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Inhibition of Cancer Derived Cell Lines Proliferation by Synthesized Hydroxylated Stilbenes and New Ferrocenyl-Stilbene Analogs. Comparison with Resveratrol
- Source :
- Molecules, Molecules; Volume 19; Issue 6; Pages: 7850-7868, Molecules, Vol 19, Iss 6, Pp 7850-7868 (2014)
- Publication Year :
- 2014
- Publisher :
- MDPI, 2014.
-
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.
- Subjects :
- Stereochemistry
Cell Survival
Pharmaceutical Science
Resveratrol
resveratrol
Article
Analytical Chemistry
lcsh:QD241-441
chemistry.chemical_compound
lcsh:Organic chemistry
Intestinal mucosa
Cell Line, Tumor
Drug Discovery
Stilbenes
methoxystilbenes
ferrocenylstilbene analogs
colon cancer
hepatoblastoma
Humans
Viability assay
Ferrous Compounds
Physical and Theoretical Chemistry
Intestinal Mucosa
Cytotoxicity
Cell Proliferation
Cell growth
Organic Chemistry
Cell Cycle
Epithelial Cells
Hep G2 Cells
Cell cycle
Biochemistry
chemistry
Chemistry (miscellaneous)
Cell culture
Cancer cell
Molecular Medicine
Colorectal Neoplasms
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 19
- Issue :
- 6
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....b675bb008a3fadfaf09567cc9ea17770