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Foldameric α/β-Peptide Analogs of the β-Sheet-Forming Antiangiogenic Anginex: Structure and Bioactivity
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The principles of beta-sheet folding and design for alpha-peptidic sequences are well established, while those for sheet mimetics containing homologated amino acid building blocks are still under investigation. To reveal the structure-function relations of beta-amino-acid-containing foldamers, we followed a top-down approach to study a series of alpha/beta-peptidic analogs of anginex, a beta-sheet-forming antiangiogenic peptide. Eight anginex analogs were developed by systematic alpha --> beta(3) substitutions and analyzed by using NMR and CD spectroscopy. The foldamers retained the beta-sheet tendency, though with a decreased folding propensity. beta-Sheet formation could be induced by a micellar environment, similarly to that of the parent peptide. The destructuring effect was higher when the alpha --> beta(3) exchange was located in the beta-sheet core. Analysis of the beta-sheet stability versus substitution pattern and the local conformational bias of the bulky beta(3)V and beta(3)I residues revealed that a mismatch between the H-bonding preferences of the alpha- and beta-residues played a minor role in the structure-breaking effect. Temperature-dependent CD and NMR measurements showed that the hydrophobic stabilization was scaled-down for the alpha/beta-peptides. Analysis of the biological activity of the foldamer peptides showed that four anginex derivatives dose-dependently inhibited the proliferation of a mouse endothelial cell line. The alpha --> beta(3) substitution strategy applied in this work can be a useful approach to the construction of bioactive beta-sheet mimetics with a reduced aggregation tendency and improved pharmacokinetic properties.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10043382"> <a href="/gui2/?type=authors&mode=browse&sel=10043382" target="_blank">Hegedus, Z</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10027663"> <a href="/gui2/?type=authors&mode=browse&sel=10027663" target="_blank">Weber, E<sup>*</sup></a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10030596"> <a href="/gui2/?type=authors&mode=browse&sel=10030596" target="_blank">Kriston-Pal, E</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10051196"> <a href="/gui2/?type=authors&mode=browse&sel=10051196" target="_blank">Makra, Ildikó</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10018848"> <a href="/gui2/?type=authors&mode=browse&sel=10018848" target="_blank">Czibula, A</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10008944"> <a href="/gui2/?type=authors&mode=browse&sel=10008944" target="_blank">Monostori, E</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001168"> <a href="/gui2/?type=authors&mode=browse&sel=10001168" target="_blank">Martinek, TA ✉</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;2459240" mtid="2459240" target="_blank">Foldameric α/β-Peptide Analogs of the β-Sheet-Forming Antiangiogenic Anginex: Structure and Bioactivity</a></div> <div class="pub-info"> <span class="journal-title">JOURNAL OF THE AMERICAN CHEMICAL SOCIETY</span> <span class="journal-volume">135</span> : <span class="journal-issue">44</span> <span class="page"> pp. 16578-16584. , 7 p. </span> <span class="year">(2013)</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="10.1021/ja408054f" target="_blank" href="https://doi.org/10.1021/ja408054f"> DOI </a> </span> <span class="id identifier oa_CLOSED" title=" Zárt "> <a style="color:black" title="60950" target="_blank" href="http://real.mtak.hu/60950"> REAL </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000326774300057" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000326774300057"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="84887699703" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-84887699703"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="24088182" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=24088182&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="http://pubs.acs.org/doi/ipdf/10.1021/ja408054f" target="_blank" href="http://pubs.acs.org/doi/ipdf/10.1021/ja408054f"> Teljes dokumentum </a> </span> <span class="id identifier oa_GREEN" title=" Green "> <a style="color:blue" title="4156" target="_blank" href="http://publicatio.bibl.u-szeged.hu/4156"> SZTE Publicatio </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:2459240 </span> <span class="status-holder"><span class="status-data status-APPROVED"> Nyilvános </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 34</span> | Független: 28 | Függő: 6 | Nem jelölt: 0 | WoS jelölt: 29 | Scopus jelölt: 33 | WoS/Scopus jelölt: 33 | DOI jelölt: 32 (Nem nyilvános: 1) </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="10043382"><a href="/gui2/?type=authors&mode=browse&sel=10043382" target="_blank">Hegedus Z (<span class="authorship-author-name">Hegedüs Zsófia</span> <span class="authorAux-mtmt"> gyógyszerkémia</span>) </a> </span> <span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/<span title="Gyógyszerkémiai Intézet">GYKI</span>/MTA-SZTE Lendület Peptidfoldamer Kutatócsoport</span> ; <span class="author-name" mtid="10027663"><a href="/gui2/?type=authors&mode=browse&sel=10027663" target="_blank">Weber E<sup>*</sup> (<span class="authorship-author-name">Wéber Edit</span> <span class="authorAux-mtmt"> gyógyszerkémia</span>) </a> </span> <span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/<span title="Gyógyszerkémiai Intézet">GYKI</span>/MTA-SZTE Lendület Peptidfoldamer Kutatócsoport</span> ; <span class="author-name" mtid="10030596"><a href="/gui2/?type=authors&mode=browse&sel=10030596" target="_blank">Kriston-Pal E (<span class="authorship-author-name">Kriston-Pál Éva</span> <span class="authorAux-mtmt"> tumorbiológia</span>) </a> </span> <span class="author-affil"><span title="MTA Szegedi Biológiai Kutatóközpont">MTA SZBK</span>/Genetikai Intézet</span> ; <span class="author-name" mtid="10051196"><a href="/gui2/?type=authors&mode=browse&sel=10051196" target="_blank">Makra Ildikó (<span class="authorship-author-name">Makra Ildikó</span> <span class="authorAux-mtmt"> biológia</span>) </a> </span> ; <span class="author-name" mtid="10018848"><a href="/gui2/?type=authors&mode=browse&sel=10018848" target="_blank">Czibula A (<span class="authorship-author-name">Czibula Ágnes</span> <span class="authorAux-mtmt"> Molekuláris genetika</span>) </a> </span> <span class="author-affil"><span title="MTA Szegedi Biológiai Kutatóközpont">MTA SZBK</span>/Genetikai Intézet</span> ; <span class="author-name" mtid="10008944"><a href="/gui2/?type=authors&mode=browse&sel=10008944" target="_blank">Monostori E (<span class="authorship-author-name">Monostori Éva</span> <span class="authorAux-mtmt"> Immunológia</span>) </a> </span> <span class="author-affil"><span title="MTA Szegedi Biológiai Kutatóközpont">MTA SZBK</span>/Genetikai Intézet</span> ; <span class="author-name" mtid="10001168"><a href="/gui2/?type=authors&mode=browse&sel=10001168" target="_blank">Martinek TA ✉ (<span class="authorship-author-name">Martinek Tamás</span> <span class="authorAux-mtmt"> Gyógyszerkémia</span>) </a> </span> <span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/<span title="Gyógyszerkémiai Intézet">GYKI</span>/MTA-SZTE Lendület Peptidfoldamer Kutatócsoport</span> </div> </div> <div class="title"><a href="/gui2/?mode=browse¶ms=publication;2459240" target="_blank">Foldameric α/β-Peptide Analogs of the β-Sheet-Forming Antiangiogenic Anginex: Structure and Bioactivity</a></div> <div> <span class="journal-title">JOURNAL OF THE AMERICAN CHEMICAL SOCIETY</span> <span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/0002-7863">0002-7863</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1520-5126">1520-5126</a>)</span>: <span class="journal-volume">135</span> <span class="journal-issue">44</span> <span class="page"> pp 16578-16584 </span> <span class="year">(2013)</span> </div> <div class="pub-footer"> <span class="language" xmlns="http://www.w3.org/1999/html">Nyelv: Angol | </span> <span class="identifiers"> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="10.1021/ja408054f" target="_blank" href="https://doi.org/10.1021/ja408054f"> DOI </a> </span> <span class="id identifier oa_CLOSED" title=" Zárt "> <a style="color:black" title="60950" target="_blank" href="http://real.mtak.hu/60950"> REAL </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000326774300057" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000326774300057"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="84887699703" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-84887699703"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="24088182" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=24088182&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:blue" title="http://pubs.acs.org/doi/ipdf/10.1021/ja408054f" target="_blank" href="http://pubs.acs.org/doi/ipdf/10.1021/ja408054f"> Teljes dokumentum </a> </span> <span class="id identifier oa_GREEN" title=" Green "> <a style="color:blue" title="4156" target="_blank" href="http://publicatio.bibl.u-szeged.hu/4156"> SZTE Publicatio </a> </span> </span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 34</span> | Független: 28 | Függő: 6 | Nem jelölt: 0 | WoS jelölt: 29 | Scopus jelölt: 33 | WoS/Scopus jelölt: 33 | DOI jelölt: 32 (Nem nyilvános: 1) </div> <div class="publication-citation"> <a target="_blank" href="/api/publication?cond=citations.related;eq;2459240&sort=publishedYear,desc&sort=title"> Idézett közlemények száma: 2 </a> </div> <div class="mtid"><span class="long-pub-mtid">Közlemény: 2459240</span> | <span class="status-data status-APPROVED"> Nyilvános </span> <span class="oldId">Régi azonosító: 2459240</span> | Forrás Idéző | <span class="type-subtype">Folyóiratcikk ( Szakcikk ) </span> | <span class="pub-category">Tudományos</span> | <span class="publication-sourceOfData">MEDLINE</span> </div> <div class="lastModified">Utolsó módosítás: 2024.02.27. 14:48 Pécsi Éva (MTMT Közp 3, admin) </div> </div></div>