TY - JOUR
T1 - Synthesis of [3′,5′-3H2]-α-fluoromethyl-tyros ine as a radioactive specific label of rat brain tyrosine hydroxylase
AU - Lafargue, Pierre
AU - Dodi, Alain
AU - Ponchant, Michel
AU - Garcia, Christine
AU - Le Cavorsin, Marion
AU - Pujol, Jean François
AU - Lellouche, Jean Paul
PY - 1994/8
Y1 - 1994/8
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0028490859&partnerID=8YFLogxK
U2 - 10.1016/s0968-0896(00)82182-3
DO - 10.1016/s0968-0896(00)82182-3
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C2 - 7894976
AN - SCOPUS:0028490859
SN - 0968-0896
VL - 2
SP - 827
EP - 835
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 8
ER -