Human skin levels of retinoic acid and cytochrome P-450-derived 4-hydroxyretinoic acid after topical application of retinoic acid in vivo compared to concentrations required to stimulate retinoic acid receptor-mediated transcription in vitro

Journal of Clinical Investigation

Volumn 90, Issue 4, 1992, Pages 1269-1274

  Duell, Elizabeth A ^a,c   Åström, Anders ^a   Griffiths, Christopher E M ^a   Chambon, Pierre ^b   Voorhees, John J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b INSTITUT DE GÉNÉTIQUE ET DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^c UNIVERSITY OF MICHIGAN HEALTH SYSTEM   (United States)

Author keywords

ED50 values; High performance liquid chromatography; P 450 inhibitors; Reporter assay

Indexed keywords

4 HYDROXYRETINOIC ACID; CARBON MONOXIDE; CHLORAMPHENICOL ACETYLTRANSFERASE; CYTOCHROME P450; DRUG METABOLITE; KETOCONAZOLE; OXYGEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RETINOIC ACID; RETINOIC ACID BINDING PROTEIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; DRUG TISSUE LEVEL; ENZYME ACTIVATION; ENZYME ACTIVITY; GENETIC TRANSCRIPTION; HUMAN; HUMAN EXPERIMENT; HUMAN TISSUE; KERATOMETRY; NONHUMAN; NORMAL HUMAN; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SKIN; SKIN BIOPSY; TOPICAL DRUG ADMINISTRATION;

ADMINISTRATION, TOPICAL; ADULT; CARRIER PROTEINS; COMPARATIVE STUDY; CYTOCHROME P-450 ENZYME SYSTEM; HUMAN; KETOCONAZOLE; RECEPTORS, RETINOIC ACID; SKIN; SUPPORT, NON-U.S. GOV'T; TRANSCRIPTION, GENETIC; TRETINOIN;

EID: 0026463579     PISSN: 00219738     EISSN: None     Source Type: Journal    
DOI: 10.1172/JCI115990     Document Type: Article

References (30)

1. Roberts, A. B., and M. B. Sporn. 1984. Cellular biology and biochemistry of the retinoids. In The Retinoids. M. B. Sporn, A. B. Roberts, and D. S. Goodman, editors. Academic Press, New York. Vol. 2, 209-286.
2. Thaller, C., and G. Eichele. 1990. Isolation of 3,4-didehydroretinoic acid, a novel morphogenetic signal in the chick wing bud. Nature (Lond.). 345:815-819.
3. Dolle, P., E. Ruberte, P. Leroy, G. Morriss-Kay, and P. Chambon. 1990. Retinoic acid receptors and cellular retinoid binding proteins. I. A systematic study of their differential pattern of transcription during mouse organogenesis. Development (Camb.). 110:1133-1151.
4. Weiss, J. S., C. N. Ellis, J. T. Headington, T. Tincoff, T. A. Hamilton, and J. J. Voorhees. 1988. Topical tretinoin improves photodamaged skin: a double blind vehicle-controlled study. JAMA (J. Am. Med. Assoc.). 259:527-532.
5. Weinstein, G. D., T. P. Migra, P. E. Pochi, R. C. Savin, A. Allan, K. Benik, E. Jeffes, L. Lufrano, and G. Thorne. 1991. Topical tretinoin for treatment of photodamaged skin. Arch. Dermatol. 127:659-665.
6. Shingleton, J. L., M. K., Skinner, and D. E. Ong. 1989. Retinol esterification in Sertoli cells by lecithin-retinol acyltransferase. Biochemistry. 28:9647-9653.
7. Torma, H., and A. Vahlquist. 1987. Retinol esterification by mouse epidermal microsomes: evidence for acyl-CoA:retinol acyltransferase activity. J. Invest. Dermatol. 88:398-402.
8. Torma, H., and A. Vahlquist. 1990. Vitamin A esterification in human epidermis: a relation to keratinocyte differentiation. J. Invest. Dermatol. 94:132-138.
9. Vahlquist, A. 1982. Vitamin A in human skin. I. Detection and identification of retinoids in normal epidermis. J. Invest. Dermatol. 79:89-93.
10. Wanek, N., D. M. Gardiner, K. Muneoka, and S. V. Bryant. 1991. Conversion by retinoic acid of anterior cells into ZPA cells in the chick wing bud. Nature (Lond.). 350:81-83.
11. Noji, S., T. Nohno, E Koyama, K. Muto, K. Ohyama, Y. Aoki, K. Tamura, K. Ohsugi, H. Ide, S. Taniguchi, and T. Saito. 1991. Retinoic acid induces polarizing activity but is unlikely to be a morphogen in the chick limb bud. Nature (Lond.). 350:83-86.
12. Krust, A., P. H. Kastner, M. Petkovich, A. Zelent, and P. Chambon. 1989. A third human retinoic acid receptor, hRAR-γ. Proc. Natl. Acad. Sci. USA. 86:5310-5314.
13. Elder, J. T., G. J. Fisher, Q. Y. Zhang, D. Eisen, A. Krust, P. Kastner, P. Chambon. and J. S. Voorhees. 1991. Retinoic acid receptor gene expression in human skin. J. Invest. Dermatol 96:425-433.
14. Elder, J. T., A. Astrom, U. Pettersson, A. Krust, P. Kastner, P. Chambon, and J. J. Voorhees. 1992. Differential regulation of retinoic acid receptors and binding proteins in human skin. J. Invest. Dermatol. 98:673-679.
15. Frolik, C. A., A. B. Roberts, T. E. Tavela, P. P. Roller, D. L. Newton, and M. B. Sporn. 1979. Isolation and identification of 4-hydroxy- and 4-oxoretinoic acid. In vitro metabolites of all-trans-retinoic acid in hamster trachea and liver. Biochemistry. 18:2092-2097.
16. Roberts, A. B., M. D. Nichols, D. L. Newton, and M. B. Sporn. 1979. In vitro metabolism of retinoic acid in hamster intestine and liver. J. Biol. Chem. 254:6296-6302.
17. Leo, M. A., S. Iida. and C. S. Lieber. 1984. Retinoic acid metabolism by a system reconstituted with cytochrome P-450. Arch. Biochem. Biophys. 234:305-312.
18. Vanden Bossche, H., G. Willemsens, and P. A. J. Janssen. 1988. Cytochrome P-450-dependent metabolism of retinoic acid in rat skin microsomes: inhibition by ketoconazole. Skin Pharmacol. 1:176-185.
19. Van Wauwe, J. P., M. C. Coene, J. Goossens, G. Van Nijen, W. Cools, and W. Lauwers. 1988. Ketoconazole inhibits the in vitro and in vivo metabolism of all-trans-retinoic acid. J. Pharm. Exp. Ther. 245:718-722.
20. Fisher, G. J., J. Esmann, C. E. M. Griffiths, H. S. Talwar, E. A. Duell, C. Hammerberg, J. T. Elder, L. J. Finkel, G. D. Karabin, B. J. Nickoloff, et al. 1991. Cellular, immunologic and biochemical characterization of topical retinoic acid-treated human skin. J. Invest. Dermatol. 96:699-707.
21. Duell, E., V. Fischer, G. Fisher, A. Astrom, and J. Voorhees. 1991. Cyclosporine A metabolism by cytochrome P-450III occurs in microsomes from rat liver but not from normal epidermis or psoriatic lesions. J. Invest. Dermatol. 96:827-831.
22. Bugge, C. J. L., L. C. Rodriguez, and F. M. Vane. 1985. Determination of isotretinoin or etretinate and their major metabolites in human blood by reversed-phase high-performance liquid chromatography. J. Pharm. Biomed. Anal. 3:269-277.
23. Astrom, A., U. Pettersson, A. Krust, P. Chambon, and J. J. Voorhees. 1990. Retinoic acid and synthetic analogs differentially activate retinoic acid receptor dependent transcription. Biochem. Biophys. Res. Commun. 173:339-345.
24. Mangelsdorf, D. J., E. S. Ong, J. A. Dyck, and R. M. Evans. 1990. Nuclear receptor that identifies a novel retinoic acid response pathway. Nature (Lond.). 345:224-229.
25. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein measurements with the Folin phenol reagent. J. Biol. Chem. 193:265-275.
26. Sietsema, W. K., and H. F. DeLuca. 1982. Retinoic acid 5,6-epoxidase. J. Biol. Chem. 257:4265-4270.
27. Watabe, T., and T. Sawahata. 1979. Biotransformation of cholesterol to cholestane-3β,5α,6β-triol via cholesterol α-epoxide (5α,6α-epoxycholestan-3β-ol) in bovine adrenal cortex. J. Biol. Chem. 254:3854-3860.
28. Roberts, E. S., A. D. N. Vaz, and M. J. Coon. 1991. Metabolism of retinoids by rabbit P-450 cytochromes. FASEB (Fed. Am. Soc. Exp. Biol.) J. 5:1514a. (Abstr.).
29. Berghard, A., K. Gradin, and R. Toftgard. 1990. Serum and extracellular calcium modulate induction of cytochrome P-450IA1 in human keratinocytes. J. Biol. Chem. 265:21086-21090.
30. Van Pelt, F. N. A. M., Y. J. M. Olde Meierink, B. J. Blaauboer, and P. J. J. M. Weterings. 1990. Immunohistochemical detection of cytochrome P-450 isozymes in cultured human epidermal cells. J. Histochem. Cytochem. 38:1847-1851.