Interactions of retinoid binding proteins and enzymes in retinoid metabolism

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1440, Issue 2-3, 1999, Pages 139-162

  Napoli, Joseph L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Metabolism; Retinoic acid biosynthesis; Retinoid

Indexed keywords

MICROSOME ENZYME; NOCICEPTIN RECEPTOR; RETINOID; RETINOID BINDING PROTEIN;

ENZYME BINDING; HUMAN; PRIORITY JOURNAL; PROTEIN METABOLISM; PROTEIN PROTEIN INTERACTION; REVIEW;

ALCOHOL DEHYDROGENASE; ALCOHOL OXIDOREDUCTASES; ALDEHYDE OXIDOREDUCTASES; ANIMALS; ESTERS; HOMEOSTASIS; HUMANS; HYDROXYSTEROID DEHYDROGENASES; RETINAL DEHYDROGENASE; RETINALDEHYDE; RETINOIDS; RETINOL-BINDING PROTEINS; TRETINOIN;

VERTEBRATA;

EID: 0032831815     PISSN: 13881981     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1388-1981(99)00117-1     Document Type: Review

References (196)

1. T. Moore, Vitamin A, Elsevier, New York, 1957.
2. Wolf G. Multiple functions of vitamin A. Physiol. Rev. 64:1984;873-937.
3. Bollag W. Vitamin A and retinoids: from nutrition to pharmacotherapy in dermatology and oncology. Lancet. 16:1983;860-863.
4. Lotan R. Retinoids in cancer chemoprevention. FASEB J. 10:1996;1031-1039.
5. Kligman A.M. The treatment of acne with topical retinoids: one man's opinions. J. Am. Acad. Dermatol. 36:1997;S92-S95.
6. Sucov H.M., Evans R.M. Retinoic acid and retinoic acid receptors in development. Mol. Neurobiol. 10:1995;169-184.
7. Chambon P. A decade of molecular biology of retinoic acid receptors. FASEB J. 10:1996;940-954.
8. Maden M. Vitamin A in embryonic development. Nutr. Rev. 52:1994;S3-S12.
9. Morriss-Kay G.M., Sokolova N. Embryonic development and pattern formation. FASEB J. 10:1996;961-968.
10. Semba R.D. The role of vitamin A and related retinoids in immune function. Nutr. Rev. 56:1998;S38-S48.
11. Maden M. Vitamin A and pattern formation in the regenerating limb. Nature. 295:1982;672-675.
12. Maden M. The effect of vitamin A on the regenerating axolotl limb. J. Embryol. Exp. Morphol. 77:1983;273-295.
13. W.S. Blaner, J.A. Olson, Retinol and retinoic acid metabolism, in: M.B. Sporn, A.B. Roberts, D.S. Goodman (Eds.), The Retinoids: Biology, Chemistry, and Medicine, 2nd edn., Raven Press, New York, 1994, pp. 229-255.
14. A.C. Ross, Vitamin A and retinoids, in: M.E. Shils, J.A. Olson, M. Skuke, A.C. Ross (Eds.), Modern Nutrition in Health and Disease, 9th edn., Williams and Wilkins, Baltimore, MD, 1999, pp. 305-327.
15. Bendich A., Olson J.A. Biological actions of carotenoids. FASEB J. 3:1989;1927-1932.
16. Thaller C., Eichele G. Isolation of 3,4-didehydroretinoic acid, a novel morphogenetic signal in the chick wing bud. Nature. 345:1990;815-819.
17. Randolph R.K., Simon M. Characterization of retinol metabolism in cultured human epidermal keratinocytes. J. Biol. Chem. 268:1993;9198-9205.
18. Buck J., Derguine F., Levi E., Nakanishi K., Hämmerling U. Intracellular signaling by 14-hydroxy-4,14-retro-retinol. Science. 254:1991;1654-1656.
19. Kitareewan S., Burka L.T., Tomer K.B., Parker C.E., Deterding L.J., Stevens R.D., Forman B.M., Mais D.E., Heyman R.A., McMorris T., Weinberger C. Phytol metabolites are circulating dietary factors that activate the nuclear receptor RXR. Mol. Biol. Cell. 7:1996;1153-1166.
20. S. Rainier, Retinol Homeostasis during Organogenesis in the Fetal Rat: Identification and Quantitation of Endogenous Fetal and Placental Retinoids and Cellular Retinoid-binding Proteins, Dissertation, Southwestern Medical School, 1985.
21. Satre M.A., Ugen K.E., Kochhar D.M. Developmental changes in endogenous retinoids during pregnancy and embryogenesis in the mouse. Biol. Reprod. 46:1992;802-810.
22. Horton C., Maden M. Endogenous distribution of retinoids during normal development and teratogenesis in the mouse embryo. Dev. Dyn. 202:1995;312-323.
23. Scott W.J., Walter R., Tzimas G., Sass J.O., Nau H., Collins M.D. Endogenous status of retinoids and their cytosolic binding proteins in limb buds of chick vs mouse embryos. Dev. Biol. 165:1995;397-409.
24. Båvik C., Ward S.J., Chambon P. Developmental abnormalities in cultured mouse embryos deprived of retinoic acid by inhibition of yolk-sac retinol binding protein synthesis. Proc. Natl. Acad. Sci. USA. 93:1996;3110-3114.
25. Horst R.L., Reinhardt T.A., Goff J.P., Koszewski N.A., Napoli J.L. 9,13-di-cis-Retinoic acid is the major circulating geometric isomer of retinoic acid during the periparturient period. Arch. Biochem. Biophys. 322:1995;235-239.
26. Horst R.L., Reinhardt T.A., Goff J.P., Nonnecke B.J., Gambhir V.K., Fiorella P.D., Napoli J.L. Identification of 9,13-di-cis-retinoic acid as a major circulating retinoid in plasma. Biochemistry. 34:1995;1203-1209.
27. Satre M.A., Kochhar D.M. Elevations in the endogenous levels of the putative morphogen retinoic acid in the embryonic mouse limb buds associated with limb dysmorphogenesis. Dev. Biol. 133:1989;529-536.
28. Creech-Kraft J., Schuh T., Juchau M.R., Kimelman D. The retinoid X receptor ligand, 9-cis-retinoic acid, is a potent regulator of early Xenopus development. Proc. Natl. Acad. Sci. USA. 91:1994;3067-3071.
29. Creech-Kraft J., Schuh T., Juchau J., Kimelman D. Temporal spatial distribution, localization and metabolism of retinol, didehydroretinol and retinal during development. Biochem. J. 301:1994;111-119.
30. Pijnappel W.W.M., Hendricks H.F.J., Folkers G.E., van den Brink C.E., Dekker E.J., Edelenbosch C., van der Saag P.J., Durston A.J. The retinoid ligand 4-oxo-retinoic acid is a highly active modulator of positional specification. Nature. 366:1990;340-344.
31. Pijnappel W.W., Fokers G.E., de Jonge W.J., Verdegem P.J., de Laat S.W., Lugtenburg J., Hendriks H.F., van der Saag P.T., Durston A.J. Metabolism to a response pathway selective retinoid ligand during axial pattern formation. Proc. Natl. Acad. Sci. USA. 95:1998;15424-15429.
32. Randolph R.K., Simon M. All-trans-retinoic acid regulates retinol and 3,4-didehydroretinol metabolism in cultured human epidermal keratinocytes. J. Invest. Dermatol. 106:1996;168-175.
33. Pfahl M., Chytil F. Regulation of metabolism by retinoic acid and its nuclear receptors. Annu. Rev. Nutr. 16:1996;257-283.
34. Lu H.C., Eichele G., Thaller C. Ligand-bound RXR can mediate retinoid signal transduction during embryogenesis. Development. 124:1997;195-203.
35. Schulman I.G., Li C., Schwabe J.W., Evans R.M. The phantom ligand effect: allosteric control of transcription by the retinoid X receptor. Genes Dev. 11:1997;299-308.
36. D.E. Ong, M.E. Newcomer, F. Chytil, Cellular retinoid-binding proteins, in: M.B. Sporn, A.B. Roberts, D.S. Goodman (Eds.), The Retinoids: Biology, Chemistry, and Medicine, 2nd edn., Raven Press, New York, 1994, pp. 303-304.
37. Newcomer M.E. Retinoid-binding proteins: structural determinants important for function. FASEB J. 9:1995;229-239.
38. Harrison E.H., Blaner W.S., Goodman D.S., Ross A.C. Subcellular localization of retinoids, retinoid-binding proteins, and acyl-CoA:retinol acyltransferase in rat liver. J. Lipid Res. 28:1987;973-981.
39. Herr F.M., Ong D.E. Differential interaction of lecithin:retinol acyltransferase with cellular retinoid-binding proteins. Biochemistry. 31:1992;6748-6755.
40. Noy N., Blaner W.S. Interactions of retinol with binding proteins: studies with rat cellular retinol-binding protein and with rat retinol-binding protein. Biochemistry. 30:1991;6380-6386.
41. 19F-NMR studies of retinol transfer between cellular retinol binding proteins and phospholipid vesicles. FEBS Lett. 402:1997;116-120.
42. Smith S.M., Levy N.S., Hayes C.E. Impaired immunity in vitamin A-deficient mice. J. Nutr. 117:1987;857-865.
43. Donovan M., Olofsson B., Gustafson A.-L., Dencker L., Eriksson U. The cellular retinoic acid binding proteins. J. Steroid Biochem. Mol. Biol. 53:1995;459-465.
44. Ong D.E., Crow J.A., Chytil F. Radioimmunochemical determination of cellular retinol- and cellular retinoic acid-binding proteins in cytosols of rat tissues. J. Biol. Chem. 257:1982;13385-13389.
45. Eriksson U., Das K., Busch C., Nordlinder H., Rask L., Sundelin J., Sällström J., Peterson P.A. Cellular retinol binding-protein: quantification and distribution. J. Biol. Chem. 259:1984;13464-13470.
46. Dollé P., Ruberte E., Leroy P., Morriss-Kay G., Chambon P. Retinoic acid receptors and cellular retinoid binding proteins. I. A systematic study of their differential pattern of transcription during mouse organogenesis. Development. 110:1990;1133-1151.
47. Ruberte E., Dolle P., Chambon P., Morriss-Kay G. Retinoic acid receptors and cellular retinoid binding proteins. II. Their differential pattern of transcription during early morphogenesis in mouse embryos. Development. 111:1991;45-60.
48. Ruberte E., Frederich V., Chambon P., Morriss-Kay G. Retinoic acid receptors and cellular retinoid binding proteins. III. Their differential transcript distribution during mouse nervous system development. Development. 118:1993;267-282.
49. Gustafson A.L., Dencker L., Eriksson U. Non-overlapping expression of CRBP I and CRABP I during pattern formation of limbs and craniofacial structures in the early mouse embryo. Development. 117:1993;451-460.
50. Lyn S., Giguére V. Localization of CRABP-I and CRABP-II mRNA in the early mouse embryo by whole-mount in situ hybridization: implications for teratogenesis and neural development. Dev. Dyn. 199:1994;280-291.
51. Fiorella P.D., Giguère V., Napoli J.L. Expression of cellular retinoic acid-binding protein (type II) in Escherichia coli: characterization and comparison to cellular retinoic acid-binding (type I). J. Biol. Chem. 268:1993;21545-21552.
52. Norris A.W., Cheng L., Giguere V., Rosenberger M., Li E. Measurement of subnanomolar retinoic acid binding affinities for cellular retinoic acid binding proteins by fluorimetric titration. Biochim. Biophys. Acta. 1209:1994;10-18.
53. Fiorella P.D., Napoli J.L. Expression of cellular retinoic acid binding protein in Escherichia coli: characterization and evidence that holo-CRABP is a substrate in retinoic acid metabolism. J. Biol. Chem. 266:1991;16572-16579.
54. Fiorella P.D., Napoli J.L. Microsomal retinoic acid metabolism: effects of cellular retinoic acid-binding protein (type I) and C18-hydroxylation as an initial step. J. Biol. Chem. 269:1994;10538-10544.
55. Boylan J.F., Gudas L.J. Overexpression of the cellular retinoic acid-binding protein-I (CRABP-I) results in a reduction in differentiation-specific gene expression in F9 teratocarcinoma cells. J. Cell Biol. 112:1991;965-979.
56. Elder J.T., Cromie M.A., Griffiths C.E., Chambon P., Voorhees J.J. Stimulus-selective induction of CRABP-II mRNA: a marker for retinoic acid action in human skin. J. Invest. Dermatol. 100:1993;356-359.
57. Bucco R.A., Zheng W.L., Davis J.T., Sierrsa-Rivera E., Osteen K.G., Chaudhary A.K., Ong D.E. Cellular retinoic acid-binding protein(II) presence in rat uterine epithelial cells correlates with their synthesis of retinoic acid. Biochemistry. 36:1997;4009-4014.
58. Chatellard-Gruaz D., Randolph R.K., Hagens G., Saurat J.H., Siegenthaler G. Differentiation of human epidermal keratinocytes is accompanied by increased expression of CRABP-II and increased cellular concentration of retinoic acids: retention of newly synthesized retinoic acid by CRABP-II. J. Lipid Res. 39:1998;1421-1429.
59. Zolfaghari R., Ross A.C. Chronic vitamin A intake affects the expression of mRNA of apolipoprotein A-1, but not for nuclear retinoid receptors, in liver of young and aging Lewis rats. Arch. Biochem. Biophys. 323:1995;258-264.
60. 1 cells: characterization of retinoic acid synthesis by an established mammalian cell line. J. Biol. Chem. 261:1986;13592-13597.
61. Sundaram M., Sivaprasadarao A., DeSousa M.M., Findlay J.B.C. The transfer of retinol from serum retinol-binding protein to cellular retinol-binding protein is mediated by a membrane receptor. J. Biol. Chem. 273:1998;3336-3342.
62. Ottonello S., Petrucco S., Maraini G. Vitamin A uptake from retinol-binding protein in a cell-free system from pigment epithelial cells of bovine retina: retinol transfer from plasma retinol-binding protein to cytoplasmic retinol-binding protein with retinyl-ester formation as the intermediate step. J. Biol. Chem. 262:1987;3975-3981.
63. Lissoos T.W., Davis A.E., Levin M.S. Vitamin A trafficking in Caco-2 cells stably transfected with cellular retinol binding proteins. Am. J. Physiol. 268:1995;G224-G231.
64. Williams J.B., Pramanik B.C., Napoli J.L. Vitamin A metabolism: analysis of steady-state neutral metabolites in rat tissues. J. Lipid Res. 25:1984;638-645.
65. Randolph R.K., Ross A.C. Regulation of retinol uptake and esterification in MCF-7 and HepG2 cells by exogenous fatty acids. J. Lipid Res. 32:1991;809-820.
66. Ong D.E., MacDonald P.N., Gubitosi A.M. Esterification of retinol in rat liver: possible participation by cellular retinol-binding protein and cellular retinol binding-protein II. J. Biol. Chem. 263:1988;5789-5796.
67. Yost R.W., Harrison E.H., Ross A.C. Esterification by rat liver microsomes of retinol bound to cellular retinol-binding protein. J. Biol. Chem. 263:1988;18693-18701.
68. Shi Y.Q., Furuyoshi S., Hubacek I., Rando R.R. Affinity labeling of lecithin retinol acyltransferase. Biochemistry. 32:1993;3077-3080.
69. Boerman M.H.E.M., Napoli J.L. Characterization of a microsomal retinol dehydrogenase: a short-chain alcohol dehydrogenase with integral and peripheral membrane forms that interacts with holo-CRBP (type I). Biochemistry. 34:1995;7027-7037.
70. Ruiz A., Winston A., Lim Y.-H., Gilbert B.A., Rando R.R., Bok D. Molecular and biochemical characterization of lecithin retinol acyltransferase (LRAT). J. Biol. Chem. 274:1999;3834-3841.
71. Ross A.C. Retinol esterification by rat liver microsomes: evidence for a fatty acyl coenzyme A:retinol acyltransferase. J. Biol. Chem. 257:1982;2453-2459.
72. Randolph R.K., Winkler K.E., Ross A.C. Fatty acyl CoA-dependent and -independent retinol esterification by rat liver and lactating mammary gland microsomes. Arch. Biochem. Biophys. 288:1991;500-508.
73. Prystowsky J.H., Smith J.E., Goodman D.S. Retinyl palmitate hydrolase activity in normal rat liver. J. Biol. Chem. 256:1981;4498-4503.
74. Boerman M.H.E.M., Napoli J.L. Cholate-independent retinyl ester hydrolysis: stimulation by apo-cellular retinol binding protein. J. Biol. Chem. 266:1991;22273-22278.
75. Napoli J.L., Pacia E.D., Salerno G.J. Cholate-independent hydrolysis of all-trans-retinyl palmitate by rat tissues: solubilization of multiple kidney microsomal hydrolases. Arch. Biochem. Biophys. 274:1989;192-199.
76. Harrison E.H., Gad M. Hydrolysis of retinyl palmitate by enzymes of rat pancreas and liver: differentiation of bile salt-dependent and bile salt-independent, neutral retinyl ester hydrolases in rat liver. J. Biol. Chem. 264:1989;17142-17147.
77. Gad M.Z., Harrison E.H. Neutral and acid retinyl ester hydrolases associated with rat liver microsomes: relationships to microsomal cholesteryl ester hydrolases. J. Lipid Res. 32:1991;685-694.
78. Sun G., Alexon S.E.H., Harrison E.H. Purification and characterization of a neutral, bile salt-independent retinyl ester hydrolase from rat liver microsomes: relationship to rat carboxylesterase ES-2. J. Biol. Chem. 272:1997;24488-24493.
79. Harrison E.H. Lipases and carboxylases: possible roles in the hepatic metabolism of retinol. Annu. Rev. Nutr. 18:1998;259-276.
80. Wei S., Lai K., Patel S., Piantedosi R., Shen H., Colantuoni V., Kraemer F.B., Blaner W.S. Retinyl ester hydrolysis and retinol efflux from BFC-1β adipocytes. J. Biol. Chem. 272:1997;14159-14165.
81. Roberts E.S., Vaz A.D.N., Coon M.J. Role of isozymes of rabbit microsomal cytochrome P-450 in the metabolism of retinoic acid, retinol, and retinal. Mol. Pharmacol. 41:1992;427-433.
82. Ottonello S., Scita G., Mantovani G., Cavazzini D., Rossi G.L. Retinol bound to cellular retinol binding-protein is a substrate for cytosolic retinoic acid synthesis. J. Biol. Chem. 268:1993;27133-27142.
83. Boerman M.H.E.M., Napoli J.L. Cellular retinol-binding protein-supported retinoic acid synthesis: relative roles of microsomes and cytosol. J. Biol. Chem. 271:1996;5610-5616.
84. Kedishvili N.Y., Gough W.H., Davis W.I., Parsons S., Li T.K., Bosron W.F. Effect of cellular retinol-binding protein on retinol oxidation by human class IV retinol/alcohol dehydrogenase and inhibition by ethanol. Biochem. Biophys. Res. Commun. 249:1998;191-196.
85. Posch K.C., Boerman M.H.E.M., Burns R.D., Napoli J.L. Holo-cellular retinol binding protein as a substrate for microsomal retinal synthesis. Biochemistry. 30:1991;6224-6230.
86. Penzes P., Napoli J.L. Holo-cellular retinol-binding protein: distinction of ligand-binding affinity from efficiency as substrate in retinal biosynthesis. Biochemistry. 38:1999;2088-2093.
87. Chai X., Boerman M.H.E.M., Zhai Y., Napoli J.L. Cloning of a cDNA for liver microsomal retinol dehydrogenase: a tissue-specific, short-chain alcohol dehydrogenase. J. Biol. Chem. 270:1995;3900-3904.
88. Chai X., Zhai Y., Popescu G., Napoli J.L. Cloning of a cDNA for a second retinol dehydrogenase, type II: expression of its mRNA relative to type I. J. Biol. Chem. 270:1995;28408-28412.
89. Chai X., Zhai Y., Napoli J.L. Cloning of a cDNA encoding a retinol dehydrogenase isozyme type III. Gene. 169:1996;219-222.
90. Romert A., Tuvendal P., Simon A., Dencker L., Eriksson U. The identification of a 9-cis-retinol dehydrogenase in the mouse embryo reveals a pathway for synthesis of 9-cis retinoic acid. Proc. Natl. Acad. Sci. USA. 95:1998;4404-4409.
91. Simon A., Hellman U., Wernstedt C., Eriksson U. The retinal pigment epithelial-specific 11-cis retinol dehydrogenase belongs to the family of short chain alcohol dehydrogenases. J. Biol. Chem. 270:1995;1107-1112.
92. Simon A., Lagercrantz J., Bajalica-Lagercrantz S., Eriksson U. Primary structure of human 11-cis retinol dehydrogenase and organization and chromosomal localization of the corresponding gene. Genomics. 36:1996;424-430.
93. Driessen C.A.G.G., Janssen B.P.M., Winkens H.J., van Vugt A.H.M., de Leeuw T.L.M., Janssen J.J.M. Cloning and expression of a cDNA encoding bovine retinal pigment epithelial 11-cis retinol dehydrogenase. Invest. Ophthalmol. Vis. Sci. 36:1995;1988-1996.
94. Mertz J.R., Shang E., Pianedosi R., Wei S., Wolgemuth D.J., Blaner W.S. Identification and characterization of a stereospecific human enzyme that catalyzes 9-cis-retinol oxidation: a possible role in 9-cis-retinoic acid formation. J. Biol. Chem. 272:1997;11744-11749.
95. Chai X., Zhai Y., Napoli J.L. cDNA cloning and characterization of a cis-retinol/3α-hydroxysterol short-chain dehydrogenase. J. Biol. Chem. 272:1997;33125-33131.
96. Su J., Chai X., Kahn B., Napoli J.L. cDNA cloning, tissue distribution, and substrate characterization of a cis-retinol/3α-hydroxysterol short-chain dehydrogenase isozyme. J. Biol. Chem. 273:1998;7910-17916.
97. Biswas M.G., Russell D.W. Expression cloning and characterization of oxidative 17β- and 3α-hydroxysteroid dehydrogenases from rat and human prostate. J. Biol. Chem. 272:1997;15959-15966.
98. Haeseleer F., Huang J., Lebioda L., Saari J.C., Palczewski K. Molecular characterization of a novel short-chain dehydrogenase/reductase. J. Biol. Chem. 273:1998;21790-21799.
99. +-dependent dehydrogenase that oxidizes all-trans-retinol and 3α-hydroxysteroids. J. Biol. Chem. 273:1998;19778-19785.
100. Wang J., Chai X., Eriksson U., Napoli J.L. Activity of human Rdh5 with steroids and retinoids and expression of its mRNA in extra-ocular human tissue. Biochem. J. 338:1999;23-27.
101. Driessen C.A., Winkens H.J., Kuhlmann E.D., Janssen A.P., van Vugt A.H., Deutman A.F., Janssen J.J. The visual cycle retinol dehydrogenase: possible involvement in the 9-cis-retinoic acid biosynthetic pathway. FEBS Lett. 428:1998;135-140.
102. V. Jurukovski, N.G. Markova, N. Karaman-Jurukovska, R.K. Randolph, J. Su, J.L. Napoli, M. Simon, Cloning and characterization of retinol dehydrogenase transcripts expressed in human epidermal keratinocytes, Mol. Genet. Metab. 67 (1999) in press.
103. Ohishi N., Imaoka S., Suzuki T., Funae Y. Characterization of two P-450 isozymes placed in the rat CYP2D subfamily. Biochim. Biophys. Acta. 1158:1993;227-236.
104. Imaoka S., Wan J., Chow T., Hire T., Eyanagi R., Shigematsu H., Funae Y. Cloning and characterization of the CYP2D1-binding protein, retinol dehydrogenase. Arch. Biochem. Biophys. 353:1998;331-336.
105. Boudou P., Chivot M., Vexiau P., Soliman H., Villette J.M., Belanger A., Fiet J. Evidence for decreased androgen 5α-reductase in skin and liver of men with severe acne after 13-cis-retinoic acid treatment. J. Clin. Endocrinol. Metab. 78:1994;1064-1069.
106. Boudou P., Soliman H., Chivot M., Villette J.M., Vexiau P., Belanger A., Fiet J. Effect of oral isotretinoin treatment on skin androgen receptor levels in male acneic patients. J. Clin. Endocrinol. Metab. 80:1995;1158-1161.
107. Huang H.F., Li M.T., Von Hagen S., Zhang Y.F., Irwin R.J. Androgen modulation of the messenger ribonucleic acid of retinoic acid receptors in the prostate seminal vesicles and kidney in the rat. Endocrinology. 138:1997;553-559.
108. Tomita S., Okuyama E., Ohnishi T., Ichikawa Y. Characteristic properties of a retinoic acid synthetic cytochrome P-450 purified from liver microsomes of 3-methylcholanthrene-induced rats. Biochim. Biophys. Acta. 1290:1996;273-281.
109. Raner M., Vaz A.D.N., Coon M.J. 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. 49:1996;515-522.
110. Duester G. Involvement of alcohol dehydrogenase, short-chain dehydrogenase/reductase, aldehyde dehydrogenase, and cytochrome P-450 in the control of retinoid signaling by activation of retinoic acid synthesis. Biochemistry. 35:1996;12221-12227.
111. Vonesch J.-L., Nakshatri H., Philippe M., Chambon P., Dollé P. Stage and tissue-specific expression of the alcohol dehydrogenase 1 (Adh-1) gene during mouse development. Dev. Dyn. 199:1994;199-213.
112. Ang H.L., Deltour L., Hayamizu T.F., Zgombic-Knight M., Duester G. Retinoic acid synthesis in mouse embryos during gastrulation and craniofacial development linked to class IV alcohol dehydrogenase gene expression. J. Biol. Chem. 271:1996;9526-9534.
113. Boleda M.D., Julia P., Moreno A., Parés X. Role of extrahepatic alcohol dehydrogenase in rat ethanol metabolism. Arch. Biochem. Biophys. 274:1989;74-81.
114. Zgombic-Knight M., Ang H.L., Foglio M.H., Duester G. Cloning of the mouse class IV alcohol dehydrogenase (retinol dehydrogenase) cDNA and tissue-specific expression patterns of the murine ADH gene family. J. Biol. Chem. 270:1995;10868-10877.
115. Deltour L., Haselbeck R.J., Ang H.L., Duester G. Localization of class I and class IV alcohol dehydrogenases in mouse testis and epididymis: potential retinol dehydrogenases for endogenous retinoic acid synthesis. Biol. Reprod. 56:1997;102-109.
116. Ang H.L., Deltour L., Zgombic-Knight M., Wagner M.A., Duester G. Expression patterns of class I and class IV alcohol dehydrogenase genes in developing epithelia suggest a role for alcohol dehydrogenase in local retinoic acid synthesis. Alcohol. Clin. Exp. Res. 20:1996;1050-1064.
117. Lee M.O., Manthey C.L., Sladek N.E. Identification of mouse liver aldehyde dehydrogenases that catalyze the oxidation of retinaldehyde to retinoic acid. Biochem. Pharmacol. 42:1991;1279-1285.
118. Posch K.C., Burns R.D., Napoli J.L. Biosynthesis of all-trans-retinoic acid from retinal: recognition of retinal bound to cellular retinol binding protein (type I) as substrate by a purified cytosolic dehydrogenase. J. Biol. Chem. 267:1992;19676-19682.
119. Dockham P.A., Lee M.O., Sladek N.E. Identification of human liver aldehyde dehydrogenases that catalyze the oxidation of aldophosphamide and retinaldehyde. Biochem. Pharmacol. 43:1992;2453-2469.
120. el Akawi Z., Napoli J.L. Rat liver cytosolic retinal dehydrogenase: comparison of 13-cis-, 9-cis-, and all-trans-retinal as substrates and effects of cellular retinoid-binding proteins and retinoic acid on activity. Biochemistry. 33:1994;1938-1943.
121. Labrecque J., Dumas F., Lacroix A., Bhat P.V. A novel isoenzyme of aldehyde dehydrogenase specifically involved in the biosynthesis of 9-cis and all-trans retinoic acid. Biochem. J. 305:1995;681-684.
122. Bhat P.V., Labrecque J., Boutin J.M., Lacroix A., Oshida A. Cloning of a cDNA encoding rat aldehyde dehydrogenase with high activity for retinal oxidation. Gene. 166:1995;303-306.
123. Saari J.C., Champer R.J., Asson-Batres M., Garwin G.G., Huang J., Crabb J.W., Milam A.H. Characterization and localization of an aldehyde dehydrogenase to amacrine cells of bovine retina. Vis. Neurosci. 12:1995;263-272.
124. Wang X., Penzes P., Napoli J.L. Cloning of a cDNA encoding an aldehyde dehydrogenase and its expression in Escherichia coli: recognition of retinal as substrate and role in retinoic acid synthesis. J. Biol. Chem. 271:1996;16288-16293.
125. Zhao D., McCaffery P., Ivins K.J., Neve R.L., Hogan P., Dräger U. Molecular identification of a major retinoic-acid-synthesizing enzyme, a retinaldehyde-specific dehydrogenase. Eur. J. Biochem. 240:1996;5-22.
126. Godbout R., Packer M., Poppema S., Dabragh L. Localization of cytosolic aldehyde dehydrogenase in the developing chick retina: in situ hybridization and immunochemical analyses. Dev. Dyn. 205:1996;319-331.
127. Penzes P., Wang X., Napoli J.L. Cloning of a cDNA encoding retinal dehydrogenase isozyme type and its expression in Escherichia coli. Gene. 191:1997;167-172.
128. Penzes P., Wang X., Napoli J.L. Enzymatic characteristics of retinal dehydrogenase type I expressed in Escherichia coli. Biochim. Biophys. Acta. 1342:1997;175-181.
129. McCaffery P., Posch K.C., Napoli J.L., Gudas L., Dräger U.C. Changing patterns of the retinoic acid system in the developing retina. Dev. Biol. 158:1993;390-399.
130. Yoshida A., Hsu L.C., Yanagawa Y. Biological role of human cytosolic aldehyde dehydrogenase 1: hormonal response, retinal oxidation and implication in testicular feminization. Enzymol. Mol. Biol. Carbonyl Metab. 4:1993;37-44.
131. Greene W.K., Bahn S., Masson N., Rabbitts T.H. The T-cell oncogenic protein Hox11 activates Aldh1 expression in NIH3T3 cells but represses its expression in mouse spleen development. Mol. Cell. Biol. 18:1998;7030-7037.
132. Niederreither K., McCaffery P., Dräger U.C., Chambon P., Dollé P. Restricted expression and retinoid acid-induced downregulation of the retinaldehyde type 2 (RALDH-2) gene during mouse development. Mech. Dev. 62:1997;67-78.
133. Sockanathan S., Jessell T.M. Motor neuron-derived retinoid signaling specifies the subtype identity of spinal motor neurons. Cell. 94:1998;503-514.
134. Yuichi O., Fukuhara N., Yoshie O. TAL1 and LIM-only proteins synergistically induce retinaldehyde dehydrogenase 2 expression in T-cell acute lymphoblastic leukemia by acting as cofactors for GATA3. Mol. Cell. Biol. 18:1998;6939-6950.
135. Lamb A.L., Wang X., Napoli J.L., Newcomer M.E. Purification, crystallization and preliminary X-ray diffraction studies of retinal dehydrogenase type II. Acta Crystallogr. D54:1998;639-642.
136. A. Lamb, M. Newcomer, The structure of retinal dehydrogenase type II at 2.7 Å resolution: implications for retinal specificity, Biochemistry 38 (1999) in press.
137. Buck J., Myc A., Garbe A., Cathomas G. Differences in the action and metabolism between retinol and retinoic acid in B lymphocytes. J. Cell Biol. 115:1991;851-859.
138. Napoli J.L., McCormick A.M. Tissue dependence of retinoic acid metabolism in vivo. Biochim. Biophys. Acta. 666:1981;165-175.
139. Williams J.B., Napoli J.L. Metabolism of retinoic acid and retinol during differentiation of F9 embryonal carcinoma cells. Proc. Natl. Acad. Sci. USA. 82:1985;4658-4662.
140. Chen A.C., Gudas L.J. An analysis of retinoic acid-induced gene expression and metabolism in AB1 embryonic stem cells. J. Biol. Chem. 271:1996;14971-14980.
141. Randolph R.K., Simon M. Metabolism of all-trans-retinoic acid by cultured human epidermal keratinocytes. J. Lipid Res. 38:1997;1374-1383.
142. Zachman R.D., Dunagin P.E. Jr., Olson J.A. Formation and enterohepatic circulation of metabolites of retinol and retinoic acid in bile duct-cannulated rats. J. Lipid Res. 7:1966;3-9.
143. Lippel K., Olson J.A. Origin of some derivatives of retinoic acid found in rat bile. J. Lipid Res. 9:1968;580-586.
144. Janick-Buckner D., Barua A.B., Olson J.A. Induction of HL-60 cell differentiation by water-soluble and nitrogen-containing conjugates of retinoic acid and retinol. FASEB J. 5:1991;320-325.
145. Formelli F., Barua A.B., Olson J.A. Bioactivities of N-(4-hydroxyphenyl)retinamide and retinoyl β-glucuronide. FASEB J. 10:1996;1014-1024.
146. Becker B., Barua A.B., Olson J.A. All-trans-retinoyl-β-glucuronide: new procedure for chemical synthesis and its metabolism in vitamin A-deficient rats. Biochem. J. 314:1996;249-252.
147. Genchi G., Napoli J.L., Olson J.A. Kinetic studies on retinyl β-glucuronide formation in the presence and absence of cellular retinoic acid binding protein. FASEB J. 12:1998;A519.
148. Napoli J.L., Khalil H., McCormick A.M. Metabolism of 5,6-epoxyretinoic acid in vivo: isolation of a major intestinal metabolite. Biochemistry. 21:1982;1942-1949.
149. Nau H., Elmazar M.M., Ruhl R., Thiel R., Sass J.O. All-trans-retinoyl-β-glucuronide is a potent teratogen in the mouse because of extensive metabolism to all-trans-retinoic acid. Teratology. 54:1996;150-156.
150. Roberts A.B., Frolik C.A., Nichols M.D., Sporn M.B. Retinoid-dependent induction of the in vivo and in vitro metabolism of retinoic acid in tissues of the vitamin A-deficient hamster. J. Biol. Chem. 254:1979;6303-6309.
151. Frolik C.A., Roberts A.B., Tavela T.E., Roller P.P., Newton D.L., Sporn M.B. Isolation and identification of 4-hydroxy- and 4-keto-retinoic acid: in vitro metabolites of all-trans-retinoic acid in hamster trachea and liver. Biochemistry. 18:1979;2092-2097.
152. Roberts A.B., Lamb L.C., Sporn M.B. Metabolism of all-trans-retinoic acid in hamster liver microsomes: oxidation of 4-hydroxy- to 4-keto-retinoic acid. Arch. Biochem. Biophys. 199:1980;374-383.
153. Frolik C.A., Roller P.P., Roberts A.B., Sporn M.B. In vitro and in vivo metabolism of all-trans- and 13-cis-retinoic acid in hamsters: identification of 13-cis-4-oxoretinoic acid. J. Biol. Chem. 255:1980;8057-8062.
154. Frolik C.A., Roller P.P., Roberts A.B., Sporn M.B. In vitro and in vivo metabolism of all-trans- and 13-cis-retinoic acid in hamsters: identification of 13-cis-4-oxoretinoic acid. J. Biol. Chem. 255:1980;8057-8062.
155. Williams J.B., Napoli J.L. Imidazole antimycotics inhibit the metabolism of retinoic acid in F9 embryonal carcinoma cells. Biochem. Pharmacol. 36:1987;1386-1388.
156. van Wauwe J.P., Coene M.-C., Goossens J., van Nyen J., Cools W., Lauwers W. Ketoconazole inhibits the in vivo and in vitro metabolism of all-trans-retinoic acid. J. Pharmacol. Exp. Ther. 245:1988;718-722.
157. van Wauwe J.P., Coene M.-C., Goossens J., Cools W., Monbaliu J. Effects of cytochrome P-450 inhibitors on the in vivo metabolism of all-trans-retinoic acid in the rats. J. Pharmacol. Exp. Ther. 252:1990;365-369.
158. Tomita S., Okuyama E., Ohnishi T., Ichikawa Y. Characteristic properties of a retinoic acid synthetic cytochrome P-450 purified from liver microsomes of 3-methylcholanthrene-induced rats. Biochim. Biophys. Acta. 1290:1996;273-281.
159. Fiorella P.D., Olson J.R., Napoli J.L. 2,3,7,8-Tetrachlorodibenzo-p-dioxin induces diverse retinoic acid metabolites in multiple tissues of the Sprague-Dawley rat. Toxicol. Appl. Pharmacol. 134:1995;222-228.
160. Fujii H., Sato T., Kaneko S., Gotoh O., Fugii-Kuriyama Y., Osawa K., Kato S., Hamada H. Metabolic inactivation of retinoic acid by a novel P450 differentially expressed in developing mouse embryos. EMBO J. 16:1997;4163-4173.
161. White J.A., Guo Y.-D., Baetz K., Beckett-Jones B., Bonasoro J., Hsu K.E., Dilworth F.J., Jones G., Petkovich M. Identification of the retinoic acid-inducible all-trans-retinoic acid 4-hydroxylase. J. Biol. Chem. 271:1996;29922-29927.
162. White J.A., Beckett-Jones B., Guo Y.-D., Dilworth F.J., Bonasoro J., Jones G., Petkovich M. cDNA cloning of human retinoic acid-metabolizing enzyme (hP450RAI) identifies a novel family of cytochromes P450 (CYP26). J. Biol. Chem. 272:1997;18538-18541.
163. Ray W.J., Bain G., Yao M., Gottlieb D.I. CYP26, a novel mammalian cytochrome P450, is induced by retinoic acid and defines a new family. J. Biol. Chem. 272:1997;18702-18708.
164. Abu-Abed S.S., Beckett B.R., Chiba H., Chithalen J.V., Jones G., Metzger D., Chambon P., Petkovich M. Mouse P450RAI (CYP26) expression and retinoic acid-inducible retinoic acid metabolism in F9 cells are regulated by retinoic acid receptor γ and retinoid X receptor α J. Biol. Chem. 273:1998;2409-2415.
165. Sonneveld E., van den Brink C.E., van der Leede B.M., Schulkes R.K., Petkovich M., van der Burg B., van der Saag P.T. Human retinoid acid (RA) 4-hydroxylase (CYP26) is highly specific for all-trans-RA and can be induced through RA receptors in human breast and colon carcinoma cells. Cell Growth Differ. 9:1998;629-637.
166. -/-) exhibit liver retinoid accumulation and reduced retinoic acid metabolism. Cancer Res. 57:1997;2835-2838.
167. Dawson M.I., Hobbs P.D., Derdzinski K.A., Chao W.R., Frenking G., Jetten A.M., Napoli J.L., Williams J.B., Sani B.P., Wille J., Schiff L.J. The effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids. J. Med. Chem. 32:1989;1504-1517.
168. van der Leede B.M., van den Brink C.E., Pijnappel W.W.M., Sonneveld E., van der Saag P.T., van der Burg B. Autoinduction of retinoic acid metabolism to polar derivatives with decreased biological activity in retinoic acid-sensitive, but not in retinoic acid-resistant human breast cancer cells. J. Biol. Chem. 272:1997;17921-17928.
169. van Heusden J., Wouters W., Ramaekers F.C., Krekels M.D., Dillen L., Borgers M., Smets G. All-trans-retinoic acid metabolites significantly inhibit the proliferation of MCF-7 human breast cancer cells in vitro. Br. J. Cancer. 77:1998;26-32.
170. Gaemers I.C., van Pelt A.M., van der Saag P.T., Hoogerbrugge J.W., Themmen A.P., de Rooij D.G. Effect of retinoid status on the messenger ribonucleic acid expression of nuclear retinoid receptors α, β, and γ, and retinoid X receptors α, β, and γ in the mouse testis. Endocrinology. 138:1997;1544-1551.
171. Dockx P., Decree J., Degreef H. Inhibition of the metabolism of endogenous retinoic acid as treatment for severe psoriasis: an open study with oral liarazole. Br. J. Dermatol. 133:1995;426-432.
172. Adedoyin A., Stiff D.D., Smith D.C., Romkes M., Bahnson R.C., Day R., Hofacker J., Branch R.A., Trump D.L. All-trans-retinoic acid modulation of drug-metabolizing enzyme activities: investigation with selective metabolic drug probes. Can. Chemother. Pharmacol. 41:1998;133-139.
173. Boylan J.F., Gudas L.J. The level of CRABP-I expression influences the amounts and types of all-trans-retinoic acid metabolites in F9 teratocarcinoma stem cells. J. Biol. Chem. 267:1992;21486-21491.
174. Wei L.-N., Lee C.-H., Chang S., Chu Y.-S. Pathogenesis in transgenic mice expressing bovine cellular retinoic acid-binding protein. Dev. Growth Differ. 34:1992;479-488.
175. Perez-Castro A.V., Tran V.T., Nguyen-Huu M.C. Defective lens fiber differentiation and pancreatic tumorigenesis caused by ectopic expression of the cellular retinoic acid-binding protein I. Development. 119:1993;363-375.
176. Wei L.-N., Chang L., Lee C.-H. Studies of over-expressing cellular retinoic acid binding protein I gene in cultured cells and transgenic mice. Transgenics. 2:1997;201-209.
177. Gorry P., Lufkin T., Dierich A., Rochette-Egly C., Decimo D., Dolle P., Mark M., Durano B., Chambon P. The cellular retinoic acid binding protein I is dispensable. Proc. Natl. Acad. Sci. USA. 91:1994;9032-9036.
178. de Bruijn D.R.H., Oerlemans F., Hendriks W., Baats E., Ploemacher R., Wieringa B., van Kessel A.G. Normal development, growth and reproduction in cellular retinoic acid binding protein I null mutant mice. Differentiation. 58:1994;141-148.
179. Fawcett D., Pascer P., Fraser R., Colbert M., Rossant J., Giguere V. Postaxial polydactylyl in forelimbs of CRABPII mutant mice. Development. 121:1995;671-679.
180. Lampron C., Egly-Rochette C., Gorry P., Dolle P., Mark M., Lufkin T., LeMeur M., Chambon P. Mice deficient in cellular retinoic acid binding II (CRABPII) or in both CRABP I and CRABP II are essentially normal. Development. 121:1995;539-548.
181. Haq R.U., Chytil F. Retinoic acid rapidly induces lung cellular retinol-binding protein mRNA levels in retinol deficient rats. Biochem. Biophys. Res. Commun. 156:1988;712-716.
182. Randolph R.K., Ross A.C. Vitamin A status regulates hepatic lecithin:retinol acyltransferase activity in rats. J. Biol. Chem. 266:1991;16453-16457.
183. Matsuura T., Ross A.C. Regulation of hepatic lecithin:retinol acyltransferase activity by retinoic acid. Arch. Biochem. Biophys. 301:1993;221-227.
184. Kurlandsky S.B., Duell E.A., Kang S., Voorhees J.J., Fisher G.J. Autoregulation of retinoic acid biosynthesis through regulation of retinol esterification in human keratinocytes. J. Biol. Chem. 271:1996;15346-15352.
185. Nagao A., Olson J.A. Enzymatic formation of 9-cis, 13-cis, and all-trans-retinals from isomers of β-carotene. FASEB J. 8:1994;968-973.
186. Urbach J., Rando R.R. Isomerization of all-trans-retinoic acid to 9-cis-retinoic acid. Biochem. J. 299:1994;459-465.
187. Tzimas G., Sass J.O., Wittfoht W., Elmazar M.M., Ehlers K., Nau H. Identification of 9,13-di-cis-retinoic acid as a major plasma metabolite of 9-cis-retinoic acid and limited transfer of 9-cis-retinoic acid and 9,13-di-cis-retinoic acid to the mouse and rat embryos. Drug Metab. Dispos. 22:1994;928-936.
188. Sass J.O., Tzimas G., Nau H. 9,13-Di-cis-retinoic acid is an isomerization product of 9-cis-retinoic acid. Drug Metab. Dispos. 25:1997;1447-1448.
189. Wang W., Napoli J.L., Ballow M. The effects of retinol on in vitro immunoglobulin synthesis by cord blood and adult peripheral blood mononuclear cells. Clin. Exp. Immunol. 92:1993;164-168.
190. Garbe A., Buck J., Hämmerling U. Retinoids are important cofactors in T cell activation. J. Exp. Med. 176:1992;109-117.
191. Buck J., Grun F., Derguini F., Chen Y., Kimura S., Noy N., Hämmerling U. Anhydroretinol: a naturally occurring inhibitor of lymphocyte physiology. J. Exp. Med. 178:1993;675-680.
192. O'Connell M.J., Chua R., Hoyos B., Buck J., Chen Y., Derguini F., Hämmerling U. Retro-retinoids in regulated growth and death. J. Exp. Med. 184:1996;549-555.
193. Chen Y., Derguini F., Buck J. Vitamin A in serum is a survival factor for fibroblasts. Proc. Natl. Acad. Sci. USA. 94:1997;10205-10208.
194. Derguini F., Nakanishi K., Hämmerling U., Chua R., Eppinger T., Levi E., Buck J. 13,14-Dihydroxy-retinol, a new bioactive retinol metabolite. J. Biol. Chem. 270:1995;18875-18880.
195. Grun F., Noy N., Hämmerling U., Buck J. Purification, cloning, and bacterial expression of retinol dehydratase from Spodoptera frugiperda. J. Biol. Chem. 271:1996;16135-16138.
196. Achkar C.C., Derguini F., Blumberg B., Langston A., Levin A.A., Speck J., Evans R.M., Bolado J. Jr., Nakanishi K., Buck J., Gudas L.J. 4-Oxoretinol, a new natural ligand and transactivator of the retinoic acid receptors. Proc. Natl. Acad. Sci. USA. 93:1996;4879-4884.