Fluorine-18 Radiochemistry: A Novel Thiol-Reactive Prosthetic Group, [18F]FBAMPy

Moore, Terrence J.; Akula, Murthy R.; Kabalka, George W.

doi:10.4236/ns.2016.81001

Cited by 2 publications

(4 citation statements)

References 15 publications

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“…T. M. Moore et al reported another derivative of this thiol-reactive prosthetic group, 2-[ 18 F]FBAMPy, with a decay corrected yield of 30 ± 4% in 80 minutes of synthesis time. 12…”

Section: Resultsmentioning

confidence: 99%

“…3,4 [ 18 F]Fluorobenzaldehydes are also used in the synthesis of maleimide functionalized fluorine-18 labeling agents, another important class of radiolabeling synthons for site specific labeling of biomolecules via coupling with a thiol group. A variety of fluorine-18 labeled maleimide functionalized prosthetic groups have been developed over the last few years, eg, 2- 12 17,18 and N-(2-(2,5-dioxo-2,5-dihydro-1Hpyrrol-1-yl)-ethyl)-6-fluoronicotinamide ([ 18 F]FNEM). 19 Preparation of any of these compounds requires a 2step or 3-step synthesis with overall preparation times ranging from 60 to 90 minutes.…”

Section: Introductionmentioning

confidence: 99%

“…[ 18 F]Fluorobenzaldehydes are also used in the synthesis of maleimide functionalized fluorine-18 labeling agents, another important class of radiolabeling synthons for site specific labeling of biomolecules via coupling with a thiol group. A variety of fluorine-18 labeled maleimide functionalized prosthetic groups have been developed over the last few years, eg, 2-[ 18 F]fluoronicotinaldehyde O -(6-(2,5-dihydro-1 H -pyrrol-1-yl)hexyl) oxime ([ 18 F]FBAMPy), 12 N-[2-(4-[ 18 F]fluorobenzamido)ethyl]maleimide ([ 18 F]FBEM), 13,14 N-[6-(4-[ 18 F]fluorobenzylidene)aminooxyhexyl]maleimide ([ 18 F]FBAM), 15 [ 18 F]FDG-maleimidehexyloxime ([ 18 F]FDG-MHO), 16 1-[3-(2-[ 18 F]fluoropyridin-3-oxy)propyl]maleimide ([ 18 F]FPyME), 17,18 and N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-ethyl)-6-fluoronicotinamide ([ 18 F]FNEM). 19…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Rapid synthesis of maleimide functionalized fluorine‐18 labeled prosthetic group using “radio‐fluorination on the Sep‐Pak” method

Basuli

Zhang

Jagoda

et al. 2018

Labelled Comp Radiopharmac

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Following our recently published fluorine-18 labeling method, "Radio-fluorination on the Sep-Pak", we have successfully synthesized 6-[ F]fluoronicotinaldehyde by passing a solution (1:4 acetonitrile: t-butanol) of its quaternary ammonium salt precursor, 6-(N,N,N-trimethylamino)nicotinaldehyde trifluoromethanesulfonate (2), through a fluorine-18 containing anion exchange cartridge (PS-HCO ). Over 80% radiochemical conversion was observed using 10 mg of precursor within 1 minute. The [ F]fluoronicotinaldehyde ([ F]5) was then conjugated with 1-(6-(aminooxy)hexyl)-1H-pyrrole-2,5-dione to prepare the fluorine-18 labeled maleimide functionalized prosthetic group, 6-[ F]fluoronicotinaldehyde O-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexyl) oxime, 6-[ F]FPyMHO ([ F]6). The current Sep-Pak method not only improves the overall radiochemical yield (50 ± 9%, decay-corrected, n = 9) but also significantly reduces the synthesis time (from 60-90 minutes to 30 minutes) when compared with literature methods for the synthesis of similar prosthetic groups.

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“…T. M. Moore et al reported another derivative of this thiol-reactive prosthetic group, 2-[ 18 F]FBAMPy, with a decay corrected yield of 30 ± 4% in 80 minutes of synthesis time. 12…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Rapid synthesis of maleimide functionalized fluorine‐18 labeled prosthetic group using “radio‐fluorination on the Sep‐Pak” method

Basuli

Zhang

Jagoda

et al. 2018

Labelled Comp Radiopharmac

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“…These prosthetic groups are catego-rized into three classes amine, thiol and carboxylic reactive. Notable thiol reactive bifunctional agents include [ 18 F] FBAM [5] [6], [ 18 F]FBOM [7], [ 18 F]FBABM [8], [ 18 F]FPyAM [9] and [ 18 F]FPyMe [10] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Semi-Automated Synthesis of [F-18]FBAM, a Thiol Reactive Prosthetic Group, Using Continuous Flow Chemistry

Akula¹,

Marepally²,

Collier³

et al. 2016

IJOC

Self Cite

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F-18]FBAM, a thiol reactive bifunctional agent, was successfully synthesized using continuous flow chemistry in a micro reactor that is part of Advion NanoTek Microfluidic Synthesizer. As the radiofluorination was carried out microfluidically, a very small amount of precursor was used and over all radiochemical yield was 38% ± 4% (n = 8, decay corrected) and the radiochemical purity was ≥98% with specific activity of 430 mC/µmol. The total reaction time including HPLC purification was 55 min that is 14 min more than manual synthesis and 6 min less than fully automated synthesis.

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Fluorine-18 Radiochemistry: A Novel Thiol-Reactive Prosthetic Group, [18F]FBAMPy

Abstract: Abstract

Cited by 2 publications

References 15 publications

Rapid synthesis of maleimide functionalized fluorine‐18 labeled prosthetic group using “radio‐fluorination on the Sep‐Pak” method

Rapid synthesis of maleimide functionalized fluorine‐18 labeled prosthetic group using “radio‐fluorination on the Sep‐Pak” method

Semi-Automated Synthesis of [F-18]FBAM, a Thiol Reactive Prosthetic Group, Using Continuous Flow Chemistry

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