Gust, Ronald and Gelbcke, Michael and Angermaier, Bernhard and Bachmann, Helmut and Krauser, Rudolf and Schönenberger, Helmut (1997) The stereoselectivity of antitumor active [1,2-diamino-1-phenylpropane]dichloroplatinum(II) complexes. INORGANICA CHIMICA ACTA, 264 (1-2). pp. 145-160. ISSN 0020-1693, 1873-3255
Full text not available from this repository.Abstract
The syntheses of enantiomeric threo- and erythro-1,2-diamino-1-phenylpropanes (Ph/Me) and of the racemic 1,2-diaminophenylethane (Ph/H) are described. These diamines and related N-2-methyl- and N-1,N-2-dimethyl-l,2-diamino-1-phenylpropanes were transformed into dichloroplatinum(II) complexes (Ph/H-PtCl2, Ph/Me-PtCl2, Ph/Me-Me-PtCl2, Ph/Me-Dime-PtCl2). For the H-1 NMR spectroscopical determination of their optical purity the diamines (Ph/Me) were converted with (R)-myrtenal into their diimines. In the test on the MCF-7 breast cancer cell line (R,R)-Ph/Me-PtCl2 produced the strongest effect of all new complexes, comparable with that of the standard cisplatin and of other Pt complexes. Its enantiomer (S,S)-Ph/Me-PtCl2 possessed a distinctly weaker inhibitory potency while the erythro-configurated counterparts were even less active [(R,R) > (S,S) > (S,R) = (R,S)]. All N-2-methylated and N-1,N-2-dimethylated complexes (Ph/Me-Me-PtCl2, Ph/Me-Dime-PtCl2) showed comparable activities equaling those of (R,S)- and (S,R)-Ph/Me-PtCl2. The molecular reasons for the differing potencies of the diastereomeric and enantiomeric Ph/Me-PtCl2 complexes are discussed in consideration of the complex conformation. (C) 1997 Elsevier Science S.A.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | TUMOR-INHIBITING PROPERTIES; ANTICANCER DRUG CISPLATIN; PLATINUM(II) COMPLEXES; CRYSTAL-STRUCTURE; MAJOR ADDUCT; DNA-ADDUCTS; ISOMERS; CIS-<PT(NH3)2(H2O)2>(NO3)2; DERIVATIVES; CHEMISTRY; antitumor activity; platinum complexes; diamine complexes; stereoselectivity |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Schönenberger |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 02 Mar 2023 09:30 |
| Last Modified: | 02 Mar 2023 09:30 |
| URI: | https://pred.uni-regensburg.de/id/eprint/50436 |
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