Synthesis of [3′,5′-3H2]-α-fluoromethyl-tyros ine as a radioactive specific label of rat brain tyrosine hydroxylase

Pierre Lafargue, Alain Dodi, Michel Ponchant, Christine Garcia, Marion Le Cavorsin, Jean François Pujol, Jean Paul Lellouche

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The [3′,5′]-ditritio-α-fluoromethyl-tyrosine 4 (specific activity 15.0 Ci/mmol) has been synthesized and used as a radioactive probe for rat neuronal tyrosine hydroxylase (TH). The route of synthesis for the preparation of 3 and 4 allowed us to not only introduce a fluorine atom into 3 4 using an inorganic source of fluorine (CsF), but also to take advantage of the high-yielding cyclization of (α,β alcohols mediated by diethylaminosulfur trifluoride (DAST) to give the corresponding oxazolines. The distribution and metabolism of 4 have been studied in control conditions within the rat locus caeruleus (LC). Intracisternal injection of 20 μCi of 4 was followed by a rapid disappearance of 4 (t 1 2 = 1.5 h) and by a specific accumulation of radioactivity into the LC anatomical limits was investigated each 140 μm along the caudo-rostral axis of the noradrenergic nucleus. In each anatomical interval, its distribution correlated nicely with already described caudo-rostral distribution of TH in noradrenergic cells. Thus, 4 may provide a reliable measure of TH activity in such catecholamine structures.

Original languageEnglish
Pages (from-to)827-835
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume2
Issue number8
DOIs
StatePublished - Aug 1994
Externally publishedYes

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