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

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

doi:10.1021/jacs.1c02229

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

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^*

^*Bijbehorende auteur voor dit werk

Onderzoeksoutput › Academic › peer review

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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.

Originele taal-2	English
Pagina's (van-tot)	10041-10047
Aantal pagina's	7
Tijdschrift	Journal of the American Chemical Society
Volume	143
Nummer van het tijdschrift	27
Vroegere onlinedatum	28-jun.-2021
DOI's	https://doi.org/10.1021/jacs.1c02229
Status	Published - 14-jul.-2021

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10.1021/jacs.1c02229Licentie: CC BY-NC-ND

Ultrafast Photoclick Reaction for Selective 18F‑Positron Emission Tomography Tracer Synthesis in FlowFinal publisher's version, 1,63 MBLicentie: CC BY-NC-ND

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Fu, Y., Helbert, H., Simeth, N. A., Crespi, S., Spoelstra, G. B., van Dijl, J. M., van Oosten, M., Nazario, L. R., van der Born, D., Luurtsema, G., Szymanski, W., Elsinga, P. H., & Feringa, B. L. (2021). Ultrafast Photoclick Reaction for Selective 18F-Positron Emission Tomography Tracer Synthesis in Flow. Journal of the American Chemical Society, 143(27), 10041-10047. https://doi.org/10.1021/jacs.1c02229

@article{2956336bc698405bafd0e2320f1f157c,

title = "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.",

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

year = "2021",

month = jul,

day = "14",

doi = "10.1021/jacs.1c02229",

language = "English",

volume = "143",

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Fu, Y, Helbert, H, Simeth, NA, Crespi, S, Spoelstra, GB , van Dijl, JM , van Oosten, M , Nazario, LR, van der Born, D, Luurtsema, G , Szymanski, W , Elsinga, PH & Feringa, BL 2021, 'Ultrafast Photoclick Reaction for Selective 18F-Positron Emission Tomography Tracer Synthesis in Flow', Journal of the American Chemical Society, vol. 143, nr. 27, blz. 10041-10047. https://doi.org/10.1021/jacs.1c02229

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T1 - Ultrafast Photoclick Reaction for Selective 18F-Positron Emission Tomography Tracer Synthesis in Flow

AU - Fu, Youxin

AU - Helbert, Hugo

AU - Simeth, Nadja A

AU - Crespi, Stefano

AU - Spoelstra, Gerbren B

AU - van Dijl, Jan Maarten

AU - van Oosten, Marleen

AU - Nazario, Luiza Reali

AU - van der Born, Dion

AU - Luurtsema, Gert

AU - Szymanski, Wiktor

AU - Elsinga, Philip H

AU - Feringa, Ben L

PY - 2021/7/14

Y1 - 2021/7/14

N2 - 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.

AB - 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.

U2 - 10.1021/jacs.1c02229

DO - 10.1021/jacs.1c02229

M3 - Article

C2 - 34181410

SN - 0002-7863

VL - 143

SP - 10041

EP - 10047

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -