TY - JOUR
T1 - Synthesis and evaluation of new 18F-labelled thienylcyclohexylpiperidine (TCP) analogues as radioligands for the NMDA receptor-channel complex
AU - Shibayama, Y.
AU - Sasaki, Shigeki
AU - Tomita, U.
AU - Nishikawa, T.
AU - Maeda, M.
PY - 1996/1/1
Y1 - 1996/1/1
N2 - We have synthesized new fluorine-18 labelled derivatives of thienylcyclohexylpiperidine (TCP), a non-competitive antagonist of NMDA receptor, which binds to the phencyclidine (PCP) binding site located within the receptor-associated ion channel. The mesylate precursors for (1S*,2R*)-2-(hydroxymethyl)- and (1S*,2R*)-2-(methoxymethyoxymethyl)-1-(N-piperidyl)-1-[2-(2'-[18F] fluoroethyl)thiophenyl]cyclohexane, [18F]4 and [18F]19, respectively, were prepared from 2-hydroxycyclo-hexanone. Radiochemical syntheses were done by displacement of the mesylates by [18F]fluoride ion with no-carrier-added [K/2.2.2]+18F in 4-4.5% radiochemical yields with specific activity of >31 GBq/mol. In the biodistribution studies with [18F]4 and [18F]19, no selective accumulation of radioactivity was observed. Low affinities of these ligands to the NMDA receptor were also shown in in vitro binding experiments.
AB - We have synthesized new fluorine-18 labelled derivatives of thienylcyclohexylpiperidine (TCP), a non-competitive antagonist of NMDA receptor, which binds to the phencyclidine (PCP) binding site located within the receptor-associated ion channel. The mesylate precursors for (1S*,2R*)-2-(hydroxymethyl)- and (1S*,2R*)-2-(methoxymethyoxymethyl)-1-(N-piperidyl)-1-[2-(2'-[18F] fluoroethyl)thiophenyl]cyclohexane, [18F]4 and [18F]19, respectively, were prepared from 2-hydroxycyclo-hexanone. Radiochemical syntheses were done by displacement of the mesylates by [18F]fluoride ion with no-carrier-added [K/2.2.2]+18F in 4-4.5% radiochemical yields with specific activity of >31 GBq/mol. In the biodistribution studies with [18F]4 and [18F]19, no selective accumulation of radioactivity was observed. Low affinities of these ligands to the NMDA receptor were also shown in in vitro binding experiments.
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U2 - 10.1002/(SICI)1099-1344(199601)38:1<77::AID-JLCR815>3.0.CO;2-X
DO - 10.1002/(SICI)1099-1344(199601)38:1<77::AID-JLCR815>3.0.CO;2-X
M3 - Article
AN - SCOPUS:0030038828
SN - 0362-4803
VL - 38
SP - 77
EP - 86
JO - Journal of Labelled Compounds and Radiopharmaceuticals
JF - Journal of Labelled Compounds and Radiopharmaceuticals
IS - 1
ER -