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Chemical Compound Review:

CHEMBL104049 (2E,4E,6E,8E)-3,7-dimethyl-9- (2,6,6...

Synonyms: HMDB06285, AC1O5MXW, LMPR01090026, LS-143473, FT-0670656, ...

Creech Kraft, J. et al., Shealy, Y.F. et al., Daly, A.K. et al., Vanden Bossche, H. et al., Spear, P.A. et al., et al.

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Disease relevance of all-trans-4-Oxo-retinoic acid

Some of these 4-oxoretinoic acid analogues showed high activity in assays in vivo for the inhibition of ornithine decarboxylase activity and carcinogen-induced papillomas in mouse skin [1].

High impact information on all-trans-4-Oxo-retinoic acid

Human plasma was analyzed by high performance liquid chromatography for the presence of retinoic acid and 4-oxoretinoic acid isomers [2].
Isolation and identification of 4-hydroxy- and 4-oxoretinoic acid. In vitro metabolites of all-trans-retinoic acid in hamster trachea and liver [3].
Our findings show that, after the microinjections of 4-oxo-all-trans-retinoic acid or 4-oxo-13-cis-retinoic acid (at these selected concentrations), 4-oxo-all-trans-retinoic acid was predominant in the embryos proper at concentrations of about 200 nM [4].
Conceptual biotransformation of 4-oxo-all-trans-retinoic acid, 4-oxo-13-cis-retinoic acid and all-trans-retinoyl-beta-glucuronide in rat whole embryo culture [4].
In the present study, we utilized HPLC techniques to analyze retinoid levels in cultured rat conceptuses, 1.5 hr after intraamniotic microinjections of 4-oxo-13-cis-retinoic acid (2500 ng/mL), 4-oxo-all-trans-retinoic acid (600 ng/mL) or all-trans-retinoyl-beta-glucuronide (4000 ng/mL) [4].

Biological context of all-trans-4-Oxo-retinoic acid

The rate of retinoic acid hydroxylation via the cytochrome P-450 system to 4-hydroxyretinoic acid plus the subsequent oxidation to 4-ketoretinoic acid was significantly elevated [5].

Anatomical context of all-trans-4-Oxo-retinoic acid

The activity of 4-oxoretinoic acid as an inducer of gap junctional communication was investigated in C3H/10T1/2 murine fibroblasts [6].
The Rf values of two major compounds correspond with those of 4-hydroxy- and 4-ketoretinoic acid, formed after incubation of hamster liver microsomes in the presence of [15-14C]-RA [7].

Gene context of all-trans-4-Oxo-retinoic acid

The ability of various retinoids to compete with all-trans-retinoic acid for binding to CRABP was assayed: 4-oxoretinoic acid and two synthetic retinoids were effective competitors, but 13-cis-retinoic acid, 3,4-didehydroretinoic acid and the acid derivative of etretinate competed poorly [8].

Analytical, diagnostic and therapeutic context of all-trans-4-Oxo-retinoic acid

New congeners of 4-oxoretinoic acid demonstrate high activity in a spectrum of bioassays [9].

References

Cancer chemopreventive 3-substituted-4-oxoretinoic acids. Shealy, Y.F., Hosmer, C.A., Riordan, J.M., Wille, J.W., Rogers, T.S., Hill, D.L. J. Med. Chem. (1994) [Pubmed]
Identification and quantitation of all-trans- and 13-cis-retinoic acid and 13-cis-4-oxoretinoic acid in human plasma. Eckhoff, C., Nau, H. J. Lipid Res. (1990) [Pubmed]
Isolation and identification of 4-hydroxy- and 4-oxoretinoic acid. In vitro metabolites of all-trans-retinoic acid in hamster trachea and liver. Frolik, C.A., Roberts, A.B., Tavela, T.E., Roller, P.P., Newton, D.L., Sporn, M.B. Biochemistry (1979) [Pubmed]
Conceptual biotransformation of 4-oxo-all-trans-retinoic acid, 4-oxo-13-cis-retinoic acid and all-trans-retinoyl-beta-glucuronide in rat whole embryo culture. Creech Kraft, J., Juchau, M.R. Biochem. Pharmacol. (1992) [Pubmed]
Increased retinoic acid metabolism following 3,3',4,4',5,5'-hexabromobiphenyl injection. Spear, P.A., Garcin, H., Narbonne, J.F. Can. J. Physiol. Pharmacol. (1988) [Pubmed]
Induction of gap junctional communication by 4-oxoretinoic acid generated from its precursor canthaxanthin. Hanusch, M., Stahl, W., Schulz, W.A., Sies, H. Arch. Biochem. Biophys. (1995) [Pubmed]
Cytochrome-P-450-dependent metabolism of retinoic acid in rat skin microsomes: inhibition by ketoconazole. Vanden Bossche, H., Willemsens, G., Janssen, P.A. Skin Pharmacol. (1988) [Pubmed]
Purification and properties of cellular retinoic acid-binding protein from neonatal rat skin. Daly, A.K., Redfern, C.P. Biochim. Biophys. Acta (1988) [Pubmed]
Synthesis and evaluation of some new retinoids for cancer chemoprevention. Shealy, Y.F. Preventive medicine. (1989) [Pubmed]

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