Biotransformation of 13-cis- and 9-cis-retinoic acid to all-trans- retinoic acid in rat conceptal homogenates: Evidence for catalysis by a conceptal isomerase

Drug Metabolism and Disposition

Volumn 26, Issue 3, 1998, Pages 222-228

  Chen, Hao ^b   Juchau, Mont R ^a  

^a UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALITRETINOIN; ISOTRETINOIN; RETINOIC ACID;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; DRUG TRANSFORMATION; EMBRYONAL TISSUE; ENZYME INACTIVATION; ENZYME INHIBITION; FETUS; ISOMERISM; NONHUMAN; PRIORITY JOURNAL; PROTEIN DETERMINATION; RAT;

ANIMALS; BIOTRANSFORMATION; FETUS; GLUTATHIONE; ISOMERISM; KINETICS; PROTEIN DENATURATION; RATS; TEMPERATURE; TRETINOIN; UREA;

EID: 0031918122     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. Bernstein PS, Law WC and Rando RR (1987a) Isomerization of all-trans-retinoids to 11-cis-retinoids in vitro. Proc Natl Acad Sci USA 84:1849-1853.
2. Bernstein PS, Law WC and Rando RR (1987b) Biochemical characterization of the retinoid isomerase system of the eye. J Biol Chem 35:16848-16857.
3. Bernstein PS and Rando RR (1990) Assay of the retinoid isomerase system of the eye. Methods Enzymol 189:494-503.
4. Chen H and Juchau MR (1997) Biotransformation of all-trans-retinal, 13-cis-retinal, and 9-cis-retinal catalyzed by conceptal cytosol and microsomes. Biochem Pharmacol 53:877-885.
5. Chen H, Namkung MJ and Juchau MR (1995) Biotransformation of all-trans-retinol and all-trans-retinal to all-trans-retinoic acid in rat conceptal homogenates. Biochem Pharmacol 50:1257-1264.
6. Creech Kraft J and Juchau MR (1992) Correlation between conceptal concentrations of all-trans-retinoic acid and dysmorphogenesis after microinjections of all-trans-retinoic acid, 13-cis-retinoic acid, all-trans-retinoyl-β-glucuronide, or retinol in cultured whole rat embryos. Drug Metab Dispos 20:218-225.
7. Creech Kraft J and Juchau MR (1993a) Conceptal biotransformation of microinjected retinoids: correlations with dysmorphogenic activities. Ann NY Acad Sci 678:338-340.
8. Creech Kraft J and Juchau MR (1993b) 9-cis-Retinoic acid: a direct-acting dysmorphogen. Biochem Pharmacol 46:709-717.
9. Creech Kraft J, Schuh T, Juchau MR and Kimelman D (1994) The retinoid X receptor ligand, 9-cis-retinoic acid, as an apparent regulator of early Xenopus development. Proc Natl Acad Sci USA 91:3067-3071.
10. Fulton BS and Rando RR (1987) Biosynthesis of 11-cis-retinoids and retinyl esters in bovine pigment epithelium membranes. Biochemistry 26:7938-7945.
11. Hamm R and Hofmann K (1965) Changes in the sulfhydryl and disulphide groups in beef muscle proteins during heating. Nature (Lond) 207:1269-1271.
12. Harris C, Fantel AG and Juchau MR (1986) Differential glutathione depletion by L-buthionine-S,R-sulfoximine in rat embryo versus visceral yolk sac in vivo and in vitro. Biochem Pharmacol 35:4437-4441.
13. Hernandez L and Lijinsky W (1989) Glutathione and lipid peroxide levels in rat liver following administration of methapyrilene and analogs. Chem-Biol Interact 69:217-224.
14. Heyman RA, Mangelsdorf DJ, Dyck JA, Stein RB, Eichele G, Evans RM and Thaller C (1992) 9-cis-Retinoic acid is a high-affinity ligand for retinoid X receptor. Cell 68:397-406.
15. Kalin JR, Starling ME and Hill DL (1981) Disposition of all-trans-retinoic acid in mice following oral doses. Drug Metab Dispos 9:196-201.
16. Kim C-I, Leo MA and Lieber CS (1992) Retinol forms retinoic acid via retinal. Arch Biochem Biophys 294:388-393.
17. Kim Y-W, Sharma RP and Li JK (1994) Characterization of heterologously expressed recombinant retinoic acid receptors with natural or synthetic retinoids. J Biochem Toxicol 9:225-234.
18. Kochhar DM and Penner JD (1987) Developmental effects of isotretinoin and 4-oxo-isotretinoin: the role of metabolism in teratogenicity. Teratology 36:67-75.
19. Kojima R, Fujimori T, Kiyota N, Toriya Y, Fukuda T, Ohashi T, Sato T, Yoshizawa Y, Takeyama K, Mano H, Masushige S and Kato S (1994) In vitro isomerization of retinoic acids: rapid isomer exchange and gene expression. J Biol Chem 269:32700-32707.
20. Levin AA (1995) Receptors as tools for understanding the toxicity of retinoids. Toxicol Lett 82/83:91-97.
21. Levin AA, Bosakowski T, Kazmer S and Grippo JF (1992) 13-cis-Retinoic acid does not bind to the retinoic acid receptors alpha, beta, and gamma. Toxicologist 12:181.
22. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
23. Mangelsdorf DJ, Umesono K and Evans RM (1994) The retinoid receptors, in The Retinoids: Biology, Chemistry and Medicine (Sporn MB, Roberts AB and Goodman DS eds) p 327, Raven Press, New York.
24. Napoli JL (1996) Retinoic acid biosynthesis and metabolism. FASEB J 10:993-1001.
25. Repa JJ, Hanson KK and Clagett-Dame M (1993) All-trans-retinol is a ligand for the retinoic acid receptors. Proc Natl Acad Sci USA 90:7293-7297.
26. Shih TW, Lin T-H, Shealy YF and Hill DL (1997) Nonenzymatic isomerization of 9-cis-retinoic acid catalyzed by sulfhydryl compounds. Drug Metab Dispos 25:27-32.
27. Shih TW, Shealy YF, Strother DL and Hill DL (1986) Nonenzymatic isomerization of all-trans- and 13-cis-retinoids catalyzed by sulfhydryl groups. Drug Metab Dispos 14:698-702.
28. Sundaresan PR and Bhat PV (1982) Ion-pair high-pressure liquid chromatography of cis-trans isomers of retinoic acid in tissues of vitamin A-sufficient rats. J Lipid Res 23:448-455.
29. Tang G-W and Russell RM (1990) 13-cis-Retinoic acid is an endogenous compound in human serum. J Lipid Res 31:175-182.
30. Urbach J and Rando RR (1994a) Isomerization of all-trans-retinoic acid to 9-cis-retinoic acid. Biochem J 299:459-465.
31. Urbach J and Rando RR (1994b) Thiol dependent isomerization of all-trans-retinoic acid to 9-cis-retinoic acid. FEBS Lett 351:429-432.
32. Zile MH, Emerick RJ and DeLuca HF (1967) Identification of 13-cis-retinoic acid in tissue extracts and its biological activity in rats. Biochim Biophys Acta 141:639-641.
33. Zile MH, Inhorn RC and DeLuca HF (1982) Metabolism in vivo of all-trans-retinoic acid: biosynthesis of 13-cis-retinoic acid and all-trans- and 13-cis-retinoyl glucuronides in the intestinal mucosa of rat. J Biol Chem 257:3544-3550.