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

Yong Leng Kelvin Tan , Pascal Pigeon (1, 2) , Siden Top (2, 1) , Eric Labbé (3) , Olivier Buriez (3) , Elisabeth A. Hillard , Anne Vessières (2) , Christian Amatore , Weng Kee Leong , Gérard Jaouen (2)

1 ENSCP - Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL
2 Laboratoire Charles Friedel
3 ENS-PSL - École normale supérieure - Paris

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 (IC50 values ranging from 0.48-1.21 mu M) than their corresponding phenolic analogues (0.57-12.7 mu M), 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 Ag2O confirms this interpretation and demonstrates the probable involvement of such oxidative metabolites in the in vitro activity of these species.

Domaines: Chimie

Yong Leng Kelvin Tan, Pascal Pigeon, Siden Top, Eric Labbé, Olivier Buriez, et al.. Ferrocenyl catechols: synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells. Dalton Transactions, 2012, 41 (25), pp.7537-7549. ⟨10.1039/c2dt30700f⟩. ⟨hal-01230385⟩