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Synthesis, radiosynthesis and in vitro studies on novel hypoxia PET tracers incorporating [18F]FDR
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dc.contributor.author | Zanda, Matteo | |
dc.contributor.author | Musolino, Manuele | |
dc.contributor.author | Fleming, Ian N. | |
dc.contributor.author | Schweiger, Lutz F. | |
dc.contributor.author | O’Hagan, David | |
dc.contributor.author | Dall’Angelo, Sergio | |
dc.date.accessioned | 2022-04-04T16:30:03Z | |
dc.date.available | 2022-04-04T16:30:03Z | |
dc.date.issued | 2021-02-22 | |
dc.identifier | 273007863 | |
dc.identifier | f4bb5703-2354-426f-9ac5-1eab92dd4868 | |
dc.identifier | 85101104812 | |
dc.identifier | 000620201500001 | |
dc.identifier.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 | en |
dc.identifier.issn | 1434-193X | |
dc.identifier.other | Jisc: 2bac56d70fa54819846f4150ef70179d | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/89627676 | |
dc.identifier.uri | https://hdl.handle.net/10023/25139 | |
dc.description | M.M. thanks SULSA for a PhD studentship. We gratefully acknowledge financial support from the EPSRC (grant EP/I034793/1). | en |
dc.description.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. | |
dc.format.extent | 1585439 | |
dc.language.iso | eng | |
dc.relation.ispartof | European Journal of Organic Chemistry | en |
dc.subject | FDR | en |
dc.subject | Hypoxia | en |
dc.subject | Positron emission | en |
dc.subject | Radiochemistry | en |
dc.subject | Tomography | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | AC | en |
dc.subject.lcc | QD | en |
dc.title | Synthesis, radiosynthesis and in vitro studies on novel hypoxia PET tracers incorporating [18F]FDR | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1002/ejoc.202001670 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | https://abdn.pure.elsevier.com/en/publications/synthesis-radiosynthesis-and-in-vitro-studies-on-novel-hypoxia-pe | en |
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