Document Detail

Preparation and evaluation of carborane analogues of tamoxifen.
MedLine Citation:
PMID:  21028825     Owner:  NLM     Status:  MEDLINE    
A stereoselective synthesis of closo carborane analogues of tamoxifen was developed where the products represent a new approach to developing metabolically robust SERMs. The A-ring found in the backbone of tamoxifen was replaced with an ortho carborane cluster; the product was determined to be the desired Z isomer, which showed superior chemical stability to tamoxifen both in solution and in the solid state. By use of microwave heating, it was possible to convert some of the Z carborane tamoxifen analogue to the corresponding E isomer. Cell growth assays using both isomers and a carborane that is known to target the ER were conducted using estrogen receptor (ER) positive and ER negative human breast cancer cells with and without the presence of estradiol (E2). The Z carborane isomer was able to inhibit cell proliferation better than tamoxifen in an E2 free environment, while the E isomer inhibited cell growth better than tamoxifen when E2 was present.
Michael L Beer; Jennifer Lemon; John F Valliant
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-10-28
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  53     ISSN:  1520-4804     ISO Abbreviation:  J. Med. Chem.     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-11-22     Completed Date:  2010-12-30     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8012-20     Citation Subset:  IM    
Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario L8S 4M1, Canada.
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MeSH Terms
Boron Compounds / chemical synthesis*,  pharmacology
Breast Neoplasms
Cell Line, Tumor
Cell Proliferation / drug effects
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Neoplasms, Hormone-Dependent
Receptors, Estrogen / metabolism
Selective Estrogen Receptor Modulators / chemical synthesis*,  pharmacology
Structure-Activity Relationship
Tamoxifen / analogs & derivatives*,  chemical synthesis*,  pharmacology
Grant Support
//Canadian Institutes of Health Research
Reg. No./Substance:
0/Boron Compounds; 0/Receptors, Estrogen; 0/Selective Estrogen Receptor Modulators; 10540-29-1/Tamoxifen

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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