3-(2-碘乙酰氨基)-PROXYL | 27048-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 3-(2-碘乙酰氨基)-PROXYL
• 中文别名: 3-(2-碘乙酰氨基)-2,2,5,5-四甲基-1-吡咯烷基氧自由基；3-(2-碘代乙酰胺基)-2,2,5,5-四甲基-1-吡咯烷基自由基
• 英文名称: 3-(2-iodoacetamido)-2,2,5,5-tetramethylpyrrolidine-1-oxyl
• 英文别名: 3-(2-iodoacetamido)-PROXYL
• CAS: 27048-01-7
• 化学式: C₁₀H₂₀IN₂O₂
• 分子量: 327.185
• InChiKey: OQIGMSGDHDTSFA-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164 °C(lit.)
• 密度：
  1.4794 (estimate)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  33.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S22,S24/25

制备方法与用途

用途
巯基基团特异性自旋标记物广泛应用于研究经臭氧处理的人和牛红细胞膜蛋白，以及在肌纤维中定位肌球蛋白亚片段。此外，含有硫代磷酸二酯的DNA片段也可通过该自旋标记物进行标记。

反应信息

• 作为反应物：
  描述：

  3-(2-碘乙酰氨基)-PROXYL 、 野靛碱 在 肼-D4 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 792.0h， 生成 N-(1-hydroxy-2,2,5,5-tetramethylpyrrolidin-3-yl)-2-{8-oxo-5,6-dihydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(2H,4H,8H)-yl}acetamide
  参考文献：
  名称：

  First spin-labeled cytisine derivatives

  摘要：

  通过仲胺的酰化和烷基化，合成了含有稳定的吡咯烷和哌啶亚硝基的自旋标记胞嘧啶衍生物。毒理学研究表明，亚硝基的引入大大降低了一般毒性。

  DOI：

  10.1007/s10600-013-0588-y
• 作为试剂：
  描述：

  在 3-(2-碘乙酰氨基)-PROXYL 、 溶剂黄146 、 三乙胺 作用下， 以 水 为溶剂， 反应 24.0h， 生成 、
  参考文献：
  名称：

  Site directed nitroxide spin labeling of oligonucleotides for NMR and EPR studies

  摘要：

  Nitroxide labels are useful probes of biomolecule structure that can be detected by NMR and EPR spectroscopy. Although many methods exist for labeling oligonucleotides with nitroxides, most require reagents that are expensive or laborious to prepare. A simpler approach is described herein using commercially available phosphorothioate oligonucleotides and 2-(3-iodoacetamidomethyl)-PROXYL. We describe semi-optimized conditions for labeling DNA and RNA oligonucleotides and methodology for purifying and identifying these reagents by MALDI-MS. The nitroxide label showed some propensity to hydrolyze at high temperature and over prolonged periods at room temperature. Nitroxide-labeled DNA oligonucleotides gave characteristic EPR spectra and caused the disappearance of bound protein signals in N-15 HSQC spectra consistent with the paramagnetic relaxation enhancement (PRE) effect. (C) 2015 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.12.056

文献信息

• [EN] NITROXIDE CONTAINING AMYLOID BINDING AGENTS FOR IMAGING AND THERAPEUTIC USES<br/>[FR] AGENTS DE LIAISON À L'AMYLOÏDE CONTENANT DU NITROXYDE UTILISÉS EN IMAGERIE ET À DES FINS THÉRAPEUTIQUES
  申请人：UNIV CALIFORNIA

  公开号：WO2017031239A1

  公开（公告）日：2017-02-23

  The present invention provides methods of using nitroxide spin-labeled amyloid beta-binding compounds to image amyloid. The present invention also provides nitroxide spin-labeled amyloid beta-binding compounds

  本发明提供了使用亚硝基自旋标记的淀粉样β结合化合物来成像淀粉样物质的方法。本发明还提供了亚硝基自旋标记的淀粉样β结合化合物。
• First spin-labeled cytisine derivatives
  作者：Yu. F. Polienko、V. I. Vinogradova、Sh. Sh. Sagdullaev、N. D. Abdullaev、Yu. V. Gatilov、I. A. Grigor′ev

  DOI：10.1007/s10600-013-0588-y

  日期：2013.5

  Spin-labeled cytisine derivatives containing stable pyrrolidine and piperidine nitroxyl radicals were synthesized by acylation and alkylation of the secondary amine. Toxicological studies showed that introduction of the nitroxyl group decreased significantly the general toxicity.

  通过仲胺的酰化和烷基化，合成了含有稳定的吡咯烷和哌啶亚硝基的自旋标记胞嘧啶衍生物。毒理学研究表明，亚硝基的引入大大降低了一般毒性。
• Site directed nitroxide spin labeling of oligonucleotides for NMR and EPR studies
  作者：Nicholas E. Shepherd、Roland Gamsjaeger、Marylène Vandevenne、Liza Cubeddu、Joel P. Mackay

  DOI：10.1016/j.tet.2014.12.056

  日期：2015.2

  Nitroxide labels are useful probes of biomolecule structure that can be detected by NMR and EPR spectroscopy. Although many methods exist for labeling oligonucleotides with nitroxides, most require reagents that are expensive or laborious to prepare. A simpler approach is described herein using commercially available phosphorothioate oligonucleotides and 2-(3-iodoacetamidomethyl)-PROXYL. We describe semi-optimized conditions for labeling DNA and RNA oligonucleotides and methodology for purifying and identifying these reagents by MALDI-MS. The nitroxide label showed some propensity to hydrolyze at high temperature and over prolonged periods at room temperature. Nitroxide-labeled DNA oligonucleotides gave characteristic EPR spectra and caused the disappearance of bound protein signals in N-15 HSQC spectra consistent with the paramagnetic relaxation enhancement (PRE) effect. (C) 2015 The Authors. Published by Elsevier Ltd.