Gabapentin hybrid peptides and bioconjugates
Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (l-Ala-Gbp, l-Val-Gbp, l-Ala-l-Phe-Gbp, Gly-l-Ala-β-Ala-Gbp). Carboxyl-activ...
Gespeichert in:
| Veröffentlicht in: | Bioorganic & medicinal chemistry 2014-02, Vol.22 (4), p.1479-1486 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1486 |
|---|---|
| container_issue | 4 |
| container_start_page | 1479 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 22 |
| creator | Lebedyeva, Iryna O. Ostrov, David A. Neubert, John Steel, Peter J. Patel, Kunal Sileno, Sean M. Goncalves, Kevin Ibrahim, Mohamed A. Alamry, Khalid A. Katritzky, Alan R. |
| description | Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (l-Ala-Gbp, l-Val-Gbp, l-Ala-l-Phe-Gbp, Gly-l-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units. |
| doi_str_mv | 10.1016/j.bmc.2013.12.017 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1516747498</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089613010110</els_id><sourcerecordid>1499141191</sourcerecordid><originalsourceid>FETCH-LOGICAL-c386t-27b5e63ed32a4a275a9b1b2792fe9dafc3acfc615a1180c46052d5a638a9b0a63</originalsourceid><addsrcrecordid>eNqFkL1OwzAURi0EoqXwACwoIwMJvrbjxGJCFRSkSiwwW459A46aH-IEqW9PqhZGmL7lfGc4hFwCTYCCvK2SorYJo8ATYAmF7IjMQUgRc67gmMypknlMcyVn5CyEilLKhIJTMmNCyFxymJOblSlMh83gm-hjW_TeRR12g3cYItO4qPCtbZtqfDcDhnNyUppNwIvDLsjb48Pr8ilev6yel_fr2PJcDjHLihQlR8eZEYZlqVEFFCxTrETlTGm5saWVkBqAnFohacpcaiTPJ5BOuyDXe2_Xt58jhkHXPljcbEyD7Rg0pCAzkQmV_48KpUAAKJhQ2KO2b0PosdRd72vTbzVQveupKz311LueGpieek6fq4N-LGp0v4-fgBNwtwdw6vHlsdfBemwsOt-jHbRr_R_6b96ihDM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1499141191</pqid></control><display><type>article</type><title>Gabapentin hybrid peptides and bioconjugates</title><source>MEDLINE</source><source>Access via ScienceDirect (Elsevier)</source><creator>Lebedyeva, Iryna O. ; Ostrov, David A. ; Neubert, John ; Steel, Peter J. ; Patel, Kunal ; Sileno, Sean M. ; Goncalves, Kevin ; Ibrahim, Mohamed A. ; Alamry, Khalid A. ; Katritzky, Alan R.</creator><creatorcontrib>Lebedyeva, Iryna O. ; Ostrov, David A. ; Neubert, John ; Steel, Peter J. ; Patel, Kunal ; Sileno, Sean M. ; Goncalves, Kevin ; Ibrahim, Mohamed A. ; Alamry, Khalid A. ; Katritzky, Alan R.</creatorcontrib><description>Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (l-Ala-Gbp, l-Val-Gbp, l-Ala-l-Phe-Gbp, Gly-l-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2013.12.017</identifier><identifier>PMID: 24468631</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Acylation ; Amines - chemistry ; Analgesics - chemistry ; Analgesics - pharmacology ; Analgesics - therapeutic use ; Animals ; Behavior, Animal - drug effects ; Benzotriazole ; Coupling ; Crystallography, X-Ray ; Cyclization ; Cyclohexanecarboxylic Acids - chemistry ; Disease Models, Animal ; Gabapentin ; gamma-Aminobutyric Acid - chemistry ; Mice ; Molecular Conformation ; Pain - drug therapy ; Peptide ; Peptides - chemistry</subject><ispartof>Bioorganic & medicinal chemistry, 2014-02, Vol.22 (4), p.1479-1486</ispartof><rights>2014</rights><rights>Copyright © 2014. Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c386t-27b5e63ed32a4a275a9b1b2792fe9dafc3acfc615a1180c46052d5a638a9b0a63</citedby><cites>FETCH-LOGICAL-c386t-27b5e63ed32a4a275a9b1b2792fe9dafc3acfc615a1180c46052d5a638a9b0a63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2013.12.017$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24468631$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lebedyeva, Iryna O.</creatorcontrib><creatorcontrib>Ostrov, David A.</creatorcontrib><creatorcontrib>Neubert, John</creatorcontrib><creatorcontrib>Steel, Peter J.</creatorcontrib><creatorcontrib>Patel, Kunal</creatorcontrib><creatorcontrib>Sileno, Sean M.</creatorcontrib><creatorcontrib>Goncalves, Kevin</creatorcontrib><creatorcontrib>Ibrahim, Mohamed A.</creatorcontrib><creatorcontrib>Alamry, Khalid A.</creatorcontrib><creatorcontrib>Katritzky, Alan R.</creatorcontrib><title>Gabapentin hybrid peptides and bioconjugates</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (l-Ala-Gbp, l-Val-Gbp, l-Ala-l-Phe-Gbp, Gly-l-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units.</description><subject>Acylation</subject><subject>Amines - chemistry</subject><subject>Analgesics - chemistry</subject><subject>Analgesics - pharmacology</subject><subject>Analgesics - therapeutic use</subject><subject>Animals</subject><subject>Behavior, Animal - drug effects</subject><subject>Benzotriazole</subject><subject>Coupling</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>Cyclohexanecarboxylic Acids - chemistry</subject><subject>Disease Models, Animal</subject><subject>Gabapentin</subject><subject>gamma-Aminobutyric Acid - chemistry</subject><subject>Mice</subject><subject>Molecular Conformation</subject><subject>Pain - drug therapy</subject><subject>Peptide</subject><subject>Peptides - chemistry</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkL1OwzAURi0EoqXwACwoIwMJvrbjxGJCFRSkSiwwW459A46aH-IEqW9PqhZGmL7lfGc4hFwCTYCCvK2SorYJo8ATYAmF7IjMQUgRc67gmMypknlMcyVn5CyEilLKhIJTMmNCyFxymJOblSlMh83gm-hjW_TeRR12g3cYItO4qPCtbZtqfDcDhnNyUppNwIvDLsjb48Pr8ilev6yel_fr2PJcDjHLihQlR8eZEYZlqVEFFCxTrETlTGm5saWVkBqAnFohacpcaiTPJ5BOuyDXe2_Xt58jhkHXPljcbEyD7Rg0pCAzkQmV_48KpUAAKJhQ2KO2b0PosdRd72vTbzVQveupKz311LueGpieek6fq4N-LGp0v4-fgBNwtwdw6vHlsdfBemwsOt-jHbRr_R_6b96ihDM</recordid><startdate>20140215</startdate><enddate>20140215</enddate><creator>Lebedyeva, Iryna O.</creator><creator>Ostrov, David A.</creator><creator>Neubert, John</creator><creator>Steel, Peter J.</creator><creator>Patel, Kunal</creator><creator>Sileno, Sean M.</creator><creator>Goncalves, Kevin</creator><creator>Ibrahim, Mohamed A.</creator><creator>Alamry, Khalid A.</creator><creator>Katritzky, Alan R.</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20140215</creationdate><title>Gabapentin hybrid peptides and bioconjugates</title><author>Lebedyeva, Iryna O. ; Ostrov, David A. ; Neubert, John ; Steel, Peter J. ; Patel, Kunal ; Sileno, Sean M. ; Goncalves, Kevin ; Ibrahim, Mohamed A. ; Alamry, Khalid A. ; Katritzky, Alan R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-27b5e63ed32a4a275a9b1b2792fe9dafc3acfc615a1180c46052d5a638a9b0a63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Acylation</topic><topic>Amines - chemistry</topic><topic>Analgesics - chemistry</topic><topic>Analgesics - pharmacology</topic><topic>Analgesics - therapeutic use</topic><topic>Animals</topic><topic>Behavior, Animal - drug effects</topic><topic>Benzotriazole</topic><topic>Coupling</topic><topic>Crystallography, X-Ray</topic><topic>Cyclization</topic><topic>Cyclohexanecarboxylic Acids - chemistry</topic><topic>Disease Models, Animal</topic><topic>Gabapentin</topic><topic>gamma-Aminobutyric Acid - chemistry</topic><topic>Mice</topic><topic>Molecular Conformation</topic><topic>Pain - drug therapy</topic><topic>Peptide</topic><topic>Peptides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lebedyeva, Iryna O.</creatorcontrib><creatorcontrib>Ostrov, David A.</creatorcontrib><creatorcontrib>Neubert, John</creatorcontrib><creatorcontrib>Steel, Peter J.</creatorcontrib><creatorcontrib>Patel, Kunal</creatorcontrib><creatorcontrib>Sileno, Sean M.</creatorcontrib><creatorcontrib>Goncalves, Kevin</creatorcontrib><creatorcontrib>Ibrahim, Mohamed A.</creatorcontrib><creatorcontrib>Alamry, Khalid A.</creatorcontrib><creatorcontrib>Katritzky, Alan R.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lebedyeva, Iryna O.</au><au>Ostrov, David A.</au><au>Neubert, John</au><au>Steel, Peter J.</au><au>Patel, Kunal</au><au>Sileno, Sean M.</au><au>Goncalves, Kevin</au><au>Ibrahim, Mohamed A.</au><au>Alamry, Khalid A.</au><au>Katritzky, Alan R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Gabapentin hybrid peptides and bioconjugates</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2014-02-15</date><risdate>2014</risdate><volume>22</volume><issue>4</issue><spage>1479</spage><epage>1486</epage><pages>1479-1486</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (l-Ala-Gbp, l-Val-Gbp, l-Ala-l-Phe-Gbp, Gly-l-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>24468631</pmid><doi>10.1016/j.bmc.2013.12.017</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2014-02, Vol.22 (4), p.1479-1486 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1516747498 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Acylation Amines - chemistry Analgesics - chemistry Analgesics - pharmacology Analgesics - therapeutic use Animals Behavior, Animal - drug effects Benzotriazole Coupling Crystallography, X-Ray Cyclization Cyclohexanecarboxylic Acids - chemistry Disease Models, Animal Gabapentin gamma-Aminobutyric Acid - chemistry Mice Molecular Conformation Pain - drug therapy Peptide Peptides - chemistry |
| title | Gabapentin hybrid peptides and bioconjugates |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T10%3A23%3A41IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Gabapentin%20hybrid%20peptides%20and%20bioconjugates&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Lebedyeva,%20Iryna%20O.&rft.date=2014-02-15&rft.volume=22&rft.issue=4&rft.spage=1479&rft.epage=1486&rft.pages=1479-1486&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/j.bmc.2013.12.017&rft_dat=%3Cproquest_cross%3E1499141191%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1499141191&rft_id=info:pmid/24468631&rft_els_id=S0968089613010110&rfr_iscdi=true |