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

Fu, Youxin; Helbert, Hugo; Simeth, Nadja A.; Crespi, Stefano; Spoelstra, Gerbren B.; van Dijl, Jan Maarten; van Oosten, Marleen; Nazario, Luiza Reali; van der Born, Dion; Luurtsema, Gert; Szymanski, Wiktor; Elsinga, Philip H.; Feringa, Ben L.

doi:10.1021/jacs.1c02229

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

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Author(s): Youxin Fu ^† , Hugo Helbert ^† ^, ^# , Nadja A. Simeth ^† , Stefano Crespi ^† , Gerbren B. Spoelstra ^# , Jan Maarten van Dijl ^§ , Marleen van Oosten ^§ , Luiza Reali Nazario ^# , Dion van der Born ^∥ , Gert Luurtsema ^# , Wiktor Szymanski ^† ^, ^⊥ ^, , Philip H. Elsinga ^# ^, , Ben L. Feringa ^† ^,

Publication date (Electronic): 28 June 2021

Journal: Journal of the American Chemical Society

Publisher: American Chemical Society

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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.

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Copper toxicity, oxidative stress, and antioxidant nutrients

L. Gaetke (2003)

Copper (Cu) is an integral part of many important enzymes involved in a number of vital biological processes. Although normally bound to proteins, Cu may be released and become free to catalyze the formation of highly reactive hydroxyl radicals. Data obtained from in vitro and cell culture studies are largely supportive of Cu's capacity to initiate oxidative damage and interfere with important cellular events. Oxidative damage has been linked to chronic Cu-overload and/or exposure to excess Cu caused by accidents, occupational hazards, and environmental contamination. Additionally, Cu-induced oxidative damage has been implicated in disorders associated with abnormal Cu metabolism and neurodegenerative changes. Interestingly, a deficiency in dietary Cu also increases cellular susceptibility to oxidative damage. A number of nutrients have been shown to interact with Cu and alter its cellular effects. Vitamin E is generally protective against Cu-induced oxidative damage. While most in vitro or cell culture studies show that ascorbic acid aggravates Cu-induced oxidative damage, results obtained from available animal studies suggest that the compound is protective. High intakes of ascorbic acid and zinc may provide protection against Cu toxicity by preventing excess Cu uptake. Zinc also removes Cu from its binding site, where it may cause free radical formation. Beta-carotene, alpha-lipoic acid and polyphenols have also been shown to attenuate Cu-induced oxidative damage. Further studies are needed to better understand the cellular effects of this essential, but potentially toxic, trace mineral and its functional interaction with other nutrients.

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68Ga-PSMA PET/CT: Joint EANM and SNMMI procedure guideline for prostate cancer imaging: version 1.0

Wolfgang P. Fendler, Matthias Eiber, Mohsen Beheshti … (2017)

The aim of this guideline is to provide standards for the recommendation, performance, interpretation and reporting of (68)Ga-PSMA PET/CT for prostate cancer imaging. These recommendations will help to improve accuracy, precision, and repeatability of (68)Ga-PSMA PET/CT for prostate cancer essentially needed for implementation of this modality in science and routine clinical practice.

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(18)F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography.

Sean M. Preshlock, Matthew Tredwell, Véronique Gouverneur (2016)

Diverse radiochemistry is an essential component of nuclear medicine; this includes imaging techniques such as positron emission tomography (PET). As such, PET can track diseases at an early stage of development, help patient care planning through personalized medicine and support drug discovery programs. Fluorine-18 is the most frequently used radioisotope in PET radiopharmaceuticals for both clinical and preclinical research. Its physical and nuclear characteristics (97% β(+) decay, 109.8 min half-life, 635 keV positron energy) and high specific activity make it an attractive nuclide for labeling and molecular imaging. Arenes and heteroarenes are privileged candidates for (18)F-incorporation as they are metabolically robust and therefore widely used by medicinal chemists and radiochemists alike. For many years, the range of (hetero)arenes amenable to (18)F-fluorination was limited by the lack of chemically diverse precursors, and of radiochemical methods allowing (18)F-incorporation in high selectivity and efficiency (radiochemical yield and purity, specific activity, and radio-scalability). The appearance of late-stage fluorination reactions catalyzed by transition metal or small organic molecules (organocatalysis) has encouraged much research on the use of these activation manifolds for (18)F-fluorination. In this piece, we review all of the reactions known to date to install the (18)F substituent and other key (18)F-motifs (e.g., CF3, CHF2, OCF3, SCF3, OCHF2) of medicinal relevance onto (hetero)arenes. The field has changed significantly in the past five years, and the current trend suggests that the radiochemical space available for PET applications will expand rapidly in the near future.

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Author and article information

Journal

Journal ID (nlm-ta): J Am Chem Soc

Journal ID (iso-abbrev): J Am Chem Soc

Journal ID (publisher-id): ja

Journal ID (coden): jacsat

Title: Journal of the American Chemical Society

Publisher: American Chemical Society

ISSN (Print): 0002-7863

ISSN (Electronic): 1520-5126

Publication date (Electronic): 28 June 2021

Publication date (Print): 14 July 2021

Volume: 143

Issue: 27

Pages: 10041-10047

Affiliations

[† ]Centre for Systems Chemistry, Stratingh Institute for Chemistry, Faculty for Science and Engineering, University of Groningen , Nijenborgh 4, 9747 AG Groningen, The Netherlands

[# ]Department of Nuclear Medicine and Molecular Imaging, University of Groningen, University Medical Centre Groningen , Hanzeplein 1, 9713 GZ Groningen, The Netherlands

[§ ]Department of Medical Microbiology and Infection Prevention, University of Groningen, University Medical Center Groningen , 9713 GZ Groningen, The Netherlands

[∥ ]FutureChemistry , Agro Business Park 10, 6708 PW Wageningen, The Netherlands

[⊥ ]Department of Radiology, Medical Imaging Center, University of Groningen, University Medical Centre Groningen , Hanzeplein 1, 9713 GZ Groningen, The Netherlands

Author notes

[* ] w.szymanski@ 123456umcg.nl

[* ] p.h.elsinga@ 123456umcg.nl

[* ] b.l.feringa@ 123456rug.nl

Author information

Youxin Fu https://orcid.org/0000-0001-6942-6534

Hugo Helbert https://orcid.org/0000-0003-0308-2841

Nadja A. Simeth https://orcid.org/0000-0001-8130-883X

Stefano Crespi https://orcid.org/0000-0002-0279-4903

Gerbren B. Spoelstra https://orcid.org/0000-0002-7063-2834

Jan Maarten van Dijl https://orcid.org/0000-0002-5688-8438

Marleen van Oosten https://orcid.org/0000-0002-7061-6324

Luiza Reali Nazario https://orcid.org/0000-0002-4983-5047

Dion van der Born https://orcid.org/0000-0001-7381-1160

Gert Luurtsema https://orcid.org/0000-0001-8599-8129

Wiktor Szymanski https://orcid.org/0000-0002-9754-9248

Philip H. Elsinga https://orcid.org/0000-0002-3365-4305

Ben L. Feringa https://orcid.org/0000-0003-0588-8435

Article

DOI: 10.1021/jacs.1c02229

PMC ID: 8283755

PubMed ID: 34181410

SO-VID: a1079314-927f-45ae-b083-6f1820c1c014

License:

Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

History

Date received : 05 March 2021

Funding

Funded by: Alexander von Humboldt-Stiftung, doi 10.13039/100005156;

Award ID: NA

Funded by: Stryker European Operations Ltd., doi NA;

Award ID: NA

Funded by: Nederlandse Organisatie voor Wetenschappelijk Onderzoek, doi 10.13039/501100003246;

Award ID: 723.014.001

Funded by: Ministerie van Onderwijs, Cultuur en Wetenschap, doi 10.13039/501100003245;

Award ID: 024.001.035

Funded by: H2020 Marie SkÃ…?odowska-Curie Actions, doi 10.13039/100010665;

Award ID: 838280

Funded by: H2020 European Research Council, doi 10.13039/100010663;

Award ID: 694345

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

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