Abstract
A novel thiol-reactive bifunctional agent, an analogue of fluorobenzaldehyde-O-[6-(2,5-dioxo-2,5- dihydro-pyrrol-1-yl)-hexyl]oxime, (FBAM) has been synthesized. The new prosthetic group, [18F]- FBAMPy, replaces the 4-fluorophenyl moiety with a 2-fluoropyridinyl moiety leading to increased polarity (FBAM analytical HPLC Rf = 6.4 min; FBAMPy Rf = 4.8 min) while retaining the sulfur-reactive pendant. By altering the polarity of the molecule, this new prosthetic group should have significant impact in coupling it with small peptides and other biomolecules.
Highlights
Biomolecules are increasingly useful in the diagnosis of disease due to their known interactions in vivo
Diseases can be diagnosed or located by employing antibodies or antibody fragments that have been radiolabeled in combination with positron emission tomography (PET) [1]
This work combines the six carbon chain heterobifunctional linker used in the synthesis of [18F]FBAM with a pyridine moiety to create a new molecule, [18F]FBAMPy (1), for the radiochemist’s repertoire of prosthetic groups which may provide an alternative to [18F]FBAM in cases where the lipophilicity of [18F]FBAM leads to poor results
Summary
Biomolecules are increasingly useful in the diagnosis of disease due to their known interactions in vivo. Diseases can be diagnosed or located by employing antibodies or antibody fragments that have been radiolabeled in combination with positron emission tomography (PET) [1] Labeling biomolecules such as peptides presents difficulties due to the number and diversity of the functional groups present. Prosthetic groups, called bifunctional labeling agents, are small organic molecules that can be radiolabeled and conjugated to sensitive biomolecules under very mild conditions. Amines are the most abundantly available functional groups in peptides or proteins and so they are commonly used to conjugate small 18F-labeled bifunctional agents. This work combines the six carbon chain heterobifunctional linker used in the synthesis of [18F]FBAM with a pyridine moiety to create a new molecule, [18F]FBAMPy (1), for the radiochemist’s repertoire of prosthetic groups which may provide an alternative to [18F]FBAM in cases where the lipophilicity of [18F]FBAM leads to poor results
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