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Preparation of 4‐ and 6‐[ 76 Br] bromometaraminol, two potential radiotracers for the study of the myocardial norepinephrine neuronal reuptake system with PET
Author(s) -
Langer Oliver,
Dollé Frédéric,
Loc'h Christian,
Halldin Christer,
Vaufrey Françoise,
Coulon Christine,
Crouzel Christian,
Någren Kjell,
Mazière Bernard
Publication year - 1997
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(199710)39:10<803::aid-jlcr27>3.0.co;2-r
Subject(s) - metaraminol , chemistry , norepinephrine , radiosynthesis , radiochemistry , positron emission tomography , nuclear medicine , medicine , dopamine , blood pressure
Metaraminol is a norepinephrine analogue which is transported with high affinity by the uptake‐1 mechanism of the sympathetic nerve terminal. Radiolabelled metaraminol and analogues are promising radiotracers to assess the integrity of the myocardial nerve system. The bromo analogues, 4‐ and 6‐bromometaraminol, were synthesized from commercially available metaraminol bitartrate. Structural assignments were made by 2D‐NMR experiments. 4‐ and 6‐[ 76 Br]Bromometaraminol were prepared from N ‐Boc‐metaraminol using [ 76 Br]NH 4 Br and peracetic acid as the brominating agent. The total radiochemical yield based on starting [ 76 Br]NH 4 Br was 17% and 38%, non‐decay‐corrected, for derivative 4‐[ 76 Br]bromometaraminol and 6‐[ 76 Br]bromometaraminol, respectively, in a synthesis time of 3.5 hours including the preparation of [ 76 Br]NH 4 Br. The specific radioactivity obtained for both radiotracers was 130 mCi/μmol (4.8 GBq/μmol). Tissue distribution studies were performed in rats and revealed a low cardiac uptake for both derivatives. These preliminary results suggest that neither 4‐ nor 6‐[ 76 Br]bromometaraminol are suitable radiotracers to study the myocardial norepinephrine neuronal reuptake system with Positron Emission Tomography. © 1997 John Wiley & Sons, Ltd.