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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 | 254619750 | |
dc.identifier | be6addd8-5ce0-4e27-a5e6-d4ba530b59f0 | |
dc.identifier | 85052610895 | |
dc.identifier | 000444798400013 | |
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 | crossref: 10.1002/cbic.201800234 | |
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.format.extent | 2030899 | |
dc.language.iso | eng | |
dc.relation.ispartof | ChemBioChem | 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.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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