| Project/Area Number |
15591297
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Radiation science
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| Research Institution | Health Sciences University of Hokkaido |
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Principal Investigator |
OHKURA Kazue Health Sciences University of Hokkaido, Pharmaceutical Sciences, Professor., 薬学部, 教授 (60094827)
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| Co-Investigator(Kenkyū-buntansha) |
TAMAKI Nagara Hokkaido University, Medical Sciences, Professor, 大学院・医学研究科, 教授 (30171888)
SEKI Koh-icin Hokkaido University, Medical Sciences, Professor, アイソトープ総合センター, 教授 (60094835)
KUGE Yiji Kyoto University, Pharmaceutical Sciences, Associate Professor, 大学院・薬学研究科, 助教授 (70321958)
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| Project Period (FY) |
2003 – 2004
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| Project Status |
Completed (Fiscal Year 2004)
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| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2004: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2003: ¥2,800,000 (Direct Cost: ¥2,800,000)
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| Keywords | hypoxia / nitroimidazole / nucleoside / single photon computed tomography / imaging / stereoselective synthesis / イメージング / 立体選択的合成 / 生体内分布 / 低酸素細胞親和性 |
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| Research Abstract |
The present work describes the synthesis of the β-isomer of 1-α-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (IAZA). Radioiodinated IAZA (123I-IAZA) has been extensively studied as a radiopharmaceutical for the diagnosis of regional and/or focal tissue hypoxia in a variety of clinical pathologies. The β-anomer of IAZA, 1-β-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (β-IAZA), was synthesized via an unconventional route starting from 1-f3-D-(ribofuranosyl)-2-nitroimidazole (AZR), with a change of configuration at the C-2'-position to afford 1-p-D-(arabinofuranosyl)-2-nitroimidazole (β-AZA). Nucleophilic iodination of the 5'-O-toluenesulfonyl-2',3'-di-O-acetyl precursor of β-AZA, followed by deprotection, afford β-IAZA in satisfactory yield. β-IAZA was also synthesized from (β-AZA using molecular iodine and triphenylphosphine.
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