Source:http://linkedlifedata.com/resource/pubmed/id/17266199
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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
3
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pubmed:dateCreated |
2007-2-1
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pubmed:abstractText |
In this study we have introduced the 11beta-methoxy group, a substituent known to increase in vivo potency in other steroidal estrogens, into the (17alpha,20E)-21-(trifluoromethylphenyl)-19-norpregna-1,3,5(10),20-tetraene-3,17beta-diols: (trifluoromethylphenyl)vinyl estradiols. Receptor binding, using the ERalpha-HBD, indicated that the 11beta-methoxy group had little effect on the relative binding affinity of the target compounds compared to the corresponding 11beta-unsubstituted analogs, however, the 11beta-methoxy derivatives were significantly more potent in stimulating uterotrophic growth in immature female rats. Molecular modeling studies suggest that while the 11beta-methoxy group does not contribute significantly to the overall binding energy of the ligand-ERalpha-HBD complex, it stabilizes residues associated with the coregulator protein binding site. Such effects would influence the dynamics of subsequent events, such as transcription and biological responses.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Feb
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
8
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pubmed:volume |
50
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
472-9
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pubmed:dateRevised |
2007-12-3
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pubmed:meshHeading |
pubmed-meshheading:17266199-Animals,
pubmed-meshheading:17266199-Binding, Competitive,
pubmed-meshheading:17266199-Binding Sites,
pubmed-meshheading:17266199-Estrogen Receptor alpha,
pubmed-meshheading:17266199-Estrogens,
pubmed-meshheading:17266199-Female,
pubmed-meshheading:17266199-Ligands,
pubmed-meshheading:17266199-Models, Molecular,
pubmed-meshheading:17266199-Norpregnatrienes,
pubmed-meshheading:17266199-Protein Structure, Tertiary,
pubmed-meshheading:17266199-Radioligand Assay,
pubmed-meshheading:17266199-Rats,
pubmed-meshheading:17266199-Stereoisomerism,
pubmed-meshheading:17266199-Structure-Activity Relationship,
pubmed-meshheading:17266199-Uterus
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pubmed:year |
2007
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pubmed:articleTitle |
Synthesis and evaluation of isomeric (17alpha,20E)-11beta-methoxy-21-(trifluoromethylphenyl)-19-norpregna-1,3,5(10),20-tetraene-3,17beta-diols as ERalpha-hormone binding domain ligands: effect of the methoxy group on receptor binding and uterotrophic growth.
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pubmed:affiliation |
Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, Massachusetts 02115, USA. r.hanson@neu.edu
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, Non-P.H.S.,
Research Support, Non-U.S. Gov't,
Research Support, N.I.H., Extramural
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