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  • Diethylstilbestrol  (2)
  • 1,1-Bis(4-hydroxyphenyl)-2-phenylethene  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Crystal structure and hormonal activity of 1,1-bis(4-hydroxyphenyl)-2-phenylethene (1993)
    Springer
    Monatshefte für Chemie 124 (1993), S. 1181-1193 
    Details
    ISSN: 1434-4475
    Keywords: 1,1-Bis(4-hydroxyphenyl)-2-phenylethene ; X-ray analysis ; Estrogenic and antiestrogenic activity ; Estrogen receptor affinity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Es wurde eine komplette dreidimensionale Röntgenstrukturanalyse von 1,1-Bis(4-hydroxyphenyl)-2-phenylethen (BHPE) durchgeführt, wobei die Reflexe bei Raumtemperatur gesammelt wurden. Nach isotroper Verfeinerung derF-Werte ergab sich einR-Wert von 0.163.BHPE kristallisiert mit 8 Molekülen in einer Einheitszelle von monokliner Symmetrie mit Raumgruppe C2/c und den Zelldimensionena=20.851,b=15.505,c=10.536 Å, β=107.54°. DasBHPE-Molekül ist nicht flach. Die aromatischen Ringe sind aus der Ethen-Ebene mit Winkeln von −30.16° (Ring B), −51.45° (Ring C) und −33.49° (Ring A) herausgedreht. Der Bindungswinkel zwischen den 1,1-ständigen, 4-hydroxysubstituierten Phenylringen beträgt 115.3°, wobei dies einen Abstand von 9.636 Å für die Hydroxylgruppen ergibt. Es stellte sich heraus, daßBHPE ein „impeded“ Estrogen mit geringer antiestrogener Wirkung ist, obwohl seine Estrogen-Receptor-Affinität sehr hoch ist (29%, Estradiol 100%). Es wird der Einfluß der räumlichen Gegebenheiten inBHPE und verwandten Substanzen im Hinblick auf ihre estrogene/antiestrogene und Brustkrebs-hemmende Wirkung diskutiert.
    Notes: Summary A complete three-dimensional X-ray crystal structure analysis of 1,1-bis(4-hydroxyphenyl)-2-phenylethene (BHPE) has been carried out. Reflexes were collected at room temperature. After isotropic refinement ofF-values by least-squares,R is 0.163.BHPE crystallizes with 8 molecules in a unit cell of monoclinic symmetry, space group C2/c and cell dimensionsa=20.851,b=15.505,c=10.536 Å, β=107.54°. The molecule ofBHPE is not flat, the aromatic rings are twisted out of the ethene plane with angles of −30.16° (ring B), −51.45° (ring C) and −33.49° (ring A). The bond angle between the 1,1-standing, 4-hydroxy-substituted phenyl rings amounts to 115.3° resulting in a distance between the hydroxy groups of 9.636 Å.BHPE proved to be a weak “impeded” estrogen with minor antiestrogenic potency, though its estrogen receptor affinity is very high (29%, estradiol 100%). A discussion of the influence of the spatial structure ofBHPE and related substances on its estrogenic/antiestrogenic and mammary tumor-inhibiting potency is given.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00810027
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  • 2
    Electronic Resource
    Electronic Resource
    Studies on the mammary tumor-inhibiting effects of diethylstilbestrol and its mono- and diphosphate (1986)
    Springer
    Journal of cancer research and clinical oncology 111 (1986), S. 110-114 
    Details
    ISSN: 1432-1335
    Keywords: Diethylstilbestrol ; Diethylstilbestrol monophosphate ; Diethylstilbestrol diphosphate ; Estrogen receptor affinity ; Estrogenic potency ; Mammary tumor inhibiting activity in vivo and in vitro
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Diethylstilbestrol (DES), diethylstilbestrol monophosphate (DES-MP) and diethylstilbestrol diphosphate (DES-DP) were tested for their estrogen receptor affinity, estrogenic potency and mammary tumor-inhibiting activity in vitro and in vivo. DES had a much higher receptor binding affinity than its mono-or diphosphate. All three compounds inhibited the growth of the hormone-dependent MCF-7 and hormone-independent MDA-MB 231 breast cancer line only at relatively high concentrations. The estrogenic potency in the immature mouse uterine weight test decreased in the order DES〉DES-MP≫DES-DP. The hormone-dependent MXT mammary tumor of the mouse was inhibited by all three compounds at a dosage of 1.0 mg/kg per week. At a dose of 0.01 mg/kg, DES, DES-MP, and DES-DP stimulated the tumor growth. Thus, for the first time, a biphasic effect on tumor growth was demonstrated in intact mature animals. As the effects of all three compounds were similar in this assay, a cleavage of the phosphate groups is likely. A decrease in estrogenic potency concomitant with a retained antitumor effect of DES-MP and DES-DP compared to DES was not demonstrable in the mature mouse using the MXT assay, only in the uterotrophic test in the immature mouse.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00400747
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  • 3
    Electronic Resource
    Electronic Resource
    The tumor-inhibiting effect of diethylstilbestrol and its diphosphate on the Nb-H and Nb-R prostatic carcinomas of the rat (1990)
    Springer
    Journal of cancer research and clinical oncology 116 (1990), S. 159-167 
    Details
    ISSN: 1432-1335
    Keywords: Diethylstilbestrol ; Honvan ; Accessory sex organs ; Noble Nb prostate tumors ; Morphometry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary For many years, diethylstilbestrol (DES) and its diphosphate (DESPP; Honvan) have been standard therapies for prostatic carcinoma. The effects of DES, its monophosphate (DESP) and of DESPP on the weights of accessory sex organs of mice and rats, and on the experimental Noble Nb-H and Nb-R prostatic carcinomas of the rat were, therefore, compared. In intact mature mice, all three compounds led to a strong and dose-dependent inhibition of seminal vesicle weights and testosterone levels, whereas only a slight antiandrogenic activity in castrated mice was found. In intact rats, DES, DESP and DESPP strongly inhibited accessory sex organ weights and testosterone levels. In castrated rats, however, no antiandrogenic activity was determinable. The prostate carcinoma-inhibiting effects of DES and DESPP were tested in comparison with castration in the transplantable hormone-sensitive Nb-H and Nb-R prostatic carcinoma in rats. Whereas castration caused only a retardation of tumor growth, DES and DESPP (3×0.1 mg/kg and 1.0 mg/kg weekly s.c.) led to an almost complete inhibition, which was significantly (P〈0.01) better than the effect of castration. As the weights of accessory sex organs were identically reduced by either castration or the estrogens, a direct tumor-inhibiting effect of DES and DESPP in addition to their testosterone-lowering activity is obvious. This was proved in an experiment with castrated rats. The only slightly inhibitory activity of castration was strongly potentiated by concomitant administration of DES. Moreover, histological examinations revealed that Nb-H and Nb-R tumors were much more damaged by treatment with DES or DESPP than after castration. Morphometry of the tumors showed that tumor reduction is associated with a decrease in the ratio of the epithelial to the stromal density, i.e. there was an even more pronounced decrease in epithelial cells than that found by merely measuring tumor area. These studies show that the prostate carcinoma-inhibiting effect of DES and DESPP in the Nb model is superior to the effect of castration and that they act directly on the tumor cells used, even in castrated rats.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01612671
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