Development of novel labeled nucleosides for spect imaging of tumor tissue.

开发用于肿瘤组织光谱成像的新型标记核苷。

• 批准号: 15591297
• 负责人: OHKURA Kazue
• 金额: $ 2.24万
• 依托单位: Health Sciences University of Hokkaido
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2003
• 资助国家: 日本
• 起止时间: 2003 至 2004
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-15591297/
• 关键词: 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

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.

本文报道了1-α-D-（5-脱氧-5-碘阿拉伯呋喃糖基）-2-硝基咪唑（IAZA）β-异构体的合成。放射性碘标记的IAZA（123 I-IAZA）作为一种放射性药物已被广泛研究，用于诊断各种临床病理学中的局部和/或局灶性组织缺氧。以1-β-D-（5-脱氧-5-碘代阿拉伯呋喃糖基）-2-硝基咪唑（AZR）为起始原料，通过非常规路线合成了1-β-D-（5-脱氧-5-碘代阿拉伯呋喃糖基）-2-硝基咪唑（β-IAZA），改变了AZR的C-2 '位构型，得到1-β-D-（5-脱氧-5-碘代阿拉伯呋喃糖基）-2-硝基咪唑（β-AZA）。β-AZA的前体5 ′-O-甲苯磺酰基-2 ′，3 ′-二-O-乙酰基经亲核碘化后脱保护，得到β-IAZA。以β-AZA为原料，用分子碘和三苯基膦合成了β-IAZA。

项目成果

Synthesis and Antiviral Activity of Novel Fluorinated 2',3'-Dideoxy-nucleoside

新型氟化2,3-双脱氧核苷的合成及抗病毒活性

• 发表时间: 2004
• 期刊: Nucleosides, Nucleotides & Nucleic Acids 23
• 作者: P.Kumar;K.Ohkura;J.Balzarini;E.De Clercq;K.Seki;L.I.Wiebe
• 通讯作者: L.I.Wiebe

P.Kumar, K.Ohkura, J.Balzarini, E.De Clercq, K.Seki, L.I.Wiebe: "Synthesis and Antiviral Activity of Novel Fluorinated 2',3'-Dideoxynucleoside"Nucleosides, Nucleotides & Nucleic Acids. 23. 7-29 (2004)

P.Kumar、K.Okura、J.Balzarini、E.De Clercq、K.Seki、L.I.Wiebe：“新型氟化 2,3-二脱氧核苷的合成和抗病毒活性”核苷、核苷酸

Synthesis and Antiviral Activity of Novel Fluorinated 2',3'-Dideoxynucleoside

新型氟化2,3-双脱氧核苷的合成及抗病毒活性

• 发表时间: 2004
• 期刊: Nucleosides, Nucleotides & Nucleic Acids 23
• 作者: P.Kumar;K.Ohkura;J.Balzarini;E.De Clercq;K.Seki;L.I.Wiebe
• 通讯作者: L.I.Wiebe

Synthesis of 1-β-D-(5-Deoxy-5-iodoaribinofuranosyl)-2-nitro-imidazole). (β-IAZA) : A Novel Marker of Tissue Hypoxoa

1-β-D-(5-脱氧-5-碘阿宾呋喃糖基)-2-硝基-咪唑) (β-IAZA) 的合成：组织缺氧的新型标记物。

• 发表时间: 2003
• 期刊: Chem.Pharm.Bull. 51
• 作者: P.Kumar;K.Ohkura;D.Beiki;L.I.Wiebe;K.Seki
• 通讯作者: K.Seki

Synthesis of 1-β-D-(5-Deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (β-IAZA): A Novel Marker of Tissue Hypoxia.

1-β-D-(5-脱氧-5-碘阿拉伯呋喃糖基)-2-硝基咪唑 (β-IAZA) 的合成：组织缺氧的新标志物。

• DOI: 10.1002/chin.200337174
• 发表时间: 2003
• 作者: Piyush Kumar;K. Ohkura;D. Beiki;L. Wiebe;K. Seki
• 通讯作者: K. Seki