Oxime formation for fluorine-18 labeling of peptides and proteins for positron emission tomography (PET) imaging: A review

Li, Xiangguo; Haaparanta, Merja; Solin, Olof

doi:10.1016/j.jfluchem.2012.07.005

Cited by 43 publications

(40 citation statements)

References 54 publications

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“…A widely used and highly chemoselective reaction, which can be carried in aqueous media and is suitable for the radiolabelling of peptides, is oxime formation between a radiofluorinated prosthetic group functionalized with an aldehyde or a ketone, and an amine from the biomolecule (8). A series of [ 18 F]prosthetic groups have been developed for labelling peptides, each one with their strengths and weaknesses in terms of ease of synthesis and reactivity with the target peptide.…”

Section: C-18 F Approachmentioning

confidence: 99%

“…However, most strategies are based on prosthetic groups directed to the amino, thiol or carboxylic acid functional groups present in the peptides (4). A widely used and highly chemoselective reaction, which can be carried in aqueous media and is suitable for the radiolabelling of peptides, is oxime formation between a radiofluorinated prosthetic group functionalized with an aldehyde or a ketone, and an amine from the biomolecule (8).…”

Section: C-18 F Approachmentioning

confidence: 99%

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Boron–¹⁸F containing positron emission tomography radiotracers: advances and opportunities

Burke

Clemente

Archibald

2014

Contrast Media & Molecular

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Standard [(18) F]fluorination methods to form carbon-fluorine bonds can have some limitations such as low yield and the requirement for harsh reaction conditions. Inorganic approaches include the formation of boron-[(18) F]fluorine bonds and have the potential to give high specific activities at room temperature forming a bond that is stable in vivo. There is considerable potential in future applications, particularly in relation to multimodal imaging and the provision of rapid efficient labelling protocols.

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Section: C-18 F Approachmentioning

confidence: 99%

Section: C-18 F Approachmentioning

confidence: 99%

Boron–¹⁸F containing positron emission tomography radiotracers: advances and opportunities

Burke

Clemente

Archibald

2014

Contrast Media & Molecular

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“…) exploits the formation of an oxime, after proper modification of the amino groups of the nanoparticle amino‐dextrane coating. As a source of a radiolabelled aldehyde, we have used the open‐chain tautomer of 2‐[ 18 F]fluoro‐2‐deoxyglucose ( 18 F‐FDG), a commercially available radioactive tracer used in the clinical setting and readily available in any PET Centre.…”

Section: Introductionmentioning

confidence: 99%

Magnetically driven nanoparticles: ¹⁸FDG‐radiolabelling and positron emission tomography biodistribution study

Simone

Panetta

Bramanti

et al. 2016

Contrast Media & Molecular

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Superparamagnetic iron oxide nanoparticles (SPIONs) have received increasing interest as contrast media in biomedical imaging and innovative therapeutic tools, in particular for loco-regional ablative treatments and drug delivery. The future of therapeutic applications would strongly benefit from improving the capability of the nanostructured constructs to reach the selected target, in particular beyond the intravascular space. Besides the decoration of SPIONs surface with ad hoc bioactive molecules, external magnetic fields are in principle able to remotely influence SPIONs' physiological biodistribution and concentrate them to a specific anatomical region or portion of a tissue. The reduction of SPIONs administered to the body and the need for defining the effective SPIONs local concentration suggest that PET/CT may be a method to quantitatively detect the nanoparticles accumulation in vivo at low concentration and assess their tridimensional distribution in response to an external magnetic field and in relation to the local anatomy highlighted by CT imaging. Here, we report on the possibility to assess the spatial distribution of magnetically-driven radiolabelled SPIONs in a peripheral tissue (mouse thigh) with microPET/CT imaging. To this aim we labelled SPIONs using F-2-fluoro-2-deoxyglucose as a synthon, by chemoselective oxime formation between its open-chain tautomer and nanoparticle amino-groups, and employed microPET/CT imaging to measure the radiolabelled construct biodistribution in a small animal model, following intravenous administration, with and without the application of a permanent magnet onto the skin. The in vivo and ex vivo results showed that micro-PET/CT was able to demonstrate the localizing action of the magnet on SPIONs and provide information, in a multimodal 3D data set, about SPIONs biodistribution taking into account the local anatomy. Copyright © 2017 John Wiley& Sons, Ltd.

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“…Additionally, it has the highest potential resolution for PET imaging, a low tissue radiation dose and a half life of 109.8 min. This makes it possible for a more complex synthesis with sufficient quantities to be delivered to centres far from its production facility [3].…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, the final product usually needs to be purified by HPLC with a low yield. In addition, the reaction between peptide and fluorinated prosthetic group is not selective and a peptide precursor should be protected [7][8][9][10][11][12][13][14][15]. To avoid side reactions, chemoselective reactions, such as oxime and hydrazone bond formation, were introduced.…”

Section: Introductionmentioning

confidence: 99%

HYNIC a bifunctional prosthetic group for the labelling of peptides with 99mTc and 18FDG

Khoshbakht

Kobarfard

Beiki

et al. 2015

J Radioanal Nucl Chem

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With regard to high reactivity and chemoselectivity of HYNIC towards carbonyl of acyclic form of 18 FDG and its stable complexes with 99m Tc, in this study, LIKKPF as the model peptide was conjugated with HYNIC and labelled with 99m Tc (RCP [90 %) and 18 FDG for the first time. The RCP of [70 % was achieved for labelling with 18 FDG, in the presence of glucose (50-250 lg/mL). Our results showed the high potential of HYNIC conjugated peptides for labelling with 99m Tc and 18 FDG as 18 Ffluorinated prosthetic group, to be clinically accepted for the radiolabelling of peptides.Keywords HYNIC Á Hydrazone bond Á 18 FDG Á 18 Ffluorinated prosthetic group Á 99m TcPositron emission tomography SPECT Single photon emission computed tomography HPLC High performance liquid chromatography TLC

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Oxime formation for fluorine-18 labeling of peptides and proteins for positron emission tomography (PET) imaging: A review

Cited by 43 publications

References 54 publications

Boron–¹⁸F containing positron emission tomography radiotracers: advances and opportunities

Boron–¹⁸F containing positron emission tomography radiotracers: advances and opportunities

Magnetically driven nanoparticles: ¹⁸FDG‐radiolabelling and positron emission tomography biodistribution study

HYNIC a bifunctional prosthetic group for the labelling of peptides with 99mTc and 18FDG

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Oxime formation for fluorine-18 labeling of peptides and proteins for positron emission tomography (PET) imaging: A review

Cited by 43 publications

References 54 publications

Boron–18F containing positron emission tomography radiotracers: advances and opportunities

Boron–18F containing positron emission tomography radiotracers: advances and opportunities

Magnetically driven nanoparticles: 18FDG‐radiolabelling and positron emission tomography biodistribution study

HYNIC a bifunctional prosthetic group for the labelling of peptides with 99mTc and 18FDG

Contact Info

Product

Resources

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Boron–¹⁸F containing positron emission tomography radiotracers: advances and opportunities

Boron–¹⁸F containing positron emission tomography radiotracers: advances and opportunities

Magnetically driven nanoparticles: ¹⁸FDG‐radiolabelling and positron emission tomography biodistribution study