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 for this work

3 Citations (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.

Original language	English
Article number	3436
Journal	Molecules
Volume	24
Issue number	19
Number of pages	7
ISSN	1431-5157
DOIs	https://doi.org/10.3390/molecules24193436
Publication status	Published - 22 Sept 2019

Keywords

Fluorine-18
Iodonium ylides
N-succinimidyl-4-[F]fluorobenzoate
PET
[F]SFB

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10.3390/molecules24193436Licence: CC BY

OA-One-Step SynthesisFinal published version, 1.03 MBLicence: CC BY

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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}",

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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

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U2 - 10.3390/molecules24193436

DO - 10.3390/molecules24193436

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AN - SCOPUS:85072572804

SN - 1431-5157

VL - 24

JO - Molecules (Print Archive Edition)

JF - Molecules (Print Archive Edition)

IS - 19

M1 - 3436

ER -

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

Abstract

Keywords

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