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Molecules 2014, 19(6), 7850-7868; doi:10.3390/molecules19067850

Inhibition of Cancer Derived Cell Lines Proliferation by Synthesized Hydroxylated Stilbenes and New Ferrocenyl-Stilbene Analogs. Comparison with Resveratrol

1
Université de Bourgogne, 21000 Dijon, France
2
Institut de Chimie Moléculaire de l'Université de Bourgogne, ICMUB UMR CNRS 6302, 9, avenue Alain Savary, 21000 Dijon, France
3
Laboratoire de Biochimie (Bio-PeroxIL) INSERM IFR 100, 6, boulevard Gabriel, Dijon, France
4
INSERM UMR 866, 7, boulevard Jeanne d'Arc, 21000 Dijon, France
*
Authors to whom correspondence should be addressed.
Received: 29 April 2014 / Revised: 27 May 2014 / Accepted: 28 May 2014 / Published: 11 June 2014
(This article belongs to the Special Issue Phytoalexins: Current Progress and Future Prospects)
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Abstract

Further advances in understanding the mechanism of action of resveratrol and its application require new analogs to identify the structural determinants for the cell proliferation inhibition potency. Therefore, we synthesized new trans-resveratrol derivatives by using the Wittig and Heck methods, thus modifying the hydroxylation and methoxylation patterns of the parent molecule. Moreover, we also synthesized new ferrocenylstilbene analogs by using an original protective group in the Wittig procedure. By performing cell proliferation assays we observed that the resveratrol derivatives show inhibition on the human colorectal tumor SW480 cell line. On the other hand, cell viability/cytotoxicity assays showed a weaker effects on the human hepatoblastoma HepG2 cell line. Importantly, the lack of effect on non-tumor cells (IEC18 intestinal epithelium cells) demonstrates the selectivity of these molecules for cancer cells. Here, we show that the numbers and positions of hydroxy and methoxy groups are crucial for the inhibition efficacy. In addition, the presence of at least one phenolic group is essential for the antitumoral activity. Moreover, in the series of ferrocenylstilbene analogs, the presence of a hidden phenolic function allows for a better solubilization in the cellular environment and significantly increases the antitumoral activity. View Full-Text
Keywords: resveratrol; methoxystilbenes; ferrocenylstilbene analogs; colon cancer; hepatoblastoma resveratrol; methoxystilbenes; ferrocenylstilbene analogs; colon cancer; hepatoblastoma
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Chalal, M.; Delmas, D.; Meunier, P.; Latruffe, N.; Vervandier-Fasseur, D. Inhibition of Cancer Derived Cell Lines Proliferation by Synthesized Hydroxylated Stilbenes and New Ferrocenyl-Stilbene Analogs. Comparison with Resveratrol. Molecules 2014, 19, 7850-7868.

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