One-step synthesis of N-succinimidyl-4-[18F]Fluorobenzoate ([18F]SFB)

Ida Nymann Petersen; Jacob Madsen; Christian Bernard Matthijs Poulie; Andreas Kjær; Matthias Manfred Herth

doi:10.3390/molecules24193436

One-step synthesis of N-succinimidyl-4-[¹⁸F]Fluorobenzoate ([¹⁸F]SFB)

Ida Nymann Petersen, Jacob Madsen, Christian Bernard Matthijs Poulie, Andreas Kjær^*, Matthias Manfred Herth

^*Corresponding author af dette arbejde

3 Citationer (Scopus)

Abstract

Herein, we present a one-step labeling procedure of N-succinimidyl-4-[18F]-fluorobenzoate ([¹⁸F]SFB) starting from spirocyclic iodonium ylide precursors. Precursor syntheses succeeded via a simple one-pot, two-step synthesis sequence, in yields of approximately 25%. Subsequent 18F-nucleophilic aromatic labeling was performed, and radiochemical incorporations (RCCs) from 5-35% were observed. Purification could be carried out using HPLC and subsequent solid phase extraction. Radiochemical purity (RCP) of >95% was determined. The total synthesis time, including purification and formulation, was no longer than 60 min. In comparison to the established 3-step synthesis route of [¹⁸F]SFB, this one-step approach avoids formation of volatile radioactive side-products and simplifies automatization.

Originalsprog	Engelsk
Artikelnummer	3436
Tidsskrift	Molecules
Vol/bind	24
Udgave nummer	19
Antal sider	7
ISSN	1431-5157
DOI	https://doi.org/10.3390/molecules24193436
Status	Udgivet - 22 sep. 2019

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10.3390/molecules24193436Licens: CC BY

OA-One-Step SynthesisForlagets udgivne version, 1,03 MBLicens: CC BY

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Citationsformater

@article{b0ae36abd33d4054bda3d893fb0f3104,

title = "One-step synthesis of N-succinimidyl-4-[18F]Fluorobenzoate ([18F]SFB)",

abstract = "Herein, we present a one-step labeling procedure of N-succinimidyl-4-[18F]-fluorobenzoate ([18F]SFB) starting from spirocyclic iodonium ylide precursors. Precursor syntheses succeeded via a simple one-pot, two-step synthesis sequence, in yields of approximately 25%. Subsequent 18F-nucleophilic aromatic labeling was performed, and radiochemical incorporations (RCCs) from 5-35% were observed. Purification could be carried out using HPLC and subsequent solid phase extraction. Radiochemical purity (RCP) of >95% was determined. The total synthesis time, including purification and formulation, was no longer than 60 min. In comparison to the established 3-step synthesis route of [18F]SFB, this one-step approach avoids formation of volatile radioactive side-products and simplifies automatization.",

keywords = "Fluorine-18, Iodonium ylides, N-succinimidyl-4-[F]fluorobenzoate, PET, [F]SFB",

author = "Petersen, {Ida Nymann} and Jacob Madsen and Poulie, {Christian Bernard Matthijs} and Andreas Kj{\ae}r and Herth, {Matthias Manfred}",

year = "2019",

month = sep,

day = "22",

doi = "10.3390/molecules24193436",

language = "English",

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T1 - One-step synthesis of N-succinimidyl-4-[18F]Fluorobenzoate ([18F]SFB)

AU - Petersen, Ida Nymann

AU - Madsen, Jacob

AU - Poulie, Christian Bernard Matthijs

AU - Kjær, Andreas

AU - Herth, Matthias Manfred

PY - 2019/9/22

Y1 - 2019/9/22

N2 - Herein, we present a one-step labeling procedure of N-succinimidyl-4-[18F]-fluorobenzoate ([18F]SFB) starting from spirocyclic iodonium ylide precursors. Precursor syntheses succeeded via a simple one-pot, two-step synthesis sequence, in yields of approximately 25%. Subsequent 18F-nucleophilic aromatic labeling was performed, and radiochemical incorporations (RCCs) from 5-35% were observed. Purification could be carried out using HPLC and subsequent solid phase extraction. Radiochemical purity (RCP) of >95% was determined. The total synthesis time, including purification and formulation, was no longer than 60 min. In comparison to the established 3-step synthesis route of [18F]SFB, this one-step approach avoids formation of volatile radioactive side-products and simplifies automatization.

AB - Herein, we present a one-step labeling procedure of N-succinimidyl-4-[18F]-fluorobenzoate ([18F]SFB) starting from spirocyclic iodonium ylide precursors. Precursor syntheses succeeded via a simple one-pot, two-step synthesis sequence, in yields of approximately 25%. Subsequent 18F-nucleophilic aromatic labeling was performed, and radiochemical incorporations (RCCs) from 5-35% were observed. Purification could be carried out using HPLC and subsequent solid phase extraction. Radiochemical purity (RCP) of >95% was determined. The total synthesis time, including purification and formulation, was no longer than 60 min. In comparison to the established 3-step synthesis route of [18F]SFB, this one-step approach avoids formation of volatile radioactive side-products and simplifies automatization.

KW - Fluorine-18

KW - Iodonium ylides

KW - N-succinimidyl-4-[F]fluorobenzoate

KW - PET

KW - [F]SFB

UR - http://www.scopus.com/inward/record.url?scp=85072572804&partnerID=8YFLogxK

U2 - 10.3390/molecules24193436

DO - 10.3390/molecules24193436

M3 - Journal article

C2 - 31546683

AN - SCOPUS:85072572804

SN - 1431-5157

VL - 24

JO - Molecules

JF - Molecules

IS - 19

M1 - 3436

ER -