5-nitro-2-[3-(5-nitro-1,3-dihydro-1,3,3-trimethyl-2H-indol-2-yliden)-1-propen-1-yl]-1,3,3-trimethyl-3H-indolium iodide | 157673-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-nitro-2-[3-(5-nitro-1,3-dihydro-1,3,3-trimethyl-2H-indol-2-yliden)-1-propen-1-yl]-1,3,3-trimethyl-3H-indolium iodide
• 英文别名: 5-nitro-2-[3-(5-nitro-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)propenyl]-1,3,3-trimethyl-3H-indolium iodide；1,3,3-Trimethyl-5-nitro-2-[3-(1,3,3-trimethyl-5-nitroindol-1-ium-2-yl)prop-2-enylidene]indole;iodide
• CAS: 157673-82-0
• 化学式: C₂₅H₂₇N₄O₄*I
• 分子量: 574.418
• InChiKey: NLMUDHQHLMGQIU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-nitro-2-[3-(5-nitro-1,3-dihydro-1,3,3-trimethyl-2H-indol-2-yliden)-1-propen-1-yl]-1,3,3-trimethyl-3H-indolium iodide 在 盐酸 、 tin(ll) chloride 、 potassium iodide 作用下， 以 水 为溶剂， 反应 2.0h， 以61%的产率得到5-amino-2-[3-(5-amino-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)propenyl]-1,3,3-trimethyl-3H-indolium iodide
  参考文献：
  名称：

  Synthesis and spectral properties of polymethine-cyanine dye–nitroxide radical hybrid compounds for use as fluorescence probes to monitor reducing species and radicals

  摘要：

  Various hybrid compounds comprised of two types of nitroxide radicals and either a pentamethine (Cy5) or trimethine cyanine (Cy3) were synthesized. The nitroxide radicals were linked either via an ester-bond to one or two N-alkyl carboxyl-terminated groups of Cy5, or via two amido-bonds (aminocarbonyl or carborylamino group) to the 5-position of the indolenine moieties of Cy5 and Cy3. Changes in fluorescence and ESR intensities of the hybrid compounds were measured before and after addition of Na ascorbate in PBS (pH 7.0) to reduce the radicals. Among the hybrid compounds synthesized, those that linked the nitroxide radicals via an aminocarbonyl residue at the 5-position of the indolenine moieties on Cy5 and Cy3 exhibited a 1.8- and 5.1-fold increase in fluorescence intensity with the reduction of the nitroxide segment by the addition of Na ascorbate, respectively. In contrast, fluorescence intensity was not enhanced in the other hybrid compounds. Thus, the hybrid compounds which exhibited an increase in fluorescent intensity with radical reduction can be used in the quantitative measurement of reducing species such as Fe(2+) and ascorbic acid, and hydroxyl radicals. Because these hybrid compounds have the advantage of fluorescing at longer wavelengths-661 (Cy5) or 568 (Cy3) nm, respectively. they can be used to measure radical-reducing species or radicals either in solution or in vivo. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2008.07.045
• 作为产物：
  描述：

  1,2,3,3-tetramethyl-5-nitro-3H-indolium iodide 、 原甲酸三乙酯 在 乙酸酐 作用下， 反应 1.0h， 生成 5-nitro-2-[3-(5-nitro-1,3-dihydro-1,3,3-trimethyl-2H-indol-2-yliden)-1-propen-1-yl]-1,3,3-trimethyl-3H-indolium iodide
  参考文献：
  名称：

  Cyanine Borate Salts that Form Penetrated Ion Pairs in Benzene Solution: Synthesis, Properties, and Structure

  摘要：

  A series of cyanine borate salts were prepared and studied by laser spectroscopy, fluorescence spectroscopy, NMR spectral methods, and computer modeling. Analysis of the chemical, physical, and spectral properties of these salts shows that, in benzene solution, they form penetrated ion pairs. The center-to-center distance between the ions is less than the sum of the individual ionic radii. We call such structures penetrated ion pairs. Penetration affects the properties of the cyanine dyes in unique ways that are described.

  DOI：

  10.1021/jo00113a022

文献信息

• COMPOUNDS FOR THE DIAGNOSIS OF NEURODEGENERATIVE DISORDERS ON THE OLFACTORY EPITHELIUM
  申请人：Schmidt Boris

  公开号：US20130287700A1

  公开（公告）日：2013-10-31

  Subject of the present invention are compounds with high affinity for the Aβ protein, α-synuclein or for Tau-PHF aggregates, which are suitable as preferably fluorescent probes for the in vivo diagnosis of neurodegenerative disorders like e.g. Alzheimer's disease and Parkinson's disease. The compounds are characterized by suitable physicochemical properties (excitation wavelength, emission wavelength, Stokes shift, extinction) as well as a high affinity and selectivity for the target proteins.

  本发明的主题是具有高亲和力的化合物，用于Aβ蛋白、α-突触核蛋白或Tau-PHF聚集物，适用于作为体内诊断神经退行性疾病（如阿尔茨海默病和帕金森病）的首选荧光探针。这些化合物具有适当的物理化学性质（激发波长、发射波长、斯托克斯位移、消光），以及对目标蛋白的高亲和力和选择性。
• Synthesis and spectral properties of polymethine-cyanine dye–nitroxide radical hybrid compounds for use as fluorescence probes to monitor reducing species and radicals
  作者：Shingo Sato、Minoru Tsunoda、Minoru Suzuki、Masahiro Kutsuna、Kiyomi Takido-uchi、Mitsuru Shindo、Hitoshi Mizuguchi、Heitaro Obara、Hiroaki Ohya

  DOI：10.1016/j.saa.2008.07.045

  日期：2009.1

  Various hybrid compounds comprised of two types of nitroxide radicals and either a pentamethine (Cy5) or trimethine cyanine (Cy3) were synthesized. The nitroxide radicals were linked either via an ester-bond to one or two N-alkyl carboxyl-terminated groups of Cy5, or via two amido-bonds (aminocarbonyl or carborylamino group) to the 5-position of the indolenine moieties of Cy5 and Cy3. Changes in fluorescence and ESR intensities of the hybrid compounds were measured before and after addition of Na ascorbate in PBS (pH 7.0) to reduce the radicals. Among the hybrid compounds synthesized, those that linked the nitroxide radicals via an aminocarbonyl residue at the 5-position of the indolenine moieties on Cy5 and Cy3 exhibited a 1.8- and 5.1-fold increase in fluorescence intensity with the reduction of the nitroxide segment by the addition of Na ascorbate, respectively. In contrast, fluorescence intensity was not enhanced in the other hybrid compounds. Thus, the hybrid compounds which exhibited an increase in fluorescent intensity with radical reduction can be used in the quantitative measurement of reducing species such as Fe(2+) and ascorbic acid, and hydroxyl radicals. Because these hybrid compounds have the advantage of fluorescing at longer wavelengths-661 (Cy5) or 568 (Cy3) nm, respectively. they can be used to measure radical-reducing species or radicals either in solution or in vivo. (C) 2008 Elsevier B.V. All rights reserved.
• Cyanine Borate Salts that Form Penetrated Ion Pairs in Benzene Solution: Synthesis, Properties, and Structure
  作者：Sean Murphy、Xiquiang Yang、Gary B. Schuster

  DOI：10.1021/jo00113a022

  日期：1995.4

  A series of cyanine borate salts were prepared and studied by laser spectroscopy, fluorescence spectroscopy, NMR spectral methods, and computer modeling. Analysis of the chemical, physical, and spectral properties of these salts shows that, in benzene solution, they form penetrated ion pairs. The center-to-center distance between the ions is less than the sum of the individual ionic radii. We call such structures penetrated ion pairs. Penetration affects the properties of the cyanine dyes in unique ways that are described.