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: Yong Leng Kelvin Tan, Pascal Pigeon, Siden Top, Eric Labbé, Olivier Buriez, Elizabeth A Hillard, Anne Vessières, Christian Amatore, Weng Kee Leong, Gérard Jaouen
• Journal: Dalton transactions (Cambridge, England : 2003) (Dalton Trans) Vol. 41 Issue 25 Pg. 7537-49 (Jul 07 2012) ISSN: 1477-9234 [Electronic] England
• PMID: 22596041 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Catechols
• Ferrous Compounds
• Metallocenes
• ferrocene

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, therapeutic use)
• Breast Neoplasms (drug therapy)
• Catechols (chemical synthesis, chemistry, therapeutic use)
• Cell Line, Tumor
• Female
• Ferrous Compounds (chemical synthesis, chemistry, therapeutic use)
• Humans
• Inhibitory Concentration 50
• Metallocenes
• Models, Molecular
• Oxidation-Reduction