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Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins
Tetrazine (Tz)–trans‐cyclooctene (TCO) ligation is an ultra‐fast and highly selective reaction and it is particularly suited to label biomolecules under physiological conditions. As such, a (3)H‐Tz based synthon would have wide applications for in vitro/ex vivo assays. In this study, we developed a...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10100488/ https://www.ncbi.nlm.nih.gov/pubmed/36333105 http://dx.doi.org/10.1002/cbic.202200539 |
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author | Radjani Bidesi, Natasha Shalina Battisti, Umberto Maria Lopes van de Broek, Sara Shalgunov, Vladimir Dall, Anne‐Mette Bøggild Kristensen, Jesper Sehlin, Dag Syvänen, Stina Moos Knudsen, Gitte Herth, Matthias Manfred |
author_facet | Radjani Bidesi, Natasha Shalina Battisti, Umberto Maria Lopes van de Broek, Sara Shalgunov, Vladimir Dall, Anne‐Mette Bøggild Kristensen, Jesper Sehlin, Dag Syvänen, Stina Moos Knudsen, Gitte Herth, Matthias Manfred |
author_sort | Radjani Bidesi, Natasha Shalina |
collection | PubMed |
description | Tetrazine (Tz)–trans‐cyclooctene (TCO) ligation is an ultra‐fast and highly selective reaction and it is particularly suited to label biomolecules under physiological conditions. As such, a (3)H‐Tz based synthon would have wide applications for in vitro/ex vivo assays. In this study, we developed a (3)H‐labeled Tz and characterized its potential for application to pretargeted autoradiography. Several strategies were explored to synthesize such a Tz. However, classical approaches such as reductive halogenation failed. For this reason, we designed a Tz containing an aldehyde and explored the possibility of reducing this group with NaBT(4). This approach was successful and resulted in [(3)H]‐(4‐(6‐(pyridin‐2‐yl)‐1,2,4,5‐tetrazin‐3‐yl)phenyl)methan‐t‐ol with a radiochemical yield of 22 %, a radiochemical purity of 96 % and a molar activity of 0.437 GBq/μmol (11.8 Ci/mmol). The compound was successfully applied to pretargeted autoradiography. Thus, we report the synthesis of the first (3)H‐labeled Tz and its successful application as a labeling building block. |
format | Online Article Text |
id | pubmed-10100488 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-101004882023-04-14 Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins Radjani Bidesi, Natasha Shalina Battisti, Umberto Maria Lopes van de Broek, Sara Shalgunov, Vladimir Dall, Anne‐Mette Bøggild Kristensen, Jesper Sehlin, Dag Syvänen, Stina Moos Knudsen, Gitte Herth, Matthias Manfred Chembiochem Research Articles Tetrazine (Tz)–trans‐cyclooctene (TCO) ligation is an ultra‐fast and highly selective reaction and it is particularly suited to label biomolecules under physiological conditions. As such, a (3)H‐Tz based synthon would have wide applications for in vitro/ex vivo assays. In this study, we developed a (3)H‐labeled Tz and characterized its potential for application to pretargeted autoradiography. Several strategies were explored to synthesize such a Tz. However, classical approaches such as reductive halogenation failed. For this reason, we designed a Tz containing an aldehyde and explored the possibility of reducing this group with NaBT(4). This approach was successful and resulted in [(3)H]‐(4‐(6‐(pyridin‐2‐yl)‐1,2,4,5‐tetrazin‐3‐yl)phenyl)methan‐t‐ol with a radiochemical yield of 22 %, a radiochemical purity of 96 % and a molar activity of 0.437 GBq/μmol (11.8 Ci/mmol). The compound was successfully applied to pretargeted autoradiography. Thus, we report the synthesis of the first (3)H‐labeled Tz and its successful application as a labeling building block. John Wiley and Sons Inc. 2022-11-04 2022-12-05 /pmc/articles/PMC10100488/ /pubmed/36333105 http://dx.doi.org/10.1002/cbic.202200539 Text en © 2022 The Authors. ChemBioChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Articles Radjani Bidesi, Natasha Shalina Battisti, Umberto Maria Lopes van de Broek, Sara Shalgunov, Vladimir Dall, Anne‐Mette Bøggild Kristensen, Jesper Sehlin, Dag Syvänen, Stina Moos Knudsen, Gitte Herth, Matthias Manfred Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins |
title | Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins |
title_full | Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins |
title_fullStr | Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins |
title_full_unstemmed | Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins |
title_short | Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins |
title_sort | development of the first tritiated tetrazine: facilitating tritiation of proteins |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10100488/ https://www.ncbi.nlm.nih.gov/pubmed/36333105 http://dx.doi.org/10.1002/cbic.202200539 |
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