title: Modification of the estrogenic properties of diphenols by the incorporation of ferrocene. Generation of antiproliferative effects in vitro.
abstract: We report here the synthesis and the strong and unexpected antiproliferative effect of the organometallic diphenolic compound 1,1-bis(4'-hydroxyphenyl)-2-ferrocenyl-but-1-ene (4) on both hormone-dependent (MCF7) and -independent (MDA-MB231) breast cancer cells (IC(50) = 0.7 and 0.6 microM). Surprisingly, 6 [1,2-bis(4'-hydroxyphenyl)-2-ferrocenyl-but-1-ene], the regioisomer of 4, shows only a modest effect on these cell lines. This pertinent organometallic modification seems to trigger an intracellular oxidation of the structurally favorable compound 4, leading to the generation of a potent cytotoxic compound.
authors.affiliation: Laboratoire de Chimie et Biochimie des Complexes Moléculaires, UMR CNRS 7576, Ecole Nationale Supérieure de Chimie de Paris, France.
authors.forename: Anne
authors.initials: A
authors.lastname: Vessières
authors.forename: Siden
authors.initials: S
authors.lastname: Top
authors.forename: Pascal
authors.initials: P
authors.lastname: Pigeon
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Hillard
authors.forename: Leila
authors.initials: L
authors.lastname: Boubeker
authors.forename: Daniela
authors.initials: D
authors.lastname: Spera
authors.forename: Gérard
authors.initials: G
authors.lastname: Jaouen
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001943:Breast Neoplasms; D045744:Cell Line, Tumor; D047628:Estrogen Receptor alpha / Q000737:chemistry / Q000378:metabolism; D047629:Estrogen Receptor beta / Q000737:chemistry / Q000378:metabolism; D004967:Estrogens / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D066298:In Vitro Techniques; D000075163:Metallocenes; D009376:Neoplasms, Hormone-Dependent; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014599:Uterus / Q000378:metabolism
chemical_list: C501751:1,1-bis(4'-hydroxyphenyl)-2-ferrocenylbut-1-ene; D000970:Antineoplastic Agents; D047628:Estrogen Receptor alpha; D047629:Estrogen Receptor beta; D004967:Estrogens; D005296:Ferrous Compounds; D000075163:Metallocenes; D009942:Organometallic Compounds; D010636:Phenols; C004998:ferrocene