Dataset Information

Ultrafast Photoclick Reaction for Selective ¹⁸F-Positron Emission Tomography Tracer Synthesis in Flow.

ABSTRACT: The development of very fast, clean, and selective methods for indirect labeling in PET tracer synthesis is an ongoing challenge. Here we present the development of an ultrafast photoclick method for the synthesis of short-lived ¹⁸F-PET tracers based on the photocycloaddition reaction of 9,10-phenanthrenequinones with electron-rich alkenes. The respective precursors are synthetically easily accessible and can be functionalized with various target groups. Using a flow photo-microreactor, the photoclick reaction can be performed in 60 s, and clinically relevant tracers for prostate cancer and bacterial infection imaging were prepared to demonstrate practicality of the method.

SUBMITTER: Fu Y

PROVIDER: S-EPMC8283755 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Ultrafast Photoclick Reaction for Selective <sup>18</sup>F-Positron Emission Tomography Tracer Synthesis in Flow.

Fu Youxin Y Helbert Hugo H Simeth Nadja A NA Crespi Stefano S Spoelstra Gerbren B GB van Dijl Jan Maarten JM van Oosten Marleen M Nazario Luiza Reali LR van der Born Dion D Luurtsema Gert G Szymanski Wiktor W Elsinga Philip H PH Feringa Ben L BL

Journal of the American Chemical Society 20210628 27

The development of very fast, clean, and selective methods for indirect labeling in PET tracer synthesis is an ongoing challenge. Here we present the development of an ultrafast photoclick method for the synthesis of short-lived <sup>18</sup>F-PET tracers based on the photocycloaddition reaction of 9,10-phenanthrenequinones with electron-rich alkenes. The respective precursors are synthetically easily accessible and can be functionalized with various target groups. Using a flow photo-microreacto ...[more]

PMID: 34181410

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Project description:IntroductionConventional methods of imaging brain tumors fail to assess metabolically active tumor regions, which limits their capabilities for tumor detection, localization, and response assessment. Positron emission tomography (PET) with 18F-fluciclovine (fluciclovine) provides regional assessment of amino acid uptake in tumors that could overcome some of the limitations of conventional imaging. However, the biological basis of enhanced fluciclovine uptake is insufficiently characterized in brain tumors, which confounds clinical interpretation and application. This study sought to address this gap by correlating multiple biologic quantities with fluciclovine PET uptake across a range of human glioblastoma xenograft models.MethodsThirty-one rats underwent orthotopic implantations with one of five different human glioblastoma cell lines. After tumors were established, fluciclovine PET and magnetic resonance imaging (MRI) scans were performed. The fluciclovine tumor-to-normal-brain (TN) uptake ratio was used to quantify fluciclovine uptake. MRI scans were used to assess tumor volume and gadolinium enhancement status. Histologic assessments quantified tumor cell proliferation, tumor cell density, and tumor cell amino acid transporters (LAT1 and ASCT2). Multivariate linear regression models related fluciclovine uptake with the other measured quantities.ResultsWithin the multivariate regression, the fluciclovine TN uptake ratio (measured 15 to 35 minutes after fluciclovine injection) was most strongly associated with tumor ASCT2 levels (β=0.64; P=0.001). The fluciclovine TN uptake ratio was also significantly associated with tumor volume (β=0.45; P=0.001) and tumor enhancement status (β=0.40; P=0.01). Tumor cell proliferation, tumor cell density, and LAT1 levels were not significantly associated with fluciclovine uptake in any of the multivariate models. In general, both enhancing and non-enhancing tumors could be visualized on fluciclovine PET images, with the median TN uptake ratio across the five tumor lines being 2.4 (range 1.1 to 8.9).ConclusionsIncreased fluciclovine PET uptake was associated with increased levels of the amino acid transporter ASCT2, suggesting fluciclovine PET may be useful for assessing brain tumor amino acid metabolism. Fluciclovine PET uptake was elevated in both enhancing and non-enhancing tumors but the degree of uptake was greater in larger tumors and tumors with enhancement, indicating these variables could confound fluciclovine metabolic measurements if not accounted for.

Dataset Information

Ultrafast Photoclick Reaction for Selective ¹⁸F-Positron Emission Tomography Tracer Synthesis in Flow.

Publications

Ultrafast Photoclick Reaction for Selective <sup>18</sup>F-Positron Emission Tomography Tracer Synthesis in Flow.

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Dataset Information

Ultrafast Photoclick Reaction for Selective 18F-Positron Emission Tomography Tracer Synthesis in Flow.

Publications

Ultrafast Photoclick Reaction for Selective <sup>18</sup>F-Positron Emission Tomography Tracer Synthesis in Flow.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets

Ultrafast Photoclick Reaction for Selective ¹⁸F-Positron Emission Tomography Tracer Synthesis in Flow.