Synthesis of (E)-N-(3-bromoprop-2-enyl)-2β-carbomethoxy-3β-(4′-tolyl) nortropane (PE2Br) and radiolabelling of [76Br]PE2Br: a potential ligand for exploration of the dopamine transporter by PET

✍ Scribed by J. Helfenbein; P. Emond; C. Loc'h; M. Bottlaender; M. Ottaviani; D. Guilloteau; B. Mazière; Y. Frangin; S. Chalon

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: French
• Weight: 281 KB
• Volume: 42
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/(sici)1099-1344(199906)42:6<581::aid-jlcr218>3.0.co;2-m

✦ Synopsis

SUMMARY
In order to study the dopamine transporter by (\mathrm{PET}), we prepared ( (E) )-N-(3-bromoprop-2-enyl)(2 \beta)-carbomethoxy-3 (\beta)-(4'-tolyl) nortropane (PE2Br) and its radiobrominated analogue. PE2Br and (\left[{ }^{76} \mathrm{Br}\right] \mathrm{PE} 2 \mathrm{Br}) were synthesized by bromodestannylation of the tributylstannyl derivative using either (\mathrm{N})-bromosuccinimide in (\mathrm{THF}) or (\left[{ }^{76} \mathrm{Br}\right] \mathrm{NH}_{4} \mathrm{Br}) with peracetic acid as oxidant respectively. After purification by HPLC, (\left[{ }^{76} \mathrm{Br}\right] \mathrm{PE} 2 \mathrm{Br}) was obtained with a radiochemical yield of (80 %), a radiochemical purity higher than (98 %) and a specific radioactivity of 20 (\mathrm{MBq} / \mathrm{nmol}). Ex vivo autoradiographic studies in rats showed that 1 hour after i.v. injection of (\left[{ }^{76} \mathrm{Br}\right] \mathrm{PE} 2 \mathrm{Br}) the highest accumulation in the brain was observed in the striata whereas no