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Chemical Compound Review

retinene     (2E,4E,6E,8E)-3,7-dimethyl-9- (2,6,6...

Synonyms: retinal, axerophthal, retinaldehyde, E-Retinal, trans-Retinal, ...
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Disease relevance of retinal


High impact information on retinal

  • Furthermore, 9-Z- and all-E-retinal isomers are biosynthetic precursors to 9-Z- and all-E-retinoic acids, ligands that mediate specific cellular responses by binding to transcriptional regulatory proteins critical in growth and development [1].
  • Exposure of human adult RPE cells to UV light at predominantly 320-400 nm (UVA light) in the presence of all-trans-retinaldehyde results in photooxidative cytotoxicity [3].
  • Light activation of rhodopsin results in its release of all-trans-retinaldehyde, which constitutes the first reactant in A2E biosynthesis [4].
  • Proof that the effects of HNE and trans-retinal are mediated by UCP is provided by examination of proton conductance in transgenic plants overexpressing UCP [5].
  • We demonstrate that 4-hydroxy-2-nonenal (HNE), a product of lipid peroxidation, and a structurally related compound, trans-retinal, stimulate a proton conductance in potato mitochondria that is inhibitable by GTP (a characteristic of UCP) [5].

Biological context of retinal


Anatomical context of retinal

  • The effect on the EECP of sequential epi-retinal (i.e. return electrode on epi-retinal surface) vs. trans-retinal (i.e. return electrode behind sclera) stimulation was compared [9].

Gene context of retinal

  • Recombinant chick ALDH6 has a K(0.5) = 0.26 microm, V(max) = 48.4 nmol/min/mg and exhibits strong positive cooperativity (H = 1.9) toward all-trans-retinaldehyde; mouse ALDH6 has similar kinetic parameters [10].
  • When coexpressed with arrestins, melanopsin could use all-trans-retinaldehyde as a chromophore, which suggests that it may function as a bireactive opsin [11].
  • The level of ATPase activity was comparable to that of trans-retinal-stimulated ABCR ATPase [12].
  • The action spectrum has a maximum of 500 nm, and the entire spectrum from 350 to 800 nm closely matches the absorption spectrum of rhodopsin, which is apparently the pigment which mediates the effects of light on phosphodiesterase activity. trans-Retinal alone does not mimic light [13].

Analytical, diagnostic and therapeutic context of retinal


  1. Altered retinoid homeostasis catalyzed by a nicotine metabolite: implications in macular degeneration and normal development. Brogan, A.P., Dickerson, T.J., Boldt, G.E., Janda, K.D. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  2. Rpe65 is a retinyl ester binding protein that presents insoluble substrate to the isomerase in retinal pigment epithelial cells. Mata, N.L., Moghrabi, W.N., Lee, J.S., Bui, T.V., Radu, R.A., Horwitz, J., Travis, G.H. J. Biol. Chem. (2004) [Pubmed]
  3. Induction of phase 2 genes by sulforaphane protects retinal pigment epithelial cells against photooxidative damage. Gao, X., Talalay, P. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  4. Treatment with isotretinoin inhibits lipofuscin accumulation in a mouse model of recessive Stargardt's macular degeneration. Radu, R.A., Mata, N.L., Nusinowitz, S., Liu, X., Sieving, P.A., Travis, G.H. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  5. Activation and function of mitochondrial uncoupling protein in plants. Smith, A.M., Ratcliffe, R.G., Sweetlove, L.J. J. Biol. Chem. (2004) [Pubmed]
  6. Retinoid specificity of interphotoreceptor retinoid-binding protein. Chen, Y., Noy, N. Biochemistry (1994) [Pubmed]
  7. Effects of bicarbonate ion on chick retinal pigment epithelium: membrane potentials and light-evoked responses. Maruiwa, F., Naoi, N., Nakazaki, S., Sawada, A. Vision Res. (1999) [Pubmed]
  8. Intravitreal ganciclovir pharmacokinetics in rabbits and man. Ashton, P., Brown, J.D., Pearson, P.A., Blandford, D.L., Smith, T.J., Anand, R., Nightingale, S.D., Sanborn, G.E. Journal of ocular pharmacology. (1992) [Pubmed]
  9. In vivo electrical stimulation of rabbit retina: effect of stimulus duration and electrical field orientation. Shah, H.A., Montezuma, S.R., Rizzo, J.F. Exp. Eye Res. (2006) [Pubmed]
  10. Aldehyde dehydrogenase 6, a cytosolic retinaldehyde dehydrogenase prominently expressed in sensory neuroepithelia during development. Grün, F., Hirose, Y., Kawauchi, S., Ogura, T., Umesono, K. J. Biol. Chem. (2000) [Pubmed]
  11. Illumination of the melanopsin signaling pathway. Panda, S., Nayak, S.K., Campo, B., Walker, J.R., Hogenesch, J.B., Jegla, T. Science (2005) [Pubmed]
  12. The C-terminal nucleotide binding domain of the human retinal ABCR protein is an adenosine triphosphatase. Biswas, E.E., Biswas, S.B. Biochemistry (2000) [Pubmed]
  13. A link between rhodopsin and disc membrane cyclic nucleotide phosphodiesterase. Action spectrum and sensitivity to illumination. Keirns, J.J., Miki, N., Bitensky, M.W., Keirns, M. Biochemistry (1975) [Pubmed]
  14. Developments in the management of uveal melanoma. Damato, B. Clin. Experiment. Ophthalmol. (2004) [Pubmed]
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