Gust, Ronald and Schönenberger, Helmut (1993) Mammary tumor inhibiting [1,2-bis(2,6-dihalo-3-hydroxyphenyl)ethylenediamine]platinum(II) complexes. III. Relationship between structure and estrogenic activity of the diamine ligands, their sulfatoplatinum(II) and diiodoplatinum(II) complexes. Archiv der Pharmazie 326 (7), pp. 405-413.
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1,2-Bis(2,6-dihalo-3-hydroxyphenyl)ethylenediamines with 2,6-Cl2, 2-F,6-Cl, 2-Cl,6-F, and 2,6-F2 substituents (meso-1 to meso-4, D,L-1 and D,L-4) and their sulfatoplatinum(II) complexes were tested in the immature mouse uterine wt. test. The only complex with marked estrogenic properties proved to be meso-1-PtSO4. Surprisingly its diamine ligand meso-1 was only marginally active. 1H-NMR spectroscopic studies on the 1,2-diphenylethylenediamine ligand reveal that the 2,6-standing Cl-atoms in meso-1 (antiperiplanar Ph residues) hinder the rotation of the arom. rings, which results in very stable conformers with different O-O distances owing to the unsym. arrangement of the ring substituents. On transformation into the Pt(II) complex the conformations of meso-1 change (synclinal Ph residues) and a delta and l interconversion takes place already at physiol. temp. (37 DegC). This process is accompanied by a rotation of Ph rings, which is supposed to allow an optimal fit for the formation of hydrogen bridges to the estrogen receptor, resulting in a marked estrogenic activity. The other ligands and complexes are inactive presumably due to a diminished hydrophobic interaction with the estrogen receptor, resulting from their R,R/S,S-configuration or the reduced no. of Cl-atoms.
|Additional information (public):||CAN 119:240909 1-3 Pharmacology 7440-06-4D (Platinum); 126735-37-3; 128413-03-6; 128413-11-6; 128413-12-7; 128413-13-8; 128524-04-9; 128524-12-9; 128524-13-0; 128524-14-1; 150390-74-2; 150447-55-5; 150448-26-3; 150520-05-1; 150520-06-2; 151037-67-1 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), BIOL (Biological study) (estrogenic activity of, mammary antitumor activity in relation to); 150412-97-8 Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), BIOL (Biological study) (estrogenic activity of, structure in relation to)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Conformation and Conformers (of hydroxyphenylethylenediamine sulfatoplatinum complexes) Molecular structure-biological activity relationship (estrogenic, of hydroxyphenylethylenediamine sulfatoplatinum complexes) Neoplasm inhibitors (mammary gland, hydroxyphenylethylenediamine sulfatoplatinum complexes as, estrogenic activity in, structure-activity relations of) Mammary gland (neoplasm, inhibitors, hydroxyphenylethylenediamine sulfatoplatinum complexes as, estrogenic activity in, structure-activity relations of) estrogenic platinum complex conformation|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Deposited On:||12 Nov 2010 06:50|
|Last Modified:||12 Nov 2010 06:50|