Tetrazine-trans-cyclooctene ligation for the rapid construction of integrin αvβ3 targeted PET tracer based on a cyclic RGD peptide
| Autor: | Peter S. Conti, Shuanglong Liu, Ryan Park, Chiun Wei Huang, Li Peng Yap, Ramajeyam Selvaraj, Joseph M. Fox, Zibo Li, Matthew Hassink |
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| Rok vydání: | 2011 |
| Předmět: |
Biodistribution
Stereochemistry Transplantation Heterologous Clinical Biochemistry Mice Nude Tetrazoles Pharmaceutical Science Biochemistry Article Catalysis Cell Line Cyclooctanes Mice Tetrazine chemistry.chemical_compound Drug Discovery Animals Radiometry Molecular Biology Chromatography High Pressure Liquid chemistry.chemical_classification Integrin alphaVbeta3 Bioconjugation Organic Chemistry Neoplasms Experimental Cyclic peptide Transplantation Kinetics chemistry Positron-Emission Tomography Biophysics Molecular Medicine Female Chemical ligation Oligopeptides Conjugate |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 21:5011-5014 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2011.04.116 |
| Popis: | Labeling biomolecules with (18)F is usually done through coupling with prosthetic groups, which generally requires several time-consuming radiosynthetic steps resulting in low labeling yield. Recently, the tetrazine-trans-cyclooctene ligation has been introduced as a method of bioconjugation that proceeds with fast reaction rates without need for catalysis. Herein, we report the development of an extremely fast and efficient method for generating (18)F labeled probes based on the tetrazine-trans-cyclooctene ligation. Starting with only 30 μg (78 μM) of a tetrazine-RGD conjugate and 2 mCi (5 μM) of (18)F-trans-cyclooctene, the (18)F labeled RGD peptide could be obtained in more than 90% yield within five minutes. The (18)F labeled RGD peptide demonstrated prominent tumor uptake in vivo. The receptor specificity was confirmed by blocking experiments. These results successfully demonstrate that the tetrazine-trans-cyclooctene ligation serves as an efficient labeling method for PET probe construction. |
| Databáze: | OpenAIRE |
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