Ferrocenyl catechols: synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells - Archive ouverte HAL Access content directly
Journal Articles Dalton Transactions Year : 2012

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

Yong Leng Kelvin Tan
  • Function : Author
Eric Labbé
Olivier Buriez
Elisabeth A. Hillard
Anne Vessières
Christian Amatore
  • Function : Author
  • PersonId : 840878
Weng Kee Leong
  • Function : Author
Gérard Jaouen

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 (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.
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Dates and versions

hal-01230385 , version 1 (18-11-2015)

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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⟩
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