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Comparative investigation of the in vitro inhibitory potencies of 13-epimeric estrones and D-secoestrones towards 17β-hydroxysteroid dehydrogenase type 1
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The inhibitory effects of 13-epimeric estrones, D-secooxime and D-secoalcohol estrone compounds on human placental 17β-hydroxysteroid dehydrogenase type 1 isozyme (17β-HSD1) were investigated. The transformation of estrone to 17β-estradiol was studied by an in vitro radiosubstrate incubation method. 13α-Estrone inhibited the enzyme activity effectively with an IC50 value of 1.2 μM, which indicates that enzyme affinity is similar to that of the natural estrone substrate. The 13β derivatives and the compounds bearing a 3-hydroxy group generally exerted stronger inhibition than the 13α and 3-ether counterparts. The 3-hydroxy-13β-D-secoalcohol and the 3-hydroxy-13α-D-secooxime displayed an outstanding cofactor dependence, i.e. more efficient inhibition in the presence of NADH than NADPH. The 3-hydroxy-13β-D-secooxime has an IC50 value of 0.070 μM and is one of the most effective 17β-HSD1 inhibitors reported to date in the literature. © 2016 Informa UK Limited, trading as Taylor & Francis Group.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10054994"> <a href="/gui2/?type=authors&mode=browse&sel=10054994" target="_blank">Herman, BE</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10037997"> <a href="/gui2/?type=authors&mode=browse&sel=10037997" target="_blank">Szabó, J</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10052580"> <a href="/gui2/?type=authors&mode=browse&sel=10052580" target="_blank">Bacsa, I</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10000356"> <a href="/gui2/?type=authors&mode=browse&sel=10000356" target="_blank">Wölfling, J</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008057"> <a href="/gui2/?type=authors&mode=browse&sel=10008057" target="_blank">Schneider, G</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10044915"> <a href="/gui2/?type=authors&mode=browse&sel=10044915" target="_blank">Bálint, M</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001657"> <a href="/gui2/?type=authors&mode=browse&sel=10001657" target="_blank">Hetényi, C</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10012035"> <a href="/gui2/?type=authors&mode=browse&sel=10012035" target="_blank">Mernyák, E ✉</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001367"> <a href="/gui2/?type=authors&mode=browse&sel=10001367" target="_blank">Szécsi, M ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;3097533" mtid="3097533" target="_blank">Comparative investigation of the in vitro inhibitory potencies of 13-epimeric estrones and D-secoestrones towards 17β-hydroxysteroid dehydrogenase type 1</a></div> <div class="pub-info"> <span class="journal-title">JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY</span> <span class="journal-volume">31</span> : <span class="journal-issue">Suppl. 3</span> <span class="page"> pp. 61-69. , 9 p. </span> <span class="year">(2016)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.1080/14756366.2016.1204610" target="_blank" href="https://doi.org/10.1080/14756366.2016.1204610"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000390581400007" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000390581400007"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="84978511849" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-84978511849"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="27424610" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=27424610&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_GREEN" title=" Green "> <a style="color:blue" title="10673" target="_blank" href="http://publicatio.bibl.u-szeged.hu/10673"> SZTE Publicatio </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="deleted-record">Locked</span> <span class="short-pub-mtid"> Publication:3097533 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Validated </span></span> <span class="pub-core">Core Citing </span> <span class="pub-type">Journal Article (Article ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Scientific</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="" class="citingPub-count">Citing papers: 13</span> | Independent citation: 4 | Self citation: 9 | Unknown citation: 0 | Number of citations in WoS: 12 | Number of citations in Scopus: 12 | WoS/Scopus assigned: 12 | Number of citations with DOI: 13 </div> </div> </div> </div><div class="JournalArticle Publication long-list">
<div class="authors">
<img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png">
<img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png">
<div class="autype autype0"> <span class="author-name" mtid="10054994"><a
href="/gui2/?type=authors&mode=browse&sel=10054994" target="_blank">Herman BE
(<span class="authorship-author-name">Herman Bianka Edina</span>
<span class="authorAux-mtmt"> Elméleti orvostudományok</span>)
</a>
</span>
<span class="author-affil"><span title="University of Szeged">SZTE</span>/<span title="Faculty of Medicine">ÁOK</span>/First Department of Internal Medicine</span>
;
<span class="author-name" mtid="10037997"><a
href="/gui2/?type=authors&mode=browse&sel=10037997" target="_blank">Szabó J
(<span class="authorship-author-name">Szabó Johanna</span>
<span class="authorAux-mtmt"> szerves kémia</span>)
</a>
</span>
<span class="author-affil"><span title="University of Szeged">SZTE</span>/<span title="Faculty of Science and Informatics">TTIK</span>/<span title="Kémiai Intézet">KI</span>/Department of Organic Chemistry</span>
;
<span class="author-name" mtid="10052580"><a
href="/gui2/?type=authors&mode=browse&sel=10052580" target="_blank">Bacsa I
(<span class="authorship-author-name">Bacsa Ildikó</span>
<span class="authorAux-mtmt"> Szerves kémia</span>)
</a>
</span>
<span class="author-affil"><span title="University of Szeged">SZTE</span>/<span title="Faculty of Science and Informatics">TTIK</span>/<span title="Kémiai Intézet">KI</span>/Department of Organic Chemistry</span>
;
<span class="author-name" mtid="10000356"><a
href="/gui2/?type=authors&mode=browse&sel=10000356" target="_blank">Wölfling J
(<span class="authorship-author-name">Wölfling János</span>
<span class="authorAux-mtmt"> Szerves kémia</span>)
</a>
</span>
<span class="author-affil"><span title="University of Szeged">SZTE</span>/<span title="Faculty of Science and Informatics">TTIK</span>/<span title="Kémiai Intézet">KI</span>/Department of Organic Chemistry</span>
;
<span class="author-name" mtid="10008057"><a
href="/gui2/?type=authors&mode=browse&sel=10008057" target="_blank">Schneider G
(<span class="authorship-author-name">Schneider Gyula</span>
<span class="authorAux-mtmt"> Szerves kémia</span>)
</a>
</span>
<span class="author-affil"><span title="University of Szeged">SZTE</span>/<span title="Faculty of Science and Informatics">TTIK</span>/<span title="Kémiai Intézet">KI</span>/Department of Organic Chemistry</span>
;
<span class="author-name" mtid="10044915"><a
href="/gui2/?type=authors&mode=browse&sel=10044915" target="_blank">Bálint M
(<span class="authorship-author-name">Bálint Mónika Enikő</span>
<span class="authorAux-mtmt"> Biokémia, Molekuláris modellezés</span>)
</a>
</span>
<span class="author-affil"><span title="Eötvös Loránd University">ELTE</span>/<span title="Faculty of Science">ELU FoS</span>/<span title="Institute of Biology">Bio_I</span>/Department of Biochemistry</span>
;
<span class="author-name" mtid="10001657"><a
href="/gui2/?type=authors&mode=browse&sel=10001657" target="_blank">Hetényi C
(<span class="authorship-author-name">Hetényi Csaba</span>
<span class="authorAux-mtmt"> Farmakoinformatika, molekulaszerkezet</span>)
</a>
</span>
<span class="author-affil"><span title="Eötvös Loránd University">ELTE</span>/<span title="Faculty of Science">ELU FoS</span>/<span title="Institute of Biology">Bio_I</span>/MTA-ELTE Molecular Biophysics Research Group</span>
;
<span class="author-name" mtid="10012035"><a
href="/gui2/?type=authors&mode=browse&sel=10012035" target="_blank">Mernyák E ✉
(<span class="authorship-author-name">Mernyák Erzsébet</span>
<span class="authorAux-mtmt"> Szerves kémia</span>)
</a>
</span>
<span class="author-affil"><span title="University of Szeged">SZTE</span>/<span title="Faculty of Science and Informatics">TTIK</span>/<span title="Kémiai Intézet">KI</span>/Department of Organic Chemistry</span>
;
<span class="author-name" mtid="10001367"><a
href="/gui2/?type=authors&mode=browse&sel=10001367" target="_blank">Szécsi M ✉
(<span class="authorship-author-name">Szécsi Mihály</span>
<span class="authorAux-mtmt"> Szteroidok analitikai kémiája és biokémiája</span>)
</a>
</span>
<span class="author-affil"><span title="University of Szeged">SZTE</span>/<span title="Faculty of Medicine">ÁOK</span>/First Department of Internal Medicine</span>
</div>
</div>
<div class="title"><a href="/gui2/?mode=browse¶ms=publication;3097533" target="_blank">Comparative investigation of the in vitro inhibitory potencies of 13-epimeric estrones and D-secoestrones towards 17β-hydroxysteroid dehydrogenase type 1</a></div> <div> <span class="journal-title">JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY</span>
<span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/1475-6366">1475-6366</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1475-6374">1475-6374</a>)</span>:
<span class="journal-volume">31</span> <span class="journal-issue">Suppl. 3</span>
<span class="page">
pp 61-69
</span> <span class="year">(2016)</span>
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<div class="pub-footer">
<span class="language" xmlns="http://www.w3.org/1999/html">Language:
English
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<span class="id identifier oa_GOLD" title=" Gold
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<a style="color:blue" title="10.1080/14756366.2016.1204610" target="_blank" href="https://doi.org/10.1080/14756366.2016.1204610">
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<div class="publication-citation" style="margin-left: 0.5cm;">
<span title="" class="citingPub-count">Citing papers: 13</span>
| Independent citation: 4
| Self citation: 9
| Unknown citation: 0
| Number of citations in WoS: 12
| Number of citations in Scopus: 12
| WoS/Scopus assigned: 12
| Number of citations with DOI: 13
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<a target="_blank" href="/api/publication?cond=citations.related;eq;3097533&sort=publishedYear,desc&sort=title">
Number of cited publications: 4
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<div class="mtid"><span class="long-pub-mtid">Publication: 3097533</span>
| <span class="status-data status-VALIDATED"> Validated
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<span class="oldId">Old id: 3097533</span> |
Core Citing
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<div class="lastModified">Last Modified: 2020.05.21. 16:06 Réka Márton (SZTE admin5-INAKTÍV)
</div>
<div class="lockedBy">Temporarily locked 2023.01.17. 09:55 Katalin Mikola (MTMT 3, admin)
</div>
<pre class="comment" style="margin-top: 0; margin-bottom: 0;"><u>Comments</u>: MTA-ELTE Molecular Biophysics Research Group, Hungarian Academy of Sciences, Budapest, Hungary</pre>
</div></div>