[125I]-meta-iodolbenzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [125I]-meta-iodolbenzoic acid
• 英文别名: 3-[(125)I]iodobenzoic acid；m-[125I]iodobenzoic acid；3-(125I)iodanylbenzoic acid
• 化学式: C₇H₅IO₂
• 分子量: 246.115
• InChiKey: KVBWBCRPWVKFQT-AAPUQBPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [125I]-meta-iodolbenzoic acid 、 N-羟基丁二酰亚胺 生成 N-succinimidyl 3-[125I]iodobenzoate
  参考文献：
  名称：

  FREUD, A.;CANFI, A.;HIRSHFELD, N., J. LABELL. COMPOUNDS AND RADIOPHARM., 30,(1991) N , C. 203

  摘要：

  DOI：
• 作为产物：
  描述：

  间溴苯甲酸 在 N-甲基吡咯烷酮 、 bis(1,5-cyclooctadiene)nickel (0) 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到[125I]-meta-iodolbenzoic acid
  参考文献：
  名称：

  镍介导的芳基和杂芳基溴化物的放射性碘化：SPECT成像示踪剂的快速合成

  摘要：

  使用镍（0）介导的卤素交换反应已实现了芳基和杂芳基溴化物的快速有效碘化。此转换可直接访问用于单光子发射计算机断层扫描（SPECT）的[ 123 I]-和[ 125 I]-成像剂，例如5- [ 123 I] -A85380（请参阅方案，Boc =叔丁氧羰基，化学需氧量= 1,5-环辛二烯，TFA =三氟乙酸）。

  DOI：

  10.1002/anie.201302800

文献信息

• BIOTIN STANNANE FOR HPLC-FREE RADIOIODINATION
  申请人：Carter Randall Lee

  公开号：US20130261311A1

  公开（公告）日：2013-10-03

  The present teachings provide methods that enable the preparation and purification of radioiodinated vectors without the need for HPLC purification, as well as novel precursors which include biotin-like substituents useful in such methods.

  本教学提供了一种方法，可以在无需HPLC纯化的情况下实现放射碘化向量的制备和纯化，同时还包括一些新颖的前体，其中包括类生物素取代基，这些前体在这些方法中非常有用。
• Methods for purifying radiolabelled compounds
  申请人：——

  公开号：US20040260073A1

  公开（公告）日：2004-12-23

  One aspect of the present invention relates to a method of purifying radiolabelled compounds comprising a) loading onto a fluorous polymer a radiolabelled compound precursor comprising a fluoroalkyl tin moiety; b) reacting the radiolabelled compound precursor with a radiolabel delivering compound to give a radiolabelled compound, wherein the fluoroalkyl tin moiety is replaced by a radiolabel; and c) eluting the radiolabelled compound from the fluorous polymer.

  本发明的一个方面涉及一种纯化放射标记化合物的方法，包括a）将含有氟烷基锡基团的放射标记化合物前体加载到氟聚合物上；b）将放射标记化合物前体与放射标记传递化合物反应，得到一个放射标记化合物，其中氟烷基锡基团被放射标记所取代；c）从氟聚合物中洗脱放射标记化合物。
• Copper‐mediated radioiodination reaction through aryl boronic acid or ester precursor and its application to direct radiolabeling of a cyclic peptide
  作者：Yuto Kondo、Hiroyuki Kimura、Chiaki Fukumoto、Yusuke Yagi、Yasunao Hattori、Hidekazu Kawashima、Hiroyuki Yasui

  DOI：10.1002/jlcr.3925

  日期：2021.6.30

  A copper-mediated radioiodination using aryl boronic precursors is attracting attention as a solution to oxidative iododestannylation and nickel-mediated radioiodination drawbacks. The copper-mediated radiolabeling method allows radioiodination at room temperature with stable aryl boronic precursors without preparing complex starting materials or reagents and can be performed in a reaction vessel exposed to air. This method has good potential in radiochemistry; however, studies on the scope of copper-mediated radioiodination through boronic precursors are insufficient. In particular, few reports have demonstrated the effect of protecting groups on radiolabeling efficiency. Therefore, the effect of the protecting group of aryl boronic acids on the copper-mediated radioiodination was investigated. In addition, this method, which does not require heating, is expected to be useful for direct radiolabeling of peptides. Thus, we attempted direct radioiodination of c(RGDyk) as an example. The resulting radioiodination method was well tolerated in various substrates and was unaffected by the pinacol ester-type protecting group. Also, c(RGDyk) was labeled with 125I via copper-mediated radioiodination using an aryl boronic acid precursor. The reaction time and yield were improved, compared with the indirect method. Furthermore, the large difference in polarity between the boronic acid precursor and the radiolabeled compound facilitated purification.

  铜介导的使用芳基硼酸前体的放射性碘化法作为解决氧化碘锡化和镍介导的放射性碘化法缺点的一种方法，正在引起人们的关注。铜介导的放射标记法可以在室温下使用稳定的芳基硼酸前体进行放射碘化，无需准备复杂的起始材料或试剂，而且可以在暴露于空气中的反应容器中进行。这种方法在放射化学领域具有很好的应用前景；然而，有关铜通过硼酸前体介导的放射性碘化范围的研究还不够充分。特别是，很少有报告证明保护基团对放射性标记效率的影响。因此，我们研究了芳基硼酸的保护基团对铜介导的放射碘化的影响。此外，这种无需加热的方法有望用于多肽的直接放射性标记。因此，我们以 c(RGDyk)为例尝试了直接放射性碘化。在各种底物中，放射性碘化方法的耐受性都很好，而且不受频哪醇酯类保护基的影响。此外，还利用芳基硼酸前体，通过铜介导的放射碘化法用 125I 标记了 c(RGDyk)。与间接法相比，反应时间和收率都有所提高。此外，硼酸前体和放射性标记化合物之间的极性差异较大，有利于纯化。
• A New Strategy for Preparing Molecular Imaging and Therapy Agents Using Fluorine-Rich (Fluorous) Soluble Supports
  作者：Amanda Donovan、Jane Forbes、Peter Dorff、Paul Schaffer、John Babich、John F. Valliant

  DOI：10.1021/ja0600375

  日期：2006.3.1

  convenient new strategy for producing radiolabeled compounds in high effective specific activity was developed using soluble fluorous supports. The reported methodology involves a fluorous linker group that is released from the substrate of interest upon reaction with radioiodine. The desired product can then be selectively separated from unreacted starting material and reaction byproducts using a simple

  使用可溶性含氟支持物开发了一种以高效比活性生产放射性标记化合物的便捷新策略。报道的方法涉及在与放射性碘反应时从感兴趣的底物释放的氟连接基团。然后可以使用简单的含氟固相萃取程序从未反应的起始材料和反应副产物中选择性地分离所需产物。通过标记一系列常用于制备分子显像剂的苯甲酸衍生物，证明了这种方法的实用性。所有化合物均以高放射化学产率、纯度和有效的比活性生产。
• Feasibility of the radioastatination of a monoclonal antibody with astatine-211 purified by wet extraction
  作者：Mickaël Bourgeois、François Guerard、Cyrille Alliot、Marie Mougin-Degraef、Holisoa Rajérison、Patricia Remaud-Le Saëc、Jean-François Gestin、François Davodeau、Michel Chérel、Jacques Barbet、Alain Faivre-Chauvet

  DOI：10.1002/jlcr.1543

  日期：2008.10.15

  Astatine-211, a most promising α-particle emitter for targeted radiotherapy, is generally obtained by high-temperature distillation. However, a liquid–liquid extraction procedure (wet extraction) has also been described. The purpose of this study was to develop and optimize the labelling of the stannylated-activated ester N-hydroxysuccinimidyl-meta-trimethylstannylbenzoate ester (MeSTB) with astatine-211 extracted in di-isopropylether (DIPE) in the presence of the oxidant N-chlorosuccinimide (NCS). The effect of final volume, incubation duration and NCS amounts on radiolabelling yield was studied. The best yields (85–90%) of N-hydroxysuccinimidyl-meta-[211At]astatobenzoate ester (SAB) were obtained with 20 nmol of MeSTB, 100 nmol of NCS in 120 µL of DIPE after 15 min. The astatine-211-labelled-activated ester was then used to radiolabel a monoclonal antibody (mAb). The labelling yield was 20–25% and the radiochemical purity was 97–99%. These results show that mAbs may be efficiently labelled with astatine-211 obtained by wet extraction, a fully automatable technique that may prove to be a useful alternative to dry distillation for high activity labelling of radiopharmaceuticals. Copyright © 2008 John Wiley & Sons, Ltd.

  Astatine-211是一种非常有前景的α粒子发射体，可用于靶向放射治疗，通常通过高温蒸馏获得。不过，也有文献描述了液-液萃取程序（湿法萃取）。本研究的目的是开发并优化N-羟基琥珀酰亚胺基-间三甲基锡苯甲酸酯（MeSTB）的标记，在氧化剂N-氯代琥珀酰亚胺（NCS）的作用下，用二异丙醚（DIPE）萃取astatine-211。研究了最终体积、孵育时间和NCS量对放射性标记产率的影响。在120微升二异丙醚中，用20毫摩尔MeSTB、100毫摩尔NCS，经过15分钟，获得了N-羟基琥珀酰亚胺基-间[211At]astatobenzoate酯（SAB）的最佳产率（85-90%）。然后，用astatine-211标记的活性酯对单克隆抗体（mAb）进行放射性标记。标记产率为20-25%，放射化学纯度为97-99%。这些结果表明，mAbs可以用湿法萃取获得的astatine-211进行有效标记，这种全自动技术可能证明是干馏法的一种有用替代