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Radiosynthesis of O-(1-[18 F]fluoropropan-2-yl)-O-(4-nitrophenyl)methylphosphonate: A novel PET tracer surrogate of sarin
- Source :
- Journal of Labelled Compounds and Radiopharmaceuticals. 61:1089-1094
- Publication Year :
- 2018
- Publisher :
- Wiley, 2018.
-
Abstract
- O-(1-Fluoropropan-2-yl)-O-(4-nitrophenyl) methylphosphonate is a reactive organophosphate ester (OP) developed as a surrogate of the chemical warfare agent sarin that forms a similar covalent adduct at the active site serine of acetylcholinesterase. The radiolabeled O-(1-[18 F]fluoropropan-2-yl)-O-(4-nitrophenyl) methylphosphonate ([18 F] fluorosarin surrogate) has not been previously prepared. In this paper, we report the first radiosynthesis of this tracer from the reaction of bis-(4-nitrophenyl) methylphosphonate with 1-[18 F]fluoro-2-propanol in the presence of DBU. The 1-[18 F]fluoro-2-propanol was prepared by reaction of propylene sulfite with Kryptofix 2.2.2 and [18 F] fluoride ion. The desired tracer O-(1-[18 F]fluoropropan-2-yl)-O-(4-nitrophenyl) methylphosphonate was obtained in a >98% radiochemical purity with a 2.4% ± 0.6% yield (n = 5, 65 minutes from start of synthesis) based on starting [18 F] fluoride ion and a molar activity of 49.9 GBq/μmol (1.349 ± 0.329 Ci/μmol, n = 3). This new facile radiosynthesis routinely affords sufficient quantities of [18 F] fluorosarin surrogate in high radiochemical purity, which will further enable the tracer development as a novel radiolabeled OP acetylcholinesterase inhibitor for assessment of OP modes of action with PET imaging in vivo.
- Subjects :
- 0301 basic medicine
Sarin
biology
Organic Chemistry
Radiosynthesis
Active site
01 natural sciences
Biochemistry
0104 chemical sciences
Analytical Chemistry
Adduct
010404 medicinal & biomolecular chemistry
03 medical and health sciences
chemistry.chemical_compound
030104 developmental biology
Sulfite
chemistry
Covalent bond
Yield (chemistry)
Drug Discovery
biology.protein
Radiology, Nuclear Medicine and imaging
Fluoride
Spectroscopy
Nuclear chemistry
Subjects
Details
- ISSN :
- 03624803
- Volume :
- 61
- Database :
- OpenAIRE
- Journal :
- Journal of Labelled Compounds and Radiopharmaceuticals
- Accession number :
- edsair.doi...........96c14636b0c4c41cac36ad40f7c0dcdf