Document Detail


First synthesis of 7alpha- and 7beta-amino-DHEA, dehydroepiandrosterone (DHEA) analogues and preliminary evaluation of their cytotoxicity on Leydig cells and TM4 Sertoli cells.
MedLine Citation:
PMID:  17350845     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Efficient syntheses of new DHEA analogues, and their apoptotic and necrotic effects on Leydig cells and TM4 Sertoli cells are described. The key step in the synthetic strategy of 7-amino-DHEA derivatives involves a bromination on C-7 position to give an epimeric mixture of bromides which were substituted by azides and reduced to give 7alpha- and 7beta-amino-3beta-hydroxyandrost-5-en-17-ones. No cytotoxic effect induced by apoptosis mechanism was observed on Leydig and TM4 Sertoli cells by treatment with these amino-DHEA analogues. A necrotic effect was induced only in TM4 Sertoli cells. The best activity was obtained with 7alpha,beta-amino-androst-5-en-3beta-ol and 7beta-amino-3beta-hydroxy-androst-5-en-17-one.
Authors:
Marc-Antoine Bazin; Carine Travert; Serge Carreau; Sylvain Rault; Laïla El Kihel
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Publication Detail:
Type:  Journal Article     Date:  2007-02-22
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  15     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2007 May 
Date Detail:
Created Date:  2007-04-02     Completed Date:  2007-06-18     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  3152-60     Citation Subset:  IM    
Affiliation:
Centre d'Etudes et de Recherche sur le Médicament de Normandie, UFR des Sciences Pharmaceutiques, Caen cedex, France.
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MeSH Terms
Descriptor/Qualifier:
Animals
Cell Survival / drug effects
Cells, Cultured
Dehydroepiandrosterone / analogs & derivatives*,  chemical synthesis*,  chemistry,  toxicity*
Dose-Response Relationship, Drug
Leydig Cells / drug effects*
Male
Molecular Conformation
Rats
Rats, Sprague-Dawley
Sertoli Cells / drug effects*
Stereoisomerism
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/7alpha-amino-dehydroepiandrosterone; 53-43-0/Dehydroepiandrosterone

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