4-(2-hydroxybenzylamino)-5-hydroxynaphthalene-2,7-disulfonic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-hydroxybenzylamino)-5-hydroxynaphthalene-2,7-disulfonic acid
• 英文别名: 4-Hydroxy-5-[(2-hydroxyphenyl)methylamino]naphthalene-2,7-disulfonic acid
• 化学式: C₁₇H₁₅NO₈S₂
• 分子量: 425.44
• InChiKey: MRYYTMDMTJKTEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  178
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 4-(2-hydroxybenzylamino)-5-hydroxynaphthalene-2,7-disulfonic acid 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到
  参考文献：
  名称：

  A copper(II) complex as selective turn-on fluorosensor for nitric oxide and its intracellular application

  摘要：

  A highly water soluble copper(II) complex, 1 of a fluorophore ligand 4-(2-hydroxybenzylamino)-5 -hydroxynaphthalene-2,7-disulfonic acid (FL1) was synthesized and characterized. In the complex, the fluorescence intensity of the ligand was found to quench due to the presence of paramagnetic Cu(II) center. In degassed methanol solution of complex 1, the Cu(II) center was found to undergo reduction in presence of nitric oxide. This resulted in the simultaneous formation of N-nitrosated ligand. In the process, the quenched fluorescence intensity of the ligand restored. The selective turn on fluorogenic nature of the complex 1 was used to study the endogenously produced NO in living cells. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.08.014
• 作为产物：
  描述：

  azomethine-H monosodium salt 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 2.0h， 以80%的产率得到4-(2-hydroxybenzylamino)-5-hydroxynaphthalene-2,7-disulfonic acid
  参考文献：
  名称：

  A copper(II) complex as selective turn-on fluorosensor for nitric oxide and its intracellular application

  摘要：

  A highly water soluble copper(II) complex, 1 of a fluorophore ligand 4-(2-hydroxybenzylamino)-5 -hydroxynaphthalene-2,7-disulfonic acid (FL1) was synthesized and characterized. In the complex, the fluorescence intensity of the ligand was found to quench due to the presence of paramagnetic Cu(II) center. In degassed methanol solution of complex 1, the Cu(II) center was found to undergo reduction in presence of nitric oxide. This resulted in the simultaneous formation of N-nitrosated ligand. In the process, the quenched fluorescence intensity of the ligand restored. The selective turn on fluorogenic nature of the complex 1 was used to study the endogenously produced NO in living cells. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.08.014

文献信息

• A copper(II) complex as selective turn-on fluorosensor for nitric oxide and its intracellular application
  作者：Kanhu Charan Rout、Sumit Kumar Chaturvedi、Rizwan Hasan Khan、Biplab Mondal

  DOI：10.1016/j.ica.2015.08.014

  日期：2015.10

  A highly water soluble copper(II) complex, 1 of a fluorophore ligand 4-(2-hydroxybenzylamino)-5 -hydroxynaphthalene-2,7-disulfonic acid (FL1) was synthesized and characterized. In the complex, the fluorescence intensity of the ligand was found to quench due to the presence of paramagnetic Cu(II) center. In degassed methanol solution of complex 1, the Cu(II) center was found to undergo reduction in presence of nitric oxide. This resulted in the simultaneous formation of N-nitrosated ligand. In the process, the quenched fluorescence intensity of the ligand restored. The selective turn on fluorogenic nature of the complex 1 was used to study the endogenously produced NO in living cells. (C) 2015 Elsevier B.V. All rights reserved.