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18F-Labelled vorozole analogues as PET tracer for aromatase

✍ Scribed by Maria Erlandsson; Farhad Karimi; Kayo Takahashi; Bengt Långström

Publisher
John Wiley and Sons
Year
2008
Tongue
French
Weight
173 KB
Volume
51
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

One‐ and two‐step syntheses for the ^18^F‐labelling of 6‐[(S)‐(4‐chlorophenyl)(1__H__‐1,2,4‐triazol‐1‐yl)methyl]‐1‐(2‐[^18^F]fluoroethyl)‐1__H__‐benzotriazole, [^18^F]FVOZ, 1 and 6‐[(S)‐(4‐chlorophenyl)(1__H__‐1,2,4‐triazol‐1‐yl)methyl]‐1‐[2‐(2‐[^18^F]fluoroethoxy)ethyl]‐1__H__‐benzotriazole, [^18^F]FVOO, 2 were developed. In the two‐step synthesis, the nucleophilic fluorination step was performed by reacting (S)‐6‐[(4‐chlorophenyl)‐(1__H__‐1,2,4‐triazol‐1‐yl)methyl]‐1__H__‐benzotriazole (VOZ) with either the ^18^F‐labelled ethane‐1,2‐diyl bis(4‐methylbenzenesulfonate) or the oxydiethane‐2,1‐diyl bis(4‐methylbenzenesulfonate). The radiochemical yields were in the range of 9–13% after the 110–120 min total syntheses and the specific radioactivities were 175±7 GBq/µmol and 56 GBq/µmol for compounds 1 and 2, respectively. In the one‐step synthesis, the precursor 2‐{6‐[(4‐chlorophenyl)(1__H__‐1,2,4‐triazol‐1‐yl)methyl]‐1__H__‐1,2,3‐benzotriazol‐1‐yl}ethyl 4‐methylbenzenesulfonate (7) or 1‐[2‐(2‐bromoethoxy)ethyl]‐6‐[(4‐chlorophenyl)(1__H__‐1,2,4‐triazol‐1‐yl)methyl]‐1__H__‐benzotriazole (8) was directly labelled via an ^18^F nucleophilic substitution to give the corresponding tracer. The labelled compounds were obtained in 36–99% radiochemical yield after 75‐min syntheses. The specific radioactivities are 100 GBq/µmol for compound 1 and 80 GBq/µmol for compound 2. In vitro autoradiography using frozen rat brains illustrated specific binding in the medial amygdala, the bed nucleus of stria terminalis and the preoptic area, all of which corresponded well to the result of ^11^C‐labelled vorozole. Copyright © 2008 John Wiley & Sons, Ltd.

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