In:
ChemBioChem, Wiley, Vol. 23, No. 23 ( 2022-12-05)
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
1439-4227
,
1439-7633
DOI:
10.1002/cbic.202200539
Language:
English
Publisher:
Wiley
Publication Date:
2022
detail.hit.zdb_id:
2020469-3
SSG:
12
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