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Chemical Compound Review

Isoretinene A     (2E,4E,6Z,8E)-3,7-dimethyl-9- (2,6,6...

Synonyms: Iso Rhodopsin, cis-9-Retinal, CHEMBL257381, HMDB06218, LMPR01090017, ...
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Disease relevance of Isoretinene A


High impact information on Isoretinene A


Biological context of Isoretinene A

  • We detect at least one novel metabolite formed from both 9-cis-retinol and 9-cis-retinal that may play a role in inhibition of MCF7 cell proliferation [7].
  • 9-cis-Retinal which occupies the binding site but does not reconstitute the chromophore was used as "caged retinal". Photoisomerization to the all-trans isomer triggers the reconstitution reaction [8].
  • The partially-purified enzyme displayed allosteric kinetics for 9-cis-retinal [K0.5 = 5.2 microM, Hill coefficient = 1.4, Vmax = 7.85 nmol min-1 (mg of protein)-1] with the ratio Vmax/K0.5 = 1 [9].
  • Administration of 9-cis-retinal increased the rate of dark adaptation and improved cone function in Rdh5(-/-)Rdh11(-/-) mice [10].
  • These data extend the kinetic characterization of mRALDH1, provide insight into the possible role of this enzyme in the biogenesis of RAs, and should give useful information on the determination of amino acid residues that play crucial roles in the catalysis of all-trans and 9-cis retinal [11].

Anatomical context of Isoretinene A


Associations of Isoretinene A with other chemical compounds


Gene context of Isoretinene A

  • Treatment of Rpe65(-/-) mice with 9-cis-retinal lowered the TPLR threshold by 2.1 log units [20].
  • Consistent with a role mediating inhibition of PC12 cell MAP kinases, NGF-stimulated ERK2 activation was suppressed considerably following pretreatment with fibroblast growth factor and 9-cis-retinal, two additional differentiation factors found to induce powerfully MKP-3 expression [21].
  • cDNA cloning and expression of a human aldehyde dehydrogenase (ALDH) active with 9-cis-retinal and identification of a rat ortholog, ALDH12 [22].
  • Rather, lumirhodopsin is converted to a new species, L' (11-cis and/or 9-cis retinal) which, on warming to room temperature, is indistinguishable from rhodopsin or isorhodopsin [23].
  • Ligand-dependent conformational changes appear to influence a newly detected difference in the bathochromic shift exhibited by bovine and human CRALBP when complexed with 9-cis-retinal [24].

Analytical, diagnostic and therapeutic context of Isoretinene A

  • Rod and cone visual function improved significantly in the mouse model of F. albipunctatus after treatment with 9-cis-retinal, suggesting a potential approach to slow the progression of cone dystrophy in affected humans [10].
  • Absorption bands in the FTIR difference spectra of the educt and product of the reaction could be assigned by comparison with a 9-cis-retinal FTIR spectrum or an FT-Raman spectrum of BR and due to band shifts observed upon deuterium exchange [8].
  • A high-performance liquid chromatographic (HPLC) procedure was developed to separate all-trans-, 13-cis-, 11-cis- and 9-cis-retinal isomers [25].


  1. Identification of 9,13-dicis-retinoic acid as a major plasma metabolite of 9-cis-retinoic acid and limited transfer of 9-cis-retinoic acid and 9,13-dicis-retinoic acid to the mouse and rat embryos. Tzimas, G., Sass, J.O., Wittfoht, W., Elmazar, M.M., Ehlers, K., Nau, H. Drug Metab. Dispos. (1994) [Pubmed]
  2. Visual adaptation: effects of externally applied retinal on the light-adapted, isolated skate retina. Pepperberg, D.R., Lurie, M., Brown, P.K., Dowling, J.E. Science (1976) [Pubmed]
  3. Incorporation of membrane proteins into large single bilayer vesicles. Application to rhodopsin. Darszon, A., Vandenberg, C.A., Ellisman, M.H., Montal, M. J. Cell Biol. (1979) [Pubmed]
  4. Intrinsically photosensitive retinal ganglion cells detect light with a vitamin A-based photopigment, melanopsin. Fu, Y., Zhong, H., Wang, M.H., Luo, D.G., Liao, H.W., Maeda, H., Hattar, S., Frishman, L.J., Yau, K.W. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  5. Rapid-flow resonance Raman spectroscopy of photolabile molecules: rhodopsin and isorhodopsin. Mathies, R., Oseroff, A.R., Stryer, L. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  6. Mouse retinal dehydrogenase 4 (RALDH4), molecular cloning, cellular expression, and activity in 9-cis-retinoic acid biosynthesis in intact cells. Lin, M., Zhang, M., Abraham, M., Smith, S.M., Napoli, J.L. J. Biol. Chem. (2003) [Pubmed]
  7. Cis-retinol dehydrogenase: 9-cis-retinol metabolism and its effect on proliferation of human MCF7 breast cancer cells. Paik, J., Blaner, W.S., Swisshelm, K. Exp. Cell Res. (2005) [Pubmed]
  8. Reconstitution of bacteriorhodopsin from the apoprotein and retinal studied by Fourier-transform infrared spectroscopy. Rüdiger, M., Tittor, J., Gerwert, K., Oesterhelt, D. Biochemistry (1997) [Pubmed]
  9. 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. el Akawi, Z., Napoli, J.L. Biochemistry (1994) [Pubmed]
  10. Improvement in Rod and Cone Function in Mouse Model of Fundus albipunctatus after Pharmacologic Treatment with 9-cis-Retinal. Maeda, A., Maeda, T., Palczewski, K. Invest. Ophthalmol. Vis. Sci. (2006) [Pubmed]
  11. Enzymatic characterization of recombinant mouse retinal dehydrogenase type 1. Gagnon, I., Duester, G., Bhat, P.V. Biochem. Pharmacol. (2003) [Pubmed]
  12. The cellular fate of mutant rhodopsin: quality control, degradation and aggresome formation. Saliba, R.S., Munro, P.M., Luthert, P.J., Cheetham, M.E. J. Cell. Sci. (2002) [Pubmed]
  13. Synthesis of rhodopsin and opsin in vitro. O'Brien, P.J., Muellenberg, C.G. Biochemistry (1975) [Pubmed]
  14. Opsin activation of transduction in the rods of dark-reared Rpe65 knockout mice. Fan, J., Woodruff, M.L., Cilluffo, M.C., Crouch, R.K., Fain, G.L. J. Physiol. (Lond.) (2005) [Pubmed]
  15. Early photolysis intermediates of gecko and bovine artificial visual pigments. Lewis, J.W., Liang, J., Ebrey, T.G., Sheves, M., Livnah, N., Kuwata, O., Jäger, S., Kliger, D.S. Biochemistry (1997) [Pubmed]
  16. Formation, conversion, and utilization of isorhodopsin, rhodopsin, and porphyropsin by rod photoreceptors in the Xenopus retina. Witkovsky, P., Engbretson, G.A., Ripps, H. J. Gen. Physiol. (1978) [Pubmed]
  17. Gene structure, expression analysis, and membrane topology of RDH4. Romert, A., Tuvendal, P., Tryggvason, K., Dencker, L., Eriksson, U. Exp. Cell Res. (2000) [Pubmed]
  18. Selectivity of retinal photoisomerization in proteorhodopsin is controlled by aspartic acid 227. Imasheva, E.S., Balashov, S.P., Wang, J.M., Dioumaev, A.K., Lanyi, J.K. Biochemistry (2004) [Pubmed]
  19. Specific reaction of 9-cis-retinoyl fluoride with bovine opsin. Wong, C.G., Rando, R.R. Biochemistry (1984) [Pubmed]
  20. Impairment of the transient pupillary light reflex in Rpe65(-/-) mice and humans with leber congenital amaurosis. Aleman, T.S., Jacobson, S.G., Chico, J.D., Scott, M.L., Cheung, A.Y., Windsor, E.A., Furushima, M., Redmond, T.M., Bennett, J., Palczewski, K., Cideciyan, A.V. Invest. Ophthalmol. Vis. Sci. (2004) [Pubmed]
  21. Induction of the mitogen-activated protein kinase phosphatase MKP3 by nerve growth factor in differentiating PC12. Camps, M., Chabert, C., Muda, M., Boschert, U., Gillieron, C., Arkinstall, S. FEBS Lett. (1998) [Pubmed]
  22. cDNA cloning and expression of a human aldehyde dehydrogenase (ALDH) active with 9-cis-retinal and identification of a rat ortholog, ALDH12. Lin, M., Napoli, J.L. J. Biol. Chem. (2000) [Pubmed]
  23. The photoconversion of lumirhodopsin at 77 degrees K. Estimation of the quantum efficiency. Becher, B. Biophys. J. (1980) [Pubmed]
  24. Structural and functional characterization of recombinant human cellular retinaldehyde-binding protein. Crabb, J.W., Carlson, A., Chen, Y., Goldflam, S., Intres, R., West, K.A., Hulmes, J.D., Kapron, J.T., Luck, L.A., Horwitz, J., Bok, D. Protein Sci. (1998) [Pubmed]
  25. A reversed-phase high-performance liquid chromatographic method to analyze retinal isomers. Cia, D., Bonhomme, B., Azim, M., Wada, A., Doly, M., Azaïs-Braesco, W. Journal of chromatography. A. (1999) [Pubmed]
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