Fluorine-18-labeled fluorine gas for synthesis of tracer molecules

doi:10.1016/S0969-8051(97)00078-4

Nuclear Medicine and Biology

Volume 24, Issue 7, October 1997, Pages 677-683

https://doi.org/10.1016/S0969-8051(97)00078-4 Get rights and content

Abstract

The aim of this work was to develop a method to produce ¹⁸F-labeled fluorine gas ([¹⁸F]F₂) with high specific radioactivity (SA, radioactivity/mass-ratio). ¹⁸F-Labeled methyl fluoride ([¹⁸F]CH₃F) was synthesized from [¹⁸F]F⁻_aq and mixed with carrier F₂ in an inert neon matrix. The constituents were atomized in an electric discharge, after which a rearrangement and ¹⁸F for ¹⁹F exchange took place. [¹⁸F]F₂ with a specific radioactivity of up to 55 GBq/μmol is available for the labeling synthesis of tracers for positron emission tomography (PET).

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Comparison of the synthesis and biological properties of no-carrier-added and carrier-added 4-borono-2-[18F]fluorophenylalanine ([18F]FBPA)
2023, Nuclear Medicine and Biology
Boron neutron capture therapy (BNCT), an attractive strategy for cancer treatment, can kill tumor cells and avoid injury to surrounding healthy cells. 4-Borono-2-[¹⁸F]fluorophenylalanine ([¹⁸F]FBPA) positron emission tomography (PET) is a reliable tool for patient screening. Due to the relatively low radiochemical yield when employing the electrophilic route, this study was able to develop a new method to produce no-carrier-added (NCA) [¹⁸F]FBPA and compare the biological characteristics with carrier-added (CA) characteristics.
By starting from 4-bromo-2-nitrobenzaldehyde, NCA [¹⁸F]FBPA was prepared using radiofluorination, alkylation, borylation, and hydrolysis. Cellular uptake analyses, microPET imaging, and biodistribution analyses were conducted to characterize the biological properties of NCA and CA [¹⁸F]FBPA.
The radiochemical yield of NCA [¹⁸F]FBPA was 20 % ± 6 % (decay corrected) with a radiochemical purity of >98 % and molar activity of 56 ± 15 GBq/μmol in a 100-min synthesis. The in vitro accumulation was significantly higher for NCA [¹⁸F]FBPA than for CA [¹⁸F]FBPA in both SAS and CT-26 cells. However, no apparent differences in tumor uptake were observed between NCA and CA [¹⁸F]FBPA-injected tumor-bearing mice.
We successfully prepared NCA [¹⁸F]FBPA through nucleophilic substitution and achieved improved radiochemical yield and purity. We also demonstrated the effects of the amount of nonradioactive FBPA on in vitro cellular uptake and in vivo imaging studies.
PET Radiochemistry
2021, Molecular Imaging: Principles and Practice
Nuclear molecular imaging is fueled by a diverse set of radiopharmaceuticals that enable the visualization of biological targets and processes in normal and disease states. Over the last 40–50 years, a rich set of radiochemistry reactions has been amassed to prepare a panoply of radiopharmaceuticals. A diverse set of positron-emitting radionuclides provides an array of physical and chemical properties that may be exploited to radiolabel small molecules to nanoparticles. Carbon, nitrogen, oxygen, and fluorine are elements that are commonly found in biomolecules and drug candidates. These four elements have radioisotopes that are near pure positron emitters with suitable imaging properties. Radiometals, typically with longer half-lives, may be conjugated to molecular agents with similar biological half-life. Creative chemistry approaches enable the preparation of radiopharmaceuticals and labeled drugs for in vivo evaluation. Herein, an overview of positron emission tomography radiochemistry is presented, highlighting the significant advances in the field covering diverse chemical and biological space.
Fluorine-18: A radionuclide with diverse range of radiochemistry and synthesis strategies for target based PET diagnosis
2020, European Journal of Medicinal Chemistry
Fluorine-18 is one of the most widely used radionuclides for the production of radiopharmaceuticals for positron emission tomography (PET). The radiolabeling methods like nucleophilic, electrophilic, Cu mediated mechanisms or prosthetic groups are widely using to achieve high regioselective radiochemical yields. It acts as a powerful tool to identify new drug targets through cellular uptake, pharmacokinetic (ADME) and pharmacodynamic parameters of the ¹⁸F labeled tracer or drug. These PET tracers have been developed based on the receptors expressed in a disease condition. A number of ¹⁸F radiotracers have been developed against the Tropomyosin Receptor Kinases (Trks), Carbonic anhydrases (CAs), Epidermal Growth Factor Receptors (EGFR), Poly ADP ribose polymerase (PARP) etc. for the diagnosis in cancer therapy. The current research also focused on the development of novel ¹⁸F radiotracers for neurological conditions for deciphering underlying physiology in diseases like Alzheimer, and Parkinson. Therefore, in this review we have focused on ¹⁸F labeling methods, and radiotracers developed against common cancers and neurological conditions.
The chemistry of labeling heterocycles with carbon-11 or fluorine-18 for biomedical imaging
2020, Advances in Heterocyclic Chemistry
Over the last half-century, the molecular imaging technique of positron emission tomography (PET) has emerged as an important tool for biomedical research, drug development and medical diagnosis. The power of PET derives from its utilization of radiotracers that can report specific information on pharmacology, biochemistry, and physiology. Many of these radiotracers are heterocycles that have been labeled with a short-lived cyclotron-produced radioisotope, either carbon-11 (t_1/2 = 20.4 min) or fluorine-18 (t_1/2 = 109.8 min). This review addresses the chemical challenges to be met in producing PET radiotracers with these radioisotope labels at heterocyclic moieties and the methods now available for doing so.
Design and implementation of an automated DT-PhotoFluor radiosynthesis module for 18F-fluorination of aliphatic, branched chain amino acids
2024, Journal of Flow Chemistry
Radiochemistry for positron emission tomography
2023, Nature Communications

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^☆: This work was supported by the Technology Development Center of Finland (TEKES).

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Nuclear Medicine and Biology

Abstract

References (28)

Radiolabelling of 2-oxoquazepam with electrophilic ¹⁸F prepared from [¹⁸F]fluoride

Appl. Radiat. Isot.

Chemical reactivity of the ¹⁸F electrophilic reagents from the ¹⁸O(p,n))¹⁸F gas target system

Nucl. Med. Biol.

Identification and quatitation of gaseous compounds of fluorine generated in [¹⁸F]F₂ target systems

Nucl. Med. Biol.

Metals suitable for fluorine gas target bodies: First use of aluminum for the production of [¹⁸F]F₂

Nucl. Med. Biol.

Production of [¹⁸F]F₂ using the $^{16} O (^{3} He,p)^{18} F$ reaction

Nucl. Med. Biol.

Evaluation of 3-[¹⁸F]fluoro-α-fluoromethyl-p-tyrosine as a tracer for striatal tyrosine hydroxylase activity

Nucl. Med. Biol.

Recommendations for fluorine-18 production

Appl. Radiat. Isot.

Presynaptic dopamine function in striatum of neuroleptic-naive schizophrenic patients

Lancet

Production of 6-[¹⁸F]fluoro-l-DOPA and its metabolism in vivo—a critical review

Nucl. Med. Biol.

[¹⁸F]Fluoro-β-fluoromethylene-m-tyrosine analogs, potential PET agents for presynaptic dopamine terminals: Synthesis and spectroscopic characterization

Appl. Radiat. Isot.

Regioselective radiofluorodestannylation with [¹⁸F]F₂ and [¹⁸F]CH₃COOF: A high-yield synthesis of 6-[¹⁸F]fluoro-l-dopa

Appl. Radiat. Isot.

An O₂ target for the production of [¹⁸F]F₂

Int. J. Appl. Radiat. Isot.

A high-power target for the production of [¹⁸F]fluoride

Nucl. Instrum. Methods

Production of ¹⁸F from water targets: Specific radioactivity and anionic contaminants

Appl. Radiat. Isot. A

Cited by (128)

Comparison of the synthesis and biological properties of no-carrier-added and carrier-added 4-borono-2-[<sup>18</sup>F]fluorophenylalanine ([<sup>18</sup>F]FBPA)

PET Radiochemistry

Fluorine-18: A radionuclide with diverse range of radiochemistry and synthesis strategies for target based PET diagnosis

The chemistry of labeling heterocycles with carbon-11 or fluorine-18 for biomedical imaging

Design and implementation of an automated DT-PhotoFluor radiosynthesis module for <sup>18</sup>F-fluorination of aliphatic, branched chain amino acids

Radiochemistry for positron emission tomography

Fluorine-18-labeled fluorine gas for synthesis of tracer molecules☆

Abstract

Appl. Radiat. Isot.

Nucl. Med. Biol.

Nucl. Med. Biol.

Nucl. Med. Biol.

Nucl. Med. Biol.

Nucl. Med. Biol.

Appl. Radiat. Isot.

Lancet

Nucl. Med. Biol.

Appl. Radiat. Isot.

Appl. Radiat. Isot.

Int. J. Appl. Radiat. Isot.

Nucl. Instrum. Methods

Appl. Radiat. Isot. A