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dc.contributor.authorZanda, Matteo
dc.contributor.authorMusolino, Manuele
dc.contributor.authorFleming, Ian N.
dc.contributor.authorSchweiger, Lutz F.
dc.contributor.authorO’Hagan, David
dc.contributor.authorDall’Angelo, Sergio
dc.identifier.citationZanda , 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 .
dc.identifier.otherPURE: 273007863
dc.identifier.otherPURE UUID: f4bb5703-2354-426f-9ac5-1eab92dd4868
dc.identifier.otherJisc: 2bac56d70fa54819846f4150ef70179d
dc.identifier.otherORCID: /0000-0002-0510-5552/work/89627676
dc.identifier.otherScopus: 85101104812
dc.identifier.otherWOS: 000620201500001
dc.descriptionM.M. thanks SULSA for a PhD studentship. We gratefully acknowledge financial support from the EPSRC (grant EP/I034793/1).en
dc.description.abstractWe 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.
dc.relation.ispartofEuropean Journal of Organic Chemistryen
dc.rightsCopyright © 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
dc.subjectPositron emissionen
dc.subjectQD Chemistryen
dc.titleSynthesis, radiosynthesis and in vitro studies on novel hypoxia PET tracers incorporating [18F]FDRen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.description.statusPeer revieweden

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