2. Academic Validation
  3. Synthesis and radiolabeling of a polar [125 I]I-1,2,4,5-tetrazine

Synthesis and radiolabeling of a polar [125 I]I-1,2,4,5-tetrazine

  • J Labelled Comp Radiopharm. 2023 Jan;66(1):22-30. doi: 10.1002/jlcr.4009.
Natasha Bidesi 1,  Vladimir Shalgunov 1 2,  Umberto Maria Battisti 1,  Lars Hvass 3,  Jesper Tranekjaer Jørgensen 3,  Christian B M Poulie 1,  Andreas I Jensen 4,  Andreas Kjaer 3,  Matthias M Herth 1 2
Affiliations

Affiliations

  • 1 Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Copenhagen, Denmark.
  • 2 Department of Clinical Physiology, Nuclear Medicine and PET, Rigshospitalet, Copenhagen, Denmark.
  • 3 Department of Clinical Physiology, Nuclear Medicine and PET & Cluster for Molecular Imaging, Copenhagen University Hospital - Rigshospitalet & Department of Biomedical Sciences, University of Copenhagen, Copenhagen, Denmark.
  • 4 Center for Nuclear Technologies (DTU Nutech), Technical University of Denmark (DTU), Roskilde, Denmark.
PMID: 36539610 DOI: 10.1002/jlcr.4009
Abstract

Pretargeting imaging has gained a lot of prominence, due to its excellent bioorthogonality and improved imaging contrast compared to conventional imaging. A new iodo tetrazine (Tz) derivative has been synthesized and further developed into the corresponding iodine-125 (125 I) analog (12), via the trimethylstannane precursor. Radiolabeling with either N-chlorosuccinimide or chloramine-T, in either MeCN or MeOH proceeded with a radiochemical conversion (RCC) of >80%. Subsequent deprotection only proved successful, among the tested conditions, when the radiolabeled Tz was stirred in 6-M HCl(aq.) at 60°C for 2.5 h. To the best of our knowledge, this is the first H-tetrazine labeled with iodine. In vivo investigations on the pretargeting ability of 12 are currently under way.

Keywords

bioorthogonal; click chemistry; idodine-125; pretargeting; tetrazine.

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