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Laboratory of Chemical Biology, United States
Institute of Biochemistry, Biological Research Centre, 62. Temesvári krt., Szeged, H-6726, Hungary
Theoretical Medicine Doctoral School, Hungary
Faculty of Medicine, University of Szeged, 97. Tisza L. krt., Szeged, H-6722, Hungary
Department of Biomolecular Chemistry, Poland
Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, Lodz, 92-215, Poland
Faculty of Chemistry, Poland
University of Wroclaw, F. Joliot-Curie 14, Wroclaw, 50-383, Poland
Export Date: 25 May 2021
CODEN: MOLEF
Correspondence Address: Janecka, A.; Department of Biomolecular ChemistryPoland; email: anna.janecka@umed.lodz.pl
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Design, Synthesis and Functional Analysis of Cyclic Opioid Peptides with Dmt-Tic Pharmacophore
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The opioid receptors are members of the G-protein-coupled receptor (GPCR) family and are known to modulate a variety of biological functions, including pain perception. Despite considerable advances, the mechanisms by which opioid agonists and antagonists interact with their receptors and exert their effect are still not completely understood. In this report, six new hybrids of the Dmt-Tic pharmacophore and cyclic peptides, which were shown before to have a high affinity for the mu-opioid receptor (MOR) were synthesized and characterized pharmacologically in calcium mobilization functional assays. All obtained ligands turned out to be selective antagonists of the delta-opioid receptor (DOR) and did not activate or block the MOR. The three-dimensional structural determinants responsible for the DOR antagonist properties of these analogs were further investigated by docking studies. The results indicate that these compounds attach to the DOR in a slightly different orientation with respect to the Dmt-Tic pharmacophore than Dmt-Tic psi[CH2-NH]Phe-Phe-NH2 (DIPP-NH2[psi]), a prototypical DOR antagonist peptide. Key pharmacophoric contacts between the DOR and the ligands were maintained through an analogous spatial arrangement of pharmacophores, which could provide an explanation for the predicted high-affinity binding and the experimentally observed functional properties of the novel synthetic ligands.
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/api/publication/31655071
<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10076528"> <a href="/gui2/?type=authors&mode=browse&sel=10076528" target="_blank">Sarkar, Arijit</a> </span> <span class="author-type"> </span> ; <span class="author-name" > Adamska-Bartlomiejczyk, Anna<sup>*</sup> </span> <span class="author-type"> </span> ; <span class="author-name" > Piekielna-Ciesielska, Justyna </span> <span class="author-type"> </span> ; <span class="author-name" > Wtorek, Karol </span> <span class="author-type"> </span> ; <span class="author-name" > Kluczyk, Alicja </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10013101"> <a href="/gui2/?type=authors&mode=browse&sel=10013101" target="_blank">Borics, Attila</a> </span> <span class="author-type"> </span> ; <span class="author-name" > Janecka, Anna ✉ </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;31655071" mtid="31655071" target="_blank">Design, Synthesis and Functional Analysis of Cyclic Opioid Peptides with Dmt-Tic Pharmacophore</a></div> <div class="pub-info"> <span class="journal-title">MOLECULES</span> <span class="journal-volume">25</span> : <span class="journal-issue">18</span> <span class="page"> Paper: 4260 </span> <span class="year">(2020)</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="10.3390/molecules25184260" target="_blank" href="https://doi.org/10.3390/molecules25184260"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000581428600001" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000581428600001"> WoS </a> </span> <span class="id identifier oa_GOLD" title=" Gold "> <a style="color:black" title="120162" target="_blank" href="http://real.mtak.hu/120162"> REAL </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="85091473007" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-85091473007"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:black" title="32957550" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=32957550&dopt=Abstract"> PubMed </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:31655071 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </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: 2</span> | Független: 2 | Függő: 0 | Nem jelölt: 0 | WoS jelölt: 2 | Scopus jelölt: 2 | WoS/Scopus jelölt: 2 | DOI jelölt: 2 </div> </div> </div> </div><div class="JournalArticle Publication long-list">
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<span class="authorAux-mtmt"> biokémia</span>)
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<span class="author-affil"><span title="Szegedi Biológiai Kutatóközpont">SZBK</span>/Biokémiai Intézet; <span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Doktori Iskolák">DI</span>/Elméleti Orvostudományok Doktori Iskola</span>
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<span class="author-name" >Wtorek Karol
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href="/gui2/?type=authors&mode=browse&sel=10013101" target="_blank">Borics Attila
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<span class="authorAux-mtmt"> Peptid- és fehérjeszerkezet</span>)
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<span class="author-affil"><span title="Szegedi Biológiai Kutatóközpont">SZBK</span>/Biokémiai Intézet</span>
;
<span class="author-name" >Janecka Anna ✉
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<div class="title"><a href="/gui2/?mode=browse¶ms=publication;31655071" target="_blank">Design, Synthesis and Functional Analysis of Cyclic Opioid Peptides with Dmt-Tic Pharmacophore</a></div> <div> <span class="journal-title">MOLECULES</span>
<span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/1420-3049">1420-3049</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1420-3049">1420-3049</a>)</span>:
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Paper 4260.
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<span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 2</span>
| Független: 2
| Függő: 0
| Nem jelölt: 0
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<div class="mtid"><span class="long-pub-mtid">Közlemény: 31655071</span>
| <span class="status-data status-VALIDATED"> Egyeztetett
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Forrás Idéző
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( Szakcikk
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<div class="lastModified">Utolsó módosítás: 2022.11.28. 14:44 Belházyné Szombathelyi Ágnes (SZTE admin5)
</div>
<pre class="comment" style="margin-top: 0; margin-bottom: 0;"><u>Megjegyzés</u>: Laboratory of Chemical Biology, United States
Institute of Biochemistry, Biological Research Centre, 62. Temesvári krt., Szeged, H-6726, Hungary
Theoretical Medicine Doctoral School, Hungary
Faculty of Medicine, University of Szeged, 97. Tisza L. krt., Szeged, H-6722, Hungary
Department of Biomolecul...</pre>
</div></div>