4-[¹²⁵I]-iodobenzyl bromide | 105644-30-2

• 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: 4-[¹²⁵I]-iodobenzyl bromide
• 英文别名: 1-(bromomethyl)-4-(125I)iodanylbenzene
• CAS: 105644-30-2
• 化学式: C₇H₆BrI
• 分子量: 295.029
• InChiKey: BQTRMYJYYNQQGK-ZRHPLBMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  美喹他嗪 、 4-[¹²⁵I]-iodobenzyl bromide 以 乙腈 为溶剂， 生成 ¹²⁵I-4-iodobenzylmequitazine
  参考文献：
  名称：

  Development of radioiodine-labeled mequitazine for evaluation of hepatic CYP2D activity

  摘要：

  Background: As drug-metabolizing enzyme activities are affected by a variety of factors, such as drug-drug interactions, a method to evaluate drug-metabolizing enzyme activities in real time is needed. In this study, we developed a novel SPECT imaging probe for evaluation of hepatic CYP2D activity.Methods: Iodine-123- and 125-labeled 4-iodobenzylmequitazine (123/125I-BMQ) was synthesized with high labeling and purity. CYP isozymes involved in the metabolism of 125I-BMQ in mouse liver microsomes were evaluated, and the utility of 123/125I-was assessed from biological distribution and SPECT imaging evaluation in normal and CYP2D-inhibited mice.Results:In vitro metabolite analysis using mouse liver microsomes showed that 125I-BMQ is specifically metabolized by CYP2D. Biological distribution and SPECT imaging of 123/125I-BMQ in normal mice showed that injection 123/125I-BMQ accumulated early in the liver and was excreted into the gallbladder and intestines. In CYP2D-inhibited mice, accumulation in the liver was increased, but accumulation in the gallbladder and intestines, the excretory organ, was delayed. Since only metabolites of 125I-BMQ are detected in bile, visualization and measuring of the accumulation of metabolites over time in the intestine, where bile is excreted, could predict the amount of metabolites produced in the body and evaluate CYP2D activity, which would be useful in determining the dosage of various drugs metabolized by CYP2D.Conclusion:123/125I-BMQ is useful as a SPECT imaging probe for comprehensive and direct assessment of hepatic CYP2D activity in a minimally invasive and simple approach.

  DOI：

  10.3389/fphar.2024.1397288
• 作为产物：
  描述：

  4-(tributylstannyl)benzyl bromide 在 叔丁基过氧化氢 、 sodium iodide 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 4-[¹²⁵I]-iodobenzyl bromide
  参考文献：
  名称：

  Development of radioiodine-labeled mequitazine for evaluation of hepatic CYP2D activity

  摘要：

  Background: As drug-metabolizing enzyme activities are affected by a variety of factors, such as drug-drug interactions, a method to evaluate drug-metabolizing enzyme activities in real time is needed. In this study, we developed a novel SPECT imaging probe for evaluation of hepatic CYP2D activity.Methods: Iodine-123- and 125-labeled 4-iodobenzylmequitazine (123/125I-BMQ) was synthesized with high labeling and purity. CYP isozymes involved in the metabolism of 125I-BMQ in mouse liver microsomes were evaluated, and the utility of 123/125I-was assessed from biological distribution and SPECT imaging evaluation in normal and CYP2D-inhibited mice.Results:In vitro metabolite analysis using mouse liver microsomes showed that 125I-BMQ is specifically metabolized by CYP2D. Biological distribution and SPECT imaging of 123/125I-BMQ in normal mice showed that injection 123/125I-BMQ accumulated early in the liver and was excreted into the gallbladder and intestines. In CYP2D-inhibited mice, accumulation in the liver was increased, but accumulation in the gallbladder and intestines, the excretory organ, was delayed. Since only metabolites of 125I-BMQ are detected in bile, visualization and measuring of the accumulation of metabolites over time in the intestine, where bile is excreted, could predict the amount of metabolites produced in the body and evaluate CYP2D activity, which would be useful in determining the dosage of various drugs metabolized by CYP2D.Conclusion:123/125I-BMQ is useful as a SPECT imaging probe for comprehensive and direct assessment of hepatic CYP2D activity in a minimally invasive and simple approach.

  DOI：

  10.3389/fphar.2024.1397288

文献信息

• Mechanism of Cu-Catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications
  作者：John J. Molloy、Kerry M. O’Rourke、Carolina P. Frias、Nikki L. Sloan、Matthew J. West、Sally L. Pimlott、Andrew Sutherland、Allan J. B. Watson

  DOI：10.1021/acs.orglett.9b00942

  日期：2019.4.5

  Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: general Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation

  报道了使用亲电子卤素试剂对铜催化的芳基硼酸卤代硼烷化反应机理的研究。提供的证据表明这是通过硼酸酯驱动的ipso取代途径发生的，并且这些过程的运行不需要Cu：一般的Lewis碱催化是可行的。这进而允许合理开发通用，简单且有效的碱催化卤代硼烷，该卤代硼烷适合制备125 I标记的SPECT应用产品。
• WILSON, A. A.;DANNALS, R. F.;RAVERT, H. T.;WAGNER, H. N. (JR), APPL. RADIAT. AND ISOTOP. A, 40,(1989) N, C. 369-373
  作者：WILSON, A. A.、DANNALS, R. F.、RAVERT, H. T.、WAGNER, H. N. (JR)

  DOI：——

  日期：——
• WILSON, ALAN A.;DANNALS, ROBERT F.;RAVERT, HAYDEN T.;FROST, J. JAMES;WAGN+, J. MED. CHEM., 32,(1989) N, C. 1057-1062
  作者：WILSON, ALAN A.、DANNALS, ROBERT F.、RAVERT, HAYDEN T.、FROST, J. JAMES、WAGN+

  DOI：——

  日期：——