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Synthesis and in vitro evaluation of 18 F‐β‐carboline alkaloids as PET ligands
Author(s) -
Blom Elisabeth,
Karimi Farhad,
Eriksson Olof,
Hall Håkan,
Långström Bengt
Publication year - 2008
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/jlcr.1519
Subject(s) - chemistry , radioligand , harmine , monoamine oxidase , stereochemistry , yield (engineering) , in vitro , organic chemistry , biochemistry , pharmacology , enzyme , medicine , materials science , metallurgy
A one‐step 18 F‐labelling strategy was used to prepare four 18 F‐labelled analogues of 7‐methoxy‐1‐methyl‐ 9H ‐β‐carboline (harmine): 7‐(2‐[ 18 F]fluoroethoxy)‐1‐methyl‐9 H ‐β‐carboline (5), 7‐(3‐[ 18 F]fluoro‐propoxy)‐1‐methyl‐9 H ‐β‐carboline (6), 7‐[2‐(2‐[ 18 F]fluoroethoxy)ethoxy]‐1‐methyl‐9 H ‐β‐carboline (7), and 7‐{2‐[2‐(2‐[ 18 F]fluoroethoxy)ethoxy]‐ethoxy}‐1‐methyl‐9 H ‐β‐carboline (8). These were synthesized as potential positron emission tomography ligands for monoamine oxidase A (MAO‐A). A solution of pure labelled compound in buffer was obtained in <70 min from end of radionuclide production, with a decay‐corrected yield of up to 23%. The average specific binding to MAO‐A in rat brain, determined by autoradiography experiments, was highest for compounds 7 and 8 (89±2 and 96±1%, respectively), which was obtained at <1 nM radioligand concentration. Copyright © 2008 John Wiley & Sons, Ltd.