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pubmed-article:1995899pubmed:abstractTextThe first example of a no-carrier-added 18F-labeled catecholamine, 6-[18F]fluoronorepinephrine (6-[18F]FNE), has been synthesized via nucleophilic aromatic substitution. The racemic mixture was resolved on a chiral HPLC column to obtain pure samples of (-)-6-[18F]FNE and (+)6-[18F]FNE. Radiochemical yields of 20% at the end of bombardment (EOB) for the racemic mixture (synthesis time 93 min), 6% for each enantiomer (synthesis time 128 min) with a specific activity of 2-5 Ci/mumol at EOB were obtained. Chiral HPLC peak assignment for the resolved enantiomers was achieved by using two independent methods: polarimetric determination and reaction with dopamine beta-hydroxylase. Positron emission tomography (PET) studies with racemic 6-[18F]FNE show high uptake and retention in the baboon heart. This work demonstrates that nucleophilic aromatic substitution by [18F]fluoride ion is applicable to systems having electron-rich aromatic rings, leading to high specific activity radiopharmaceuticals. Furthermore, the suitably protected dihydroxynitrobenzaldehyde 1 may serve as a useful synthetic precursor for the radiosynthesis of other complex 18F-labeled radiotracers.lld:pubmed
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pubmed-article:1995899pubmed:authorpubmed-author:GatleyS JSJlld:pubmed
pubmed-article:1995899pubmed:authorpubmed-author:FowlerJ SJSlld:pubmed
pubmed-article:1995899pubmed:authorpubmed-author:WolfA PAPlld:pubmed
pubmed-article:1995899pubmed:authorpubmed-author:DeweyS LSLlld:pubmed
pubmed-article:1995899pubmed:authorpubmed-author:DingY SYSlld:pubmed
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pubmed-article:1995899pubmed:volume34lld:pubmed
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pubmed-article:1995899pubmed:pagination767-71lld:pubmed
pubmed-article:1995899pubmed:dateRevised2008-11-21lld:pubmed
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pubmed-article:1995899pubmed:articleTitleSynthesis of high specific activity (+)- and (-)-6-[18F]fluoronorepinephrine via the nucleophilic aromatic substitution reaction.lld:pubmed
pubmed-article:1995899pubmed:affiliationChemistry Department, Brookhaven National Laboratory, Upton, New York 11973.lld:pubmed
pubmed-article:1995899pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:1995899pubmed:publicationTypeResearch Support, U.S. Gov't, P.H.S.lld:pubmed
pubmed-article:1995899pubmed:publicationTypeResearch Support, U.S. Gov't, Non-P.H.S.lld:pubmed
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