Disease relevance of hexestrol

• It is tentatively concluded that there is a mediating or co-operative pituitary influence involved in the significant hepatic, uterine and adrenal weight gains caused by hexoestrol [1].
• Subacute toxicity of diethylstilboestrol and hexoestrol in the female rat, and the effects of clomiphene pretreatment [2].
• Four young (23 kg body weight) and two mature wethers (52 and 92 kg body weight) were subcutaneously injected with hexestrol (HX) or HX dicaprylate (HX-D) and killed 41 d later [3].
• Overwhelming toxoplasmosis with increased mortality was found in the hexoestrol-treated mice after infection, probably resulting from a depression of cell-mediated immunity caused by hexoestrol [4].

High impact information on hexestrol

• We studied the action of E-diethylstilbestrol (E-DES), erythro-hexestrol (erythro-HES), and E,E-dienestrol (E,E-DIES) on microtubule formation [5].
• Conformational analysis of nonsteroidal estrogens: The effect of conformer populations on the binding affinity of meso- and dl-hexestrol to the estrogen receptor [6].
• The endothelial cells react to Hexoestrol similarly in male and female mice, by increasing their height and becoming more heavily structured, with an effect particularly on the Golgi apparatus [7].
• The endothelial cells of male and female control and gonadectomised mice were higher after infection with Toxoplasma while in the infected hexoestrol-treated animals, lower cells were seen [8].
• The number of lymphocytes passing through the post-capillary venule wall was increased by gonadectomy and decreased by hexoestrol administration in both sexes [8].

Biological context of hexestrol

• Metabolic activation and formation of DNA adducts of hexestrol, a synthetic nonsteroidal carcinogenic estrogen [9].
• The synthetic oestrogens diethylstilboestrol, hexoestrol and 17 alpha-ethynyloestradiol are known to be carcinogenic, yet they all exert antioxidant properties in vitro in that they are good inhibitors of iron ion-dependent lipid peroxidation [10].
• The synthetic oestrogens diethylstilboestrol, hexoestrol and 17 alpha-ethynyloestradiol are known to be good antioxidants, and we now report that they decrease membrane fluidity, in ox-brain phospholipid liposomes [11].
• Diethylstilbestrol, dienestrol, hexestrol, beta-estradiol, ethynylestradiol and estriol caused significant increase in aneuploidy within a narrow range of high concentrations in recovering cell populations [12].
• The Thrombotest clotting times of the hexoestrol-treated rats were prolonged [2].

Anatomical context of hexestrol

• On the first and second days after Hexoestrol administration there is an increase in the number of ribosomes and polyribosomes lying free in the cytoplasm of the endothelial cells [13].
• Diethylstilbestrol (DES) and four derivatives, viz. tetrafluoro-DES, 3'-hydroxy-DES, Z,Z-dienestrol and hexestrol, were examined for their abilities to form superoxide radicals and to induce DNA strand breaks in the presence of horseradish peroxidase/hydrogen peroxide metabolism in a cell-free system [14].
• High doses of hexoestrol produced a loss of contractility of the papillary muscle without significant alterations of the amplitude and shape of the electrical activity recorded extracellularly [15].
• These results indicate that hexoestrol probably acts by blocking certain steps in the process by which extracellular and/or superficially bound Ca ions move to the contractile machinery in cardiac and in smooth muscle cells [15].
• The synthetic oestrogen hexoestrol, administered at 60 mg/kg/day for 4 days to female rats in 3 studies, caused the following mean changes in the relative weights of some of the principal organs: liver (+37%), spleen (-11%), adrenals (+43%), kidneys (+3%), pituitary (+23%), uterus (+49%), and ovaries (+13%) [1].

Associations of hexestrol with other chemical compounds

• Estrogen photoaffinity labels. 2. Reversible binding and covalent attachment of photosensitive hexestrol derivatives to the uterine estrogen receptor [16].
• Photolysis of 3,5-diiodohexestrol in methanol results in rapid deiodination to 3-iodohexestrol; further reduction to hexestrol is slower [17].
• Ketononestrol aziridine [(6R,TS)1-(N-aziridinyl)6,7-bis-(4-hydroxyphenyl)5-nonamone (KNA)], an aziridine derivative of hexestrol, is an estrogenic affinity label for the estrogen receptor (ER) [18].
• On the other hand, meso-hexestrol was distinguished from others by inhibition of microtubule assembly and formation of a large amount of aggregates from purified tubulin in the presence of MgCl2 and DMSO [19].
• Our preliminary findings showed that geiparvarin and some derivatives obtained from its conjugation with diethylstilboestrol and meso-hexestrol significantly inhibit taxol-induced in vitro polymerization of both tubulin and microtubular protein [20].

Gene context of hexestrol

• Only meso-3,4-bis(2,4-dihydroxyphenyl)hexane (16) showed an estrogen receptor binding affinity comparable to that of hexestrol (32 and 27%, respectively) [21].
• Two groups, each of ten female rats, were orally dosed with the synthetic oestrogens diethylstilboestrol (DES; 6 mg/kg day) and hexoestrol (60 mg/kg/day) for 6 wk [2].
• By in vitro experiments using the lignin-degrading enzyme manganese peroxidase (MnP), BPA was metabolized to phenol, 4-isopropenylphenol, 4-isopropylphenol, and hexestrol [22].

Analytical, diagnostic and therapeutic context of hexestrol

• Initial examinations for purity by gas-liquid chromatography, thin-layer chromatography, and isotope dilution did not show the presence of hexestrol [23].
• A radioimmunoassay method is described for the detection and measurement of residues of hexoestrol and other stilbenes in tissues of poultry [24].
• Determination of hexoestrol residues in animal tissues based on enzyme-linked immunosorbent assay and comparison with liquid chromatography-tandem mass spectrometry [25].
• Combination of the high resolution of the HPLC with a specific RIA is a suitable method to discriminate between the presence of different stilbene derivatives like diethylstilboestrol (DES), dienoestrol (DE) and hexoestrol (HEX) or other unknown compounds interfering in the celite-RIA used in the screening [26].

References