Synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[ 18F]fluoropyridin-4-yl)pyridine ([18F]NIDA 522131), a novel potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by PET

Yi Zhang, Andrew Horti

Research output: Contribution to journalArticle

Abstract

6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[18F]fluoropyridin- 4-yl)pyridine ([18F]NIDA 522131), a potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by positron-emission tomography, was synthesized via no-carrier-added nucleophilic [ 18F]fluorination of 6-chloro-3-((1-(tert-butoxycarbonyl)-2-(S)- azetidinyl) methoxy)-5-(2-iodopyridin-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 4-8% (non-decay-corrected), the specific radioactivity was in the range of 167-33 GBq/μmol (4500-9000 mCi/μmol) and the radiochemical purity was greater than 99%. Preparation of [18F]NIDA522131 via corresponding bromo-derivative 2 is also described.

Original languageEnglish (US)
Pages (from-to)947-952
Number of pages6
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume47
Issue number13
DOIs
StatePublished - Nov 2004
Externally publishedYes

Fingerprint

Nicotinic Receptors
Fluorination
Positron emission tomography
Halogenation
Radioactivity
Positron-Emission Tomography
Derivatives
N-nitrosoiminodiacetic acid
pyridine

Keywords

  • F
  • Nicotinic acetylcholine receptors
  • Nucleophilic halogen-exchange
  • Positron emission tomography

ASJC Scopus subject areas

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

Cite this

@article{498da278e06e4ffc840a2c1cd0261410,
title = "Synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[ 18F]fluoropyridin-4-yl)pyridine ([18F]NIDA 522131), a novel potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by PET",
abstract = "6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[18F]fluoropyridin- 4-yl)pyridine ([18F]NIDA 522131), a potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by positron-emission tomography, was synthesized via no-carrier-added nucleophilic [ 18F]fluorination of 6-chloro-3-((1-(tert-butoxycarbonyl)-2-(S)- azetidinyl) methoxy)-5-(2-iodopyridin-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 4-8{\%} (non-decay-corrected), the specific radioactivity was in the range of 167-33 GBq/μmol (4500-9000 mCi/μmol) and the radiochemical purity was greater than 99{\%}. Preparation of [18F]NIDA522131 via corresponding bromo-derivative 2 is also described.",
keywords = "F, Nicotinic acetylcholine receptors, Nucleophilic halogen-exchange, Positron emission tomography",
author = "Yi Zhang and Andrew Horti",
year = "2004",
month = "11",
doi = "10.1002/jlcr.883",
language = "English (US)",
volume = "47",
pages = "947--952",
journal = "Journal of Labelled Compounds and Radiopharmaceuticals",
issn = "0362-4803",
publisher = "John Wiley and Sons Ltd",
number = "13",

}

TY - JOUR

T1 - Synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[ 18F]fluoropyridin-4-yl)pyridine ([18F]NIDA 522131), a novel potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by PET

AU - Zhang, Yi

AU - Horti, Andrew

PY - 2004/11

Y1 - 2004/11

N2 - 6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[18F]fluoropyridin- 4-yl)pyridine ([18F]NIDA 522131), a potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by positron-emission tomography, was synthesized via no-carrier-added nucleophilic [ 18F]fluorination of 6-chloro-3-((1-(tert-butoxycarbonyl)-2-(S)- azetidinyl) methoxy)-5-(2-iodopyridin-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 4-8% (non-decay-corrected), the specific radioactivity was in the range of 167-33 GBq/μmol (4500-9000 mCi/μmol) and the radiochemical purity was greater than 99%. Preparation of [18F]NIDA522131 via corresponding bromo-derivative 2 is also described.

AB - 6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[18F]fluoropyridin- 4-yl)pyridine ([18F]NIDA 522131), a potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by positron-emission tomography, was synthesized via no-carrier-added nucleophilic [ 18F]fluorination of 6-chloro-3-((1-(tert-butoxycarbonyl)-2-(S)- azetidinyl) methoxy)-5-(2-iodopyridin-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 4-8% (non-decay-corrected), the specific radioactivity was in the range of 167-33 GBq/μmol (4500-9000 mCi/μmol) and the radiochemical purity was greater than 99%. Preparation of [18F]NIDA522131 via corresponding bromo-derivative 2 is also described.

KW - F

KW - Nicotinic acetylcholine receptors

KW - Nucleophilic halogen-exchange

KW - Positron emission tomography

UR - http://www.scopus.com/inward/record.url?scp=10344222720&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=10344222720&partnerID=8YFLogxK

U2 - 10.1002/jlcr.883

DO - 10.1002/jlcr.883

M3 - Article

AN - SCOPUS:10344222720

VL - 47

SP - 947

EP - 952

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

SN - 0362-4803

IS - 13

ER -