dopamine semiquinone anion radical | 88466-19-7

• 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: dopamine semiquinone anion radical
• CAS: 88466-19-7
• 化学式: C₈H₁₀NO₂
• 分子量: 152.173
• InChiKey: MEPFRGURKIZZAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dopamine semiquinone anion radical 生成 多巴胺苯醌
  参考文献：
  名称：

  Mechanism of the Manganese-Catalyzed Autoxidation of Dopamine

  摘要：

  Manganese is an essential trace element for human metabolism, but at higher concentrations it is a potent neurotoxin that presents clinical symptoms similar to those of Parkinson's disease. Since the toxicity of manganese may be related to its ability to accelerate the oxidation of catecholamines, we have examined the effect of aqueous Mn2+ on the formation and decay of the dopamine semiquinone radical ion. ESR spectroscopy was used to measure the kinetics of the disappearance of the semiquinone radical spectrum and the simultaneous appearance of the six-line spectrum of aqueous Mn2+ in Tris buffer. From the proposed mechanism for the autoxidation of dopamine to the quinone, the rate expression for semiquinone radical disappearance has the functional form -rate = k'[D(OH)(2)][Mn2+] at constant pH and molecular oxygen concentration, while the pH dependence is given by -log(rate) = log(constant) + (2 x pH), in agreement with the experimental results. The autoxidation of dopamine is catalyzed by manganese through the formation of a highly reactive complex. The effect of manganese is due to the fact that it can participate in a redox cycle which involves intramolecular electron transfer between manganese and the dopamine ligand.

  DOI：

  10.1021/tx00043a015
• 作为产物：
  描述：

  dopamine 在 Cl₂ radical anion 作用下， 生成 dopamine semiquinone anion radical
  参考文献：
  名称：

  Maity, Dilip K.; Mohan, Hari; Mittal, Jai P., Journal of the Chemical Society. Perkin transactions II, 1994, # 4, p. 919 - 924

  摘要：

  DOI：

文献信息

• Mechanism of the oxidation of dopamine by the hydroxyl radical in aqueous solution
  作者：Helen W. Richter、Walter H. Waddell

  DOI：10.1021/ja00354a041

  日期：1983.8

  from the adducts to H/sub 2/O, HPO/sub 4//sup 2more » -/, HO/sup -/, and PO/sub 4//sup 3 -/ were 1.7 x 10/sup 2/, 6.5 x 10/sup 8/, less than or equal to1.5 x 10/sup 11/, and less than or equal to7.0 x 10/sup 11/ M/sup -1/ s/sup -1/, respectively; for the fast reaction, rate constants for H/sub 2/O and HPO/sub 4//sup 2 -/ were 1.1 x 10/sup 3/ and 2.2 x 10/sup 8/ M/sup -1/ s/sup -1/, respectively.« less

  羟基自由基（HOin 平衡）与多巴胺（4-（2-氨基乙基）-1,2-苯二醇）通过单电子氧化反应产生邻半醌和邻半醌阴离子自由基，k = 5.9 x 10/sup 9/ M/sup -1/ s/sup -1/。H2O 的反应。与质子化多巴胺 (H/sup +/QH/sub 2/) 的反应通过添加到芳环进行，而与去质子化多巴胺 (H/sup +/QH/sup -/) 的反应通过直接的单电子氧化进行。通过加入 H2O 形成异构的羟基环己二烯基。到 H/sup +/QH/sub 2/ 产生三个动力学可区分的基团（1-和 2-，或 3- 和 6-，或 4- 和 5- 羟基环己二烯基），以产生半醌自由基的水消除速率; 脱水是“非常快”（将 H2O. ipso 添加到 OH 基团）、“快”或“慢”。快速和慢速反应是酸和碱催化的，在 pH 4-5 时速率最低。酸催化似乎是特定的，而碱催化是通用的。光谱是为 H2O
• Maity, Dilip K.; Mohan, Hari; Mittal, Jai P., Journal of the Chemical Society. Perkin transactions II, 1994, # 4, p. 919 - 924
  作者：Maity, Dilip K.、Mohan, Hari、Mittal, Jai P.

  DOI：——

  日期：——
• Mechanism of the Manganese-Catalyzed Autoxidation of Dopamine
  作者：Roger V. Lloyd

  DOI：10.1021/tx00043a015

  日期：1995.1

  Manganese is an essential trace element for human metabolism, but at higher concentrations it is a potent neurotoxin that presents clinical symptoms similar to those of Parkinson's disease. Since the toxicity of manganese may be related to its ability to accelerate the oxidation of catecholamines, we have examined the effect of aqueous Mn2+ on the formation and decay of the dopamine semiquinone radical ion. ESR spectroscopy was used to measure the kinetics of the disappearance of the semiquinone radical spectrum and the simultaneous appearance of the six-line spectrum of aqueous Mn2+ in Tris buffer. From the proposed mechanism for the autoxidation of dopamine to the quinone, the rate expression for semiquinone radical disappearance has the functional form -rate = k'[D(OH)(2)][Mn2+] at constant pH and molecular oxygen concentration, while the pH dependence is given by -log(rate) = log(constant) + (2 x pH), in agreement with the experimental results. The autoxidation of dopamine is catalyzed by manganese through the formation of a highly reactive complex. The effect of manganese is due to the fact that it can participate in a redox cycle which involves intramolecular electron transfer between manganese and the dopamine ligand.