Please use this identifier to cite or link to this item:
http://doi.org/10.25358/openscience-7442Full metadata record
| DC Field | Value | Language |
|---|---|---|
| dc.contributor.author | Schieferstein, Hanno | - |
| dc.contributor.author | Betzel, Thomas | - |
| dc.contributor.author | Fischer, Cindy R. | - |
| dc.contributor.author | Ross, Tobias | - |
| dc.date.accessioned | 2022-07-15T10:02:25Z | - |
| dc.date.available | 2022-07-15T10:02:25Z | - |
| dc.date.issued | 2013 | - |
| dc.identifier.uri | https://openscience.ub.uni-mainz.de/handle/20.500.12030/7456 | - |
| dc.description.abstract | Background The folate receptor (FR) is a well-established target for tumor imaging and therapy. To date, only a few 18 F-folate conjugates via 18 F-prosthetic group labeling for positron emission tomography (PET) imaging have been developed. To some extent, they all lack the optimal balance between efficient radiochemistry and favorable in vivo characteristics. Methods A new clickable olate precursor was synthesized by regioselective coupling of folic acid to 11-azido-3,6,9-trioxaundecan-1-amine at the γ-position of the glutamic acid residue. The non-radioactive reference compound was synthesized via copper-catalyzed azide-alkyne cycloaddition of 3-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)prop-1-yne and γ-(11-azido-3,6,9-trioxaundecanyl)folic acid amide. The radiosynthesis was accomplished in two steps: at first a 18 F-fluorination of 2-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)ethyl-4-methylbenzenesulfonate, followed by a 18 F-click reaction with the γ-azido folate. The in vitro, ex vivo, and in vivo behaviors of the new 18 F-folate were investigated using FR-positive human KB cells in displacement assays and microPET studies using KB tumor-bearing mice. Results The new 18 F-folate with oligoethylene spacers showed reduced lipophilicity in respect to the previously developed 18 F-click folate with alkyl spacers and excellent affinity (Ki = 1.6 nM) to the FR. Combining the highly efficient 18 F-click chemistry and a polar oligoethylene-based 18 F-prosthetic group facilitated these results. The overall radiochemical yield of the isolated and formulated product averages 8.7%. In vivo PET imaging in KB tumor-bearing mice showed a tumor uptake of 3.4% ID/g tissue, which could be reduced by FR blockade with native folic acid. Although the new 18 F-oligoethyleneglycole (OEG)-folate showed reduced hepatobiliary excretion over time, a distinct unspecific abdominal background was still observed. Conclusions A new 18 F-folate was developed, being available in very high radiochemical yields via a fast and convenient two-step radiosynthesis. The new 18 F-OEG-folate showed good in vivo behavior and lines up with several recently evaluated 18 F-labeled folates. | en_GB |
| dc.description.sponsorship | DFG, Open Access-Publizieren Universität Mainz / Universitätsmedizin | de |
| dc.language.iso | eng | de |
| dc.relation.ispartofseries | EJNMMI Research | - |
| dc.rights | CC BY | * |
| dc.rights.uri | https://creativecommons.org/licenses/by/2.0/ | * |
| dc.subject.ddc | 540 Chemie | de_DE |
| dc.subject.ddc | 540 Chemistry and allied sciences | en_GB |
| dc.title | 18F-click labeling and preclinical evaluation of a new 18F-folate for PET imaging | en_GB |
| dc.title.alternative | <sup>18</sup>F-click labeling and preclinical evaluation of a new <sup>18</sup>F-folate for PET imaging | de_DE |
| dc.type | Zeitschriftenaufsatz | de |
| dc.identifier.doi | http://doi.org/10.25358/openscience-7442 | - |
| jgu.type.dinitype | article | en_GB |
| jgu.type.version | Published version | de |
| jgu.type.resource | Text | de |
| jgu.organisation.department | FB 09 Chemie, Pharmazie u. Geowissensch. | de |
| jgu.organisation.number | 7950 | - |
| jgu.organisation.name | Johannes Gutenberg-Universität Mainz | - |
| jgu.rights.accessrights | openAccess | - |
| jgu.journal.title | EJNMMI Research | de |
| jgu.journal.volume | 3 | de |
| jgu.pages.alternative | Art. 68 | de |
| jgu.publisher.year | 2013 | - |
| jgu.publisher.name | Springer | de |
| jgu.publisher.place | Berlin | de |
| jgu.publisher.uri | http://dx.doi.org/10.1186/2191-219X-3-68 | de |
| jgu.publisher.issn | 2191-219X | de |
| jgu.organisation.place | Mainz | - |
| jgu.subject.ddccode | 540 | de |
| opus.date.modified | 2018-08-06T10:29:49Z | - |
| opus.subject.dfgcode | 06-301 | - |
| opus.organisation.string | FB 09: Chemie, Pharmazie und Geowissenschaften: Institut für Kernchemie | de_DE |
| opus.identifier.opusid | 24291 | - |
| opus.institute.number | 0904 | - |
| opus.metadataonly | false | - |
| opus.type.contenttype | Keine | de_DE |
| opus.type.contenttype | None | en_EN |
| opus.affiliated | Schieferstein, Hanno | - |
| opus.affiliated | Ross, Tobias | - |
| jgu.publisher.doi | 10.1186/2191-219X-3-68 | de |
| jgu.organisation.ror | https://ror.org/023b0x485 | - |
| Appears in collections: | DFG-OA-Publizieren (2012 - 2017) | |
Files in This Item:
| File | Description | Size | Format | ||
|---|---|---|---|---|---|
 | 18fclick_labeling_and_preclin-20220714111456125.pdf | 1.3 MB | Adobe PDF | View/Open |