Synthesis of 1-[11c]methylpiperidin-4-yl propionate ([11c]pmp) for in vivo measurements of acetylcholinesterase activity
| Autor: | Scott E. Snyder, David E. Kuhl, Michael R. Kilbourn, Douglas M. Jewett, Thinh B. Nguyen, Louis Tluczek |
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| Rok vydání: | 1998 |
| Předmět: |
Cancer Research
Carbamate Stereochemistry medicine.medical_treatment High-performance liquid chromatography Catalysis Acylation chemistry.chemical_compound medicine Humans Radiology Nuclear Medicine and imaging Carbon Radioisotopes Chromatography High Pressure Liquid Methyl trifluoromethanesulfonate Mesylates chemistry.chemical_classification Brain Total synthesis Dimethylformamide chemistry Isotope Labeling Acetylcholinesterase Propionate Molecular Medicine Amine gas treating Hydrogenation Propionates Radiopharmaceuticals Tomography Emission-Computed Nuclear chemistry |
| Zdroj: | Nuclear Medicine and Biology. 25:751-754 |
| ISSN: | 0969-8051 |
| DOI: | 10.1016/s0969-8051(98)00045-6 |
| Popis: | Synthesis of 1-[ 11 C]methylpiperidin-4-yl propionate ([ 11 C]PMP), an in vivo substrate for acetylcholinesterase, is reported. An improved preparation of 4-piperidinyl propionate (PHP), the immediate precursor for radiolabeling, was accomplished in three steps from 4-hydroxypiperidine by (a) protection of the amine as the benzyl carbamate, (b) acylation with propionyl chloride, and (c) deprotection of the carbamate by catalytic hydrogenation. The final product was obtained in an overall 82% yield. Reaction of the free base form of PHP with [ 11 C]methyl trifluoromethanesulfonate at room temperature in N,N -dimethylformamide, followed by high performance liquid chromatography (HPLC) purification, provided [ 11 C]PMP in 57% radiochemical yield, >99% radiochemical purity, and >1500 Ci/mmol at the end of synthesis. The total synthesis time from end-of-bombardment was 35 min. [ 11 C]PMP can thus be reliably prepared for routine clinical studies of acetylcholinesterase in human brain using positron emission tomography. |
| Databáze: | OpenAIRE |
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