2-amino-4-chloro-1-{[1-(2-aminophenoxymethyl)oct-7-en-2-yl]oxy}benzene | 945225-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-amino-4-chloro-1-{[1-(2-aminophenoxymethyl)oct-7-en-2-yl]oxy}benzene
• 英文别名: 2-[1-(2-Aminophenoxy)oct-7-en-2-yloxy]-5-chloroaniline；2-[1-(2-aminophenoxy)oct-7-en-2-yloxy]-5-chloroaniline
• CAS: 945225-31-0
• 化学式: C₂₀H₂₅ClN₂O₂
• 分子量: 360.884
• InChiKey: AIWKLKLTGQWSAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  556.1±50.0 °C(predicted)
• 密度：
  1.166±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-chloro-1-{[1-(2-aminophenoxymethyl)oct-7-en-2-yl]oxy}benzene 在 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 44.5h， 生成 [(2-{(2-[2-bis(methoxycarbonylmethyl)amino-4-chlorophenoxy]oct-7-en-2-yl)oxy}-4-formylphenyl)(methoxycarbonylmethyl)amino]acetic acid methyl ester
  参考文献：
  名称：

  Calcium Rubies: A Family of Red-Emitting Functionalizable Indicators Suitable for Two-Photon Ca²⁺ Imaging

  摘要：

  We designed Calcium Rubies, a family of functionalizable BAPTA-based red-fluorescent calcium (Ca2+) indicators as new tools for biological Ca2+ imaging. The specificity of this Ca2+-indicator family is its side arm, attached on the ethylene glycol bridge that allows coupling the indicator to various groups while leaving open the possibility of aromatic substitutions on the BAPTA core for tuning the Ca2+-binding affinity. Using this possibility we now synthesize and characterize three different CaRubies with affinities between 3 and 22 mu M. Their long excitation and emission wavelengths (peaks at 586/604 nm) allow their use in otherwise challenging multicolor experiments, e.g., when combining Ca2+ uncaging or optogenetic stimulation with Ca2+ imaging in cells expressing fluorescent proteins. We illustrate this capacity by the detection of Ca2+ transients evoked by blue light in cultured astrocytes expressing CatCh, a light-sensitive Ca2+-translocating channelrhodopsin linked to yellow fluorescent protein. Using time-correlated single-photon counting, we measured fluorescence lifetimes for all CaRubies and demonstrate a 10-fold increase in the average lifetime upon Ca2+ chelation. Since only the fluorescence quantum yield but not the absorbance of the CaRubies is Ca2+-dependent, calibrated two-photon fluorescence excitation measurements of absolute Ca2+ concentrations are feasible.

  DOI：

  10.1021/ja304018d
• 作为产物：
  描述：

  4-氯-2-硝基苯酚 在 盐酸 、 tin(II) chloride dihdyrate 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 2-amino-4-chloro-1-{[1-(2-aminophenoxymethyl)oct-7-en-2-yl]oxy}benzene
  参考文献：
  名称：

  Calcium Rubies: A Family of Red-Emitting Functionalizable Indicators Suitable for Two-Photon Ca²⁺ Imaging

  摘要：

  We designed Calcium Rubies, a family of functionalizable BAPTA-based red-fluorescent calcium (Ca2+) indicators as new tools for biological Ca2+ imaging. The specificity of this Ca2+-indicator family is its side arm, attached on the ethylene glycol bridge that allows coupling the indicator to various groups while leaving open the possibility of aromatic substitutions on the BAPTA core for tuning the Ca2+-binding affinity. Using this possibility we now synthesize and characterize three different CaRubies with affinities between 3 and 22 mu M. Their long excitation and emission wavelengths (peaks at 586/604 nm) allow their use in otherwise challenging multicolor experiments, e.g., when combining Ca2+ uncaging or optogenetic stimulation with Ca2+ imaging in cells expressing fluorescent proteins. We illustrate this capacity by the detection of Ca2+ transients evoked by blue light in cultured astrocytes expressing CatCh, a light-sensitive Ca2+-translocating channelrhodopsin linked to yellow fluorescent protein. Using time-correlated single-photon counting, we measured fluorescence lifetimes for all CaRubies and demonstrate a 10-fold increase in the average lifetime upon Ca2+ chelation. Since only the fluorescence quantum yield but not the absorbance of the CaRubies is Ca2+-dependent, calibrated two-photon fluorescence excitation measurements of absolute Ca2+ concentrations are feasible.

  DOI：

  10.1021/ja304018d

文献信息

• Synthesis and Characterization of a New Red-Emitting Ca²⁺ Indicator, Calcium Ruby
  作者：Stéphane Gaillard、Aleksey Yakovlev、Camilla Luccardini、Martin Oheim、Anne Feltz、Jean-Maurice Mallet

  DOI：10.1021/ol070648h

  日期：2007.7.1

  Calcium Ruby m-Cl (X = H, Y = Cl) is a visible-light excited red-emitting calcium concentration ([Ca2+]) indicator dye (579/598 nm peak excitation/emission) with a side arm for conjugation via EDC or click chemistry. Its large molar extinction and high quantum yield rank it among the brightest long-wavelength Ca2+ indicators. Calcium Ruby is a promising alternative to existing dyes for imaging [Ca2+] in multicolor fluorescence applications or in the presence of yellow-green cellular autofluorescence.
• Calcium Rubies: A Family of Red-Emitting Functionalizable Indicators Suitable for Two-Photon Ca²⁺ Imaging
  作者：Mayeul Collot、Christina Loukou、Aleksey V. Yakovlev、Christian D. Wilms、Dongdong Li、Alexis Evrard、Alsu Zamaleeva、Laurent Bourdieu、Jean-François Léger、Nicole Ropert、Jens Eilers、Martin Oheim、Anne Feltz、Jean-Maurice Mallet

  DOI：10.1021/ja304018d

  日期：2012.9.12

  We designed Calcium Rubies, a family of functionalizable BAPTA-based red-fluorescent calcium (Ca2+) indicators as new tools for biological Ca2+ imaging. The specificity of this Ca2+-indicator family is its side arm, attached on the ethylene glycol bridge that allows coupling the indicator to various groups while leaving open the possibility of aromatic substitutions on the BAPTA core for tuning the Ca2+-binding affinity. Using this possibility we now synthesize and characterize three different CaRubies with affinities between 3 and 22 mu M. Their long excitation and emission wavelengths (peaks at 586/604 nm) allow their use in otherwise challenging multicolor experiments, e.g., when combining Ca2+ uncaging or optogenetic stimulation with Ca2+ imaging in cells expressing fluorescent proteins. We illustrate this capacity by the detection of Ca2+ transients evoked by blue light in cultured astrocytes expressing CatCh, a light-sensitive Ca2+-translocating channelrhodopsin linked to yellow fluorescent protein. Using time-correlated single-photon counting, we measured fluorescence lifetimes for all CaRubies and demonstrate a 10-fold increase in the average lifetime upon Ca2+ chelation. Since only the fluorescence quantum yield but not the absorbance of the CaRubies is Ca2+-dependent, calibrated two-photon fluorescence excitation measurements of absolute Ca2+ concentrations are feasible.