title: Synthesis, oxidation chemistry and cytotoxicity studies on ferrocene derivatives of diethylstilbestrol.
abstract: A series of compounds is described in which one of the ethyl groups in diethylstilbestrol has been replaced by a ferrocenyl substituent.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.
authors.affiliation: Laboratoire Charles Friedel, UMR CNRS 7223, Ecole Nationale Supérieure de Chimie de Paris, 11 rue Pierre et Marie Curie, 75231, Paris Cedex 05, France.
authors.forename: Yong Leng Kelvin
authors.initials: YL
authors.lastname: Tan
authors.forename: Pascal
authors.initials: P
authors.lastname: Pigeon
authors.forename: Elizabeth A
authors.initials: EA
authors.lastname: Hillard
authors.forename: Siden
authors.initials: S
authors.lastname: Top
authors.forename: Marie-Aude
authors.initials: MA
authors.lastname: Plamont
authors.forename: Anne
authors.initials: A
authors.lastname: Vessières
authors.forename: Michael J
authors.initials: MJ
authors.lastname: McGlinchey
authors.forename: Helge
authors.initials: H
authors.lastname: Müller-Bunz
authors.forename: Gérard
authors.initials: G
authors.lastname: Jaouen
mesh_terms: 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
chemical_list: D000970:Antineoplastic Agents; D056831:Coordination Complexes; D005296:Ferrous Compounds; D000075163:Metallocenes; D004054:Diethylstilbestrol; C004998:ferrocene