Retinoid binding-proteins redirect retinoid metabolism: Biosynthesis and metabolism of retinoic acid

Seminars in Cell and Developmental Biology

Volumn 8, Issue 4, 1997, Pages 403-415

  Napoli, Joseph L ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

Binding protein; Embryo; Retinal; Retinoic acid; Retinol

Indexed keywords

VERTEBRATA;

EID: 0000640253     PISSN: 10849521     EISSN: None     Source Type: Journal    
DOI: 10.1006/scdb.1997.0164     Document Type: Article

References (90)

1. Rainier S (1985) 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
2. Satre MA, Ugen KE, Kochhar DM (1992) Developmental changes in endogenous retinoids during pregnancy and embryogenesis in the mouse. Biol Reprod 46:802-810
3. Horton C, Maden M (1995) Endogenous distribution of retinoids during normal development and teratogenesis in the mouse embryo. Dev Dynam 202:312-323
4. Scott WJ, Walter R, Tzimas G, Sass JO, Nau H, Collins MD (1996) Endogenous status of retinoids and their cytosolic binding proteins in limb buds of chick vs mouse embryos. Dev Biol 165:397-409
5. Båvik C, Ward SJ, Chambon P (1996) Developmental abnormalities in cultured mouse embryos deprived of retinoic acid by inhibition of yolk-sac retinol binding protein synthesis. Proc Natl Acad Sci USA 93:3110-3114
6. Satre MA, Kochhar DM (1989) Elevations in the endogenous levels of the putative morphogen retinoic acid in the embryonic mouse limb buds associated with limb dysmorphogenesis. Dev Biol 133:529-536
7. Fiorella PD, Napoli JL (1994) Microsomal retinoic acid metabolism: effects of cellular retinoic acid-binding protein (type I) and C18-hydroxylation as an initial step. J Biol Chem 269:10538-10544
8. Thaller C, Eichele G (1990) Isolation of 3,4-didehydroretinoic acid, a novel morphogenetic signal in the chick wing bud. Nature 345:815-819
9. Creech Kraft J, Schuh T, Juchau MR, Kimelman D (1994) The retinoid X receptor ligand, 9-cis-retinoic acid, is a potent regulator of early Xenopus development. Proc Natl Acad Sci USA 91:3067-3071
10. Creech Kraft J, Schuh T, Juchau J, Kimelman D (1994) Temporal spatial distribution, localization and metabolism of retinol, didehydroretinol and retinal during development. Biochem J 301:111-119
11. Pijnappel WWM, Hendricks HFJ, Folkers GE, van den Brink CE, Dekker EJ, Edelenbosch C, van der Saag PJ, Durston AJ (1990) The retinoid ligand 4-xroretinoic acid is a highly active modulator of positional specification. Nature 366:340-344
12. Ong DE, Newcomer ME, Chytil F (1994) Cellular retinoid-binding proteins, in The Retinoids: Biology, Chemistry, and Medicine (Sporn MB, Roberts AB, Goodman DS, eds) pp 303-304 2nd Ed.. Raven Press, New York
13. Newcomer ME (1995) Retinoid-binding proteins: structural determinants important for function. FASEB J 9:229-239
14. Li E, Norris AW (1996) Structure/function of cytoplasmic vitamin A-binding proteins. Annu Rev Nutrition 16:205-234
15. Kleyweft G, Bergfors T, Senn H, Le Motte P, Gsell B, Shudo K, Jones TA (1994) Crystal structures of cellular retinoic acid binding proteins I and II in complex with all-trans-retinoic acid and a synthetic retinoid. Structure 2:1241-1258
16. Thompson JR, Bratt JM, Banaszak LJ (1995) Crystal structure of cellular retinoic acid binding protein I shows increased access to the binding cavity due to formation of an intermolecular β-sheet. J Mol Biol 252:433-446
17. Perez-Castro AV, Toth-Rogler LE, Wei L, Nguyen-Huu MC (1989) Spatial and temporal pattern of expression of the cellular retinoic acid-binding protein and the cellular retinol-binding protein during mouse embryogenesis. Proc Natl Acad Sci 86:8813-8817
18. Dollé P, Ruberte E, Leroy P, Morriss-Kay G, Chambon P (1990) Retinoic acid receptors and cellular retinoid binding proteins I. A systematic study of their differential pattern of transcription during mouse organogenesis. Development 110:1133-1151
19. Ruberte E, Dollé P, Chambon P, Morriss-Kay G (1991) Retinoic acid receptors and cellular retinoid binding proteins II. Their differential pattern of transcription during early morphogenesis in mouse embryos. Development 111:45-60
20. Ruberte E, Frederich V, Chambon P, Morriss-Kay G (1993) Retinoic acid receptors and cellular retinoid binding proteins III. Their differential transcript distribution during mouse nervous system development. Development 118:267-282
21. Gustafson AL, Dencker L, Eriksson U (1993) Non-overlapping expression of CRBP I and CRABP I during pattern formation of limbs and craniofacial structures in the early mouse embryo. Development 117:451-460
22. Lyn S, Giguere V (1994) 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 Dynam 199:280-291
23. Harrison EH, Blaner WS, Goodman DS, Ross AC (1987) Subcellular localization of retinoids, retinoid-binding proteins, and acyl-CoA:retinol acyltransferase in rat liver. J Lipid Res 28:973-981
24. Hendriks HF, Blaner WS, Wennekers HM, Piantedosi R, Brouwer A, DeLeeuw AM, Goodman DS, Knook DL (1988) Distributions of retinoids, retinoid-binding proteins and related parameters in different types of liver cells isolated from young and old rats. Eur J Biochem 171:237-244
25. Li E, Qian SJ, Winter NS, d'Avignon A, Levin MS, Gordon JI (1991) Fluorine nuclear magnetic resonance analysis of the ligand binding properties of two homologous rat cellular retinol-binding proteins expressed in Escherichia coli. J Biol Chem 266:3622-3629
26. Norris AW, Cheng L, Giguere V, Rosenberger M, Li E (1994) Measurement of subnanomolar retinoic acid binding affinities for cellular retinoic acid binding proteins by fluorimetric titration. Biochim Biophys Acta 1209:10-18
27. Saari JC, Bredberg L, Garwin G (1982) Identification of the endogenous retinoids associated with three cellular retinoid-binding proteins from bovine retina and retinal pigment epithelium. J Biol Chem 257:13329-13333
28. de Bruijn DR, Oerlemans F, Hendriks W, Baats E, Ploemacher R, Wieringa B, Guerts, van Kessel A (1994) Normal development, growth and reproduction in cellular retinoic acid binding protein-I (CRABPI) null mutant mice. Differentiation 58:141-148
29. Lampron C, Rochette-Egly C, Gorry P, Dollé P, Mark M, Lufkin T, LeMeur M, Chambon P (1995) Mice deficient in cellular retinoic acid binding protein II (CRABPII) or in both CRABPI and CRABPII are essentially normal. Development 121:539-548
30. Wei LN, Lee CH, Chang SL, Chu YS (1992) Pathogenesis in transgenic mice expressing bovine cellular retinoic acid-binding protein. Dev Growth Diff 34:479-488
31. Perez-Castro AV, Tran VT, Nguyen-Huu MC (1993) Defective lens fiber differentiation and pancreatic tumorigenesis caused by ectopic expression of the cellular retinoic acid-binding protein I. Development 119:363-375
32. Boylan JF, Gudas LJ (1991) Overexpression of the cellular retinoic acid binding protein-I (CRABP-I) results in a reduction in differentiation-specific gene expression in F9 teratocarcinoma cell. J Cell Biol 112:965-969
33. Wei S, Episkopou V, Piantedosi R, Maeda S, Shimada K, Gottesman ME, Blaner WE (1995) Studies on the metabolism of retinol and retinol-binding protein in transthyretin-deficient mice produced by homologous recombination. J Biol Chem 270:866-870
34. Ross AC (1982) Retinol esterification by rat liver microsomes: evidence for a fatty acyl coenzyme A:retinol acyltransferase. J Biol Chem 257:2453-2459
35. Ong DE, MacDonald PN, Gubitosi AM (1988) Esterification of retinol in rat liver: possible participation by cellular retinol-binding protein and cellular retinol binding-protein II. J Biol Chem 263:5789-5796
36. Yost RW, Harrison EH, Ross AC (1988) Esterification by rat liver microsomes of retinol bound to cellular retinol-binding protein. J Biol Chem 263:18693-18701
37. Kakkad BP, Ong DE (1988) Reduction of retinaldehyde bound to cellular retinol binding protein (type II) by microsomes from rat small intestine. J Biol Chem 263:12916-12919
38. Harrison EH (1993) Enzymes catalyzing the hydrolysis of retinyl esters. Biochem Biophys Acta 1170:99-108
39. Napoli JL, Pacia EB, Salerno GJ (1989) Cholate-independent hydrolysis of all-trans-retinyl palmitate by rat tissues: solubilization of multiple kidney microsomal hydrolases. Arch Biochem Biophys 274:192-199
40. Harrison EH, Gad M (1989) 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 264:17142-17147
41. Gad MZ, Harrison EH (1991) Neutral and acid retinyl ester hydrolases associated with rat liver microsomes: relationships to microsomal cholesteryl ester hydrolases. J Lipid Res 32:685-694
42. Ottonello S, Petrucco S, Maraini G (1987) 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 262:3975-3939
43. Boerman MHEM, Napoli JL (1991) Cholate-independent retinyl ester hydrolysis: stimulation by apo-cellular retinol binding protein. J Biol Chem 266:22273-22278
44. Napoli JL, Race KR (1987) Biosynthesis of retinoic acid from retinol by rat tissues in vitro. Arch Biochem Biophys 255:95-101
45. Napoli JL, Race KR (1990) Microsomes convert retinol and retinal into retinoic acid and interfere in the conversions catalyzed by cytosol. Biochim Biophys Acta 1034:228-232
46. Posch KC, Napoli JL (1992) Multiple retinoid dehydrogenases in testes cytosol from alcohol dehydrogenase negative or positive deermice. Biochem Pharmacol 43:2296-2298
47. Posch KC, Boerman MHEM, Burns RD, Napoli JL (1991) Holocellular retinol binding protein as a substrate for microsomal retinal synthesis. Biochemistry 30:6224-6230
48. Napoli JL, Posch KC, Burns RD (1992) Microsomal retinal synthesis: retinol vs. holo-CRBP as substrate and evaluation of NADP, NAD and NADPH as cofactors. Biochim Biophys Acta 1120:183-186
49. Ottonello S, Scita G, Mantovani G, Cavazzini D, Rossi GL (1993) Retinol bound to cellular retinol-binding protein is as substrate for cytosolic retinoic acid synthesis. J Biol Chem 268:27133-27142
50. Napoli JL (1994) Retinoic acid homeostasis: roles of β-Carotene, retinol, holoCRBP, and holoCRABP, in Basic Science and Clinical Aspects of Vitamin A in Health and Disease (Blomhoff R, ed) pp 135-188 Chapt 6. Marcel Dekker, New York
51. Boerman MHEM, Napoli JL (1995) 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 34:7027-7037
52. Cavazzini D, Galdieri M, Ottonello S (1996) Retinoic acid synthesis in the somatic cells of rat seminiferous tubules. Biochim Biophys Acta 1313:139-145
53. Grün F, Noy N, Hämmerling U, Buck J (1996) Purification, cloning and bacterial expression of retinol dehydratase from Spodoptera frugiperda. J Biol Chem 271:16165-16138
54. Boerman MHEM, Napoli JL (1996) Cellular retinol-binding protein-supported retinoic acid synthesis: relative roles of microsomes and cytosol. J Biol Chem 271:5610-5616
55. Herr F, Ong DE (1992) Differential interaction of lecithin-retinol acyltransferase with cellular retinol binding proteins. Biochemistry 31:6748-6755
56. Williams JB, Napoli JL (1985) Metabolism of retinoic acid and retinol during differentiation of F9 embryonal carcinoma cells. Proc Natl Acad Sci USA 82:4658-4662
57. 1 cells: characterization of retinoic acid synthesis by an established mammalian cell line. J Biol Chem 261:13592-13597
58. Randolph RK, Simon M (1993) Characterization of retinol metabolism in cultured human epidermal keratinocytes. J Biol Chem 268:9198-9205
59. Posch KC, Burns RD, Napoli JL (1992) 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 267:19676-19682
60. Zolfaghari R, Ross AC (1995) Chronic vitamin A intake affects the expression of mRNA of apoliprotein A-1, but not for nuclear retinoid receptors, in liver of young and aging Lewis rats. Arch Biochem Biophys 323:258-264
61. Malpeli G, Stoppini M, Zapponi MC, Folli C, Berni R (1995) Interactions with retinol and retinoids of bovine cellular retinol-binding protein. Eur J Biochem 229:486-493
62. Lissoos TW, Davis AE, Levin MS (1995) Vitamin A trafficking in Caco-2 cells stably transfected with cellular retinol binding proteins. Am J Physiol 268:G224-G231
63. Haq RU, Chytil F (1988) Retinoic acid rapidly induces lung cellular retinol-binding protein mRNA levels in retinol deficient rats. Biochem Biophys Res Commun 156:712-716
64. Randolph RK, Ross AC (1991) Vitamin A status regulates hepatic lecithin:retinol acyltransferase activity in rats. J Biol Chem 266:16453-16457
65. Matuura T, Ross AC (1993) Regulation of hepatic lecithin:retinol acyltransferase activity by retinoic acid. Arch Biochem Biophys 301:211-227
66. Roberts AB, Nichols MD, Newton DL, Sporn MB (1979) In vitro metabolism of retinoic acid in hamster intestine and liver. J Biol Chem 254:6296-6302
67. Fiorella PD, Napoli JL (1991) 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 266:16572-16579
68. Takatsuka J, Takahashi N, De Luca LM (1996) Retinoic acid metabolism and inhibition of cell proliferation: an unexpected liaison. Cancer Res 56:675-678
69. Boylan JF, Lufkin T, Achkar CC, Taneja R, Chambon P, Gudas LJ (1995) Targeted disruption of retinoic acid receptor alpha (RAR alpha) and RAR gamma results in receptor-specific alterations in retinoic acid-mediated differentiation and retinoic acid metabolism. Mol Cell Biol 15:843-851
70. White JA, Guo YD, Baetz K, Beckett-Jones B, Bonasoro J, Hsu KE, Dilworth RJ, Jones G, Petkovich M (1996). J Biol Chem 272:29922-29927
71. Donovan M, Olofsson B, Gustafson AL, Dencker L, Eriksson U (1995) The cellular retinoic acid binding proteins. J Steroid Biochem Mol Biol 53:459-465
72. Kurlandsky SB, Gamble MV, Ramakrishnan R, Blaner WS (1995) Plasma delivery of retinoic acid to tissues in the rat. J Biol Chem 270:17850-17857
73. Kurlandsky SB, Duell EA, Kang S, Voorhees JJ, Fisher GJ (1996) Auto-regulation of retinoic acid biosynthesis through regulation of retinol esterification in human keratinocytes. J Biol Chem 271:15346-15352
74. Kurlandsky SB, Xiao JH, Duell EA, Voorhees JJ, Fisher GJ (1994) Biological activity of all-trans-retinol requires metabolic conversion to all-tarans-retinoic acid and is mediated through activation of nuclear retinoid receptors in human keratinocytes. J Biol Chem 269:32281-32287
75. Chai X, Boerman MHEM, Zhai Y, Napoli JL (1995) Cloning of a cDNA for liver microsomal retinol dehydrogenase: a tissue-specific, short-chain alcohol dehydrogenase. J Biol Chem 270:3900-3904
76. Chai X, Zhai Y, Popescu G, Napoli JL (1995) Cloning of a cDNA for a second retinol dehydrogenase, type II: expression of its mRNA relative to type I. J Biol Chem 270:28408-28412
77. Chai X, Zhai Y, Napoli JL (1996) Cloning of a cDNA encoding a retinol dehydrogenase isozyme type III. Gene 169:219-222
78. Baker ME (1995) Unusual evolution of 11β- and 17β-hydroxysteroid and retinol dehydrogenases. BioEssays 18:63-70
79. Jörnvall H, Persson B, Krook M, Atrian S, Gonzàlex-Duarte , Jeffery J, Ghosh D (1995) Short-chain dehydrogenases/reductases (SDR). Biochemistry 34:6003-6013
80. Lee MO, Manthey CL, Sladek NE (1991) Identification of mouse liver aldehyde dehydrogenases that catalyze the oxidation of retinaldehyde to retinoic acid. Biochem Pharmacol 42:1279-1285
81. Dockham PA, Lee MO, Sladek NE (1992) Identification of human liver aldehyde dehydrogenases that catalyze the oxidation of aldophosphamide and retinaldehyde. Biochem Pharmacol 43:2453-2469
82. Wang X, Penzes P, Napoli JL (1996) 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 271:16288-16293
83. Penzes P, Wang X, Napoli JL (1997) Cloning of a cDNA encoding retinal dehydrogenase isozyme type and its expression in Escherichia coli. Gene in press:
84. Bhat PV, Labrecque J, Boutin JM, Lacroix A, Yoshida A (1995) Cloning of a cDNA encoding rat aldehyde dehydrogenase with high activity for retinal oxidation. Gene 166:303-306
85. El Akawi Z, Napoli JL (1994) 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 33:1938-1943
86. Labrecque J, Dumas F, Lacroix A, Bhat PV (1995) A novel isoenzyme of aldehyde dehydrogenase specifically involved in the biosynthesis of 9-cis and all-trans retinoic acid. Biochem J 305:681-684
87. Zhao D, McCaffery P, Ivins KJ, Neve RL, Hogan P, Chin WW, Drager (1996) Molecular identification of a major retinoic-acid-synthesizing enzyme, a retinaldehyde-specific dehydrogenase. Eur J Biochem 240:15-22
88. Yamamoto M, McCaffery P, Dräger UC (1996) Influence of the choroid plexis on cerebellar development: analysis of retinoic acid synthesis. Dev Brain Res 93:182-190
89. Saari JC, Champer RJ, Asson-Batres M, Garwin GG, Huang J, Crabb JW, Milam AH (1995) Characterization and localization of an aldehyde dehydrogenase to amacrine cells of bovine retina. Vis Neurosci 12:263-272
90. Godbout R, Packer M, Poppema S, Dabragh L (1996) Localization of cytosolic aldehyde dehydrogenase in the developing chick retina: in situ hybridization and immunochemical analyses. Dev Dynamics 205:319-331