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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
22
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pubmed:dateCreated |
2006-10-9
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pubmed:abstractText |
The 17beta-hydroxysteroid dehydrogenases (17beta-HSDs) modulate the biological potency of estrogens and androgens by interconversion of inactive 17-keto-steroids and their active 17beta-hydroxy- counterparts. We have shown previously that flavonoids are potentially useful lead compounds for developing inhibitors of 17beta-HSDs. In this paper, we describe the synthesis and biochemical evaluation of structurally analogous inhibitors, the trans-cinnamic acid esters and related compounds. Additionally, quantitative structure-activity relationship (QSAR) and modelling studies were performed to rationalize the results and to suggest further optimization. The results stress the importance of a hydrogen bond with Asn154 and hydrophobic interactions with the aromatic side chain of Tyr212 for optimal molecular recognition.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Nov
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pubmed:issn |
0968-0896
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
15
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pubmed:volume |
14
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
7404-18
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pubmed:dateRevised |
2010-11-18
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pubmed:meshHeading |
pubmed-meshheading:16891119-17-Hydroxysteroid Dehydrogenases,
pubmed-meshheading:16891119-Binding Sites,
pubmed-meshheading:16891119-Cinnamates,
pubmed-meshheading:16891119-Esters,
pubmed-meshheading:16891119-Flavonoids,
pubmed-meshheading:16891119-Fungi,
pubmed-meshheading:16891119-Humans,
pubmed-meshheading:16891119-Hydrophobic and Hydrophilic Interactions,
pubmed-meshheading:16891119-Models, Molecular,
pubmed-meshheading:16891119-Molecular Structure,
pubmed-meshheading:16891119-Oxidation-Reduction,
pubmed-meshheading:16891119-Protein Binding,
pubmed-meshheading:16891119-Quantitative Structure-Activity Relationship
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pubmed:year |
2006
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pubmed:articleTitle |
Flavonoids and cinnamic acid esters as inhibitors of fungal 17beta-hydroxysteroid dehydrogenase: a synthesis, QSAR and modelling study.
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pubmed:affiliation |
Faculty of Pharmacy, University of Ljubljana, Askerceva 7, 1000 Ljubljana, Slovenia.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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