2-Jod-östron und 2-Jod-östradiol

Hillmann-Elies, Anneliese; Hillmann, Günther; Schiedt, Ulrich

doi:10.1515/znb-1953-0807

Cited by 21 publications

(5 citation statements)

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“…The presence in small quantities of the wrong antipode of glutamic acid was also ascertained by experiments of Hillmann and collaborators (19). According to these experiments, small quantities of Dglutamic acid are found in rats after administration per os of various normal proteins from plants or from animals, while, in agreement with findings of Kogl, greater quantities of this aniino acid appear after administration of liver metastases to the test animals.…”

Section: Attempts To Determine By Direct Experiments the Limitasupporting

confidence: 52%

Possible Relation Between Optical Activity and Aging

Kühn¹

1959

Advances in Enzymology - And Related Areas of Molecular Biology

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Section: Attempts To Determine By Direct Experiments the Limitasupporting

confidence: 52%

Possible Relation Between Optical Activity and Aging

Kühn¹

1959

Advances in Enzymology - And Related Areas of Molecular Biology

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“…Preliminary studies indicated that the solubility of [3H]-I-Hex in pH 7.4 TEA buffer was exceedingly low, several orders of magnitude below that of estradiol (ca. 10-5 M;Hahnel, 1971).…”

Section: Resultsmentioning

confidence: 99%

“…) Aliphatic iodine compounds have a high susceptibility toward substitution and elimination reactions (Gould, 1959); therefore, on the grounds of chemical stability, we considered it preferable to have the iodine bonded to an aryl group. The preparation of both 2-and 4-monoiodo-17/3-estradiol and 2,4-diiodo-17/3-estradiol (Albert et al, 1949;Hillmann-Elies et al, 1953;Nambara et al, 1971; Matkovics et al, 1971) had been reported. Although the iodine in these derivatives appeared to be metabolically stable, these compounds showed either low or negligible uterotrophic activity (Albert et al, 1949;Hillmann-Elies, 1953;Peck et al, 1961), and they were not taken up selectively by the uterus (Albert et al, 1949).…”

Section: Discussionmentioning

confidence: 99%

“…The preparation of both 2-and 4-monoiodo-17/3-estradiol and 2,4-diiodo-17/3-estradiol (Albert et al, 1949;Hillmann-Elies et al, 1953;Nambara et al, 1971; Matkovics et al, 1971) had been reported. Although the iodine in these derivatives appeared to be metabolically stable, these compounds showed either low or negligible uterotrophic activity (Albert et al, 1949;Hillmann-Elies, 1953;Peck et al, 1961), and they were not taken up selectively by the uterus (Albert et al, 1949). It is not certain whether this was the result of the failure to satisfy criteria 2 or 3, but as the estrogen receptor is known to be relatively intolerant of bulk at A-ring positions 2 and 4 (Katzenellenbogen et al, 1973b), it appeared that functionalization of these positions in a steroidal ligand was not consistent with high receptor binding (criterion 2).…”

Section: Discussionmentioning

confidence: 99%

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Iodohexestrols. II. Characterization of the binding and estrogenic activity of iodinated hexestrol derivatives, in vitro and in vivo

et al. 1975

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The affinity of ortho-iodinated hexestrols for the estrogen binding protein from rat uterus, determined by competitive binding assay, decreases with progressive iodine substitution; 3-iodohexestrol (I-Hex) has a binding affinity 42% that of estradiol. Analysis of [3-H]-I-Hex binding in rat uterine cytosol by sucrose density gradient centrifugation shows both an estrogen-specific binding component (8 S) and a more abundant component (4 S) that is not estrogen specific. Scatchard analysis indicates that this latter binding is of high affinity (Kd equals to 3.7-8.3 times 10- minus-9 M) but is not uterine specific. Polyacrylamide gel electrophoresis shows that most of the [3-H]-I-Hex binding activity in serum and uterine cytosol is distinct from and anodic to the principal protein component (albumin), and that is comigrates with [14-C]thyroxine binding activity. In in vitro incubation of rat uteri, I-Hex can block the specific uptake of [3-H]estradiol into the nuclear fraction; it itself causes a translocation of estrogen-specific binding capacity (as measured by exchange) from cytoplasm to nuclei, and can induce the synthesis of an estrogen-specific uterine protein, all under conditions where it is not metabolically deiodinated to hexestrol. The uterotrophic activities of the iodohexestrols are in most cases comparable to that expected on the basis of their competitive binding affinities. However, selective, estrogen-specific uptake of [3-H]-I-Hex into rat uterus, either in vitro or in vivo, cannot be demonstrated.

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“…THE PAST, workers (2,4,5,6) have studied the positions of substituents on the aromatic ring of estratriens. This laboratory would like to confirm these assignments, by means of their nuclear magnetic resonance spectra.…”

mentioning

confidence: 99%