3-(N,N-bis(methoxycarbonylmethyl)-(2-(2-amino-5-methoxyphenoxy))-1-ethoxy)-4-(N'-methoxycarbonylmethyl)aminobenzaldehyde | 404335-92-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(N,N-bis(methoxycarbonylmethyl)-(2-(2-amino-5-methoxyphenoxy))-1-ethoxy)-4-(N'-methoxycarbonylmethyl)aminobenzaldehyde
• 英文别名: Methyl 2-[2-[2-[2-[bis(2-methoxy-2-oxoethyl)amino]-5-methoxyphenoxy]ethoxy]-4-formylanilino]acetate
• CAS: 404335-92-8
• 化学式: C₂₅H₃₀N₂O₁₀
• 分子量: 518.521
• InChiKey: BHVWJRUNROEVFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(N,N-bis(methoxycarbonylmethyl)-(2-(2-amino-5-methoxyphenoxy))-1-ethoxy)-4-(N'-methoxycarbonylmethyl)aminobenzaldehyde 在 氢氧化钾 、 甲烷磺酸 、 四氯苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 反应 16.0h， 生成 fluozin-3, tetrapotassium salt
  参考文献：
  名称：

  Detection and Imaging of Zinc Secretion from Pancreatic β-Cells Using a New Fluorescent Zinc Indicator

  摘要：

  A novel Zn2+-selective visible wavelength fluoroionophore (FluoZin-3, 9) was synthesized. The chelating portion of the molecule resembles known EGTA-based Ca2+-selective fluoroionophores, except that one of the N-acetic acid moieties has been deleted in 9. FluoZin-3 is virtually non-fluorescent in the absence of Zn2+, and exhibits a several hundred-fold fluorescence increase upon saturation with Zn2+( approximately 100 nM), with a Kd = 15 +/- 2 nM. A 1:1 binding stoichiometry of 9:Zn2+ was determined, and the fluorescence of the complex is pH-independent at pH > 6. FluoZin-3 was used to monitor Zn2+ that was co-secreted with insulin from pancreatic beta-cells by exocytosis following stimulation with glucose. The total Zn2+ concentration near the cells reached 600 nM, and Zn2+ was detectable at least 15 mum away from secreting cells. Heterogeneity in secretion among cells was indicated in that some cells in a cluster did not release Zn2+. Also, within secreting cells some regions of the cell membrane gave rise to secretion while others did not, suggesting active zones of secretion on the cell surface.

  DOI：

  10.1021/ja011774y
• 作为产物：
  描述：

  3-(2-(5-methoxy-2-nitrophenoxy)-1-ethoxy)-4-nitrobenzaldehyde dioxolane 在 platinum(IV) oxide 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、137.9 kPa 条件下， 反应 8.0h， 生成 3-(N,N-bis(methoxycarbonylmethyl)-(2-(2-amino-5-methoxyphenoxy))-1-ethoxy)-4-(N'-methoxycarbonylmethyl)aminobenzaldehyde
  参考文献：
  名称：

  Detection and Imaging of Zinc Secretion from Pancreatic β-Cells Using a New Fluorescent Zinc Indicator

  摘要：

  A novel Zn2+-selective visible wavelength fluoroionophore (FluoZin-3, 9) was synthesized. The chelating portion of the molecule resembles known EGTA-based Ca2+-selective fluoroionophores, except that one of the N-acetic acid moieties has been deleted in 9. FluoZin-3 is virtually non-fluorescent in the absence of Zn2+, and exhibits a several hundred-fold fluorescence increase upon saturation with Zn2+( approximately 100 nM), with a Kd = 15 +/- 2 nM. A 1:1 binding stoichiometry of 9:Zn2+ was determined, and the fluorescence of the complex is pH-independent at pH > 6. FluoZin-3 was used to monitor Zn2+ that was co-secreted with insulin from pancreatic beta-cells by exocytosis following stimulation with glucose. The total Zn2+ concentration near the cells reached 600 nM, and Zn2+ was detectable at least 15 mum away from secreting cells. Heterogeneity in secretion among cells was indicated in that some cells in a cluster did not release Zn2+. Also, within secreting cells some regions of the cell membrane gave rise to secretion while others did not, suggesting active zones of secretion on the cell surface.

  DOI：

  10.1021/ja011774y

文献信息

• ZINC BINDING COMPOUNDS AND THEIR METHOD OF USE
  申请人：Gee Kyle R.

  公开号：US20090181364A1

  公开（公告）日：2009-07-16

  The present invention provides a metal chelator and methods that facilitate binding, detecting, monitoring and quantitating of zinc ions in a sample. The metal chelating moiety of the zinc-binding compound is an analog of the well-known calcium chelator, BAPTA (1,2-bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid), wherein the chelating moiety has been modified from a tetraacetic acid moiety to a tri- di- or monoacetic moiety. This change in acetic acid groups on the metal chelating moiety results in the selective bindings of zinc ions in the presence of calcium ions, both of which are present in biological fluids and intracellular cytosolic fluid and organelles.
• Zinc binding compounds and their method of use
  申请人：GEE Kyle R.

  公开号：US20110159517A1

  公开（公告）日：2011-06-30

  The present invention provides a metal chelator and methods that facilitate binding, detecting, monitoring and quantitating of zinc ions in a sample. The metal chelating moiety of the zinc-binding compound is an analog of the well-known calcium chelator, BAPTA (1,2-bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid), wherein the chelating moiety has been modified from a tetraacetic acid moiety to a tri- di- or monoacetic moiety. This change in acetic acid groups on the metal chelating moiety results in the selective bindings of zinc ions in the presence of calcium ions, both of which are present in biological fluids and intracellular cytosolic fluid and organelles.
• US8445702B2
  申请人：——

  公开号：US8445702B2

  公开（公告）日：2013-05-21