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: | , , , , , , , , , |
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| 其他作者: | |
| 格式: | Article |
| 語言: | English |
| 出版: |
2013
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| 在線閱讀: | https://hdl.handle.net/10356/96342 http://hdl.handle.net/10220/10868 |
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| 總結: | 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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