The inverse electron demand Diels–Alder cycloaddition with carbon‐11 and fluorine‐18: A gateway to pretargeted imaging across the blood–brain barrier

Zientek, Simon H; Thompson, Stephen; Sephton, Selena Milicevic; Aigbirhio, Franklin I.

doi:10.1002/jlcr.4029

Labelled Comp Radiopharmac

2023

DOI: 10.1002/jlcr.4029

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The inverse electron demand Diels–Alder cycloaddition with carbon‐11 and fluorine‐18: A gateway to pretargeted imaging across the blood–brain barrier

Simon H Zientek

Stephen Thompson

Selena Milicevic Sephton

et al.

Abstract: How to cite this article: Zientek SH, Thompson S, Sephton SM, Aigbirhio FI. The inverse electron demand Diels-Alder cycloaddition with carbon-11 and fluorine-18: A gateway to pretargeted imaging across the blood-brain barrier.

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2024

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Cited by 3 publications

References 76 publications

(223 reference statements)

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Potential of miRNA as Imaging Targets for PET

Zientek,

Thompson,

Aigbirhio

et al. 2024

Helvetica Chimica Acta

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Positron Emission Tomography (PET) is an important part of the medical imaging field which is continually exploring novel biological targets as exemplified by PET imaging of neuroinflammation. Due to limitations stemming from either sub‐optimal biological targets or a lack of available selective radiotracers, alternative biomarkers and PET imaging agent candidates are considered. One such possible target is microRNA (miRNA) and herein, we discuss the potential of miRNA for PET imaging. With the aim of addressing key strategies for imaging miRNA with PET, we identify three distinct approaches as follows: small molecules directly targeting miRNA, small molecules indirectly targeting Argonaute 2 (AGO2)‐protein complexes, and direct chemical modification of antisense oligonucleotides. The radiosynthetic approaches are based on the methods of direct radiolabelling of respective antisense oligonucleotides and several examples are described herein, showcasing the potential of miRNA in PET imaging. Whilst these approaches offer different radiolabelling strategies, application of these radiolabelled molecules towards PET imaging of miRNA are scarce with only one, limited example applied to bone remodeling reported in the literature.

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Potential of miRNA as Imaging Targets for PET

Zientek,

Thompson,

Aigbirhio

et al. 2024

Helvetica Chimica Acta

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Tetrazine–trans-cyclooctene ligation: Unveiling the chemistry and applications within the human body

Tomarchio,

Turnaturi,

Saccullo

et al. 2024

Bioorganic Chemistry

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Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

Maujean,

Ramanoudjame,

Riché

et al. 2024

Molecules

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Radiolabeled peptides are valuable tools for diagnosis or therapies; they are often radiofluorinated using an indirect approach based on an F-18 prosthetic group. Herein, we are reporting our results on the F-18 radiolabeling of three peptides using two different methods based on click reactions. The first one used the well-known CuAAC reaction, and the second one is based on our recently reported hetero-Diels–Alder (HDA) using a dithioesters (thia-Diels–Alder) reaction. Both methods have been automated, and the 18F-peptides were obtained in similar yields and synthesis time (37–39% decay corrected yields by both methods in 120–140 min). However, to obtain similar yields, the CuAAC needs a large amount of copper along with many additives, while the HDA is a catalyst and metal-free reaction necessitating only an appropriate ratio of water/ethanol. The HDA can therefore be considered as a minimalist method offering easy access to fluorine-18 labeled peptides and making it a valuable additional tool for the indirect and site-specific labeling of peptides or biomolecules.

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The inverse electron demand Diels–Alder cycloaddition with carbon‐11 and fluorine‐18: A gateway to pretargeted imaging across the blood–brain barrier

Abstract: How to cite this article: Zientek SH, Thompson S, Sephton SM, Aigbirhio FI. The inverse electron demand Diels-Alder cycloaddition with carbon-11 and fluorine-18: A gateway to pretargeted imaging across the blood-brain barrier.

Cited by 3 publications

References 76 publications

Potential of miRNA as Imaging Targets for PET

Potential of miRNA as Imaging Targets for PET

Tetrazine–trans-cyclooctene ligation: Unveiling the chemistry and applications within the human body

Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

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