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Enzymatic fluorination of biotin and tetrazine conjugates for pretargeting approaches to PET imaging
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dc.contributor.author | Lowe, Phillip T. | |
dc.contributor.author | Dall'angelo, Sergio | |
dc.contributor.author | Devine, Andrew | |
dc.contributor.author | Zanda, Matteo | |
dc.contributor.author | O'Hagan, David | |
dc.date.accessioned | 2019-08-07T23:41:21Z | |
dc.date.available | 2019-08-07T23:41:21Z | |
dc.date.issued | 2018-08-08 | |
dc.identifier.citation | Lowe , P T , Dall'angelo , S , Devine , A , Zanda , M & O'Hagan , D 2018 , ' Enzymatic fluorination of biotin and tetrazine conjugates for pretargeting approaches to PET imaging ' , ChemBioChem , vol. In press . https://doi.org/10.1002/cbic.201800234 | en |
dc.identifier.issn | 1439-4227 | |
dc.identifier.other | PURE: 254619750 | |
dc.identifier.other | PURE UUID: be6addd8-5ce0-4e27-a5e6-d4ba530b59f0 | |
dc.identifier.other | crossref: 10.1002/cbic.201800234 | |
dc.identifier.other | Scopus: 85052610895 | |
dc.identifier.other | WOS: 000444798400013 | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/68281242 | |
dc.identifier.other | ORCID: /0000-0003-1568-0750/work/122719947 | |
dc.identifier.uri | https://hdl.handle.net/10023/18268 | |
dc.description | The authors thank the Engineering and Physical Sciences Research Council, UK, for a research grant (EP/M01262X/1). | en |
dc.description.abstract | The use of radiolabelled antibodies and antibody‐derived recombinant constructs has shown promise for both imaging and therapeutic use. In this context, the biotin–avidin/streptavidin pairing, along with the inverse‐electron‐demand Diels–Alder (iEDDA) reaction, have found application in pretargeting approaches for positron emission tomography (PET). This study reports the fluorinase‐mediated transhalogenation [5′‐chloro‐5′‐deoxyadenosine (ClDA) substrates to 5′‐fluoro‐5′‐deoxyadenosine (FDA) products] of two antibody pretargeting tools, a FDA‐PEG‐tetrazine and a [18F]FDA‐PEG‐biotin, and each is assessed either for its compatibility towards iEDDA ligation to trans‐cyclooctene or for its affinity to avidin. A protocol to avoid radiolytically promoted oxidation of biotin during the synthesis of [18F]FDA‐PEG‐biotin was developed. The study adds to the repertoire of conjugates for use in fluorinase‐catalysed radiosynthesis for PET and shows that the fluorinase will accept a wide range of ClDA substrates tethered at C‐2 of the adenine ring with a PEGylated cargo. The method is exceptional because the nucleophilic reaction with [18F]fluoride takes place in water at neutral pH and at ambient temperature. | |
dc.language.iso | eng | |
dc.relation.ispartof | ChemBioChem | en |
dc.rights | © 2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version 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/cbic.201800234 | en |
dc.subject | Fluorinase | en |
dc.subject | Amide bioconjugation | en |
dc.subject | Tetrazine | en |
dc.subject | Biotin | en |
dc.subject | 18F labelling | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Enzymatic fluorination of biotin and tetrazine conjugates for pretargeting approaches to PET imaging | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.description.version | Postprint | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | https://doi.org/10.1002/cbic.201800234 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-08-08 | |
dc.identifier.grantnumber | EP/I034734/1 | en |
dc.identifier.grantnumber | EP/M01262X/1 | en |
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