Identification of CJC-1131-albumin bioconjugate as a stable and bioactive GLP-1(7–36) analog
A series of analogs of GLP-1(7–36) amide containing a Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)-lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabili...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2004-09, Vol.14 (17), p.4395-4398 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Léger, Roger Thibaudeau, Karen Robitaille, Martin Quraishi, Omar van Wyk, Pieter Bousquet-Gagnon, Nathalie Carette, Julie Castaigne, Jean-Paul Bridon, Dominique P. |
| description | A series of analogs of GLP-1(7–36) amide containing a
Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)-lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabilizing effect of bioconjugation in the presence of DPP-IV as well as GLP-1 receptor binding and activation. Compound
9 (CJC-1131) having the point of attachment to albumin at the
C-terminal of GLP-1 and a
d-alanine substitution at position 8 was identified as having the best combination of stability and bioactivity.
▪
A series of analogs of GLP-1(7–36) amide containing a
Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabilizing effect of bioconjugation in the presence of DPP-IV as well as GLP-1 receptor binding and activation. Compound
9 (CJC-1131) having the point of attachment to albumin at the
C-terminal of GLP-1 and a
d-alanine substitution at position 8 was identified as having the best combination of stability and bioactivity. |
| doi_str_mv | 10.1016/j.bmcl.2004.06.066 |
| format | Article |
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Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)-lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabilizing effect of bioconjugation in the presence of DPP-IV as well as GLP-1 receptor binding and activation. Compound
9 (CJC-1131) having the point of attachment to albumin at the
C-terminal of GLP-1 and a
d-alanine substitution at position 8 was identified as having the best combination of stability and bioactivity.
▪
A series of analogs of GLP-1(7–36) amide containing a
Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabilizing effect of bioconjugation in the presence of DPP-IV as well as GLP-1 receptor binding and activation. Compound
9 (CJC-1131) having the point of attachment to albumin at the
C-terminal of GLP-1 and a
d-alanine substitution at position 8 was identified as having the best combination of stability and bioactivity.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2004.06.066</identifier><identifier>PMID: 15357960</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Albumin conjugate ; Amino Acid Sequence - genetics ; Animals ; Biological and medical sciences ; CHO Cells ; Cricetinae ; DPP-IV ; GLP-1 ; Glucagon ; Glucagon-Like Peptide 1 ; Glucagon-Like Peptides ; Humans ; Maleimides - chemistry ; Maleimides - metabolism ; Medical sciences ; Miscellaneous ; Molecular Sequence Data ; Peptide Fragments - chemistry ; Peptide Fragments - genetics ; Peptide Fragments - metabolism ; Peptides - chemistry ; Peptides - metabolism ; Pharmacology. Drug treatments ; Protein Binding - physiology ; Serum Albumin - metabolism</subject><ispartof>Bioorganic & medicinal chemistry letters, 2004-09, Vol.14 (17), p.4395-4398</ispartof><rights>2004 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c382t-62bd7836346a7d7c034de0905d77688a19168de8998dc9bc099ced1f0f0e0ab03</citedby><cites>FETCH-LOGICAL-c382t-62bd7836346a7d7c034de0905d77688a19168de8998dc9bc099ced1f0f0e0ab03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2004.06.066$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16002519$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15357960$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Léger, Roger</creatorcontrib><creatorcontrib>Thibaudeau, Karen</creatorcontrib><creatorcontrib>Robitaille, Martin</creatorcontrib><creatorcontrib>Quraishi, Omar</creatorcontrib><creatorcontrib>van Wyk, Pieter</creatorcontrib><creatorcontrib>Bousquet-Gagnon, Nathalie</creatorcontrib><creatorcontrib>Carette, Julie</creatorcontrib><creatorcontrib>Castaigne, Jean-Paul</creatorcontrib><creatorcontrib>Bridon, Dominique P.</creatorcontrib><title>Identification of CJC-1131-albumin bioconjugate as a stable and bioactive GLP-1(7–36) analog</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of analogs of GLP-1(7–36) amide containing a
Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)-lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabilizing effect of bioconjugation in the presence of DPP-IV as well as GLP-1 receptor binding and activation. Compound
9 (CJC-1131) having the point of attachment to albumin at the
C-terminal of GLP-1 and a
d-alanine substitution at position 8 was identified as having the best combination of stability and bioactivity.
▪
A series of analogs of GLP-1(7–36) amide containing a
Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabilizing effect of bioconjugation in the presence of DPP-IV as well as GLP-1 receptor binding and activation. Compound
9 (CJC-1131) having the point of attachment to albumin at the
C-terminal of GLP-1 and a
d-alanine substitution at position 8 was identified as having the best combination of stability and bioactivity.</description><subject>Albumin conjugate</subject><subject>Amino Acid Sequence - genetics</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>CHO Cells</subject><subject>Cricetinae</subject><subject>DPP-IV</subject><subject>GLP-1</subject><subject>Glucagon</subject><subject>Glucagon-Like Peptide 1</subject><subject>Glucagon-Like Peptides</subject><subject>Humans</subject><subject>Maleimides - chemistry</subject><subject>Maleimides - metabolism</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Molecular Sequence Data</subject><subject>Peptide Fragments - chemistry</subject><subject>Peptide Fragments - genetics</subject><subject>Peptide Fragments - metabolism</subject><subject>Peptides - chemistry</subject><subject>Peptides - metabolism</subject><subject>Pharmacology. Drug treatments</subject><subject>Protein Binding - physiology</subject><subject>Serum Albumin - metabolism</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFq3DAQhkVpaTZpX6CH4ktDevB2ZMmyBLmEpU1TFtJDCz1VjKVx0GJbqWUHess79A37JNWyC7kVBmbg_2aQPsbecFhz4OrDbt0Orl9XAHINKpd6xlZcKlkKCfVztgKjoNRG_jhhpyntALgEKV-yE16Lusnhiv288TTOoQsO5xDHInbF5sum5FzwEvt2GcJYtCG6OO6WO5ypwFRgkWZs-zyPfh-im8MDFdfbryW_aP4-_hHqfc6wj3ev2IsO-0Svj_2Mff_08dvmc7m9vb7ZXG1LJ3Q1l6pqfaOFElJh4xsHQnoCA7VvGqU1csOV9qSN0d6Z1oExjjzvoAMCbEGcsfPD3fsp_loozXYIyVHf40hxSVYpXRsJOoPVAXRTTGmizt5PYcDpt-Vg91btzu6t2r1VCyqXyktvj9eXdiD_tHLUmIF3RwCTw76bcHQhPXEKoKq5ydzlgaPs4iHQZJMLNOa_hIncbH0M_3vHPyUvk8w</recordid><startdate>20040906</startdate><enddate>20040906</enddate><creator>Léger, Roger</creator><creator>Thibaudeau, Karen</creator><creator>Robitaille, Martin</creator><creator>Quraishi, Omar</creator><creator>van Wyk, Pieter</creator><creator>Bousquet-Gagnon, Nathalie</creator><creator>Carette, Julie</creator><creator>Castaigne, Jean-Paul</creator><creator>Bridon, Dominique P.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><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></search><sort><creationdate>20040906</creationdate><title>Identification of CJC-1131-albumin bioconjugate as a stable and bioactive GLP-1(7–36) analog</title><author>Léger, Roger ; Thibaudeau, Karen ; Robitaille, Martin ; Quraishi, Omar ; van Wyk, Pieter ; Bousquet-Gagnon, Nathalie ; Carette, Julie ; Castaigne, Jean-Paul ; Bridon, Dominique P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c382t-62bd7836346a7d7c034de0905d77688a19168de8998dc9bc099ced1f0f0e0ab03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Albumin conjugate</topic><topic>Amino Acid Sequence - genetics</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>CHO Cells</topic><topic>Cricetinae</topic><topic>DPP-IV</topic><topic>GLP-1</topic><topic>Glucagon</topic><topic>Glucagon-Like Peptide 1</topic><topic>Glucagon-Like Peptides</topic><topic>Humans</topic><topic>Maleimides - chemistry</topic><topic>Maleimides - metabolism</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Molecular Sequence Data</topic><topic>Peptide Fragments - chemistry</topic><topic>Peptide Fragments - genetics</topic><topic>Peptide Fragments - metabolism</topic><topic>Peptides - chemistry</topic><topic>Peptides - metabolism</topic><topic>Pharmacology. Drug treatments</topic><topic>Protein Binding - physiology</topic><topic>Serum Albumin - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Léger, Roger</creatorcontrib><creatorcontrib>Thibaudeau, Karen</creatorcontrib><creatorcontrib>Robitaille, Martin</creatorcontrib><creatorcontrib>Quraishi, Omar</creatorcontrib><creatorcontrib>van Wyk, Pieter</creatorcontrib><creatorcontrib>Bousquet-Gagnon, Nathalie</creatorcontrib><creatorcontrib>Carette, Julie</creatorcontrib><creatorcontrib>Castaigne, Jean-Paul</creatorcontrib><creatorcontrib>Bridon, Dominique P.</creatorcontrib><collection>Pascal-Francis</collection><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><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Léger, Roger</au><au>Thibaudeau, Karen</au><au>Robitaille, Martin</au><au>Quraishi, Omar</au><au>van Wyk, Pieter</au><au>Bousquet-Gagnon, Nathalie</au><au>Carette, Julie</au><au>Castaigne, Jean-Paul</au><au>Bridon, Dominique P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of CJC-1131-albumin bioconjugate as a stable and bioactive GLP-1(7–36) analog</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2004-09-06</date><risdate>2004</risdate><volume>14</volume><issue>17</issue><spage>4395</spage><epage>4398</epage><pages>4395-4398</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of analogs of GLP-1(7–36) amide containing a
Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)-lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabilizing effect of bioconjugation in the presence of DPP-IV as well as GLP-1 receptor binding and activation. Compound
9 (CJC-1131) having the point of attachment to albumin at the
C-terminal of GLP-1 and a
d-alanine substitution at position 8 was identified as having the best combination of stability and bioactivity.
▪
A series of analogs of GLP-1(7–36) amide containing a
Nε-(2-{2-[2-(3-maleimidopropylamido)ethoxy]ethoxy}acetyl)lysine has been synthesized and the resulting derivatives were bioconjugated to Cys34 of human serum albumin (HSA). The GLP-1-HSA bioconjugates were analyzed in vitro to assess the stabilizing effect of bioconjugation in the presence of DPP-IV as well as GLP-1 receptor binding and activation. Compound
9 (CJC-1131) having the point of attachment to albumin at the
C-terminal of GLP-1 and a
d-alanine substitution at position 8 was identified as having the best combination of stability and bioactivity.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15357960</pmid><doi>10.1016/j.bmcl.2004.06.066</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2004-09, Vol.14 (17), p.4395-4398 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_66859408 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Albumin conjugate Amino Acid Sequence - genetics Animals Biological and medical sciences CHO Cells Cricetinae DPP-IV GLP-1 Glucagon Glucagon-Like Peptide 1 Glucagon-Like Peptides Humans Maleimides - chemistry Maleimides - metabolism Medical sciences Miscellaneous Molecular Sequence Data Peptide Fragments - chemistry Peptide Fragments - genetics Peptide Fragments - metabolism Peptides - chemistry Peptides - metabolism Pharmacology. Drug treatments Protein Binding - physiology Serum Albumin - metabolism |
| title | Identification of CJC-1131-albumin bioconjugate as a stable and bioactive GLP-1(7–36) analog |
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