• 1
    Blomhoff, R. (1994) Transport and metabolism of vitamin A. Nutr. Rev. 52, S13S23.
  • 2
    Clagett-Dame, M. & DeLuca, H.F. (2002) The role of vitamin A in mammalian reproduction and embryonic development. Ann. Rev. Nutr. 22, 347381.
  • 3
    Allenby, G., Bocqel, M.-T., Saunders, M., Kazmer, S., Speck, J., Resenberger, M., Lovey, A., Kastner, P., Grippo, J.F., Chambon, P. & Levin, A.A. (1993) Retinoic acid receptors and retinoid-receptors: interactions with endogenous retinoic acids. Proc. Natl Acad. Sci. USA 90, 3034.
  • 4
    Chambon, P. (1996) A decade of molecular biology of retinoic acid receptors. FASEB J. 10, 940954.
  • 5
    Duester, G. (2000) Families of retinoid dehydrogenases regulating vitamin A function. Production of visual pigment and retinoic acid. Eur. J. Biochem. 267, 43154324.
  • 6
    Eklund, H. & Brändén, C.-I. (1987) Alcohol dehydrogenase. In Biological Macromolecules and Assemblies (Jurnak, F.A. & McPherson, A., eds), Vol. 3, pp. 73142. John Wiley & Sons Inc, London.
  • 7
    Szalai, G., Duester, G., Friedman, R., Jia, H., Lin, S., Roe, B.A. & Felder, M.R. (2002) Organization of six functional mouse alcohol dehydrogenase genes on two overlapping bacterial artificial chromosomes. Eur. J. Biochem. 269, 224232.
  • 8
    Molotkov, A., Deltour, L., Foglio, M.H., Cuenca, A.E. & Duester, G. (2002) Retinol/ethanol drug interaction during acute alcohol intoxication in mice involves inhibition of retinol metabolism to retinoic acid by alcohol dehydrogenase. J. Biol. Chem. 277, 1380413811.
  • 9
    Höög, J.-O., Hedberg, J.J., Strömberg, P. & Svensson, S. (2001) Mammalian alcohol dehydrogenase – functional and structural implications. J. Biomed. Sci. 8, 7176.
  • 10
    Molotkov, A., Fan, X., Deltour, L., Foglio, M.H., Martras, S., Farrés, J., Parés, X. & Duester, G. (2002) Stimulation of retinoic acid production and growth by ubiquitously expressed alcohol dehydrogenase Adh3. Proc. Natl Acad. Sci. USA 99, 53375342.
  • 11
    Ang, H.L., Deltour, L., Hayamizu, T.F., Zgombic-Knight, M. & Duester, G. (1996) Retinoic acid synthesis in mouse embryos during gastrulation and craniofacial development linked to class IV alcohol dehydrogenase gene expression. J. Biol. Chem. 271, 95269536.
  • 12
    Haselbeck, R.J. & Duester, G. (1997) Regional restriction of alcohol/retinol dehydrogenases along the mouse gastrointestinal epithelium. Alcohol. Clin. Exp. Res. 21, 14841490.
  • 13
    Jörnvall, H., Persson, B., Krook, M., Atrián, S., González-Duarte, R., Jeffery, J. & Ghosh, D. (1995) Short-chain dehydrogenases/reductases (SDR). Biochemistry 34, 60036013.
  • 14
    Napoli, J.L., Posch, K.C. & Burns, R.D. (1992) Microsomal retinal synthesis: retinol vs. holo-CRBP as substrate and evaluation of NADP, NAD and NADPH as cofactors. Biochim. Biophys. Acta 1120, 183186.
  • 15
    Lapshina, E.A., Belyaeva, O.V., Chumakova, O.V. & Kedishvili, N.Y. (2003) Differential recognition of the free versus bound retinol by human microsomal retinol/sterol dehydrogenases: characterization of the holo-CRBP dehydrogenase activity of RoDH-4. Biochemistry 42, 776784.
  • 16
    Ghyselinck, N.B., Bavik, C., Sapin, V., Mark, M., Bonnie, D., Hindelang, C., Dierich, A., Nilsson, C.B., Hakansson, H., Sauvant, P., Azaïs-Braesco, V., Frasson, M., Picaud, S. & Chambon, P. (1999) Cellular retinol-binding protein I is essential for vitamin A homeostasis. EMBO J. 18, 49034914.
  • 17
    Kedishvili, N.Y., Gough, W.H., Davis, W.I., Parsons, S., Li, T.-K. & Bosron, W.F. (1998) 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, 191196.
  • 18
    McBee, J.K., Palczewski, K., Baehr, W. & Pepperberg, D.R. (2001) Confronting complexity: the interlink of phototransduction and retinoid metabolism in the vertebrate retina. Prog. Retin. Eye Res. 20, 469529 .
  • 19
    Mata, N.L., Radu, R.A., Clemmons, R.S. & Travis, G.H. (2002) Isomerization and oxidation of vitamin A in cone-dominant retinas: a novel pathway for visual-pigment regeneration in daylight. Neuron 36, 6980.
  • 20
    Berson, D.M., Dunn, F.A. & Motoharu, T. (2002) Phototransduction by retinal ganglion cells that set the circadian clock. Science 295, 10701073.
  • 21
    McCaffery, P., Wagner, E., O'Neil, J., Petkovic, M. & Dräger, U.C. (1999) Dorsal and ventral retinal territories defined by retinoic acid synthesis, break-down and nuclear receptor expression. Mech. Dev. 82, 119130.
  • 22
    Bitzer, M., Feldkaemper, M. & Schaeffel, F. (2000) Visually induced changes in components of the retinoic acid system in fundal layers of the chick. Exp. Eye Res. 70, 97106.
  • 23
    Weiler, R., Pottek, M., He, S. & Vaney, D.I. (2000) Modulation of coupling between retinal horizontal cells by retinoic acid and endogenous dopamine. Brain Res. Rev. 32, 121129.
  • 24
    Julià, P., Farrés, J. & Parés, X. (1983) Purification and partial characterization of a rat retina alcohol dehydrogenase active with ethanol and retinol. Biochem. J. 213, 547550.
  • 25
    Julià, P., Farrés, J. & Parés, X. (1986) Ocular alcohol dehydrogenase in the rat: regional distribution and kinetics of the ADH-1 isoenzyme with retinol and retinal. Exp. Eye Res. 42, 305314.
  • 26
    Plapp, B.V., Mitchell, J.L. & Berst, K.B. (2001) Mouse alcohol dehydrogenase 4: kinetic mechanism, substrate specificity and simulation of effects of ethanol on retinoid metabolism. Chemico-Biol. Interact. 130–132, 445456.
  • 27
    Hedén, L.-O., Höög, J.-O., Larsson, K., Lake, M., Lagerholm, E., Holmgren, A., Vallee, B.L., Jörnvall, H. & Von Bahr-Lindström, H. (1986) cDNA clones coding for the β-subunit of human liver alcohol dehydrogenase have differently 3′-non-coding regions. FEBS Lett. 194, 327332.
  • 28
    Allali-Hassani, A., Peralba, J.M., Martras, S., Farrés, J. & Parés, X. (1998) Retinoids, ω-hydroxyfatty acids and cytotoxic aldehydes as physiological substrates, and H2-receptor antagonists as pharmacological inhibitors, of human class IV alcohol dehydrogenase. FEBS Lett. 426, 362366.
  • 29
    Deltour, L., Haselbeck, R.J., Ang, H.L. & Duester, G. (1997) 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, 102109.
  • 30
    Bradford, M.M. (1976) A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248254.
  • 31
    Crosas, B., Allali-Hassani, A., Martínez, S.E., Martras, S., Persson, B., Jörnvall, H., Parés, X. & Farrés, J. (2000) Molecular basis for differential substrate specificity in class IV alcohol dehydrogenase. J. Biol. Chem. 275, 2518025187.
  • 32
    Alvarez, R., Domínguez, B. & de Lera, A. (2001) An expedient stereocontrolled synthesis of 7-cis-retinoids. Synth. Commun. 31, 20832087.
  • 33
    Hosoda, A., Taguchi, T. & Kobayashi, Y. (1987) Highly cis-slective witting reaction of oxido-allylic phosphorane with aldehyde. An efficient synthesis of 11-cis-retinoids. Tetrahedron Lett. 28, 6568.
  • 34
    Fatiadi, A.J. (1976) Active manganese dioxide oxidation in organic chemistry – part I. Synthesis 2, 65104.
  • 35
    Xie, P., Parssons, S.H., Speckhard, D.C., Bosron, W.F. & Hurley, T.D. (1997) X-ray structure of human class IV σσ alcohol dehydrogenase. J. Biol. Chem. 272, 1855818563.
  • 36
    Hurley, T.D., Bosron, W.F., Hamilton, J.A. & Amzel, L.M. (1991) Structure of human β1β1 alcohol dehydrogenase: catalytic effects of non-active-site substitutions. Proc. Natl Acad. Sci. USA 88, 81498153.
  • 37
    Xie, P.T. & Hurley, T.D. (1999) Methionine-141 directly influences the binding of 4-methylpyrazole in human σσ alcohol dehydrogenase. Protein Sci. 8, 26392644.
  • 38
    Vaglenova, J., Martínez, S.E., Porté, S., Duester, G., Farrés, J. & Parés, X. (2003) Expression, localization and potential physiological significance of alcohol dehydrogenase in the gastrointestinal tract. Eur. J. Biochem. 270, 26522662.
  • 39
    Wagner, F.W., Burger, A.R. & Vallee, B.L. (1983) Kinetic properties of human liver alcohol dehydrogenase: oxidation of alcohols by class I isoenzymes. Biochemistry 22, 18571863.
  • 40
    Yin, S.-J., Bosron, W.F., Magnes, L.J. & Li, T.-K. (1984) Human liver alcohol dehydrogenase: purification and kinetic characterization of the β2β2, β2β1, αβ2, and β2γ1‘oriental isoenzymes’. Biochemistry 23, 58475853.
  • 41
    Algar, E.M., Seeley, T.-L. & Holmes, R.S. (1983) Purification and molecular properties of mouse alcohol dehydrogenase isozymes. Eur. J. Biochem. 137, 139147.
  • 42
    Boleda, M.D., Saubi, N., Farrés, J. & Parés, X. (1993) Physiological substrates for rat alcohol dehydrogenase classes: aldehydes of lipid peroxidation, ω-hydroxyfatty acids, and retinoids. Arch. Biochem. Biophys. 307, 8590.
  • 43
    Yang, Z.-N., Davis, G.J., Hurley, T.D., Stone, C.L., Li, T.-K. & Bosron, W.F. (1994) Catalytic efficiency of human alcohol dehydrogenases for retinol oxidation and retinal reduction. Alcohol. Clin. Exp. Res. 18, 587591.
  • 44
    Moreno, A. & Parés, X. (1991) Purification and characterization of a new alcohol dehydrogenase from human stomach. J. Biol. Chem. 266, 11281133.
  • 45
    Han, C.L., Liao, C.S., Wu, C.W., Hwong, C.L., Lee, A.R. & Yin, S.J. (1998) Contribution to first-pass metabolism of ethanol and inhibition by ethanol for retinol oxidation in human alcohol dehydrogenase family. Eur. J. Biochem. 254, 2531.
  • 46
    Yin, S.-J., Chou, C.-F., Lai, C.-L., Lee, S.-L. & Han, C.-L. (2003) Human class IV alcohol dehydrogenase: kinetic mechanism, functional roles and medical relevance. Chem. Biol. Interact. 143–144, 219227.
  • 47
    Ang. H.L., Deltour, L., Zgombic-Knight, M., Wagner, M.A. & Duester, G. (1996) 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, 10501064.
  • 48
    Molotkov, A., Fan, X. & Duester, G. (2002) Excessive vitamin A toxicity in mice genetically deficient in either alcohol dehydrogenase Adh1 or Adh3. Eur. J. Biochem. 269, 26072612.
  • 49
    Bifone, A., de Groot, H.J.M. & Buda, F. (1996) Ab initio molecular dynamics of retinals. Chem. Phys. Lett. 248, 165172.
  • 50
    Buss, V., Weingart, O. & Sugihara, M. (2000) Fast photoisomerization of a rhodopsin model – an ab initio molecular dynamics study. Angew. Chem. Int. Ed. 39, 27842786.
  • 51
    Deigner, P.S., Law, W.C., Canada, F.J. & Rando, R.R. (1989) Membranes as the energy source in the endergonic transformation of vitamin A to 11-cis-retinol. Science 244, 968971.
  • 52
    Yamamoto, H., Simon, A., Eriksson, U., Harris, E., Berson, E.L. & Dryja, T.P. (1999) Mutations in the gene encoding 11-cis retinol dehydrogenase cause delayed dark adaptation and fundus albipunctatus. Nature Genet. 22, 188191.
  • 53
    Cideciyan, A.V., Haeseleer, F., Fariss, R.N., Aleman, T.S., Jang, G.F., Verlinde, C.L., Marmor, M.F., Jacobson, S.G. & Palczewski, K. (2000) Rod and cone visual cycle consequences of a null mutation in the 11-cis-retinol dehydrogenase gene in man. Vis. Neurosci. 17, 667678.
  • 54
    Driessen, C.A.G.G., Winkens, H.J., Hoffmann, K., Kuhlmann, L.D., Janssen, B.P.M., van Vugt, A.H.M., van Hooser, J.P., Wieringa, B.E., Deutman, A.F., Palczewski, K., Ruether, K. & Janssen, J.J.M. (2000) Disruption of the 11-cis-retinol dehydrogenase gene leads to accumulation of cis-retinols and cis-retinyl esters. Mol. Cell. Biol. 20, 42754287.
  • 55
    Shang, E., Lai, K., Packer, A.I., Paik, J., Blaner, W.S., Vieira, M.M., Gouras, P. & Wolgemuth, D.J. (2002) Targeted disruption of the mouse cis-retinol dehydrogenase gene: visual and nonvisual functions. J. Lipid. Res. 43, 590597.
  • 56
    Golovleva, I., Bhattacharya, S., Wu, Z., Shaw, N., Yang, Y., Andrabi, K., West, K.A., Burstedt, M.S., Forsman, K., Holmgren, G., Sandgren, O., Noy, N., Qin, J. & Crabb, J.W. (2003) Disease-causing mutations in the cellular retinaldehyde binding protein tighten and abolish ligand interactions. J. Biol. Chem. 278, 1239712402.
  • 57
    Saari, J.C. & Bredberg, D.L. (1982) Enzymatic reduction of 11-cis-retinal bound to cellular retinal-binding protein. Biochim. Biophys. Acta 716, 266272.
  • 58
    Donmoyer, C.M., Lai, K., Kong, J., Duester, G., Molotkov, A., Blaner, W.S. & Gouras, P. (2002)Impairment of dark adaptation in ADH4–/–RDH5–/– double knockout mice.Invest. Ophthalmol. Vis. Sci. 43, E–Abstract 3681.
  • 59
    Chen, P., Lee, T.D. & Fong, H.K.W. (2001) Interaction of 11-cis-retinol dehydrogenase with the chromophore of retinal G protein-coupled receptor opsin. J. Biol. Chem. 276, 2109821104.
  • 60
    De Leeuw, A.M., Gaur, V.P., Saari, J.C. & Milam, A.H. (1990) Immunolocalization of cellular retinol-, retinaldehyde- and retinoic acid-binding proteins in rat retina during pre- and postnatal development. J. Neurocytol. 19, 253264.
  • 61
    Milam, A.H., Possin, D.E., Huang, J., Fariss, R.N., Flannery, J.G. & Saari, J.C. (1997) Characterization of aldehyde dehydrogenase-positive amacrine cells restricted in distribution to the dorsal retina. Vis. Neurosci. 14, 601608.