[123I]-(E)-5-(2-iodovinyl)-2'-fluoro-2'-deoxyuridine | 178179-44-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [123I]-(E)-5-(2-iodovinyl)-2'-fluoro-2'-deoxyuridine
• 英文别名: 1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-2-(123I)iodanylethenyl]pyrimidine-2,4-dione
• CAS: 178179-44-7
• 化学式: C₁₁H₁₂FIN₂O₅
• 分子量: 394.225
• InChiKey: PZPQPNSQTAMTEX-VOLROXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-5-(2-(trimethylsilyl)vinyl)-2'-fluoro-2'-deoxyuridine 在 sodium hydroxide 、 sodium iodide 、 双氧水 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 生成 [123I]-(E)-5-(2-iodovinyl)-2'-fluoro-2'-deoxyuridine
  参考文献：
  名称：

  In Vivo Evaluation of the Uptake of [123I]FIAU, [123I]IVFRU and [123I]IVFAU by Normal Mouse Brain: Potential For Noninvasive Assessment of HSV-1 Thymidine Kinase Gene Expression in Gliomas

  摘要：

  Radioiodinated 5-iodo-1-(2-fluoro-2-deoxy--D-arabinofuranosyl)uracil (F *IAU) is most commonly used for noninvasive assessment of herpes simplex virus type 1 thymidine kinase (HSV-1-tk) gene expression. However, it does not permeate the intact blood-brain barrier (BBB) because of its moderate lipophilicity. In this work, three iodo-nucleosides, FIAU, IVFRU, and IVFAU, were radiolabeled with iodine-123 and tested for permeation of the BBB in mice and for potential measurement of HSV-1-tk gene expression in gliomas. The results demonstrate that brain uptake and retention of these nucleosides is not directly related to their lipophilicity. The low brain uptake of IVFAU, in conjunction with its higher and constant brain/blood ratio, may reflect greater stability against hydrolysis of the N-glycosidic bond. In vivo PET evaluations of [124I]IVFRU and [124I]IVFAU in tumor-bearing mice are warranted.

  DOI：

  10.1080/15257770701571933

文献信息

• In Vivo Evaluation of the Uptake of [123I]FIAU, [123I]IVFRU and [123I]IVFAU by Normal Mouse Brain: Potential For Noninvasive Assessment of HSV-1 Thymidine Kinase Gene Expression in Gliomas
  作者：H. -F. Li、A. Winkeler、S. Moharram、E. E. Knaus、K. Dittmar、M. Stockle、W. D. Heiss、L. I. Wiebe、A. J. Jacob

  DOI：10.1080/15257770701571933

  日期：2008.1

  Radioiodinated 5-iodo-1-(2-fluoro-2-deoxy--D-arabinofuranosyl)uracil (F *IAU) is most commonly used for noninvasive assessment of herpes simplex virus type 1 thymidine kinase (HSV-1-tk) gene expression. However, it does not permeate the intact blood-brain barrier (BBB) because of its moderate lipophilicity. In this work, three iodo-nucleosides, FIAU, IVFRU, and IVFAU, were radiolabeled with iodine-123 and tested for permeation of the BBB in mice and for potential measurement of HSV-1-tk gene expression in gliomas. The results demonstrate that brain uptake and retention of these nucleosides is not directly related to their lipophilicity. The low brain uptake of IVFAU, in conjunction with its higher and constant brain/blood ratio, may reflect greater stability against hydrolysis of the N-glycosidic bond. In vivo PET evaluations of [124I]IVFRU and [124I]IVFAU in tumor-bearing mice are warranted.