Site-selective radiolabeling of peptides by (18)F-fluorobenzoylation with [(18F)]SFB in solution and on solid phase: a comparative study
Research output: Contribution to journal › Research article › Contributed › peer-review
Contributors
Abstract
Peptides labeled with short-lived positron-emitting radionuclides are of outstanding interest as probes for molecular imaging by positron emission tomography (PET). Herein, the site-selective incorporation of fluorine-18 into lysine-containing peptides using the prosthetic labeling agent N-succinimidyl 4-[(18)F]fluorobenzoate ([(18)F]SFB) is described. The reaction of [(18)F]SFB with four biologically relevant resin-bound peptides was studied and optimized. For comparison, each peptide was 18F-fluorobenzoylated in solution under different conditions and the product distribution was analyzed confirming the advantages of the solid-phase approach. The method's feasibility for selective radiolabeling either at the N-terminus or at the lysine side chain was demonstrated. Labeling on solid phase with [(18)F]SFB resulted in crude (18)F-fluorobenzoylpeptides whose radiochemical purities were typically greater than 90% and that could be prepared in synthesis times from 65 to 76 min.
Details
Original language | English |
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Pages (from-to) | 1431-1443 |
Number of pages | 13 |
Journal | Amino acids |
Volume | 43 |
Issue number | 4 |
Publication status | Published - Oct 2012 |
Peer-reviewed | Yes |
Externally published | Yes |
External IDs
Scopus | 84867574516 |
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ORCID | /0000-0002-6432-5694/work/146644247 |
Keywords
Keywords
- Benzoates/chemistry, Fluorine Radioisotopes/chemistry, Humans, Immobilized Proteins/chemistry, Isotope Labeling/methods, Lysine/chemistry, Peptides/chemistry, Positron-Emission Tomography, Radiopharmaceuticals/chemical synthesis, Solid-Phase Synthesis Techniques/methods, Solutions, Succinimides/chemistry