Preparation of 10B-enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia-targeting boron-neutron capture therapy
We report a novel drug that can be used for the treatment of tumor hypoxic cells by boron neutron capture therapy. We attempted to modify p‑boronophenylalanine, a agent for this therapy in practical use, with a hypoxia-accumulating functional group, 2-nitroimidazole derivative to form p‑boronophenyl...
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| Format: | Article |
| Language: | English |
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Elsevier
2025-05-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715625002280 |
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| author | Tatsuya Ozasa Miu Mizutani Tatsuya Nishihara Minoru Suzuki Kazuhito Tanabe |
| author_facet | Tatsuya Ozasa Miu Mizutani Tatsuya Nishihara Minoru Suzuki Kazuhito Tanabe |
| author_sort | Tatsuya Ozasa |
| collection | DOAJ |
| description | We report a novel drug that can be used for the treatment of tumor hypoxic cells by boron neutron capture therapy. We attempted to modify p‑boronophenylalanine, a agent for this therapy in practical use, with a hypoxia-accumulating functional group, 2-nitroimidazole derivative to form p‑boronophenylalanine with nitroimidazole group (BPA-NI). We successfully prepared 10B-enriched BPA-NI by using click chemistry between azide-modified p‑boronophenylalanine and alkyne-modified nitroimidazole in the presence of copper catalysis. This functional molecule showed selective accumulation in hypoxic cells, and therefore showed robust cytotoxic effects toward hypoxic cells upon thermal neutron irradiation. |
| format | Article |
| id | doaj-art-2c1e4aab6c7b4a0cb4485c8cc40326e0 |
| institution | OA Journals |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-2c1e4aab6c7b4a0cb4485c8cc40326e02025-08-20T02:09:18ZengElsevierResults in Chemistry2211-71562025-05-011510224510.1016/j.rechem.2025.102245Preparation of 10B-enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia-targeting boron-neutron capture therapyTatsuya Ozasa0Miu Mizutani1Tatsuya Nishihara2Minoru Suzuki3Kazuhito Tanabe4Department of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara 252-5258, JapanDepartment of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara 252-5258, JapanDepartment of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara 252-5258, JapanInstitute for Integrated Radiation and Nuclear Science, Kyoto University, Asashiro-Nishi, Kumatori-cho, Sennan-gun, 590-0494, JapanDepartment of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara 252-5258, Japan; Corresponding author.We report a novel drug that can be used for the treatment of tumor hypoxic cells by boron neutron capture therapy. We attempted to modify p‑boronophenylalanine, a agent for this therapy in practical use, with a hypoxia-accumulating functional group, 2-nitroimidazole derivative to form p‑boronophenylalanine with nitroimidazole group (BPA-NI). We successfully prepared 10B-enriched BPA-NI by using click chemistry between azide-modified p‑boronophenylalanine and alkyne-modified nitroimidazole in the presence of copper catalysis. This functional molecule showed selective accumulation in hypoxic cells, and therefore showed robust cytotoxic effects toward hypoxic cells upon thermal neutron irradiation.http://www.sciencedirect.com/science/article/pii/S2211715625002280Hypoxic cellsBNCTNitroimidazoleBoronophenylalanineClick reaction |
| spellingShingle | Tatsuya Ozasa Miu Mizutani Tatsuya Nishihara Minoru Suzuki Kazuhito Tanabe Preparation of 10B-enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia-targeting boron-neutron capture therapy Results in Chemistry Hypoxic cells BNCT Nitroimidazole Boronophenylalanine Click reaction |
| title | Preparation of 10B-enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia-targeting boron-neutron capture therapy |
| title_full | Preparation of 10B-enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia-targeting boron-neutron capture therapy |
| title_fullStr | Preparation of 10B-enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia-targeting boron-neutron capture therapy |
| title_full_unstemmed | Preparation of 10B-enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia-targeting boron-neutron capture therapy |
| title_short | Preparation of 10B-enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia-targeting boron-neutron capture therapy |
| title_sort | preparation of 10b enriched nitroimidazole derivative by click reaction as a functional drug for hypoxia targeting boron neutron capture therapy |
| topic | Hypoxic cells BNCT Nitroimidazole Boronophenylalanine Click reaction |
| url | http://www.sciencedirect.com/science/article/pii/S2211715625002280 |
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