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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Main 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
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
Online Access:https://hdl.handle.net/10356/96342
http://hdl.handle.net/10220/10868
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Institution: Nanyang Technological University
Language: English
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spelling 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.
institution Nanyang Technological University
building NTU Library
country Singapore
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language English
description 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.
author2 School of Physical and Mathematical Sciences
author_facet 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
format Article
author Hillard, Elizabeth A.
Tan, Kelvin Yong Leng
Pigeon, Pascal
Top, Siden
Labbé, Eric
Buriez, Olivier
Vessières, Anne
Amatore, Christian
Leong, Weng Kee
Jaouen, Gérard
spellingShingle 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
publishDate 2013
url https://hdl.handle.net/10356/96342
http://hdl.handle.net/10220/10868
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