Synthesis and evaluation of new 18F-labelled thienylcyclohexylpiperidine (TCP) analogues as radioligands for the NMDA receptor-channel complex

Y. Shibayama, Shigeki Sasaki, U. Tomita, T. Nishikawa, M. Maeda

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)77-86
Number of pages10
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume38
Issue number1
DOIs
Publication statusPublished - Jan 1 1996

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and evaluation of new 18F-labelled thienylcyclohexylpiperidine (TCP) analogues as radioligands for the NMDA receptor-channel complex'. Together they form a unique fingerprint.

Cite this