Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution
Abstract Astatine-211 (211At)-labeled phenylalanine is expected to be a promising agent for targeted alpha-particle therapy for the treatment of patients with glioma. The existing reactions to prepare the labeled compound usually require organic solvents and metals that are toxic and hazardous to th...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2021-06-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-021-92476-6 |
| _version_ | 1818978325359493120 |
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| author | Yoshifumi Shirakami Tadashi Watabe Honoka Obata Kazuko Kaneda Kazuhiro Ooe Yuwei Liu Takahiro Teramoto Atsushi Toyoshima Atsushi Shinohara Eku Shimosegawa Jun Hatazawa Koichi Fukase |
| author_facet | Yoshifumi Shirakami Tadashi Watabe Honoka Obata Kazuko Kaneda Kazuhiro Ooe Yuwei Liu Takahiro Teramoto Atsushi Toyoshima Atsushi Shinohara Eku Shimosegawa Jun Hatazawa Koichi Fukase |
| author_sort | Yoshifumi Shirakami |
| collection | DOAJ |
| description | Abstract Astatine-211 (211At)-labeled phenylalanine is expected to be a promising agent for targeted alpha-particle therapy for the treatment of patients with glioma. The existing reactions to prepare the labeled compound usually require organic solvents and metals that are toxic and hazardous to the environment. In this study, we developed a novel method wherein astatination was realized via the substitution of 211At for a dihydroxyboryl group coupled to phenylalanine. [211At]4-astato-L-phenylalanine was obtained as the carrier-free product in aqueous medium in high radiochemical yields (98.1 ± 1.9%, n = 5). The crude reaction mixture was purified by solid-phase extraction, and the radiochemical purity of the product was 99.3 ± 0.7% (n = 5). The high yield and purity were attributed to the formation of [211At]AtI and AtI2 − as the reactive intermediates in the astatination reaction. The reaction did not require any organic solvents or toxic reagents, suggesting that this method is suitable for clinical applications. |
| first_indexed | 2024-12-20T16:41:50Z |
| format | Article |
| id | doaj.art-c725b93b6496492c9ff9377e5a3890d6 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-12-20T16:41:50Z |
| publishDate | 2021-06-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-c725b93b6496492c9ff9377e5a3890d62022-12-21T19:33:01ZengNature PortfolioScientific Reports2045-23222021-06-011111710.1038/s41598-021-92476-6Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solutionYoshifumi Shirakami0Tadashi Watabe1Honoka Obata2Kazuko Kaneda3Kazuhiro Ooe4Yuwei Liu5Takahiro Teramoto6Atsushi Toyoshima7Atsushi Shinohara8Eku Shimosegawa9Jun Hatazawa10Koichi Fukase11Institute for Radiation Sciences, Osaka UniversityInstitute for Radiation Sciences, Osaka UniversityDepartment of Chemistry, Graduate School of Science, Osaka UniversityInstitute for Radiation Sciences, Osaka UniversityInstitute for Radiation Sciences, Osaka UniversityDepartment of Tracer Kinetics and Nuclear Medicine, Graduate School of Medicine, Osaka UniversityInstitute for Radiation Sciences, Osaka UniversityInstitute for Radiation Sciences, Osaka UniversityInstitute for Radiation Sciences, Osaka UniversityDepartment of Molecular Imaging in Medicine, Osaka University Graduate School of MedicineResearch Center for Nuclear Physics, Osaka UniversityInstitute for Radiation Sciences, Osaka UniversityAbstract Astatine-211 (211At)-labeled phenylalanine is expected to be a promising agent for targeted alpha-particle therapy for the treatment of patients with glioma. The existing reactions to prepare the labeled compound usually require organic solvents and metals that are toxic and hazardous to the environment. In this study, we developed a novel method wherein astatination was realized via the substitution of 211At for a dihydroxyboryl group coupled to phenylalanine. [211At]4-astato-L-phenylalanine was obtained as the carrier-free product in aqueous medium in high radiochemical yields (98.1 ± 1.9%, n = 5). The crude reaction mixture was purified by solid-phase extraction, and the radiochemical purity of the product was 99.3 ± 0.7% (n = 5). The high yield and purity were attributed to the formation of [211At]AtI and AtI2 − as the reactive intermediates in the astatination reaction. The reaction did not require any organic solvents or toxic reagents, suggesting that this method is suitable for clinical applications.https://doi.org/10.1038/s41598-021-92476-6 |
| spellingShingle | Yoshifumi Shirakami Tadashi Watabe Honoka Obata Kazuko Kaneda Kazuhiro Ooe Yuwei Liu Takahiro Teramoto Atsushi Toyoshima Atsushi Shinohara Eku Shimosegawa Jun Hatazawa Koichi Fukase Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution Scientific Reports |
| title | Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution |
| title_full | Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution |
| title_fullStr | Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution |
| title_full_unstemmed | Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution |
| title_short | Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution |
| title_sort | synthesis of 211at 4 astato l phenylalanine by dihydroxyboryl astatine substitution reaction in aqueous solution |
| url | https://doi.org/10.1038/s41598-021-92476-6 |
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