identification of 9-cis, 13-cis-retinoic acid as a major circulating retinoid in plasma. Biochemistry 34, 1203-1209 (1995).
26. G. Wolf, S. G. Kahn, and B. C. Johnson: Metabolism studies with radio-active vitamin A. J. Am. Chem. Soc. 79, 1208-1212 (1957).
27. A. B. Roberts and H. F. DeLuca: Pathways of retinol and retinoic acid metabolism in the rat. Biochem. J. 102, 600-605 (1967).
28. P. R. Sundaresan and H. N. Bhagavan: Metabolic studies on retinoic acid in the rat. Biochem. J. 122, 1-4 (1971).
29. R. Hanni, F. Bigler, W. Meister, and G. Englert: Isolation and identification of three urinary metabolites of retinoic acid in the rat. Helv. Chim. Acta 59, 2221-2227 (1976).
30. 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).
31. P. E. Dunagin, Jr., R. D. Zachman, and J. A. Olson: The identification of metabolites of retinal and retinoic acid in rat bile. Biochim. Biophys. Acta 124, 71-85 (1966).
32. 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).
33. J. O. Sass, G. Tzimas, and H. Nau: 9-cis-retinoyl-β-D-glucuronide is a major metabolite of 9-cis-retinoic acid. Life Sci. 54, 69-74 (1994).
34. J. O. Sass, E. Masgrau, J.-H. Saurat, and H. Nau: Metabolism of oral 9-cis-retinoic acid in the human: identification of 9-cis-retinoyl-β-glucuronide and 9-cis-4-oxo-retinoyl-β-glucuronide as urinary metabolites. Drug Metab. Dispos. 23, 887-891 (1995).
35. K. L. Skare, H. K. Schnoes, and H. F. DeLuca: Biliary metabolites of all-trans retinoic acid in the rat: isolation and identification of a novel polar metabolite. Biochemistry 21, 3308-3317 (1982).
36. 3H]-9-cis-retinoic acid and its application for identifying retinoids with unusual binding properties. J. Med. Chem. 37, 408-414 (1994).
37. 3]-9-cis-retinoic acid. J. Labelled Compd. Radiopharm. 36, 755-763 (1995).
38. M. N. Marchetti, H. Bun, J. M. Geiger, and A. Durand: Determination of a new retinoid: 9-cis retinoic acid in plasma by HPLC. Analyt. Lett. 27, 1847-1862 (1994).
39. J. R. Dyer "Applications of Absorption Spectroscopy of Organic Compounds." Prentice-Hall, New Jersey. 1965.
40. M. A. Shirley, X. Guan, D. G. Kaiser, G. W. Halstead, and T. A. Baillie: Taurine conjugation of ibuprofen in humans and in rat liver in vitro: relationship to metabolic chiral inversion. J. Pharmacol. Exp. Ther. 269, 1166-1175 (1994).
41. D. A. Vessey: The biochemical basis for conjugation of bile acids with either glycine or taurine. Biochem. J. 174, 621-626 (1978).
42. R. Hanni, F. Bigler, W. Vetter, G. Englert, and P. Loeliger: Der Metabolismus des retinoids Ro 10-9359: Isolierung und Identifizierung der hauptmetabiliten aus plasma, urin und faeces des menschen sowie aus der galle der ratte synthese von drei urinmetaboliten. Helv. Chim. Acta 60, 2309-2325 (1977).
43. H. F. DeLuca and A. B. Roberts: Pathways of retinoic acid and retinol metabolism. Am, J. Clin. Nutr. 22, 945-952 (1969).
44. C. E. Mize, D. Steinberg, J. Avigan, and H. M Fales: A pathway for oxidative degradation of phytanic acid in mammals. Biochem. Biophys. Res. Commun. 25, 359-365 (1966).
45. G. Vanhove, P. P. Van Veldhoven, F. Vanhoutte, G. Parmentier, H. J. Eyssen, and G. P. Mannaerts: Mitochondrial and peroxisomal β oxidation of the branched chain fatty acid 2-methylpalmitate in rat liver. J. Biol. Chem. 266, 24670-24675 (1991).
46. G. A. D. Haselwood: Bile salt evolution. J. Lipid Res. 8, 535-550 (1967).
47. A. J. Hutt and J. Caldwell: Amino acid conjugation. In "Conjugation Reactions in Drug Metabolism" (G. J. Mulder, ed.), pp. 273-305. Taylor and Francis, London, 1990.
48. J. L. Napoli, B. C. Pramanik, J. B. Williams, M. I. Dawson, and P. D. Hobbs: Quantification of retinoic acid by gas-liquid chromatography-mass spectrometry: total versus all-trans-retinoic acid in plasma. J. Lipid Res. 26, 387-392 (1985).
49. 34S]omeprazole. Rapid Commun. Mass Spectrom. 6, 192-196 (1992).