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Synthesis of 1‐( trans ‐[ 123 I]Iodopropen‐2‐yl)‐4‐(4‐cyanophenoxy‐methyl)piperidine: A selective sigma receptor radioligand for SPECT
Author(s) -
Waterhouse Rikki N.,
Collier T. Lee,
O'Brien Joanne C.
Publication year - 1996
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199603)38:3<215::aid-jlcr834>3.0.co;2-f
Subject(s) - chemistry , radioligand , lipophilicity , sigma receptor , piperidine , ligand (biochemistry) , biodistribution , stereochemistry , chemical synthesis , electrophile , receptor , in vitro , biochemistry , catalysis
1‐( trans ‐[ 123 I]Iodopropen‐2‐yl)‐4‐(4‐cyanophenoxymethyl)piperidine has been prepared as a novel sigma receptor ligand for SPECT. This ligand was found to be selective in vitro for the sigma receptor site (Ki(σ) = 21.7 nM) when tested in a variety of neuroreceptor binding assays. The lipophilicity of this ligand (log P 7.5 = 3.36) is appropriate for good brain uptake and relatively low non‐specific binding. Radioiodination was accomplished using classical electrophilic iododestannylation methods and specific activity of the purified product was >2100 mCi/μmole. Radiochemical yields were 60–80% EOS and radiochemical purities were >99%. The average time of synthesis and purification was 35 minutes.