ArticleTheranostics2016
Conformationally Strained trans-Cyclooctene (sTCO) Enables the Rapid Construction of (18)F-PET Probes via Tetrazine Ligation.
Article in Theranostics, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed.
- Biological Evaluation of Molecular Spherical Nucleic Acids: Targeting Tumors via a Hybridization-Based Folate Decoration.ACS omega · 2025Article
- Trans-cyclooctene-a Swiss army knife for bioorthogonal chemistry: exploring the synthesis, reactivity, and applications in biomedical breakthroughs.EJNMMI radiopharmacy and chemistry · 2024Review
- Development ofChemical communications (Cambridge, England) · 2023Article
- Click Chemistry and Radiochemistry: An Update.Bioconjugate chemistry · 2023Review
- Characterization of Structurally DiverseACS omega · 2023Article
- Readily Accessible Strained Difunctionalized trans-Cyclooctenes with Fast Click and Release Capabilities.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- The role of radiolabeling in BNCT tracers for enhanced dosimetry and treatment planning.Theranostics · 2023Review
- Matrix Adhesiveness Regulates Myofibroblast Differentiation from Vocal Fold Fibroblasts in a Bio-orthogonally Cross-linked Hydrogel.ACS applied materials & interfaces · 2022Article
- OrganometallicBioconjugate chemistry · 2022Article
- Synthesis and Luminescent Properties ofMolecules (Basel, Switzerland) · 2022Article
- Novel ConjugatedMolecules (Basel, Switzerland) · 2022Article
- Origin of Increased Reactivity in Rhenium-Mediated Cycloadditions of Tetrazines.The Journal of organic chemistry · 2021Article
- IEDDA: An Attractive Bioorthogonal Reaction for Biomedical Applications.Molecules (Basel, Switzerland) · 2021Review
- Ultrafast Photoclick Reaction for SelectiveJournal of the American Chemical Society · 2021Article
- Synthesis and Evaluation of Novel Ring-Strained Noncanonical Amino Acids for Residue-Specific Bioorthogonal Reactions in Living Cells.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- A Cleavable CJournal of the American Chemical Society · 2020Article
- Metabolism of a Bioorthogonal PET Tracer Candidate [Molecular pharmaceutics · 2020Article
- Development of Antibody Immuno-PET/SPECT Radiopharmaceuticals for Imaging of Oncological Disorders-An Update.Cancers · 2020Review
- Improving Tumor-to-Background Contrast through Hydrophilic Tetrazines: The Construction ofChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Preclinical Evaluation of a NovelACS omega · 2020Article
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10 authors.
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Abstract
The bioorthogonal reaction between tetrazines and trans-cyclooctenes is a method for the rapid construction of F-18 probes for PET imaging. Described here is a second generation (18)F-labeling system based on a conformationally strained trans-cyclooctene (sTCO)-a dienophile that is approximately 2 orders of magnitude more reactive than conventional TCO dienophiles. Starting from a readily prepared tosylate precursor, an (18)F labeled sTCO derivative ((18)F-sTCO) could be synthesized in 29.3 +/- 5.1% isolated yield and with high specific activity. Tetrazine ligation was carried out with a cyclic RGD-conjugate of a diphenyl-s-tetrazine analogue (RGD-Tz) chosen from a diene class with an excellent combination of fast reactivity and stability both for the diene as well as the Diels-Alder adduct. For both the tetrazine and the sTCO, mini-PEG spacers were included to enhance solubility and improve the in vivo distribution profile of the resulting probe. Extremely fast reactivity (up to 2.86 x 10(5) M(-1)s(-1) at 25 °C in water) has been observed in kinetic studies in the reaction of sTCO with diphenyl-s-tetrazine derivatives. A kinetic study on sTCO diastereomers in 55:45 MeOH:water showed that the syn-diastereomer displayed slightly faster reactivity than the anti-diastereomer. An (18)F-sTCO conjugate with RGD-Tz demonstrated prominent and persistent tumor uptake in vivo with good tumor-to-background contrast. Unlike most radiolabeled RGD peptides, the tumor uptake of this PET agent increased from 5.3 +/- 0.2% ID/g at 1 h post injection (p.i.), to 8.9 +/- 0.5% ID/g at 4 h p.i., providing evidence for prolonged blood circulation. These findings suggest that tetrazine ligations employing (18)F-sTCO should serve as a powerful and general platform for the rapid construction of peptide or protein derived PET agents.
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