Development of the First Tritiated Tetrazine: Facilitating Tritiation of Proteins
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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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.
I: ChemBioChem, Bind 23, Nr. 23, e202200539, 2022.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Development of the First Tritiated Tetrazine
T2 - Facilitating Tritiation of Proteins
AU - Radjani Bidesi, Natasha Shalina
AU - Battisti, Umberto Maria
AU - Lopes van de Broek, Sara
AU - Shalgunov, Vladimir
AU - Dall, Anne-Mette
AU - Bøggild Kristensen, Jesper
AU - Sehlin, Dag
AU - Syvänen, Stina
AU - Moos Knudsen, Gitte
AU - Herth, Matthias Manfred
N1 - © 2022 The Authors. ChemBioChem published by Wiley-VCH GmbH.
PY - 2022
Y1 - 2022
N2 - 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.
AB - 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.
U2 - 10.1002/cbic.202200539
DO - 10.1002/cbic.202200539
M3 - Journal article
C2 - 36333105
VL - 23
JO - ChemBioChem
JF - ChemBioChem
SN - 1439-4227
IS - 23
M1 - e202200539
ER -
ID: 325102102