Document Detail

Structural determinants of resveratrol for cell proliferation inhibition potency: experimental and docking studies of new analogs.
MedLine Citation:
PMID:  20395019     Owner:  NLM     Status:  MEDLINE    
Resveratrol is the subject of intense research because of the abundance of this compound in the human diet and as one of the most valuable natural chemopreventive agents. Further advances require new resveratrol analogs be used to identify the structural determinants of resveratrol for the inhibition potency of cell proliferation by comparing experimental and docking studies. Therefore, we synthesized new trans/(E)- and cis/(Z)-resveratrol - analogs not reported to date - by modifying the hydroxylation pattern of resveratrol and a double bond geometry. We included them in a larger panel of 14 molecules, including (Z)-3,5,4'-trimethoxystilbene, the most powerful molecule that is used as reference. Using a docking model complementary to experimental studies on the proliferation inhibition of the human colorectal tumor SW480 cell line, we show that methylation is the determinant substitution in inhibition efficacy, but only in molecules bearing a Z configuration. Most of the synthetic methylated derivatives (E or Z) stop mitosis at the M phase and lead to polyploid cells, while (E)-resveratrol inhibits cells at the S phase. Docking studies show that almost all of the docked structures of (Z)-polymethoxy isomers, but not most of the (E)-polymethoxy isomers substantially overlap the docked structure of combretastatin A-4, taken as reference ligand at the colchicine-tubulin binding site.
Frédéric Mazué; Didier Colin; Jessica Gobbo; Maria Wegner; Antonio Rescifina; Carmela Spatafora; Dominique Fasseur; Dominique Delmas; Philippe Meunier; Corrado Tringali; Norbert Latruffe
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-03-25
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  45     ISSN:  1768-3254     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2010 Jul 
Date Detail:
Created Date:  2010-05-17     Completed Date:  2010-08-17     Revised Date:  2013-06-03    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  2972-80     Citation Subset:  IM    
Copyright Information:
Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.
INSERM U 866, University of Burgundy, Laboratory of Biochemistry of Metabolism and Nutrition, 6, Bd Gabriel, F-21000 Dijon, France.
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MeSH Terms
Binding Sites
Cell Cycle / drug effects
Cell Line, Tumor
Cell Proliferation / drug effects
Colchicine / metabolism
DNA / metabolism
Hydroxides / chemistry
Models, Molecular
Stilbenes / chemical synthesis,  chemistry*,  metabolism,  pharmacology*
Tubulin / chemistry,  metabolism
Reg. No./Substance:
0/Hydroxides; 0/Stilbenes; 0/Tubulin; 64-86-8/Colchicine; 9007-49-2/DNA; 9159UV381P/hydroxide ion; Q369O8926L/resveratrol

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