Post-radiolabeling thioether oxidation to enhance the bioorthogonal reactivity of 18F-tetrazines
Radiolabeled 1,2,4,5-tetrazines are powerful heterocyclic agents for bioorthogonal PET imaging due to their fast cycloaddition with trans -cyclooctenes. However, fluorine-18 radiolabeling of highly reactive tetrazines is often not feasible due to limited compound stability. We demonstrate that post-...
Gespeichert in:
| Veröffentlicht in: | Monatshefte für Chemie 2023-12, Vol.154 (12), p.1441-1457 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1457 |
|---|---|
| container_issue | 12 |
| container_start_page | 1441 |
| container_title | Monatshefte für Chemie |
| container_volume | 154 |
| creator | Wilkovitsch, Martin Svatunek, Dennis Mikula, Hannes Denk, Christoph |
| description | Radiolabeled 1,2,4,5-tetrazines are powerful heterocyclic agents for bioorthogonal PET imaging due to their fast cycloaddition with
trans
-cyclooctenes. However, fluorine-18 radiolabeling of highly reactive tetrazines is often not feasible due to limited compound stability. We demonstrate that post-radiolabeling oxidation of thioether functionalities is a viable and transferable strategy to avoid these limitations, enabling the synthesis of highly reactive
18
F-tetrazines.
Graphical abstract |
| doi_str_mv | 10.1007/s00706-023-03140-w |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2892980298</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2892980298</sourcerecordid><originalsourceid>FETCH-LOGICAL-c293t-d70f4c0556b44b4d6fc173ce84c6e78f9a2698e774d925bbfab5885aa0c0b6d33</originalsourceid><addsrcrecordid>eNp9kEFLAzEQhYMoWKt_wNOC5-hskt1kj1KsCgU96Dkm2Ww3Zd3UJLXWX2-0gjcPM8Mw7z2GD6HzEi5LAH4Vc4MaA6EYaMkAbw_QpGSUYcZ4dYgmAKTGDWH8GJ3EuIK8M6AT9PLoY8JBtc4PStvBjcsi9c7b1NtQ-A_XquT8WCRf2LFXo7H5bAvtvA-p90s_qqEIVpnk3l3aFb4rSjHHyaagPt1o4yk66tQQ7dnvnKLn-c3T7A4vHm7vZ9cLbEhDE245dMxAVdWaMc3aujMlp8YKZmrLRdcoUjfCcs7ahlRad0pXQlRKgQFdt5RO0cU-dx3828bGJFd-E_J3URLRkEZArqwie5UJPsZgO7kO7lWFnSxBfpOUe5Iyk5Q_JOU2m-jeFLN4XNrwF_2P6wscVniX</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2892980298</pqid></control><display><type>article</type><title>Post-radiolabeling thioether oxidation to enhance the bioorthogonal reactivity of 18F-tetrazines</title><source>SpringerLink Journals - AutoHoldings</source><creator>Wilkovitsch, Martin ; Svatunek, Dennis ; Mikula, Hannes ; Denk, Christoph</creator><creatorcontrib>Wilkovitsch, Martin ; Svatunek, Dennis ; Mikula, Hannes ; Denk, Christoph</creatorcontrib><description>Radiolabeled 1,2,4,5-tetrazines are powerful heterocyclic agents for bioorthogonal PET imaging due to their fast cycloaddition with
trans
-cyclooctenes. However, fluorine-18 radiolabeling of highly reactive tetrazines is often not feasible due to limited compound stability. We demonstrate that post-radiolabeling oxidation of thioether functionalities is a viable and transferable strategy to avoid these limitations, enabling the synthesis of highly reactive
18
F-tetrazines.
Graphical abstract</description><identifier>ISSN: 0026-9247</identifier><identifier>EISSN: 1434-4475</identifier><identifier>DOI: 10.1007/s00706-023-03140-w</identifier><language>eng</language><publisher>Vienna: Springer Vienna</publisher><subject>Analytical Chemistry ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Cycloaddition ; Fluorine ; Fluorine isotopes ; Inorganic Chemistry ; Organic Chemistry ; Original Paper ; Oxidation ; Physical Chemistry ; Positron emission ; Radiolabelling ; Theoretical and Computational Chemistry</subject><ispartof>Monatshefte für Chemie, 2023-12, Vol.154 (12), p.1441-1457</ispartof><rights>The Author(s) 2023</rights><rights>The Author(s) 2023. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c293t-d70f4c0556b44b4d6fc173ce84c6e78f9a2698e774d925bbfab5885aa0c0b6d33</citedby><cites>FETCH-LOGICAL-c293t-d70f4c0556b44b4d6fc173ce84c6e78f9a2698e774d925bbfab5885aa0c0b6d33</cites><orcidid>0000-0002-9218-9722 ; 0000-0002-2328-542X ; 0000-0002-6809-6972 ; 0000-0003-1101-2376</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00706-023-03140-w$$EPDF$$P50$$Gspringer$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00706-023-03140-w$$EHTML$$P50$$Gspringer$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Wilkovitsch, Martin</creatorcontrib><creatorcontrib>Svatunek, Dennis</creatorcontrib><creatorcontrib>Mikula, Hannes</creatorcontrib><creatorcontrib>Denk, Christoph</creatorcontrib><title>Post-radiolabeling thioether oxidation to enhance the bioorthogonal reactivity of 18F-tetrazines</title><title>Monatshefte für Chemie</title><addtitle>Monatsh Chem</addtitle><description>Radiolabeled 1,2,4,5-tetrazines are powerful heterocyclic agents for bioorthogonal PET imaging due to their fast cycloaddition with
trans
-cyclooctenes. However, fluorine-18 radiolabeling of highly reactive tetrazines is often not feasible due to limited compound stability. We demonstrate that post-radiolabeling oxidation of thioether functionalities is a viable and transferable strategy to avoid these limitations, enabling the synthesis of highly reactive
18
F-tetrazines.
Graphical abstract</description><subject>Analytical Chemistry</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Cycloaddition</subject><subject>Fluorine</subject><subject>Fluorine isotopes</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Oxidation</subject><subject>Physical Chemistry</subject><subject>Positron emission</subject><subject>Radiolabelling</subject><subject>Theoretical and Computational Chemistry</subject><issn>0026-9247</issn><issn>1434-4475</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>C6C</sourceid><recordid>eNp9kEFLAzEQhYMoWKt_wNOC5-hskt1kj1KsCgU96Dkm2Ww3Zd3UJLXWX2-0gjcPM8Mw7z2GD6HzEi5LAH4Vc4MaA6EYaMkAbw_QpGSUYcZ4dYgmAKTGDWH8GJ3EuIK8M6AT9PLoY8JBtc4PStvBjcsi9c7b1NtQ-A_XquT8WCRf2LFXo7H5bAvtvA-p90s_qqEIVpnk3l3aFb4rSjHHyaagPt1o4yk66tQQ7dnvnKLn-c3T7A4vHm7vZ9cLbEhDE245dMxAVdWaMc3aujMlp8YKZmrLRdcoUjfCcs7ahlRad0pXQlRKgQFdt5RO0cU-dx3828bGJFd-E_J3URLRkEZArqwie5UJPsZgO7kO7lWFnSxBfpOUe5Iyk5Q_JOU2m-jeFLN4XNrwF_2P6wscVniX</recordid><startdate>20231201</startdate><enddate>20231201</enddate><creator>Wilkovitsch, Martin</creator><creator>Svatunek, Dennis</creator><creator>Mikula, Hannes</creator><creator>Denk, Christoph</creator><general>Springer Vienna</general><general>Springer Nature B.V</general><scope>C6C</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-9218-9722</orcidid><orcidid>https://orcid.org/0000-0002-2328-542X</orcidid><orcidid>https://orcid.org/0000-0002-6809-6972</orcidid><orcidid>https://orcid.org/0000-0003-1101-2376</orcidid></search><sort><creationdate>20231201</creationdate><title>Post-radiolabeling thioether oxidation to enhance the bioorthogonal reactivity of 18F-tetrazines</title><author>Wilkovitsch, Martin ; Svatunek, Dennis ; Mikula, Hannes ; Denk, Christoph</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c293t-d70f4c0556b44b4d6fc173ce84c6e78f9a2698e774d925bbfab5885aa0c0b6d33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Analytical Chemistry</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Cycloaddition</topic><topic>Fluorine</topic><topic>Fluorine isotopes</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Oxidation</topic><topic>Physical Chemistry</topic><topic>Positron emission</topic><topic>Radiolabelling</topic><topic>Theoretical and Computational Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wilkovitsch, Martin</creatorcontrib><creatorcontrib>Svatunek, Dennis</creatorcontrib><creatorcontrib>Mikula, Hannes</creatorcontrib><creatorcontrib>Denk, Christoph</creatorcontrib><collection>Springer Nature OA Free Journals</collection><collection>CrossRef</collection><jtitle>Monatshefte für Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wilkovitsch, Martin</au><au>Svatunek, Dennis</au><au>Mikula, Hannes</au><au>Denk, Christoph</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Post-radiolabeling thioether oxidation to enhance the bioorthogonal reactivity of 18F-tetrazines</atitle><jtitle>Monatshefte für Chemie</jtitle><stitle>Monatsh Chem</stitle><date>2023-12-01</date><risdate>2023</risdate><volume>154</volume><issue>12</issue><spage>1441</spage><epage>1457</epage><pages>1441-1457</pages><issn>0026-9247</issn><eissn>1434-4475</eissn><abstract>Radiolabeled 1,2,4,5-tetrazines are powerful heterocyclic agents for bioorthogonal PET imaging due to their fast cycloaddition with
trans
-cyclooctenes. However, fluorine-18 radiolabeling of highly reactive tetrazines is often not feasible due to limited compound stability. We demonstrate that post-radiolabeling oxidation of thioether functionalities is a viable and transferable strategy to avoid these limitations, enabling the synthesis of highly reactive
18
F-tetrazines.
Graphical abstract</abstract><cop>Vienna</cop><pub>Springer Vienna</pub><doi>10.1007/s00706-023-03140-w</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0002-9218-9722</orcidid><orcidid>https://orcid.org/0000-0002-2328-542X</orcidid><orcidid>https://orcid.org/0000-0002-6809-6972</orcidid><orcidid>https://orcid.org/0000-0003-1101-2376</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0026-9247 |
| ispartof | Monatshefte für Chemie, 2023-12, Vol.154 (12), p.1441-1457 |
| issn | 0026-9247 1434-4475 |
| language | eng |
| recordid | cdi_proquest_journals_2892980298 |
| source | SpringerLink Journals - AutoHoldings |
| subjects | Analytical Chemistry Chemistry Chemistry and Materials Science Chemistry/Food Science Cycloaddition Fluorine Fluorine isotopes Inorganic Chemistry Organic Chemistry Original Paper Oxidation Physical Chemistry Positron emission Radiolabelling Theoretical and Computational Chemistry |
| title | Post-radiolabeling thioether oxidation to enhance the bioorthogonal reactivity of 18F-tetrazines |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T01%3A02%3A31IST&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=Post-radiolabeling%20thioether%20oxidation%20to%20enhance%20the%20bioorthogonal%20reactivity%20of%2018F-tetrazines&rft.jtitle=Monatshefte%20f%C3%BCr%20Chemie&rft.au=Wilkovitsch,%20Martin&rft.date=2023-12-01&rft.volume=154&rft.issue=12&rft.spage=1441&rft.epage=1457&rft.pages=1441-1457&rft.issn=0026-9247&rft.eissn=1434-4475&rft_id=info:doi/10.1007/s00706-023-03140-w&rft_dat=%3Cproquest_cross%3E2892980298%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=2892980298&rft_id=info:pmid/&rfr_iscdi=true |