Efficient synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-((E)-2-(2- [18F]fluoropyridin-4-yl)vinyl)pyridine ([18F]NIDA 52289), a very high affinity radioligand for nicotinic acetylcholine receptors

Yi Zhang, Andrew W. Hall, Andrew Horti

Research output: Contribution to journalArticle

Abstract

6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-((E)-2-(2- [18F] fluoropyridin-4-yl)vinyl)pyridine ([18F]NIDA 52289), a very high affinity radioligand for studying nicotinic acetylcholine receptors (nAChRs) by positron-emission tomography, was synthesized through Kryptofix 222 assisted no-carrier-added nucleophilic [18F]fluorination of 6-choro-3-((l-(tert-butoxycarbonyl)-2-(S)-azetidinyl)methoxy)-5-((E) -2-(2-bromopyri-din-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 10% (non-decay-corrected), the specific radioactivity was in the range of 93-326 GBq/μmol (2.5-8.8mCi/μmol) and the radiochemical purity was greater than 99%.

Original languageEnglish (US)
Pages (from-to)385-392
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume47
Issue number6
DOIs
StatePublished - May 2004
Externally publishedYes

Fingerprint

Nicotinic Receptors
Fluorination
Positron emission tomography
Halogenation
Radioactivity
Positron-Emission Tomography
N-nitrosoiminodiacetic acid
pyridine
cryptating agent 222

Keywords

  • F
  • A-85380
  • Nicotinic acetylcholine receptors
  • Positron-emission tomography

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Clinical Biochemistry
  • Molecular Medicine
  • Pharmacology

Cite this

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title = "Efficient synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-((E)-2-(2- [18F]fluoropyridin-4-yl)vinyl)pyridine ([18F]NIDA 52289), a very high affinity radioligand for nicotinic acetylcholine receptors",
abstract = "6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-((E)-2-(2- [18F] fluoropyridin-4-yl)vinyl)pyridine ([18F]NIDA 52289), a very high affinity radioligand for studying nicotinic acetylcholine receptors (nAChRs) by positron-emission tomography, was synthesized through Kryptofix 222 assisted no-carrier-added nucleophilic [18F]fluorination of 6-choro-3-((l-(tert-butoxycarbonyl)-2-(S)-azetidinyl)methoxy)-5-((E) -2-(2-bromopyri-din-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 10{\%} (non-decay-corrected), the specific radioactivity was in the range of 93-326 GBq/μmol (2.5-8.8mCi/μmol) and the radiochemical purity was greater than 99{\%}.",
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author = "Yi Zhang and Hall, {Andrew W.} and Andrew Horti",
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TY - JOUR

T1 - Efficient synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-((E)-2-(2- [18F]fluoropyridin-4-yl)vinyl)pyridine ([18F]NIDA 52289), a very high affinity radioligand for nicotinic acetylcholine receptors

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AU - Hall, Andrew W.

AU - Horti, Andrew

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AB - 6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-((E)-2-(2- [18F] fluoropyridin-4-yl)vinyl)pyridine ([18F]NIDA 52289), a very high affinity radioligand for studying nicotinic acetylcholine receptors (nAChRs) by positron-emission tomography, was synthesized through Kryptofix 222 assisted no-carrier-added nucleophilic [18F]fluorination of 6-choro-3-((l-(tert-butoxycarbonyl)-2-(S)-azetidinyl)methoxy)-5-((E) -2-(2-bromopyri-din-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 10% (non-decay-corrected), the specific radioactivity was in the range of 93-326 GBq/μmol (2.5-8.8mCi/μmol) and the radiochemical purity was greater than 99%.

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