title: Ferrocenyl catechols: synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells.
abstract: The synthesis and anti-tumoral properties of a series of compounds possessing a ferrocenyl group tethered to a catechol via a conjugated system is presented. On MDA-MB-231 breast cancer cell lines, the catechol compounds display a similar or greater anti-proliferative potency (IC(50) values ranging from 0.48-1.21 μM) than their corresponding phenolic analogues (0.57-12.7 μM), with the highest activity found for species incorporating the [3]ferrocenophane motif. On the electrochemical timescale, phenolic compounds appear to oxidize to the quinone methide, while catechol moieties form the o-quinone by a similar mechanism. Chemical oxidation of selected compounds with Ag(2)O confirms this interpretation and demonstrates the probable involvement of such oxidative metabolites in the in vitro activity of these species.
authors.affiliation: ENSCP Chimie Paris Tech, Laboratoire Charles Friedel (LCF), 75005 Paris, France.
authors.forename: Yong Leng Kelvin
authors.initials: YL
authors.lastname: Tan
authors.forename: Pascal
authors.initials: P
authors.lastname: Pigeon
authors.forename: Siden
authors.initials: S
authors.lastname: Top
authors.forename: Eric
authors.initials: E
authors.lastname: Labbé
authors.forename: Olivier
authors.initials: O
authors.lastname: Buriez
authors.forename: Elizabeth A
authors.initials: EA
authors.lastname: Hillard
authors.forename: Anne
authors.initials: A
authors.lastname: Vessières
authors.forename: Christian
authors.initials: C
authors.lastname: Amatore
authors.forename: Weng Kee
authors.initials: WK
authors.lastname: Leong
authors.forename: Gérard
authors.initials: G
authors.lastname: Jaouen
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D001943:Breast Neoplasms / Q000188:drug therapy*; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D045744:Cell Line, Tumor; D005260:Female; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D006801:Humans; D020128:Inhibitory Concentration 50; D000075163:Metallocenes; D008958:Models, Molecular; D010084:Oxidation-Reduction
chemical_list: D000970:Antineoplastic Agents; D002396:Catechols; D005296:Ferrous Compounds; D000075163:Metallocenes; C004998:ferrocene