Labeling Strategies with F-18 for Positron Emission Tomography Imaging

Gu, Yonghong; Huang, Dong; Liu, Zhiguo; Huang, Jiaguo; Zeng, Wenbin

doi:10.2174/157340611796799140

Cited by 7 publications

(7 citation statements)

References 92 publications

(89 reference statements)

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“…When radiotracers are based on tumor-specific peptides, proteins or antibodies [34–35], mild and fast methods for radiolabeling are mandatory because of the short half-live of [ 18 F]fluoride ( t 1/2 : 110 min). In most cases, indirect radiolabeling is used for these more sensitive biomacromolecules due to the harsh conditions (i.e., organic solvents, high temperatures and basic conditions) for the direct incorporation of [ 18 F]fluoride, which can alter the biological/pharmacological behavior or, at least, destroy sensitive biomolecules [36–38].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

Mamat

Pretze

Gott

et al. 2016

Beilstein J. Org. Chem.

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Novel, functionalized piperazine derivatives were successfully synthesized and fully characterized by 1H/13C/19F NMR, MS, elemental analysis and lipophilicity. All piperazine compounds occur as conformers resulting from the partial amide double bond. Furthermore, a second conformational shape was observed for all nitro derivatives due to the limited change of the piperazine chair conformation. Therefore, two coalescence points were determined and their resulting activation energy barriers were calculated using 1H NMR. To support this result, single crystals of 1-(4-nitrobenzoyl)piperazine (3a, monoclinic, space group C2/c, a = 24.587(2), b = 7.0726(6), c = 14.171(1) Å, β = 119.257(8)°, V = 2149.9(4) Å3, Z = 4, D obs = 1.454 g/cm3) and the alkyne derivative 4-(but-3-yn-1-yl)-1-(4-fluorobenzoyl)piperazine (4b, monoclinic, space group P21/n, a = 10.5982(2), b = 8.4705(1), c = 14.8929(3) Å, β = 97.430(1)°, V = 1325.74(4) Å3, Z = 4, D obs = 1.304 g/cm3) were obtained from a saturated ethyl acetate solution. The rotational conformation of these compounds was also verified by XRD. As proof of concept for future labeling purposes, both nitropiperazines were reacted with [18F]F–. To test the applicability of these compounds as possible 18F-building blocks, two biomolecules were modified and chosen for conjugation either using the Huisgen-click reaction or the traceless Staudinger ligation.

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Section: Resultsmentioning

confidence: 99%

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

Mamat

Pretze

Gott

et al. 2016

Beilstein J. Org. Chem.

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“…The suitability of the 18 F radioisotope in anatomical alterations of a certain disease are detected [5][6][7][8]. The suitability of the 18 F radioisotope in PET has encouraged radiochemists to invest much effort in the development of efficient 18 Ffluorination and 18 F-fluoroalkylation strategies [9][10][11][12][13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

“…Catalysts 2020,10, x FOR PEER REVIEW 13 of 23 radical C-H 18 F-difluoromethylation of the substrates 7a-7g in favourable reaction site(s) would result in the formation of [ 18 F]heteroaryl-CF2H radical intermediates. Subsequent oxidation by fac-Ir IV (ppy)3 and deprotonation would afford the corresponding [ 18 F]heteroaryl-CF2H derivatives […”

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confidence: 99%

Radical C–H 18F-Difluoromethylation of Heteroarenes with [18F]Difluoromethyl Heteroaryl-Sulfones by Visible Light Photoredox Catalysis

et al. 2020

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The 18 F-labeling of CF 2 H groups has been recently studied in radiopharmaceutical chemistry owing to the favorable nuclear and physical characteristics of the radioisotope 18 F for positron emission tomography (PET). Following up on the reported efficiency of the [ 18 F]difluoromethyl benzothiazolyl-sulfone ([ 18 F]1) as a 18 F-difluoromethylating reagent, we investigated the influence of structurally-related [ 18 F]difluoromethyl heteroaryl-sulfones in the reactivity toward the photoredox C-H 18 F-difluoromethylation of heteroarenes under continuous-flow conditions. In the present work, six new [ 18 F]difluoromethyl heteroaryl-sulfones [ 18 F]5a-[ 18 F]5f were prepared and, based on the overall radiochemical yields (RCYs), three of these reagents ([ 18 F]5a, [ 18 F]5c, and [ 18 F]5f) were selected for the fully automated radiosynthesis on a FASTlab TM synthesizer (GE Healthcare) at high level of starting radioactivity. Subsequently, their efficiency as 18 F-difluoromethylating reagents was evaluated using the antiherpetic drug acyclovir as a model substrate. Our results showed that the introduction of molecular modifications in the structure of [ 18 F]1 influenced the amount of fac-Ir III (ppy) 3 and the residence time needed to ensure a complete C-H 18 F-difluoromethylation process. The photocatalytic C-H 18 F-difluoromethylation reaction with the reagents [ 18 F]5a, [ 18 F]5c, and [ 18 F]5f was extended to other heteroarenes. Radical-trapping experiments demonstrated the likely involvement of radical species in the C-H 18 F-difluoromethylation process.

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“…To radiolabel peptides or proteins, 18 F is brought within a prosthetic group, which is then coupled to the vector molecule. Isotope exchange methods using silyl [26,27], phosphorous or boron-containing derivatives [28,29,30] also represent attractive alternatives [31,32,33]. Covalent 18 F-radiolabeling of a molecule is a multi-step process [34] that may involve quite drastic reaction conditions (use of anhydrous organic solvents, heating at high temperatures).…”

Section: Introductionmentioning

confidence: 99%

A Comprehensive Review of Non-Covalent Radiofluorination Approaches Using Aluminum [18F]fluoride: Will [18F]AlF Replace 68Ga for Metal Chelate Labeling?

et al. 2019

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Due to its ideal physical properties, fluorine-18 turns out to be a key radionuclide for positron emission tomography (PET) imaging, for both preclinical and clinical applications. However, usual biomolecules radiofluorination procedures require the formation of covalent bonds with fluorinated prosthetic groups. This drawback makes radiofluorination impractical for routine radiolabeling, gallium-68 appearing to be much more convenient for the labeling of chelator-bearing PET probes. In response to this limitation, a recent expansion of the 18F chemical toolbox gave aluminum [18F]fluoride chemistry a real prominence since the late 2000s. This approach is based on the formation of an [18F][AlF]2+ cation, complexed with a 9-membered cyclic chelator such as NOTA, NODA or their analogs. Allowing a one-step radiofluorination in an aqueous medium, this technique combines fluorine-18 and non-covalent radiolabeling with the advantage of being very easy to implement. Since its first reports, [18F]AlF radiolabeling approach has been applied to a wide variety of potential PET imaging vectors, whether of peptidic, proteic, or small molecule structure. Most of these [18F]AlF-labeled tracers showed promising preclinical results and have reached the clinical evaluation stage for some of them. The aim of this report is to provide a comprehensive overview of [18F]AlF labeling applications through a description of the various [18F]AlF-labeled conjugates, from their radiosynthesis to their evaluation as PET imaging agents.

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Labeling Strategies with F-18 for Positron Emission Tomography Imaging

Cited by 7 publications

References 92 publications

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

Radical C–H 18F-Difluoromethylation of Heteroarenes with [18F]Difluoromethyl Heteroaryl-Sulfones by Visible Light Photoredox Catalysis

A Comprehensive Review of Non-Covalent Radiofluorination Approaches Using Aluminum [18F]fluoride: Will [18F]AlF Replace 68Ga for Metal Chelate Labeling?

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