[125I]-Fialuridine

• 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: [125I]-Fialuridine
• 英文别名: (125)I-1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-5-iodouracil；[¹²⁵I]1-(2-deoxy-2-fluoro-1-darabinofuranosyl)-5-iodouracil；2'-fluoro-2'-deoxy-5-[(125)I]iodo-1-β-D-arabinofuranosyluracil；2'-fluoro-2'-deoxy-1-β-D-arabinofuranosyl-5-(125)iodo-uracil；1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(125I)iodanylpyrimidine-2,4-dione
• 化学式: C₉H₁₀FIN₂O₅
• 分子量: 370.187
• InChiKey: IPVFGAYTKQKGBM-UNLWNXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  1-(2-脱氧-2-氟-beta-D-阿拉伯呋喃基)尿嘧啶 在 sodium iodide 、 硝酸 作用下， 以 水 为溶剂， 反应 0.75h， 生成 [125I]-Fialuridine
  参考文献：
  名称：

  [EN] IMAGING INFECTION WITH COMPOUNDS THAT BIND TO THYMIDINE KINASE
  [FR] VISUALISATION D'UNE INFECTION AVEC DES COMPOSES SE LIANT A LA THYMIDINE KINASE

  摘要：

  公开号：

  WO2006002142A3

文献信息

• A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of ¹²⁵I-Labeled Molecular Probes
  作者：Ran Yan、Kerstin Sander、Eva Galante、Vineeth Rajkumar、Adam Badar、Mathew Robson、Ethaar El-Emir、Mark F. Lythgoe、R. Barbara Pedley、Erik Årstad

  DOI：10.1021/ja307926g

  日期：2013.1.16

  biological activity. Herein, we report a one-pot, three-component, copper(II)-mediated reaction of azides, alkynes, and [(125)I]iodide to yield 5-[(125)I]iodo-1,2,3-triazoles. Using a selection of azides and alkynes in a combinatorial approach, we have synthesized a library of structurally diverse (125)I-labeled triazoles functionalized with bioconjugation groups, fluorescent dyes, and biomolecules. Our

  核成像与放射性示踪剂相结合，可以对体内生化事件进行无创测量。然而，由于缺乏快速组装具有先决生物活性的放射性标记分子的方法，对示踪剂的获取仍然有限。在此，我们报道了一种单锅、三组分、铜 (II) 介导的叠氮化物、炔烃和 [(125)I] 碘化物反应生成 5-[(125)I]iodo-1,2,3 -三唑类。我们在组合方法中使用选择的叠氮化物和炔烃，合成了一个结构多样的 (125) I 标记的三唑库，这些三唑具有生物共轭基团、荧光染料和生物分子功能化。我们的初步生物学评估表明，5-[(125)I]iodo-1,2,3-triazoles 在体内对脱碘具有抗性，无论是作为小分子探针还是作为抗体偶联物。
• A Convenient Method for the Preparation of Fluorous Tin Derivatives for the Fluorous Labeling Strategy
  作者：Jason W. McIntee、Chitra Sundararajan、Amanda C. Donovan、Michael S. Kovacs、Alfredo Capretta、John F. Valliant

  DOI：10.1021/jo8013287

  日期：2008.11.7

  A convenient method for the preparation of fluorous aryl stannanes was developed as a means of expanding the general utility of the fluorous labeling strategy (FLS). Following the synthesis of a novel fluorous distannane, a palladium-catalyzed cross-coupling reaction was used to prepare the target compounds from aryl halides. The scope of the reaction was investigated by preparing a small library of

  开发一种方便的制备氟代芳基锡烷的方法，作为扩大氟标记策略（FLS）通用性的一种手段。在合成新型的氟二萘嵌苯之后，使用钯催化的交叉偶联反应从芳基卤化物制备目标化合物。通过制备小的模型化合物库来研究反应范围，该模型库的反应收率与使用六甲基或六丁基二锡烷的类似方法所报道的收率相似。通过成功地将氟前体合成为两种已建立的分子成像和治疗剂（FIAU，IUdR），证明了所报告方法的实用性。将它们用碘125放射性标记，并以高收率和有效的比活性分离出所需的产物。
• Synthesis and in Vitro Evaluation of 5-[¹⁸F]Fluoroalkyl Pyrimidine Nucleosides for Molecular Imaging of Herpes Simplex Virus Type 1 Thymidine Kinase Reporter Gene Expression
  作者：Ann-Marie Chacko、Wenchao Qu、Hank F. Kung

  DOI：10.1021/jm800501d

  日期：2008.9.25

  Two novel series of 5-fluoroalkyl-2'-deoxyuridines (FPrDU, FBuDU, FPeDU) and 2'-fluoro-2'-deoxy-5-fluoroalkylarabinouridines (FFPrAU, FFBuAU, FFPeAU) that have three, four, or five methylene units (propyl, butyl, or pentyl) at C-5 were prepared and tested as reporter probes for imaging herpes simplex virus type I thymidine kinase (HSV1-tk) gene expression. The Negishi coupling methodology was employed in efficiently synthesizing the radiolabeling precursors. All six 5-[F-18]fluoroalkyl pyrimidines were readily prepared from 3-N-benzoyl-3',5'-di-O-benzoyl-protected 5-O-mesylate Precursors in 17-35% radiochemical yield (decay-corrected). In vitro studies highlighted that all six [F-18]-labeled nucleosides selectively accumulated in cells expressing the HSV1-TK protein and there was negligible uptake in control cells. [F-18]FPrDU, [F-18]FBuDU, [F-18]FPeDU, and [F-18]FFBuAU had the best uptake profiles. Despite their selective accumulation in HSV1-tk-expressing cells, all 5-fluoroalkyl pyrimidine nucleosides had low-to-negligible cytotoxic activity (CC50 > 1000-1209 mu M). Ultimately, the results demonstrated that 5-[F-18]fluoropropyl, [F-18]fluorobutyl, and [F-18]fluoropentyl pyrimidine nucleosides have the potential to be in vivo HSV1-TK PET reporter probes over a dynamic range of reporter gene expression levels.