Synthesis, oxidation chemistry and cytotoxicity studies on ferrocene derivatives of diethylstilbestrol.
A series of compounds is described in which one of the ethyl groups in diethylstilbestrol has been replaced by a ferrocenyl substituent. Only those derivatives incorporating phenol moieties underwent isomerisation from the Z to the E form, and some of them could be chemically oxidized to a quinone species. The compounds were less cytotoxic against hormone-independent MDA-MB-231 breast cancer cell lines than their corresponding ferrocenyl phenyl or phenol isomers in which the ferrocene and ethyl moieties are linked to the same carbon atom. The biochemical results were evaluated in conjunction with information obtained from electrochemical and chemical oxidation experiments.
Tan
Yong Leng Kelvin
YL
Laboratoire Charles Friedel, UMR CNRS 7223, Ecole Nationale Supérieure de Chimie de Paris, 11 rue Pierre et Marie Curie, 75231, Paris Cedex 05, France.
Pigeon
Pascal
P
Hillard
Elizabeth A
EA
Top
Siden
S
Plamont
Marie-Aude
MA
Vessières
Anne
A
McGlinchey
Michael J
MJ
Müller-Bunz
Helge
H
Jaouen
Gérard
G
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D045744:Cell Line, Tumor; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D018360:Crystallography, X-Ray; D004054:Diethylstilbestrol / Q000031:analogs & derivatives* / Q000737:chemistry; D005296:Ferrous Compounds / Q000737:chemistry*; D006801:Humans; D000075163:Metallocenes; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D056831:Coordination Complexes; D005296:Ferrous Compounds; D000075163:Metallocenes; D004054:Diethylstilbestrol; C004998:ferrocene