Direct Cu-mediated aromatic18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging

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Standard

Direct Cu-mediated aromatic18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging. / García-Vázquez, Rocío; Battisti, Umberto M.; Jørgensen, Jesper T.; Shalgunov, Vladimir; Hvass, Lars; Stares, Daniel L.; Petersen, Ida N.; Crestey, François; Löffler, Andreas; Svatunek, Dennis; Kristensen, Jesper L.; Mikula, Hannes; Kjaer, Andreas; Herth, Matthias M.

I: Chemical Science, Bind 12, Nr. 35, 2021, s. 11668-11675.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Harvard

García-Vázquez, R, Battisti, UM, Jørgensen, JT, Shalgunov, V, Hvass, L, Stares, DL, Petersen, IN, Crestey, F, Löffler, A, Svatunek, D, Kristensen, JL, Mikula, H, Kjaer, A & Herth, MM 2021, 'Direct Cu-mediated aromatic18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging', Chemical Science, bind 12, nr. 35, s. 11668-11675. https://doi.org/10.1039/d1sc02789a

APA

García-Vázquez, R., Battisti, U. M., Jørgensen, J. T., Shalgunov, V., Hvass, L., Stares, D. L., Petersen, I. N., Crestey, F., Löffler, A., Svatunek, D., Kristensen, J. L., Mikula, H., Kjaer, A., & Herth, M. M. (2021). Direct Cu-mediated aromatic18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging. Chemical Science, 12(35), 11668-11675. https://doi.org/10.1039/d1sc02789a

Vancouver

García-Vázquez R, Battisti UM, Jørgensen JT, Shalgunov V, Hvass L, Stares DL o.a. Direct Cu-mediated aromatic18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging. Chemical Science. 2021;12(35):11668-11675. https://doi.org/10.1039/d1sc02789a

Author

García-Vázquez, Rocío ; Battisti, Umberto M. ; Jørgensen, Jesper T. ; Shalgunov, Vladimir ; Hvass, Lars ; Stares, Daniel L. ; Petersen, Ida N. ; Crestey, François ; Löffler, Andreas ; Svatunek, Dennis ; Kristensen, Jesper L. ; Mikula, Hannes ; Kjaer, Andreas ; Herth, Matthias M. / Direct Cu-mediated aromatic18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging. I: Chemical Science. 2021 ; Bind 12, Nr. 35. s. 11668-11675.

Bibtex

@article{c9571b21be204492a7756e4afe633a36,
title = "Direct Cu-mediated aromatic18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging",
abstract = "Pretargeted imaging can be used to visualize and quantify slow-accumulating targeting vectors with short-lived radionuclides such as fluorine-18 - the most popular clinically applied Positron Emission Tomography (PET) radionuclide. Pretargeting results in higher target-to-background ratios compared to conventional imaging approaches using long-lived radionuclides. Currently, the tetrazine ligation is the most popular bioorthogonal reaction for pretargeted imaging, but a direct18F-labeling strategy for highly reactive tetrazines, which would be highly beneficial if not essential for clinical translation, has thus far not been reported. In this work, a simple, scalable and reliable direct18F-labeling procedure has been developed. We initially studied the applicability of different leaving groups and labeling methods to develop this procedure. The copper-mediated18F-labeling exploiting stannane precursors showed the most promising results. This approach was then successfully applied to a set of tetrazines, including highly reactive H-tetrazines, suitable for pretargeted PET imaging. The labeling succeeded in radiochemical yields (RCYs) of up to approx. 25%. The new procedure was then applied to develop a pretargeting tetrazine-based imaging agent. The tracer was synthesized in a satisfactory RCY ofca.10%, with a molar activity of 134 ± 22 GBq μmol−1and a radiochemical purity of >99%. Further evaluation showed that the tracer displayed favorable characteristics (target-to-background ratios and clearance) that may qualify it for future clinical translation.",
author = "Roc{\'i}o Garc{\'i}a-V{\'a}zquez and Battisti, {Umberto M.} and J{\o}rgensen, {Jesper T.} and Vladimir Shalgunov and Lars Hvass and Stares, {Daniel L.} and Petersen, {Ida N.} and Fran{\c c}ois Crestey and Andreas L{\"o}ffler and Dennis Svatunek and Kristensen, {Jesper L.} and Hannes Mikula and Andreas Kjaer and Herth, {Matthias M.}",
year = "2021",
doi = "10.1039/d1sc02789a",
language = "English",
volume = "12",
pages = "11668--11675",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "Royal Society of Chemistry",
number = "35",

}

RIS

TY - JOUR

T1 - Direct Cu-mediated aromatic18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging

AU - García-Vázquez, Rocío

AU - Battisti, Umberto M.

AU - Jørgensen, Jesper T.

AU - Shalgunov, Vladimir

AU - Hvass, Lars

AU - Stares, Daniel L.

AU - Petersen, Ida N.

AU - Crestey, François

AU - Löffler, Andreas

AU - Svatunek, Dennis

AU - Kristensen, Jesper L.

AU - Mikula, Hannes

AU - Kjaer, Andreas

AU - Herth, Matthias M.

PY - 2021

Y1 - 2021

N2 - Pretargeted imaging can be used to visualize and quantify slow-accumulating targeting vectors with short-lived radionuclides such as fluorine-18 - the most popular clinically applied Positron Emission Tomography (PET) radionuclide. Pretargeting results in higher target-to-background ratios compared to conventional imaging approaches using long-lived radionuclides. Currently, the tetrazine ligation is the most popular bioorthogonal reaction for pretargeted imaging, but a direct18F-labeling strategy for highly reactive tetrazines, which would be highly beneficial if not essential for clinical translation, has thus far not been reported. In this work, a simple, scalable and reliable direct18F-labeling procedure has been developed. We initially studied the applicability of different leaving groups and labeling methods to develop this procedure. The copper-mediated18F-labeling exploiting stannane precursors showed the most promising results. This approach was then successfully applied to a set of tetrazines, including highly reactive H-tetrazines, suitable for pretargeted PET imaging. The labeling succeeded in radiochemical yields (RCYs) of up to approx. 25%. The new procedure was then applied to develop a pretargeting tetrazine-based imaging agent. The tracer was synthesized in a satisfactory RCY ofca.10%, with a molar activity of 134 ± 22 GBq μmol−1and a radiochemical purity of >99%. Further evaluation showed that the tracer displayed favorable characteristics (target-to-background ratios and clearance) that may qualify it for future clinical translation.

AB - Pretargeted imaging can be used to visualize and quantify slow-accumulating targeting vectors with short-lived radionuclides such as fluorine-18 - the most popular clinically applied Positron Emission Tomography (PET) radionuclide. Pretargeting results in higher target-to-background ratios compared to conventional imaging approaches using long-lived radionuclides. Currently, the tetrazine ligation is the most popular bioorthogonal reaction for pretargeted imaging, but a direct18F-labeling strategy for highly reactive tetrazines, which would be highly beneficial if not essential for clinical translation, has thus far not been reported. In this work, a simple, scalable and reliable direct18F-labeling procedure has been developed. We initially studied the applicability of different leaving groups and labeling methods to develop this procedure. The copper-mediated18F-labeling exploiting stannane precursors showed the most promising results. This approach was then successfully applied to a set of tetrazines, including highly reactive H-tetrazines, suitable for pretargeted PET imaging. The labeling succeeded in radiochemical yields (RCYs) of up to approx. 25%. The new procedure was then applied to develop a pretargeting tetrazine-based imaging agent. The tracer was synthesized in a satisfactory RCY ofca.10%, with a molar activity of 134 ± 22 GBq μmol−1and a radiochemical purity of >99%. Further evaluation showed that the tracer displayed favorable characteristics (target-to-background ratios and clearance) that may qualify it for future clinical translation.

U2 - 10.1039/d1sc02789a

DO - 10.1039/d1sc02789a

M3 - Journal article

C2 - 34659701

AN - SCOPUS:85115162973

VL - 12

SP - 11668

EP - 11675

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

IS - 35

ER -

ID: 281602615