Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes
We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully u...
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| Veröffentlicht in: | Angewandte Chemie 2017-12, Vol.129 (49), p.15818-15822 |
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| container_title | Angewandte Chemie |
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| creator | Bernard, Sabrina Audisio, Davide Riomet, Margaux Bregant, Sarah Sallustrau, Antoine Plougastel, Lucie Decuypere, Elodie Gabillet, Sandra Kumar, Ramar Arun Elyian, Jijy Trinh, Minh Nguyet Koniev, Oleksandr Wagner, Alain Kolodych, Sergii Taran, Frédéric |
| description | We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target‐fishing applications. This click‐and‐release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.
Klick und ab: Iminosydnone reagieren unter physiologischen Bedingungen ohne Kupferzusatz glatt mit Cycloalkinen zu Klick‐Pyrazolen; als weiteres Produkt entsteht ein Harnstoffderivat. Die Anwendungsmöglichkeiten dieser Reaktion zur Wirkstoff‐Freisetzung und Proteinmarkierung wurden in Beispielexperimenten evaluiert. |
| doi_str_mv | 10.1002/ange.201708790 |
| format | Article |
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Klick und ab: Iminosydnone reagieren unter physiologischen Bedingungen ohne Kupferzusatz glatt mit Cycloalkinen zu Klick‐Pyrazolen; als weiteres Produkt entsteht ein Harnstoffderivat. Die Anwendungsmöglichkeiten dieser Reaktion zur Wirkstoff‐Freisetzung und Proteinmarkierung wurden in Beispielexperimenten evaluiert.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201708790</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Bioorthogonale Reaktionen ; Chemische Biologie ; Chemistry ; Design modifications ; Drug delivery systems ; Fishing ; Klick-Chemie ; Mesoionische Verbindungen ; Proteins ; Spaltungsreaktionen</subject><ispartof>Angewandte Chemie, 2017-12, Vol.129 (49), p.15818-15822</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1620-5c402b120570935f8d524c51868cf50a165f1c0f770be142732deb188e8b67d73</citedby><cites>FETCH-LOGICAL-c1620-5c402b120570935f8d524c51868cf50a165f1c0f770be142732deb188e8b67d73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201708790$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201708790$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Bernard, Sabrina</creatorcontrib><creatorcontrib>Audisio, Davide</creatorcontrib><creatorcontrib>Riomet, Margaux</creatorcontrib><creatorcontrib>Bregant, Sarah</creatorcontrib><creatorcontrib>Sallustrau, Antoine</creatorcontrib><creatorcontrib>Plougastel, Lucie</creatorcontrib><creatorcontrib>Decuypere, Elodie</creatorcontrib><creatorcontrib>Gabillet, Sandra</creatorcontrib><creatorcontrib>Kumar, Ramar Arun</creatorcontrib><creatorcontrib>Elyian, Jijy</creatorcontrib><creatorcontrib>Trinh, Minh Nguyet</creatorcontrib><creatorcontrib>Koniev, Oleksandr</creatorcontrib><creatorcontrib>Wagner, Alain</creatorcontrib><creatorcontrib>Kolodych, Sergii</creatorcontrib><creatorcontrib>Taran, Frédéric</creatorcontrib><title>Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes</title><title>Angewandte Chemie</title><description>We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target‐fishing applications. This click‐and‐release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.
Klick und ab: Iminosydnone reagieren unter physiologischen Bedingungen ohne Kupferzusatz glatt mit Cycloalkinen zu Klick‐Pyrazolen; als weiteres Produkt entsteht ein Harnstoffderivat. Die Anwendungsmöglichkeiten dieser Reaktion zur Wirkstoff‐Freisetzung und Proteinmarkierung wurden in Beispielexperimenten evaluiert.</description><subject>Alkynes</subject><subject>Bioorthogonale Reaktionen</subject><subject>Chemische Biologie</subject><subject>Chemistry</subject><subject>Design modifications</subject><subject>Drug delivery systems</subject><subject>Fishing</subject><subject>Klick-Chemie</subject><subject>Mesoionische Verbindungen</subject><subject>Proteins</subject><subject>Spaltungsreaktionen</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkMFLwzAUxoMoOKdXzwXPne-lSZMeZ5lzOBREzyFN0y1b18ymMvrf2zHRo6cPHt_v4_Ej5BZhggD0XjcrO6GAAqTI4IyMkFOME8HFORkBMBZLyrJLchXCBgBSKrIReX5w3rfd2q98o-sor53ZRropozdbWx3skNp0zjeRr6LFzjU-9GXjGxuig-vWUd6b2ut62w-Xa3JR6TrYm58ck4_H2Xv-FC9f54t8uowNphRibhjQAilwAVnCK1lyygxHmUpTcdCY8goNVEJAYZFRkdDSFiillUUqSpGMyd1pd9_6zy8bOrXxX-3wflCYpZJBisiG1uTUMq0PobWV2rdup9teIaijMHUUpn6FDUB2Ag6utv0_bTV9mc_-2G9JGG5L</recordid><startdate>20171204</startdate><enddate>20171204</enddate><creator>Bernard, Sabrina</creator><creator>Audisio, Davide</creator><creator>Riomet, Margaux</creator><creator>Bregant, Sarah</creator><creator>Sallustrau, Antoine</creator><creator>Plougastel, Lucie</creator><creator>Decuypere, Elodie</creator><creator>Gabillet, Sandra</creator><creator>Kumar, Ramar Arun</creator><creator>Elyian, Jijy</creator><creator>Trinh, Minh Nguyet</creator><creator>Koniev, Oleksandr</creator><creator>Wagner, Alain</creator><creator>Kolodych, Sergii</creator><creator>Taran, Frédéric</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20171204</creationdate><title>Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes</title><author>Bernard, Sabrina ; Audisio, Davide ; Riomet, Margaux ; Bregant, Sarah ; Sallustrau, Antoine ; Plougastel, Lucie ; Decuypere, Elodie ; Gabillet, Sandra ; Kumar, Ramar Arun ; Elyian, Jijy ; Trinh, Minh Nguyet ; Koniev, Oleksandr ; Wagner, Alain ; Kolodych, Sergii ; Taran, Frédéric</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1620-5c402b120570935f8d524c51868cf50a165f1c0f770be142732deb188e8b67d73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkynes</topic><topic>Bioorthogonale Reaktionen</topic><topic>Chemische Biologie</topic><topic>Chemistry</topic><topic>Design modifications</topic><topic>Drug delivery systems</topic><topic>Fishing</topic><topic>Klick-Chemie</topic><topic>Mesoionische Verbindungen</topic><topic>Proteins</topic><topic>Spaltungsreaktionen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bernard, Sabrina</creatorcontrib><creatorcontrib>Audisio, Davide</creatorcontrib><creatorcontrib>Riomet, Margaux</creatorcontrib><creatorcontrib>Bregant, Sarah</creatorcontrib><creatorcontrib>Sallustrau, Antoine</creatorcontrib><creatorcontrib>Plougastel, Lucie</creatorcontrib><creatorcontrib>Decuypere, Elodie</creatorcontrib><creatorcontrib>Gabillet, Sandra</creatorcontrib><creatorcontrib>Kumar, Ramar Arun</creatorcontrib><creatorcontrib>Elyian, Jijy</creatorcontrib><creatorcontrib>Trinh, Minh Nguyet</creatorcontrib><creatorcontrib>Koniev, Oleksandr</creatorcontrib><creatorcontrib>Wagner, Alain</creatorcontrib><creatorcontrib>Kolodych, Sergii</creatorcontrib><creatorcontrib>Taran, Frédéric</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bernard, Sabrina</au><au>Audisio, Davide</au><au>Riomet, Margaux</au><au>Bregant, Sarah</au><au>Sallustrau, Antoine</au><au>Plougastel, Lucie</au><au>Decuypere, Elodie</au><au>Gabillet, Sandra</au><au>Kumar, Ramar Arun</au><au>Elyian, Jijy</au><au>Trinh, Minh Nguyet</au><au>Koniev, Oleksandr</au><au>Wagner, Alain</au><au>Kolodych, Sergii</au><au>Taran, Frédéric</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes</atitle><jtitle>Angewandte Chemie</jtitle><date>2017-12-04</date><risdate>2017</risdate><volume>129</volume><issue>49</issue><spage>15818</spage><epage>15822</epage><pages>15818-15822</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target‐fishing applications. This click‐and‐release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.
Klick und ab: Iminosydnone reagieren unter physiologischen Bedingungen ohne Kupferzusatz glatt mit Cycloalkinen zu Klick‐Pyrazolen; als weiteres Produkt entsteht ein Harnstoffderivat. Die Anwendungsmöglichkeiten dieser Reaktion zur Wirkstoff‐Freisetzung und Proteinmarkierung wurden in Beispielexperimenten evaluiert.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201708790</doi><tpages>5</tpages></addata></record> |
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| subjects | Alkynes Bioorthogonale Reaktionen Chemische Biologie Chemistry Design modifications Drug delivery systems Fishing Klick-Chemie Mesoionische Verbindungen Proteins Spaltungsreaktionen |
| title | Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes |
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