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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Archiv der Pharmazie | ||||
| Verlag: | Wiley | ||||
| Band: | 326 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 12 | ||||
| Seitenbereich: | S. 967-976 | ||||
| Datum: | 1993 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 120:182470 1-6 Pharmacology 128413-04-7; 128413-05-8 Role: BIOL (Biological study) (crystal structure of and estrogenic activity of, cancer inhibition in relation to); 111112-54-0; 153697-92-8; 153697-93-9; 153697-94-0; 153697-95-1 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), BIOL (Biological study) (estrogenic activity of, structure in relation to) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Entpflichtete oder im Ruhestand befindliche Professoren > Prof. Schönenberger | ||||
| Sonstige Projekte: | SFB 234 | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Estrogens Role: BIOL (Biological study) ([(hydroxyphenyl)ethylenediamine]platinum(II) complexes as, structure in relation to) Conformation and Conformers (of [(halohydroxyphenyl)ethylenediamine]platinum(II) complexes) Crystal structure (of [(halohydroxyphenyl)ethylenediamine]platinum(II) complexes, estrogenicity in relation to) Molecular structure-biological activity relationship (estrogenic, of [(hydroxyphenyl)ethylenediamine]platinum(II) complexes) Neoplasm inhibitors (mammary gland, [(hydroxyphenyl)ethylenediamine]platinum(II) complexes as, estrogenic activity in relation to) Mammary gland Prostate gland (neoplasm, inhibitors, [(hydroxyphenyl)ethylenediamine]platinum(II) complexes as, estrogenic activity in relation to) Neoplasm inhibitors (prostate gland, [(hydroxyphenyl)ethylenediamine]platinum(II) complexes as, estrogenic activity in relation to) phenylethylenediamine platinum complex estrogenic crystal structure conformation phenylethylenediamine platinum complex estrogenic activity mammary cancer inhibitor phenylethylenediamine platinum complex | ||||
| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status: | Veröffentlicht | ||||
| Begutachtet: | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden: | Ja | ||||
| Dokumenten-ID: | 17700 |
Zusammenfassung
Complete three-dimensional x-ray crystal structure analyses of estrogenic [erythro-1-(2,6-dichloro-4-hydroxyphenyl)-2-(2-halo-4-hydroxyphenyl)ethylenediamine]diiodoplatinum(II) complexes [halo = fluoro:erythro-8-PtI2 (I) and halo = chloro:erythro-9-PtI2 (II)] which were synthesized for application in breast and prostate cancer, have been carried out. The 6239 as well as the 6521 reflexes were ...
Zusammenfassung
Complete three-dimensional x-ray crystal structure analyses of estrogenic [erythro-1-(2,6-dichloro-4-hydroxyphenyl)-2-(2-halo-4-hydroxyphenyl)ethylenediamine]diiodoplatinum(II) complexes [halo = fluoro:erythro-8-PtI2 (I) and halo = chloro:erythro-9-PtI2 (II)] which were synthesized for application in breast and prostate cancer, have been carried out. The 6239 as well as the 6521 reflexes were measured and refined to an R-value of 0.105 and 0.066, resp. The mols. of erythro-8-PtI2 are displayed laterally from a possible Pt-Pt axis sepd., alternatingly, by Pt-Pt-distances of 3.62 .ANG. and 6.27 .ANG.. A comparable structure possesses erythro-9-PtI2 with Pt-Pt-distances of 3.59 .ANG. and 6.32 .ANG.. The ethylenediamine ligands of erythro-8-PtI2 and erythro-9-PtI2 are puckered and exist in half chair conformations. For both complexes, the 2,6-dichloro-4-hydroxyphenyl ring is equatorially arranged, while the 2-halo-4-hydroxyphenyl ring is nearly perpendicular to the N-Pt-N plane. The O-O-distance between the phenolic oxygens amts. to 8.1 .ANG. in erythro-8-PtI2 and to 7.8 .ANG. in erythro-9-PtI2. Though these O-O-distances differ strongly from that (12.1 .ANG.), which is considered to be necessary for the binding of an estrogen to its receptor, [1-(2,6-dichloro-4-hydroxyphenyl)-2-(2-halo-4-hydroxyphenyl)ethylenediamine]platinum(II) complexes show estrogenic effects which are, however, strongly reduced compared to that of therapeutically used estrogens like diethylstilbestrol. The relation between mol. structure and estrogenicity as well as the significance of the latter for antitumor activity and untoward side effects are thoroughly discussed.
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