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Synthesis, radiosynthesis and in vitro studies on novel hypoxia PET tracers incorporating [18F]FDR

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Date
22/02/2021
Author
Zanda, Matteo
Musolino, Manuele
Fleming, Ian N.
Schweiger, Lutz F.
O’Hagan, David
Dall’Angelo, Sergio
Keywords
FDR
Hypoxia
Positron emission
Radiochemistry
Tomography
QD Chemistry
DAS
AC
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Abstract
We report the synthesis of five radiotracers incorporating different oxyamine spacers between the hypoxia‐reactive 2‐nitroimidazole moiety and the 5‐[18F]‐fluorodeoxyribose ([18F]FDR, 12 ) prosthetic group: three linear alkyl chains with 3, 5, 7 carbon atoms ( 15 a – c ), a cyclopropyl ring ( 15 d ) and a 1,4‐disubstituted‐1,2,3‐triazole ( 15 e ). Experiments in hypoxic cells showed that 15 d displays superior uptake kinetics – and similar selectivity for hypoxic cells – relative to the gold standard hypoxia tracers [18F]fluoroazomycin arabinoside ([18F]FAZA) and [18F]fluoromisonidazole ([18F]FMISO). Lipophilicity and structural rigidity have strong influence on the selectivity of tracers 15 towards hypoxic cells: the lead tracer 15 d displays a logP=0.38 and the most rigid spacer. A sixth radiotracer ( 15 f ), with a 2‐H‐imidazole replacing the 2‐nitroimidazole moiety of 15 d , was used to demonstrate that the cyclopropyl group does not play a meaningful role in the sensitivity towards hypoxia.
Citation
Zanda , M , Musolino , M , Fleming , I N , Schweiger , L F , O’Hagan , D & Dall’Angelo , S 2021 , ' Synthesis, radiosynthesis and in vitro studies on novel hypoxia PET tracers incorporating [ 18 F]FDR ' , European Journal of Organic Chemistry , vol. Early View . https://doi.org/10.1002/ejoc.202001670
Publication
European Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1002/ejoc.202001670
ISSN
1434-193X
Type
Journal article
Rights
Copyright © 2021 Wiley-VCH GmbH. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/ejoc.202001670.
Description
M.M. thanks SULSA for a PhD studentship. We gratefully acknowledge financial support from the EPSRC (grant EP/I034793/1).
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  • University of St Andrews Research
URL
https://abdn.pure.elsevier.com/en/publications/synthesis-radiosynthesis-and-in-vitro-studies-on-novel-hypoxia-pe
URI
http://hdl.handle.net/10023/25139

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