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Structure-activity relationships of resveratrol and derivatives in breast cancer cells.

Abstract
Resveratrol (RSV) is classified as a phytoestrogen due to its ability to interact with estrogen receptors (ERs). We assessed structure-activity relationships of RSV and the analogs 4,4'-dihydroxystilbene (4,4'-DHS), 3,5-dihydroxystilbene (3,5-DHS), 3,4'-dihydroxystilbene (3,4'-DHS), 4-hydroxystilbene (4-HS) using as model systems the ERalpha-positive and negative MCF7 and SkBr3 breast cancer cells, respectively. In binding assays and transfection experiments RSV and the analogs showed the following order of agonism for ERalpha: 3,4'-DHS > 4,4'-DHS > 4-HS > RSV, while 3,5-DHS did not elicit any ligand properties. Computational docking analysis and real-time PCR revealed for each analog a distinct ERalpha binding orientation and estrogen target gene expression profile. Interestingly, the aforementioned order of ligand activity was confirmed in proliferation assays which also showed the lack of growth stimulation by 3,5-DHS. Our data suggest that subtle changes in the structure of the RSV derivatives examined may be responsible for the different ERalpha-mediated biological responses observed in estrogen-sensitive cancer cells.
AuthorsRosamaria Lappano, Camillo Rosano, Antonio Madeo, Lidia Albanito, Pierluigi Plastina, Bartolo Gabriele, Luca Forti, Lucia Anna Stivala, Domenico Iacopetta, Vincenza Dolce, Sebastiano Andò, Vincenzo Pezzi, Marcello Maggiolini
JournalMolecular nutrition & food research (Mol Nutr Food Res) Vol. 53 Issue 7 Pg. 845-58 (Jul 2009) ISSN: 1613-4133 [Electronic] Germany
PMID19496085 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • ESR1 protein, human
  • Estrogen Receptor alpha
  • Stilbenes
  • Resveratrol
Topics
  • Binding Sites
  • Breast Neoplasms (pathology)
  • Cell Line, Tumor
  • Estrogen Receptor alpha (chemistry, physiology)
  • Gene Expression Regulation, Neoplastic (drug effects)
  • Humans
  • Models, Molecular
  • Resveratrol
  • Stilbenes (pharmacology)
  • Structure-Activity Relationship

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