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Radioiodinated (+)‐4‐[(αR)‐α‐[(2S5R)‐4‐(iodopropen‐2‐yl)‐2,5‐dimethyl‐1‐piperazinyl]‐3‐hydroxybenzyl]‐N,N‐diethylbenzamide: a potential ligand for in vitro and in vivo investigations of δ‐opioid receptors
Author(s) -
Waterhouse Rikki N.,
Campa Michael J.,
Park Jason,
Patz Edward F.
Publication year - 1998
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(1998090)41:9<801::aid-jlcr130>3.0.co;2-c
Subject(s) - chemistry , receptor , in vivo , ligand (biochemistry) , opioid , stereochemistry , radiosynthesis , in vitro , antagonist , chemical synthesis , derivative (finance) , opioid receptor , selectivity , biochemistry , catalysis , microbiology and biotechnology , economics , financial economics , biology
(+)‐4‐[(αR)‐α‐[(2S, 5R)‐4‐(Iodopropen‐2‐yl)‐2,5‐dimethyl‐1‐piperazinyl]‐3‐hydroxybenzyl]‐N,N‐diethylbenzamide ( 1 ), a novel radioiodinated derivative of the selective δ‐opioid antagonist (+)‐BW373U86, was synthesized and evaluated in vitro for binding to opioid receptor subtypes. This new compound was found to have high affinity (Ki=0.57±0.10 nM) and good selectivity for delta (δ) opioid receptors over mu (μ) (Ki μ/δ=13.6) and kappa (κ) (Ki κ/δ=175) receptors. The corresponding 123 I and 125 I derivatives were prepared by oxidative radioiododestannylation from a trans ‐vinyltributyltin precursor. The radiochemical yield was 72–78% EOS (74.3±2.6%, n=3) for 125 I‐ 1 and 40–62% EOS (53.9±9.8%, n=3) for 123 I‐ 1 . The specific activities were 200–300 mCi/μmol and >5,000 mCi/μmol for the 125 I and 123 I‐labeled traces, respectively. © 1998 John Wiley & Sons, Ltd.