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Chemical Compound Review

Dienestrol, (Z,Z)-Isomer     4-[(2Z,4Z)-4-(4- hydroxyphenyl)hexa-2,4...

Synonyms: Z,Z-Dienestrol, CHEMBL72364, CCRIS 7090, ZINC04742540, ZINC38664631, ...
 
 
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Disease relevance of dienestrol

  • 4-OT, from Pseudomonas putida mt-2, catalyzes the conversion of 2-oxo-4-hexenedioate to 2-oxo-3-hexenedioate through the dienol intermediate 2-hydroxymuconate in a catabolic pathway for aromatic hydrocarbons [1].
  • The dietary dienestrol diacetate also resulted in increased body weights at 30 and 46 wk in one experiment [2].
 

High impact information on dienestrol

  • Substituted phenols bind tightly to the active site of the D38N mutant of KSI, and are analogs of the intermediate dienol [3].
  • The free energy profile for the D38E enzyme was determined from a combination of steady state kinetics and stopped-flow kinetics with the independently generated dienol intermediate (2) [4].
  • The utility of this derivatization is illustrated for the delta 7,14 TMS dienol ethers of the 3-deoxy, 3-keto, 3 alpha-hydroxy, and 3 beta-methoxy analogs of 1 and for delta 8(14)-15-ketosterols in mixtures obtained from incubations of 1 with rat liver mitochondria in the presence of NADPH [5].
  • Inhibitors of sterol synthesis. Characterization of trimethylsilyl dienol ethers of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one. Applications in the analysis of mitochondrial metabolites of the 15-ketosterol by gas chromatography-mass spectrometry [5].
  • This activity was increased by Z,Z-dienestrol, with minimal estrogen receptor occupancy, and did not result in stimulation of DNA synthesis [6].
 

Biological context of dienestrol

  • Hydroxylation leading to epoxyalcohols with a cis, trans-conjugated dienol occurs at carbons 5, 8, 9, or 12 [7].
  • Selective protection of the A-ring enone system as the dienol ether followed by ethynylation and deprotection under base and acid hydrolysis condition gave 7alpha-cyano-17alpha-ethynyl-19-nortestosterone [8].
  • Rhenium(I)-catalyzed intramolecular geminal carbofunctionalization of alkynes: tandem cyclization of omega-acetylenic dienol silyl ethers [9].
 

Anatomical context of dienestrol

  • 3. Hepatic microsomes from untreated and 7,8-BF-pretreated hamsters metabolize E-diethylstilboestrol (E-DES) to its stereoisomer Z-DES and to several oxidative metabolites, of which 3-hydroxy-DES and Z,Z-dienestrol were unambiguously identified by g.l.c.-mass spectrometry [10].
 

Associations of dienestrol with other chemical compounds

 

Gene context of dienestrol

  • With the use of radio gas chromatography and gas chromatography--mass spectrometry, the major urinary and biliary metabolites were tentatively identified as hydroxy and methoxy derivatives of DES and dienestrol, of which the relative amounts excreted depended largely on the species [15].
 

Analytical, diagnostic and therapeutic context of dienestrol

  • The TMS dienol ethers showed reduced artefact formation, improved chromatographic resolution, and increased sensitivity relative to the delta 8(14)-15-ketosterols, properties that improve the detection and identification of minor components in analyses of complex biological mixtures [5].
  • A high-performance liquid chromatographic (HPLC) analysis is described for dienestrol as a drug substance and in cream, foam, and tablet dosage forms [16].
  • Analysis of dienestrol and its dosage forms by high-performance liquid chromatography [16].

References

  1. Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural consequences of the L8R mutation in 4-oxalocrotonate tautomerase. Poelarends, G.J., Almrud, J.J., Serrano, H., Darty, J.E., Johnson, W.H., Hackert, M.L., Whitman, C.P. Biochemistry (2006) [Pubmed]
  2. Performance of Leghorn type hens fed two levels of energy and a synthetic estrogen during the growing period. Douglas, C.R., Harms, R.H., Carpenter, M.D., Chaille, T.B. Poult. Sci. (1989) [Pubmed]
  3. Substituent effects on the binding of phenols to the D38N mutant of 3-oxo-delta5-steroid isomerase. A probe for the nature of hydrogen bonding to the intermediate. Petrounia, I.P., Pollack, R.M. Biochemistry (1998) [Pubmed]
  4. Reaction energetics of a mutant 3-oxo-delta 5-steroid isomerase with an altered active site base (D38E). Zawrotny, M.E., Pollack, R.M. Biochemistry (1994) [Pubmed]
  5. Inhibitors of sterol synthesis. Characterization of trimethylsilyl dienol ethers of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one. Applications in the analysis of mitochondrial metabolites of the 15-ketosterol by gas chromatography-mass spectrometry. St Pyrek, J., Wilson, W.K., Numazawa, S., Schoepfer, G.J. J. Lipid Res. (1991) [Pubmed]
  6. Estrogen stimulation of phosphatidylinositol metabolism in mouse uterine tissue. Grove, R.I., Korach, K.S. Endocrinology (1987) [Pubmed]
  7. NADPH-dependent microsomal metabolism of 14,15-epoxyeicosatrienoic acid to diepoxides and epoxyalcohols. Capdevila, J.H., Mosset, P., Yadagiri, P., Lumin, S., Falck, J.R. Arch. Biochem. Biophys. (1988) [Pubmed]
  8. Synthesis of the 7alpha-cyano-(17alpha,20E/Z)-[125I]iodovinyl-19-nortestosterones: potential radioligands for androgen and progesterone receptors. Ali, H., Rousseau, J., Ahmed, N., Guertin, V., Hochberg, R.B., van Lier, J.E. Steroids (2003) [Pubmed]
  9. Rhenium(I)-catalyzed intramolecular geminal carbofunctionalization of alkynes: tandem cyclization of omega-acetylenic dienol silyl ethers. Kusama, H., Yamabe, H., Onizawa, Y., Hoshino, T., Iwasawa, N. Angew. Chem. Int. Ed. Engl. (2005) [Pubmed]
  10. The effects of pretreatment with 7,8-benzoflavone on drug-metabolizing enzymes and diethylstilboestrol metabolism in male hamster liver microsomal preparations. Blaich, G., Metzler, M. Xenobiotica (1988) [Pubmed]
  11. Analysis of diethylstilbestrol, dienestrol and hexestrol in biological samples by immunoaffinity extraction and gas chromatography-negative-ion chemical ionization mass spectrometry. Bagnati, R., Castelli, M.G., Airoldi, L., Paleologo Oriundi, M., Ubaldi, A., Fanelli, R. J. Chromatogr. (1990) [Pubmed]
  12. Chemiexcitation in the peroxidative metabolism of diethylstilbestrol. Metabolic products. Knudsen, F.d.a. .S., Cilento, G. Photochem. Photobiol. (1992) [Pubmed]
  13. Hormonal replacement therapy in patients after cervical cancer treatment. Ploch, E. Gynecol. Oncol. (1987) [Pubmed]
  14. Biotransformation of diethylstilbestrol in the rhesus monkey and the chimpanzee. Metzler, M., Müller, W., Hobson, W.C. Journal of toxicology and environmental health. (1977) [Pubmed]
  15. Diethylstilbestrol: evidence for metabolic activation in man, rat, and hamster. Metzler, M. National Cancer Institute monograph. (1979) [Pubmed]
  16. Analysis of dienestrol and its dosage forms by high-performance liquid chromatography. Bailey, L.C., Bailey, C.A. Journal of pharmaceutical sciences. (1979) [Pubmed]
 
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