Role of aromatic substituents on the antiproliferative effects of diphenyl ferrocenyl butene compounds

We have been exploring the cytotoxic effects of conjugated phenylferrocene systems on breast cancer cells. Complexes with p-OH, p-NH(2), and p-NHC(O)CH(3) substitution show particularly high activity, with IC(50) values in the low or sub micromolar range for both the hormone-dependent MCF-7 and horm...

Full description

Saved in:
Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2009-01, Vol.22 (22), p.4318-4326
Main Authors: Zekri, Ouardia, Hillard, Elizabeth A, Top, Siden, Vessières, Anne, Pigeon, Pascal, Plamont, Marie-Aude, Huché, Michel, Boutamine, Sultana, McGlinchey, Michael J, Müller-Bunz, Helge, Jaouen, Gérard
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents, Hormonal - chemical synthesis
Antineoplastic Agents, Hormonal - chemistry
Antineoplastic Agents, Hormonal - pharmacology
Antineoplastic Agents, Hormonal - therapeutic use
Breast Neoplasms - drug therapy
Butanes - chemical synthesis
Butanes - chemistry
Butanes - pharmacology
Butanes - therapeutic use
Cancer
Cell Line, Tumor
Cell Survival - drug effects
Chemical Sciences
Crystallography, X-Ray
Electrochemistry
Estrogen Receptor alpha - metabolism
Estrogen Receptor beta - metabolism
Female
Ferrous Compounds - chemical synthesis
Ferrous Compounds - chemistry
Ferrous Compounds - pharmacology
Ferrous Compounds - therapeutic use
Humans
Life Sciences
Models, Molecular
Molecular Structure
Protein Binding
Quantitative Methods
Sheep
Structure-Activity Relationship
Uterus - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We have been exploring the cytotoxic effects of conjugated phenylferrocene systems on breast cancer cells. Complexes with p-OH, p-NH(2), and p-NHC(O)CH(3) substitution show particularly high activity, with IC(50) values in the low or sub micromolar range for both the hormone-dependent MCF-7 and hormone-independent MDA-MB-231 breast cancer cell lines. We now present the synthesis, X-ray crystal structures and biochemical studies of analogous halogen or pseudo-halogen para-substituted compounds with R = Cl, (Z)-7a; Br, (Z)-7b; CF(3), (E)-7c; and CN, (E)-7d and (Z)-7d. Lacking hydrogen bonding groups, the compounds have low, but non-zero, relative binding affinity values for the oestrogen receptor alpha (RBA
ISSN:1477-9226
1477-9234
DOI:10.1039/b819812h