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Chemical Compound Review:

CPD-13538 (2Z,4E,6Z,8E)-3,7-dimethyl-9- (2,6,6...

Synonyms: AC1NS4TF, 2052-63-3, 22737-97-9, Retinol, 9-cis-, Retinol, 13-cis-

Paik, J. et al., Shang, E. et al., Wang, J. et al., Parish, C.A. et al., Dew, S.E. et al., et al.

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Disease relevance of Retinol, 9-cis-

Cis-retinol dehydrogenase: 9-cis-retinol metabolism and its effect on proliferation of human MCF7 breast cancer cells [1].

High impact information on Retinol, 9-cis-

By using 5% of the extract from individual aged human eyes, this protocol has led to the quantification of A2E and the characterization of iso-A2E, a new A2E double bond isomer; all-trans-retinol and 13-cis-retinol also have been identified in these HPLC chromatograms [2].
Interestingly, the cytosolic alcohol dehydrogenase 4 failed to efficiently catalyze 9-cis-retinol oxidation [3].
Intense ALDH12 mRNA expression in adult and fetal liver and kidney, two organs that reportedly have relatively high concentrations of 9-cis-retinol, reinforces this notion [4].
We have obtained a 1.4-kilobase cDNA clone from a normalized human breast tissue library, which when expressed in CHO cells encodes a protein that avidly catalyzes oxidation of 9-cis-retinol to 9-cis-retinaldehyde [5].
LRDHSN/MCF7 cells showed a marked reduction in cell numbers (60-80%) upon treatment with 9-cis-retinol compared to vehicle alone [1].

Biological context of Retinol, 9-cis-

To investigate this hypothesis, MCF7 human breast carcinoma cells were transduced with cRDH cDNA (LRDHSN/MCF7), and the growth kinetics and retinoid profiles of cells were examined following treatment with 9-cis-retinol [1].
Esterification of 9-cis-retinol occurred in both cell types, likely by acyl-CoA:retinol acyltransferase and lecithin:retinol acyltransferase [6].
Considered along with the identical nucleotide sequences in the untranslated regions of human Rdh5 and human 9-cis-retinol dehydrogenase cDNAs and the nearly identical nucleotide sequences overall (99% identity), the current results suggest that the two cDNAs represent a single gene product [7].

Anatomical context of Retinol, 9-cis-

Both cell lines accumulate similar amounts of 9-cis-retinol provided in the medium [6].
We investigated the specificity of that process by determining the absorption of all-trans-, 13-cis-, and 9-cis-retinol, 3-dehydroretinol, and retinal (vitamin A aldehyde) by gut sheets from the small intestine of suckling rats [8].

Associations of Retinol, 9-cis- with other chemical compounds

It has been proposed that cis-retinol dehydrogenase (cRDH) acts within the body to catalyze the oxidation of 9-cis-retinol, an oxidative step needed for 9-cis-retinoic acid synthesis, the oxidation of 11-cis-retinol [an oxidative step needed for 11-cis-retinal (visual chromophore) synthesis], and 3 alpha-hydroxysteroid transformations [9].
This oxidative 3 alpha-hydroxysteroid dehydrogenase (3 alpha-HSD) activity of RoDH-4 is competitively inhibited by retinol and 13-cis-retinol [10].

Gene context of Retinol, 9-cis-

There is little information regarding either the biochemical properties of cRDH or how its 9-cis-retinol substrate is formed [11].
Analysis of rat cytosolic 9-cis-retinol dehydrogenase activity and enzymatic characterization of rat ADHII [12].
(CRAD2 does not recognize 9-cis-retinol as a substrate) [13].
This conclusion is inconsistent with earlier literature indicating that 11cRDH is expressed solely in the eye and does not utilize 9-cis-retinol as a substrate [14].

References

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]
Isolation and one-step preparation of A2E and iso-A2E, fluorophores from human retinal pigment epithelium. Parish, C.A., Hashimoto, M., Nakanishi, K., Dillon, J., Sparrow, J. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
Biosynthesis of 9-cis-retinoic acid in vivo. The roles of different retinol dehydrogenases and a structure-activity analysis of microsomal retinol dehydrogenases. Tryggvason, K., Romert, A., Eriksson, U. J. Biol. Chem. (2001) [Pubmed]
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]
Identification and characterization of a stereospecific human enzyme that catalyzes 9-cis-retinol oxidation. A possible role in 9-cis-retinoic acid formation. Mertz, J.R., Shang, E., Piantedosi, R., Wei, S., Wolgemuth, D.J., Blaner, W.S. J. Biol. Chem. (1997) [Pubmed]
9-cis-retinoids: biosynthesis of 9-cis-retinoic acid. Paik, J., Vogel, S., Piantedosi, R., Sykes, A., Blaner, W.S., Swisshelm, K. Biochemistry (2000) [Pubmed]
Activity of human 11-cis-retinol dehydrogenase (Rdh5) with steroids and retinoids and expression of its mRNA in extra-ocular human tissue. Wang, J., Chai, X., Eriksson, U., Napoli, J.L. Biochem. J. (1999) [Pubmed]
Specificity of the retinol transporter of the rat small intestine brush border. Dew, S.E., Ong, D.E. Biochemistry (1994) [Pubmed]
Targeted disruption of the mouse cis-retinol dehydrogenase gene: visual and nonvisual functions. Shang, E., Lai, K., Packer, A.I., Paik, J., Blaner, W.S., de Morais Vieira, M., Gouras, P., Wolgemuth, D.J. J. Lipid Res. (2002) [Pubmed]
13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Karlsson, T., Vahlquist, A., Kedishvili, N., Törmä, H. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
Biochemical properties, tissue expression, and gene structure of a short chain dehydrogenase/ reductase able to catalyze cis-retinol oxidation. Gamble, M.V., Shang, E., Zott, R.P., Mertz, J.R., Wolgemuth, D.J., Blaner, W.S. J. Lipid Res. (1999) [Pubmed]
Analysis of rat cytosolic 9-cis-retinol dehydrogenase activity and enzymatic characterization of rat ADHII. Popescu, G., Napoli, J.L. Biochim. Biophys. Acta (2000) [Pubmed]
cis-Retinol/androgen dehydrogenase, isozyme 3 (CRAD3): a short-chain dehydrogenase active in a reconstituted path of 9-cis-retinoic acid biosynthesis in intact cells. Zhuang, R., Lin, M., Napoli, J.L. Biochemistry (2002) [Pubmed]
Substrate specificities and 13-cis-retinoic acid inhibition of human, mouse and bovine cis-retinol dehydrogenases. Gamble, M.V., Mata, N.L., Tsin, A.T., Mertz, J.R., Blaner, W.S. Biochim. Biophys. Acta (2000) [Pubmed]

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