Synthesis of a radiotracer for studying nicotinic acetylcholine receptors: (+/-)-Exo-2-(2-[18F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane

Andrew Horti; Hayden T Ravert; Edythe D. Londoni; Robert F. Dannals

doi:10.1002/(SICI)1099-1344(199604)38:4<355::AID-JLCR842>3.0.CO;2-3

Synthesis of a radiotracer for studying nicotinic acetylcholine receptors: (+/-)-Exo-2-(2-[¹⁸F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane

Andrew Horti
, Hayden T Ravert
, Edythe D. Londoni
, Robert F. Dannals

School of Medicine

Research output: Contribution to journal › Article › peer-review

65 Scopus citations

Abstract

The radiochemical synthesis of (+/-)-exo-2-(2-[¹⁸F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane ([¹⁸F]1) was accomplished by Kryptofix® 222 assisted nucleophilic no-carrier-added [¹⁸F]fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl)-7-azabicyclo[2.2.1] heptane (3a). The average radiochemical yield of the final product was 10% and the average specific activity was greater than >2000 mCi/μmol, calculated at end-of-synthesis. The stable fluorine ligand ([¹⁹F]1) was prepared by Kryptofix® 222 assisted nucleophilic fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl) - 7- methoxycarbonyl - 7 - azabicyclo[2.2.1]heptane (3b) followed by acid deprotection.

Original language	English (US)
Pages (from-to)	355-365
Number of pages	11
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	38
Issue number	4
DOIs	https://doi.org/10.1002/(SICI)1099-1344(199604)38:4<355::AID-JLCR842>3.0.CO;2-3
State	Published - 1996

Keywords

Acetylcholine
Epibatidine
F
Fluorination
Halogen-exchange
Nicotinic receptors
Positron emission
Radiotracer
Tomography

ASJC Scopus subject areas

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

Access to Document

10.1002/(SICI)1099-1344(199604)38:4<355::AID-JLCR842>3.0.CO;2-3

Cite this

@article{9883ef5a12f04ceead791319c81c58b6,

title = "Synthesis of a radiotracer for studying nicotinic acetylcholine receptors: (+/-)-Exo-2-(2-[18F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane",

abstract = "The radiochemical synthesis of (+/-)-exo-2-(2-[18F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane ([18F]1) was accomplished by Kryptofix{\textregistered} 222 assisted nucleophilic no-carrier-added [18F]fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl)-7-azabicyclo[2.2.1] heptane (3a). The average radiochemical yield of the final product was 10\% and the average specific activity was greater than >2000 mCi/μmol, calculated at end-of-synthesis. The stable fluorine ligand ([19F]1) was prepared by Kryptofix{\textregistered} 222 assisted nucleophilic fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl) - 7- methoxycarbonyl - 7 - azabicyclo[2.2.1]heptane (3b) followed by acid deprotection.",

keywords = "Acetylcholine, Epibatidine, F, Fluorination, Halogen-exchange, Nicotinic receptors, Positron emission, Radiotracer, Tomography",

author = "Andrew Horti and Ravert, \{Hayden T\} and Londoni, \{Edythe D.\} and Dannals, \{Robert F.\}",

year = "1996",

doi = "10.1002/(SICI)1099-1344(199604)38:4<355::AID-JLCR842>3.0.CO;2-3",

language = "English (US)",

volume = "38",

pages = "355--365",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

issn = "0362-4803",

publisher = "John Wiley and Sons Ltd",

number = "4",

}

TY - JOUR

T1 - Synthesis of a radiotracer for studying nicotinic acetylcholine receptors

T2 - (+/-)-Exo-2-(2-[18F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane

AU - Horti, Andrew

AU - Ravert, Hayden T

AU - Londoni, Edythe D.

AU - Dannals, Robert F.

PY - 1996

Y1 - 1996

N2 - The radiochemical synthesis of (+/-)-exo-2-(2-[18F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane ([18F]1) was accomplished by Kryptofix® 222 assisted nucleophilic no-carrier-added [18F]fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl)-7-azabicyclo[2.2.1] heptane (3a). The average radiochemical yield of the final product was 10% and the average specific activity was greater than >2000 mCi/μmol, calculated at end-of-synthesis. The stable fluorine ligand ([19F]1) was prepared by Kryptofix® 222 assisted nucleophilic fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl) - 7- methoxycarbonyl - 7 - azabicyclo[2.2.1]heptane (3b) followed by acid deprotection.

AB - The radiochemical synthesis of (+/-)-exo-2-(2-[18F]fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane ([18F]1) was accomplished by Kryptofix® 222 assisted nucleophilic no-carrier-added [18F]fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl)-7-azabicyclo[2.2.1] heptane (3a). The average radiochemical yield of the final product was 10% and the average specific activity was greater than >2000 mCi/μmol, calculated at end-of-synthesis. The stable fluorine ligand ([19F]1) was prepared by Kryptofix® 222 assisted nucleophilic fluorination of (+/-)-exo-2-(2-bromo-5-pyridyl) - 7- methoxycarbonyl - 7 - azabicyclo[2.2.1]heptane (3b) followed by acid deprotection.

KW - Acetylcholine

KW - Epibatidine

KW - F

KW - Fluorination

KW - Halogen-exchange

KW - Nicotinic receptors

KW - Positron emission

KW - Radiotracer

KW - Tomography

UR - https://www.scopus.com/pages/publications/0029880960

UR - https://www.scopus.com/pages/publications/0029880960#tab=citedBy

U2 - 10.1002/(SICI)1099-1344(199604)38:4<355::AID-JLCR842>3.0.CO;2-3

DO - 10.1002/(SICI)1099-1344(199604)38:4<355::AID-JLCR842>3.0.CO;2-3

M3 - Article

AN - SCOPUS:0029880960

SN - 0362-4803

VL - 38

SP - 355

EP - 365

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

IS - 4

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