Development of the First Aliphatic F-18-Labeled Tetrazine Suitable for Pretargeted PET Imaging.Expanding the Bioorthogonal Tool Box

Pretargeted imaging of nanomedicines have attracted considerable interest because it has the potential to increase imaging contrast while reducing radiation burden to healthy tissue. Currently, the tetrazine ligation is the fastest bioorthogonal reaction for this strategy and, consequently, the stat...

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Published inJournal of medicinal chemistry Vol. 64; no. 20; pp. 15297 - 15312
Main Authors Battisti, Umberto M., Bratteby, Klas, Jorgensen, Jesper T., Hvass, Lars, Shalgunov, Vladimir, Mikula, Hannes, Kjaer, Andreas, Herth, Matthias Manfred
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 28.10.2021
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Abstract Pretargeted imaging of nanomedicines have attracted considerable interest because it has the potential to increase imaging contrast while reducing radiation burden to healthy tissue. Currently, the tetrazine ligation is the fastest bioorthogonal reaction for this strategy and, consequently, the state-of-art choice for in vivo chemistry. We have recently identified key properties for tetrazines in pretargeting. We have also developed a method to F-18-label reactive tetrazines using an aliphatic nucleophilic substitution strategy. Here, we combined this knowledge and developed an F-18-labeled tetrazine for pretargeted imaging. In order to develop this ligand, a small SAR study was performed. The most promising compound was selected for labeling and subsequent positronemission-tomography in vivo imaging. Radiolabeling was achieved in satisfactory yields, molar activities, and high radiochemical purities. [F-18]15 displayed favorable pharmacokinetics and remarkable target-to-background ratios.as early as 1 h post injection. We believe that this agent could be a promising candidate for translation into clinical studies.
AbstractList Pretargeted imaging of nanomedicines have attracted considerable interest because it has the potential to increase imaging contrast while reducing radiation burden to healthy tissue. Currently, the tetrazine ligation is the fastest bioorthogonal reaction for this strategy and, consequently, the state-of-art choice for in vivo chemistry. We have recently identified key properties for tetrazines in pretargeting. We have also developed a method to F-18-label reactive tetrazines using an aliphatic nucleophilic substitution strategy. Here, we combined this knowledge and developed an F-18-labeled tetrazine for pretargeted imaging. In order to develop this ligand, a small SAR study was performed. The most promising compound was selected for labeling and subsequent positronemission-tomography in vivo imaging. Radiolabeling was achieved in satisfactory yields, molar activities, and high radiochemical purities. [F-18]15 displayed favorable pharmacokinetics and remarkable target-to-background ratios.as early as 1 h post injection. We believe that this agent could be a promising candidate for translation into clinical studies.
Author Mikula, Hannes
Jorgensen, Jesper T.
Shalgunov, Vladimir
Hvass, Lars
Battisti, Umberto M.
Herth, Matthias Manfred
Kjaer, Andreas
Bratteby, Klas
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  start-page: 3375
  year: 2010
  ident: WOS:000277656100024
  article-title: In Vivo Chemistry for Pretargeted Tumor Imaging in Live Mice
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200906294
  contributor:
    fullname: Rossin, R
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Snippet Pretargeted imaging of nanomedicines have attracted considerable interest because it has the potential to increase imaging contrast while reducing radiation...
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StartPage 15297
SubjectTerms Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Science & Technology
Title Development of the First Aliphatic F-18-Labeled Tetrazine Suitable for Pretargeted PET Imaging.Expanding the Bioorthogonal Tool Box
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