19F/18F exchange synthesis for a novel [18F]S1P3‐radiopharmaceutical

Rokka, Johanna; Federico, Cesare; Jurttila, Jori; Snellman, Anniina; Haaparanta, Merja; Rinne, Juha O.; Solin, Olof

doi:10.1002/jlcr.3055

Cited by 9 publications

(8 citation statements)

References 21 publications

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“…More importantly, this strategy would enable direct translation of readily available uorinated therapeutics into 18 F-labeled radiopharmaceuticals though simple late-stage 19 F to 18 F conversion [34][35][36] .…”

Section: Introductionmentioning

confidence: 99%

Arene radiofluorination enabled by photoredox-mediated halide interconversion

et al. 2021

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Positron emission tomography (PET) is a powerful imaging technology that could visualize and measure metabolic processes in vivo and/or obtain unique information about drug candidates at early stages. Identi cation of new and improved molecular probes plays a critical role in PET, but its progress is limited in many situations due to the lack of e cient and simple labeling methods to modify biologically active small molecules and/or drugs. Although various approaches have been reported, current methods to radio uorinate unactivated arenes are still limited. Here we document the discovery of a robust method for constructing C-18F bonds through direct halide/18F conversion in electron-rich halo(hetero)arene substrates. Based on readily available halide precursors and mild photoredox conditions, [18F]F-is e ciently introduced into a broad spectrum of organic molecules, including pharmaceutical compounds in a site-selective manner. Notably, the direct 19F/18F conversion method is demonstrated to be a simple and robust protocol for PET probe screening/preparation: this methodology not only identi es a new cancer imaging agent L-61-18F-COOH after a rapid screening of a tyrosine isomer library; but also allows the simple and high-yielding synthesis of the widely used PET agent L-[18F]FDOPA. Taken together, photoredox-mediated halide/18F interconversion strategies represent an innovative chemical tool to prepare new and clinically signi cant PET agents that are synthetically inaccessible or cumbersome to achieve by traditional methods.

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Section: Introductionmentioning

confidence: 99%

Arene radiofluorination enabled by photoredox-mediated halide interconversion

et al. 2021

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“…In view of the important role of S1PR1 in the occurrence, development and metastasis of tumors, noninvasive monitoring of the expression of S1PR1 in malignant tumors has important clinical significance in formulating tumor treatment plans, monitoring treatment effects, and evaluating prognosis. In some recent studies, Tu's and Haufe's groups have designed and synthesized a series of S1PRs, including specific carbon-11and fluorine-18-labeled radiotracers highly targeted to S1PR1 (16)(17)(18)(19)(20)(21). They have shown promising cell membrane binding assays in vitro towards S1PRs.…”

Section: Introductionmentioning

confidence: 99%

A Novel Radioimmune 99mTc-Labeled Tracer for Imaging Sphingosine 1-Phosphate Receptor 1 in Tumor Xenografts: An In Vitro and In Vivo Study

Gai

et al. 2021

Front. Immunol.

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Sphingosine-1-phosphate (S1P) is a phospholipid that regulates pleiotropic biological activities and exerts extracellular functions by binding to five specific G-protein-coupled receptors, S1P receptors (S1PR) 1–5. When activated by S1P, S1PR promote the proliferation and invasion of tumor cells by inducing the formation of new blood vessels. We developed and assessed a new monoclonal antibody imaging probe 99mTc-HYNIC-S1PR1mAb, to explore the feasibility of targeting the S1PR1 in vitro and in vivo. S1PR1mAb was prepared and followed by technetium-99m labeling with succinimidyl 6-hydraziniumnicotinate hydrochloride. Cell uptake and blocking studies were performed to investigate the binding specificity of 99mTc-HYNIC-S1PR1mAb in vitro. 99mTc-HYNIC-S1P1mAb was also tested in vivo in mice xenografted with SK-HEP-1 (high-expression of S1PR1) and MCF-7 (low-expression of S1PR1) using single-photon emission-computed tomography (SPECT). Ex vivo gamma counting of tissues from tumor-bearing mice was used to evaluate 99mTc-HYNIC-S1PR1mAb biodistribution. The biodistribution study results showed significantly higher uptake in SK-HEP-1 tumors than in MCF-7 tumors (P < 0.001). Reduced uptake of 99mTc-HYNIC-S1PR1mAb in SK-HEP-1 was observed in tumor-bearing nude mice pretreated with fingolimod, which binds competitively to the receptors, especially S1PR1. 99mTc-HYNIC-S1PR1mAb can be synthesized and specifically targeted to S1PR1 in vitro and in vivo, allowing S1PR1 expression assessment with SPECT imaging.

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“…We further evaluated the application of direct 19 F/ 18 F conversion in electron rich arenes, due to its exceptional e ciency and simplicity. Although the resulting PET agents may have reduced molar activity, it still represents a broadly useful technology for studying the pharmacokinetics/pharmacodynamics of uorine-containing drugs [34][35][36] or imaging transporter-mediated processes 53,54 , such as synthesizing uorinated amino acid agents for large neutral amino acid transporter (LAT1) imaging 39,41 . We were particularly interested in synthesizing 18 F-labeled tyrosine analogs.…”

Section: Resultsmentioning

confidence: 99%

Arene Radiofluorination Enabled by Photoredox-Mediated Halide Interconversion

Chen¹,

Wang²,

Tay³

et al. 2020

Preprint

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Positron emission tomography (PET) is a powerful imaging technology that could visualize and measure metabolic processes in vivo and/or obtain unique information about drug candidates at early stages. Identification of new and improved molecular probes plays a critical role in PET, but its progress is limited in many situations due to the lack of efficient and simple labeling methods to modify biologically active small molecules and/or drugs. Although various approaches have been reported, current methods to radiofluorinate unactivated arenes are still limited. Here we document the discovery of a robust method for constructing C–18F bonds through direct halide/18F conversion in electron-rich halo(hetero)arene substrates. Based on readily available halide precursors and mild photoredox conditions, [18F]F- is efficiently introduced into a broad spectrum of organic molecules, including pharmaceutical compounds in a site-selective manner. Notably, the direct 19F/18F conversion method is demonstrated to be a simple and robust protocol for PET probe screening/preparation: this methodology not only identifies a new cancer imaging agent L-61-18F-COOH after a rapid screening of a tyrosine isomer library; but also allows the simple and high-yielding synthesis of the widely used PET agent L-[18F]FDOPA. Taken together, photoredox-mediated halide/18F interconversion strategies represent an innovative chemical tool to prepare new and clinically significant PET agents that are synthetically inaccessible or cumbersome to achieve by traditional methods.

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¹⁹F/¹⁸F exchange synthesis for a novel [¹⁸F]S1P₃‐radiopharmaceutical

Cited by 9 publications

References 21 publications

Arene radiofluorination enabled by photoredox-mediated halide interconversion

Arene radiofluorination enabled by photoredox-mediated halide interconversion

A Novel Radioimmune 99mTc-Labeled Tracer for Imaging Sphingosine 1-Phosphate Receptor 1 in Tumor Xenografts: An In Vitro and In Vivo Study

Arene Radiofluorination Enabled by Photoredox-Mediated Halide Interconversion

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