(2-boronobenzyl)triphenylphosphonium | 1247338-12-0

• 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: (2-boronobenzyl)triphenylphosphonium
• CAS: 1247338-12-0
• 化学式: C₂₅H₂₃BO₂P
• 分子量: 397.241
• InChiKey: LTTFZFVTVHROPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2-boronobenzyl)triphenylphosphonium 在 双氧水 作用下， 生成 (2-hydroxybenzyl)triphenylphosphonium
  参考文献：
  名称：

  Mitigation of NADPH Oxidase 2 Activity as a Strategy to Inhibit Peroxynitrite Formation

  摘要：

  Using high throughput screening-compatible assays for superoxide and hydrogen peroxide, we identified potential inhibitors of the NADPH oxidase (Nox2) isoform from a small library of bioactive compounds. By using multiple probes (hydroethidine, hydropropidine, Amplex Red, and coumarin boronate) with well defined redox chemistry that form highly diagnostic marker products upon reaction with superoxide (O2 arrange=stack.), hydrogen peroxide (H2O2), and peroxynitrite (ONOO-), the number of false positives was greatly decreased. Selected hits for Nox2 were further screened for their ability to inhibit ONOO- formation in activated macrophages. A new diagnostic marker product for ONOO- is reported. We conclude that the newly developed high throughput screening/reactive oxygen species assays could also be used to identify potential inhibitors of ONOO- formed from Nox2-derived O2. and nitric oxide synthase-derived nitric oxide.

  DOI：

  10.1074/jbc.m115.702787

文献信息

• Reaction between Peroxynitrite and Triphenylphosphonium-Substituted Arylboronic Acid Isomers: Identification of Diagnostic Marker Products and Biological Implications
  作者：Adam Sikora、Jacek Zielonka、Jan Adamus、Dawid Debski、Agnieszka Dybala-Defratyka、Bartosz Michalowski、Joy Joseph、Richard C. Hartley、Michael P. Murphy、Balaraman Kalyanaraman

  DOI：10.1021/tx300499c

  日期：2013.6.17

  (TPP) group on the reaction between ONOO– and mitochondria-targeted arylboronate isomers (o-, m-, and p-MitoPhB(OH)2). Results from the electron paramagnetic resonance (EPR) spin-trapping experiments unequivocally showed the presence of a phenyl radical intermediate from meta and para isomers, and not from the ortho isomer. The yield of o-MitoPhNO2 formed from the reaction between o-MitoPhB(OH)2 and ONOO–

  芳族硼酸与过氧亚硝酸盐 (ONOO – ) 快速反应生成酚类作为主要产物。该反应用于监测细胞系统中 ONOO的形成。此前，我们提出ONOO -和芳基硼酸酯(PhB(OH) 2 ) 之间的反应产生酚类产物（主要途径）和自由基对PhB(OH) 2 O •– ··· • NO 2（次要途径）。[西科拉，A.等。( 2011 )化学。水库。毒理学。24 , 687-697]。在这项研究中，我们研究了庞大的三苯基鏻 (TPP) 基团对 ONOO与线粒体靶向芳基硼酸酯异构体（o-、m-和p -MitoPhB(OH) 2）之间反应的影响。电子顺磁共振 (EPR) 自旋捕获实验的结果明确表明存在来自间位和对位异构体的苯基自由基中间体，而不是来自邻位异构体。o -MitoPhNO 2的产率由它们之间的反应形成o -MitoPhB(OH) 2和 ONOO –没有被苯基自由基清除剂减少，这表明o -MitoPhB(OH)