CBTF: New Amine-to-Thiol Coupling Reagent for Preparation of Antibody Conjugates with Increased Plasma Stability
Amine-to-thiol coupling is the most common route for the preparation of antibody–drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were recently revealed...
Gespeichert in:
| Veröffentlicht in: | Bioconjugate chemistry 2015-02, Vol.26 (2), p.197-200 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 200 |
|---|---|
| container_issue | 2 |
| container_start_page | 197 |
| container_title | Bioconjugate chemistry |
| container_volume | 26 |
| creator | Kolodych, Sergii Koniev, Oleksandr Baatarkhuu, Zoljargal Bonnefoy, Jean-Yves Debaene, François Cianférani, Sarah Van Dorsselaer, Alain Wagner, Alain |
| description | Amine-to-thiol coupling is the most common route for the preparation of antibody–drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were recently revealed to have limited stability in blood circulation, which can compromise therapeutic efficacy of the conjugate. To address this issue, we have developed a heterobifunctional reagent, sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate (CBTF), for amine-to-thiol coupling. It comprises a recently described 3-arylpropionitrile (APN) function in replacement of maleimide and allows for the preparation of remarkably stable conjugates. A series of antibody–dye conjugates have been prepared using this reagent and shown superior stability in human blood plasma compared to maleimide-derived conjugates. |
| doi_str_mv | 10.1021/bc500610g |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_04847661v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1709179169</sourcerecordid><originalsourceid>FETCH-LOGICAL-a410t-fed20c01d18b3e2fbc7b1f3ea31bea89e01cc8d40d1fb0a94a0147398472ba023</originalsourceid><addsrcrecordid>eNqF0U2P0zAQBuAIgdhl4cAfQJYQEhwCM86Xw61ULLtSBSso52icTFpXSZy1HVb996TqUhAcONmyHr0e-42i5whvESS-03UGkCNsHkTnmEmIU4Xy4byHNIlRgTyLnni_A4ASlXwcncksx7RMsvNoXH5YX74Xn_lOLHozcBxsvN4a24mlncbODBvxlWnDQxCtdeLG8UiOgrGDsK1YDMFo2-xnPOymDQX24s6ErbgeasfkuRE3HfmexLdA2nQm7J9Gj1rqPD-7Xy-i75cf18urePXl0_VysYopRQhxy42EGrBBpROWra4LjW3ClKBmUiUD1rVqUmiw1UBlSoBpkZQqLaQmkMlF9OaYu6WuGp3pye0rS6a6Wqyqwxmks81z_IGzfX20o7O3E_tQ9cbX3HU0sJ18hcX8cUWJefl_mmdFIjNVFDN9-Rfd2ckN86MPSkGmcsTfc9bOeu-4PQ2LUB3arU7tzvbFfeKke25O8ledM3h1BFT7P277J-gngpWo-A</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1658058611</pqid></control><display><type>article</type><title>CBTF: New Amine-to-Thiol Coupling Reagent for Preparation of Antibody Conjugates with Increased Plasma Stability</title><source>MEDLINE</source><source>American Chemical Society Publications</source><creator>Kolodych, Sergii ; Koniev, Oleksandr ; Baatarkhuu, Zoljargal ; Bonnefoy, Jean-Yves ; Debaene, François ; Cianférani, Sarah ; Van Dorsselaer, Alain ; Wagner, Alain</creator><creatorcontrib>Kolodych, Sergii ; Koniev, Oleksandr ; Baatarkhuu, Zoljargal ; Bonnefoy, Jean-Yves ; Debaene, François ; Cianférani, Sarah ; Van Dorsselaer, Alain ; Wagner, Alain</creatorcontrib><description>Amine-to-thiol coupling is the most common route for the preparation of antibody–drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were recently revealed to have limited stability in blood circulation, which can compromise therapeutic efficacy of the conjugate. To address this issue, we have developed a heterobifunctional reagent, sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate (CBTF), for amine-to-thiol coupling. It comprises a recently described 3-arylpropionitrile (APN) function in replacement of maleimide and allows for the preparation of remarkably stable conjugates. A series of antibody–dye conjugates have been prepared using this reagent and shown superior stability in human blood plasma compared to maleimide-derived conjugates.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc500610g</identifier><identifier>PMID: 25614935</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amines - chemistry ; Benzene Derivatives - chemistry ; Biochemistry, Molecular Biology ; Cell Line ; Chemistry ; Cross-Linking Reagents - chemistry ; Drugs ; Halogenation ; Humans ; Immunoconjugates - blood ; Immunoconjugates - chemistry ; Life Sciences ; Maleimides - chemistry ; Plasma ; Reagents ; Sulfhydryl Compounds - chemistry</subject><ispartof>Bioconjugate chemistry, 2015-02, Vol.26 (2), p.197-200</ispartof><rights>Copyright © 2015 American Chemical Society</rights><rights>Copyright American Chemical Society Feb 18, 2015</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-fed20c01d18b3e2fbc7b1f3ea31bea89e01cc8d40d1fb0a94a0147398472ba023</citedby><cites>FETCH-LOGICAL-a410t-fed20c01d18b3e2fbc7b1f3ea31bea89e01cc8d40d1fb0a94a0147398472ba023</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bc500610g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc500610g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25614935$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-04847661$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Kolodych, Sergii</creatorcontrib><creatorcontrib>Koniev, Oleksandr</creatorcontrib><creatorcontrib>Baatarkhuu, Zoljargal</creatorcontrib><creatorcontrib>Bonnefoy, Jean-Yves</creatorcontrib><creatorcontrib>Debaene, François</creatorcontrib><creatorcontrib>Cianférani, Sarah</creatorcontrib><creatorcontrib>Van Dorsselaer, Alain</creatorcontrib><creatorcontrib>Wagner, Alain</creatorcontrib><title>CBTF: New Amine-to-Thiol Coupling Reagent for Preparation of Antibody Conjugates with Increased Plasma Stability</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>Amine-to-thiol coupling is the most common route for the preparation of antibody–drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were recently revealed to have limited stability in blood circulation, which can compromise therapeutic efficacy of the conjugate. To address this issue, we have developed a heterobifunctional reagent, sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate (CBTF), for amine-to-thiol coupling. It comprises a recently described 3-arylpropionitrile (APN) function in replacement of maleimide and allows for the preparation of remarkably stable conjugates. A series of antibody–dye conjugates have been prepared using this reagent and shown superior stability in human blood plasma compared to maleimide-derived conjugates.</description><subject>Amines - chemistry</subject><subject>Benzene Derivatives - chemistry</subject><subject>Biochemistry, Molecular Biology</subject><subject>Cell Line</subject><subject>Chemistry</subject><subject>Cross-Linking Reagents - chemistry</subject><subject>Drugs</subject><subject>Halogenation</subject><subject>Humans</subject><subject>Immunoconjugates - blood</subject><subject>Immunoconjugates - chemistry</subject><subject>Life Sciences</subject><subject>Maleimides - chemistry</subject><subject>Plasma</subject><subject>Reagents</subject><subject>Sulfhydryl Compounds - chemistry</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U2P0zAQBuAIgdhl4cAfQJYQEhwCM86Xw61ULLtSBSso52icTFpXSZy1HVb996TqUhAcONmyHr0e-42i5whvESS-03UGkCNsHkTnmEmIU4Xy4byHNIlRgTyLnni_A4ASlXwcncksx7RMsvNoXH5YX74Xn_lOLHozcBxsvN4a24mlncbODBvxlWnDQxCtdeLG8UiOgrGDsK1YDMFo2-xnPOymDQX24s6ErbgeasfkuRE3HfmexLdA2nQm7J9Gj1rqPD-7Xy-i75cf18urePXl0_VysYopRQhxy42EGrBBpROWra4LjW3ClKBmUiUD1rVqUmiw1UBlSoBpkZQqLaQmkMlF9OaYu6WuGp3pye0rS6a6Wqyqwxmks81z_IGzfX20o7O3E_tQ9cbX3HU0sJ18hcX8cUWJefl_mmdFIjNVFDN9-Rfd2ckN86MPSkGmcsTfc9bOeu-4PQ2LUB3arU7tzvbFfeKke25O8ledM3h1BFT7P277J-gngpWo-A</recordid><startdate>20150218</startdate><enddate>20150218</enddate><creator>Kolodych, Sergii</creator><creator>Koniev, Oleksandr</creator><creator>Baatarkhuu, Zoljargal</creator><creator>Bonnefoy, Jean-Yves</creator><creator>Debaene, François</creator><creator>Cianférani, Sarah</creator><creator>Van Dorsselaer, Alain</creator><creator>Wagner, Alain</creator><general>American Chemical Society</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><scope>1XC</scope></search><sort><creationdate>20150218</creationdate><title>CBTF: New Amine-to-Thiol Coupling Reagent for Preparation of Antibody Conjugates with Increased Plasma Stability</title><author>Kolodych, Sergii ; Koniev, Oleksandr ; Baatarkhuu, Zoljargal ; Bonnefoy, Jean-Yves ; Debaene, François ; Cianférani, Sarah ; Van Dorsselaer, Alain ; Wagner, Alain</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-fed20c01d18b3e2fbc7b1f3ea31bea89e01cc8d40d1fb0a94a0147398472ba023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amines - chemistry</topic><topic>Benzene Derivatives - chemistry</topic><topic>Biochemistry, Molecular Biology</topic><topic>Cell Line</topic><topic>Chemistry</topic><topic>Cross-Linking Reagents - chemistry</topic><topic>Drugs</topic><topic>Halogenation</topic><topic>Humans</topic><topic>Immunoconjugates - blood</topic><topic>Immunoconjugates - chemistry</topic><topic>Life Sciences</topic><topic>Maleimides - chemistry</topic><topic>Plasma</topic><topic>Reagents</topic><topic>Sulfhydryl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kolodych, Sergii</creatorcontrib><creatorcontrib>Koniev, Oleksandr</creatorcontrib><creatorcontrib>Baatarkhuu, Zoljargal</creatorcontrib><creatorcontrib>Bonnefoy, Jean-Yves</creatorcontrib><creatorcontrib>Debaene, François</creatorcontrib><creatorcontrib>Cianférani, Sarah</creatorcontrib><creatorcontrib>Van Dorsselaer, Alain</creatorcontrib><creatorcontrib>Wagner, Alain</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kolodych, Sergii</au><au>Koniev, Oleksandr</au><au>Baatarkhuu, Zoljargal</au><au>Bonnefoy, Jean-Yves</au><au>Debaene, François</au><au>Cianférani, Sarah</au><au>Van Dorsselaer, Alain</au><au>Wagner, Alain</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>CBTF: New Amine-to-Thiol Coupling Reagent for Preparation of Antibody Conjugates with Increased Plasma Stability</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>2015-02-18</date><risdate>2015</risdate><volume>26</volume><issue>2</issue><spage>197</spage><epage>200</epage><pages>197-200</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>Amine-to-thiol coupling is the most common route for the preparation of antibody–drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were recently revealed to have limited stability in blood circulation, which can compromise therapeutic efficacy of the conjugate. To address this issue, we have developed a heterobifunctional reagent, sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate (CBTF), for amine-to-thiol coupling. It comprises a recently described 3-arylpropionitrile (APN) function in replacement of maleimide and allows for the preparation of remarkably stable conjugates. A series of antibody–dye conjugates have been prepared using this reagent and shown superior stability in human blood plasma compared to maleimide-derived conjugates.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25614935</pmid><doi>10.1021/bc500610g</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1043-1802 |
| ispartof | Bioconjugate chemistry, 2015-02, Vol.26 (2), p.197-200 |
| issn | 1043-1802 1520-4812 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_04847661v1 |
| source | MEDLINE; American Chemical Society Publications |
| subjects | Amines - chemistry Benzene Derivatives - chemistry Biochemistry, Molecular Biology Cell Line Chemistry Cross-Linking Reagents - chemistry Drugs Halogenation Humans Immunoconjugates - blood Immunoconjugates - chemistry Life Sciences Maleimides - chemistry Plasma Reagents Sulfhydryl Compounds - chemistry |
| title | CBTF: New Amine-to-Thiol Coupling Reagent for Preparation of Antibody Conjugates with Increased Plasma Stability |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T09%3A22%3A06IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=CBTF:%20New%20Amine-to-Thiol%20Coupling%20Reagent%20for%20Preparation%20of%20Antibody%20Conjugates%20with%20Increased%20Plasma%20Stability&rft.jtitle=Bioconjugate%20chemistry&rft.au=Kolodych,%20Sergii&rft.date=2015-02-18&rft.volume=26&rft.issue=2&rft.spage=197&rft.epage=200&rft.pages=197-200&rft.issn=1043-1802&rft.eissn=1520-4812&rft_id=info:doi/10.1021/bc500610g&rft_dat=%3Cproquest_hal_p%3E1709179169%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1658058611&rft_id=info:pmid/25614935&rfr_iscdi=true |