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Title: Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells
Authors: Hillard, Elizabeth A.
Tan, Kelvin Yong Leng
Pigeon, Pascal
Top, Siden
Labbé, Eric
Buriez, Olivier
Vessières, Anne
Amatore, Christian
Leong, Weng Kee
Jaouen, Gérard
Issue Date: 2012
Source: Tan, K. Y. L., Pigeon, P., Top, S., Labbé, E., Buriez, O., Hillard, E. A., et al. (2012). Ferrocenyl catechols: synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells. Dalton Transactions, 41(25), 7537-7549.
Series/Report no.: Dalton transactions
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 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 Ag2O confirms this interpretation and demonstrates the probable involvement of such oxidative metabolites in the in vitro activity of these species.
ISSN: 1477-9226
DOI: 10.1039/c2dt30700f
Rights: © 2012 The Royal Society of Chemistry.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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