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Aqua[1,1‐bis(4‐hydroxyphenyl)‐1,2‐diamino‐2‐phenylethane]‐sulfatoplatinum(II), a New Compound for the Treatment of the Mammary Carcinoma
Author(s) -
Gust Ronald
Publication year - 1994
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19943270109
Subject(s) - diamine , chemistry , ligand (biochemistry) , ether , ether cleavage , chelation , stereochemistry , estrogen receptor , derivative (finance) , estrogen , medicinal chemistry , receptor , breast cancer , cancer , medicine , biochemistry , organic chemistry , financial economics , economics
The highly estrogen receptor(ER)‐affinic compound 1,1‐bis(4‐hydroxy‐phenyl)‐2‐phenylethene (BHPE) was used as carrier ligand for a new cis‐platin derivative, aqua[1,1‐bis(4‐hydroxyphenyl)‐1,2‐diamino‐2‐phenyl‐ethane]sulfatoplatinum(II) ( 3 ‐PtSO 4 ) for the therapy of the ER‐positive ( i.e. hormone sensitive) breast cancer. The diamine ligand 1,1‐bis(4‐hydroxyphenyl)‐1,2‐diamino‐2‐phenylethane ( 3 ) was synthesized by transformation of the O ‐methyl ether derivative of BHPE into the 1,2‐bisazido compound 3b with IN 3 /NaN 3 , reduction of both N 3 residues into NH 2 groups [ 3a ] and subsequent ether cleavage with BBr 3 . From the diamine ligand 3 and K 2 PtI 4 a five‐membered chelate 3 ‐PtI 2 was obtained which was transformed into 3 ‐PtSO 4 with Ag 2 SO 4 . In comparison to BHPE the ER‐affinity of 3 ‐PtSO 4 is markedly reduced. 3 ‐PtSO 4 possesses, however, weak cytotoxic activity (P388) and antiestrogenic, but no estrogenic properties. 3 ‐PtSO 4 is comparable with BHPE in terms of its activity on the hormone sensitive MXT‐M 3.2 breast cancer of the mouse.