Ferrocenyl catechols: synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells.

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.
AuthorsYong Leng Kelvin Tan, Pascal Pigeon, Siden Top, Eric Labbé, Olivier Buriez, Elizabeth A Hillard, Anne Vessières, Christian Amatore, Weng Kee Leong, Gérard Jaouen
JournalDalton transactions (Cambridge, England : 2003) (Dalton Trans) Vol. 41 Issue 25 Pg. 7537-49 (Jul 7 2012) ISSN: 1477-9234 [Electronic] England
PMID22596041 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Antineoplastic Agents
  • Catechols
  • Ferrous Compounds
  • ferrocene
  • 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
  • Models, Molecular
  • Oxidation-Reduction

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