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 (IC50 values ranging fr...
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sg-ntu-dr.10356-963422020-03-07T12:34:41Z Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells Hillard, Elizabeth A. Tan, Kelvin Yong Leng Pigeon, Pascal Top, Siden Labbé, Eric Buriez, Olivier Vessières, Anne Amatore, Christian Leong, Weng Kee Jaouen, Gérard School of Physical and Mathematical Sciences 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. 2013-07-01T07:13:45Z 2019-12-06T19:29:17Z 2013-07-01T07:13:45Z 2019-12-06T19:29:17Z 2012 2012 Journal Article 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. 1477-9226 https://hdl.handle.net/10356/96342 http://hdl.handle.net/10220/10868 10.1039/c2dt30700f en Dalton transactions © 2012 The Royal Society of Chemistry. |
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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. |
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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Hillard, Elizabeth A. Tan, Kelvin Yong Leng Pigeon, Pascal Top, Siden Labbé, Eric Buriez, Olivier Vessières, Anne Amatore, Christian Leong, Weng Kee Jaouen, Gérard |
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Article |
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Hillard, Elizabeth A. Tan, Kelvin Yong Leng Pigeon, Pascal Top, Siden Labbé, Eric Buriez, Olivier Vessières, Anne Amatore, Christian Leong, Weng Kee Jaouen, Gérard |
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Hillard, Elizabeth A. Tan, Kelvin Yong Leng Pigeon, Pascal Top, Siden Labbé, Eric Buriez, Olivier Vessières, Anne Amatore, Christian Leong, Weng Kee Jaouen, Gérard Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells |
author_sort |
Hillard, Elizabeth A. |
title |
Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells |
title_short |
Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells |
title_full |
Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells |
title_fullStr |
Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells |
title_full_unstemmed |
Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells |
title_sort |
ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on mda-mb-231 breast cancer cells |
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2013 |
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https://hdl.handle.net/10356/96342 http://hdl.handle.net/10220/10868 |
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1681042375923728384 |