4-trimethylammonium-2,2,6,6-tetramethyl-piperidine-1-oxyl | 64525-01-5

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-trimethylammonium-2,2,6,6-tetramethyl-piperidine-1-oxyl
• 英文别名: 4-(trimethylammonium)-2,2,6,6-tetramethylpiperidinyl-1-oxy iodide salt；CAT-1
• CAS: 64525-01-5
• 化学式: C₁₂H₂₆N₂O
• 分子量: 214.351
• InChiKey: GGKNTGJPGZQNID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  4.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-trimethylammonium-2,2,6,6-tetramethyl-piperidine-1-oxyl 在 苯肼 作用下， 生成 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl-trimethylammonium
  参考文献：
  名称：

  [EN] A SOLUTION OF TEMPO-DERIVATIVES FOR USE AS ELECTROLYTE IN REDOX-FLOW CELLS
  [FR] SOLUTION DE DÉRIVÉS DE TEMPO DESTINÉE À ÊTRE UTILISÉE EN TANT QU'ÉLECTROLYTE DANS DES CELLULES À FLUX CONTINU RÉDOX

  摘要：

  本发明涉及一种包含水和不同的2,2,6,6-四甲基哌啶氧基自由基(TEMPO)衍生物的溶液，制备该溶液的方法，制备以该溶液作为电解质的氧化还原流动电池的方法，包括该溶液作为电池中一个腔室的氧化还原流动电池，以及使用该氧化还原流动电池存储电能的方法。

  公开号：

  WO2021197876A1
• 作为产物：
  描述：

  1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yltrimethylammonium chloride 在 二乙烯三胺五醋酸 、 sodium chloride 、 xanthine oxidase 、 黄嘌呤 作用下， 生成 4-trimethylammonium-2,2,6,6-tetramethyl-piperidine-1-oxyl
  参考文献：
  名称：

  EPR detection of cellular and mitochondrial superoxide using cyclic hydroxylamines

  摘要：

  Superoxide (O(2)(center dot-)) has been implicated in the pathogenesis of many human diseases, but detection of the O(2)(center dot-) radicals in biological systems is limited due to inefficiency of O(2)(center dot-) spin trapping and lack of site-specific information. This work studied production of extracellular, intracellular and mitochondrial O(2)(center dot-) in neutrophils, cultured endothelial cells and isolated mitochondria using a new set of cationic, anionic and neutral hydroxylamine spin probes with various lipophilicity and cell permeability. Cyclic hydroxylamines rapidly react with O(2)(center dot-), producing stable nitroxides and allowing site-specific O(2)(center dot-) detection in intracellular, extracellular and mitochondrial compartments. Negatively charged 1-hydroxy-4-phosphono-oxy-2,2,6, 6-tetramethylpiperidine (PP-H) and positively charged 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl-trimethylammonium (CAT1-H) detected only extramitochondrial O(2)(center dot-). Inhibition of EPR signal by SOD2 over-expression showed that mitochondria targeted mitoTEMPO-H detected intramitochondrial O(2)(center dot-) both in isolated mitochondria and intact cells. Both 1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine (CP-H) and 1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (CM-H) detected an increase in cytoplasm O(2)(center dot-) stimulated by PMA, but only CM-H and mitoTEMPO-H showed an increase in rotenone-induced mitochondrial O(2)(center dot-). These data show that a new set of hydroxylamine spin probes provide unique information about site-specific production of the O(2)(center dot-) radical in extracellular or intracellular compartments, cytoplasm or mitochondria.

  DOI：

  10.3109/10715762.2010.540242

文献信息

• [EN] A SOLUTION OF TEMPO-DERIVATIVES FOR USE AS ELECTROLYTE IN REDOX-FLOW CELLS<br/>[FR] SOLUTION DE DÉRIVÉS DE TEMPO DESTINÉE À ÊTRE UTILISÉE EN TANT QU'ÉLECTROLYTE DANS DES CELLULES À FLUX CONTINU RÉDOX
  申请人：BASF SE

  公开号：WO2021197876A1

  公开（公告）日：2021-10-07

  The present invention relates to a solution comprising water and different 2,2,6,6-tetramethyl-piperidinyl-oxyl (TEMPO)-derivatives, a process for the production of this solution, a process for making a redox-flow cell comprising the solution as electrolyte, a redox-flow cell comprising the solution as an electrolyte in one chamber of the cell and the use of the redox-flow cell for storing electrical energy.

  本发明涉及一种包含水和不同的2,2,6,6-四甲基哌啶氧基自由基(TEMPO)衍生物的溶液，制备该溶液的方法，制备以该溶液作为电解质的氧化还原流动电池的方法，包括该溶液作为电池中一个腔室的氧化还原流动电池，以及使用该氧化还原流动电池存储电能的方法。
• [EN] A SOLUTION OF TEMPO-DERIVATIVES FOR USE AS ELECTROLYTE IN REDOX-FLOW CELLS<br/>[FR] SOLUTION DE DÉRIVÉS DE TEMPO POUR UNE UTILISATION EN TANT QU'ÉLECTROLYTE DANS DES ÉLÉMENTS REDOX
  申请人：BASF SE

  公开号：WO2021197877A1

  公开（公告）日：2021-10-07

  The present invention relates to a solution comprising water and different 2,2,6,6-tetramethyl-piperidinyl-oxyl (TEMPO)-derivatives, a process for the production of this solution, a process for making a redox-flow cell comprising the solution as electrolyte, the redox-flow cell comprising the solution as an electrolyte in one chamber of the cell and the use of the redox-flow cell for storing electrical energy.

  本发明涉及一种包括水和不同的2,2,6,6-四甲基哌啶氧化物(TEMPO)衍生物的溶液，以及制备该溶液的方法、制备包括该溶液作为电解质的氧化还原流动电池的方法，该氧化还原流动电池包括该溶液作为电池的一个腔室的电解质，以及利用该氧化还原流动电池储存电能的方法。
• EPR detection of cellular and mitochondrial superoxide using cyclic hydroxylamines
  作者：Sergey I. Dikalov、Igor A. Kirilyuk、Maxim Voinov、Igor A. Grigor'ev

  DOI：10.3109/10715762.2010.540242

  日期：2011.4

  Superoxide (O(2)(center dot-)) has been implicated in the pathogenesis of many human diseases, but detection of the O(2)(center dot-) radicals in biological systems is limited due to inefficiency of O(2)(center dot-) spin trapping and lack of site-specific information. This work studied production of extracellular, intracellular and mitochondrial O(2)(center dot-) in neutrophils, cultured endothelial cells and isolated mitochondria using a new set of cationic, anionic and neutral hydroxylamine spin probes with various lipophilicity and cell permeability. Cyclic hydroxylamines rapidly react with O(2)(center dot-), producing stable nitroxides and allowing site-specific O(2)(center dot-) detection in intracellular, extracellular and mitochondrial compartments. Negatively charged 1-hydroxy-4-phosphono-oxy-2,2,6, 6-tetramethylpiperidine (PP-H) and positively charged 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl-trimethylammonium (CAT1-H) detected only extramitochondrial O(2)(center dot-). Inhibition of EPR signal by SOD2 over-expression showed that mitochondria targeted mitoTEMPO-H detected intramitochondrial O(2)(center dot-) both in isolated mitochondria and intact cells. Both 1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine (CP-H) and 1-hydroxy-3-methoxycarbonyl-2,2,5,5-tetramethylpyrrolidine (CM-H) detected an increase in cytoplasm O(2)(center dot-) stimulated by PMA, but only CM-H and mitoTEMPO-H showed an increase in rotenone-induced mitochondrial O(2)(center dot-). These data show that a new set of hydroxylamine spin probes provide unique information about site-specific production of the O(2)(center dot-) radical in extracellular or intracellular compartments, cytoplasm or mitochondria.