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-...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 R<sub>f</sub> = 6.4 min;FBAMPy R<sub>f</sub> = 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.展开更多
Peptides have an important role in organism and its high quantity present in tumors leading to development of radiolabeled peptides for tumor-specific imaging. Once the traditional methodologies used for radiofluorina...Peptides have an important role in organism and its high quantity present in tumors leading to development of radiolabeled peptides for tumor-specific imaging. Once the traditional methodologies used for radiofluorination do not work with peptides, due to their harsh conditions, other radiolabeling strategies had to be developed to supply the need. Direct radiofluorination is either an inefficient method, and the use of bidirectional groups, or prosthetic groups, is needed to enable the binding between the radionuclide fluorine-18 and a peptide functionalized. New peptides radiolabeling strategies have been developed sourcing increase the synthesis yield, its chemoselectivity, and the binding stability, and reduce the total process time and the number of steps required. The progress of radiofluorination methodologies led to development of the amidation, acylation, imidation, and alkylation techniques, the use of thiol groups, photochemical conjugation, chemoselective reactions, and “click chemistry”, in addition to use of FDG molecule and heteroatoms as linkers. This paper presents the main strategies used for peptides radiofluorination, presenting their positive and negative points, and the prosthetic groups most used in each method.展开更多
文摘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 R<sub>f</sub> = 6.4 min;FBAMPy R<sub>f</sub> = 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.
文摘Peptides have an important role in organism and its high quantity present in tumors leading to development of radiolabeled peptides for tumor-specific imaging. Once the traditional methodologies used for radiofluorination do not work with peptides, due to their harsh conditions, other radiolabeling strategies had to be developed to supply the need. Direct radiofluorination is either an inefficient method, and the use of bidirectional groups, or prosthetic groups, is needed to enable the binding between the radionuclide fluorine-18 and a peptide functionalized. New peptides radiolabeling strategies have been developed sourcing increase the synthesis yield, its chemoselectivity, and the binding stability, and reduce the total process time and the number of steps required. The progress of radiofluorination methodologies led to development of the amidation, acylation, imidation, and alkylation techniques, the use of thiol groups, photochemical conjugation, chemoselective reactions, and “click chemistry”, in addition to use of FDG molecule and heteroatoms as linkers. This paper presents the main strategies used for peptides radiofluorination, presenting their positive and negative points, and the prosthetic groups most used in each method.
