methyl 2-[2-[7-azido-2-[2-[bis(2-methoxy-2-oxoethyl)amino]-4-chlorophenoxy]octoxy]-N-(2-methoxy-2-oxoethyl)-4-(3-oxa-23-aza-9-azoniaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-16-yl)anilino]acetate | 1185947-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 2-[2-[7-azido-2-[2-[bis(2-methoxy-2-oxoethyl)amino]-4-chlorophenoxy]octoxy]-N-(2-methoxy-2-oxoethyl)-4-(3-oxa-23-aza-9-azoniaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-16-yl)anilino]acetate
• CAS: 1185947-26-5
• 化学式: C₅₇H₆₇ClN₇O₁₁
• 分子量: 1061.65
• InChiKey: XOUFXXCIVFUKPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  76
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  160
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 2-[2-[7-azido-2-[2-[bis(2-methoxy-2-oxoethyl)amino]-4-chlorophenoxy]octoxy]-N-(2-methoxy-2-oxoethyl)-4-(3-oxa-23-aza-9-azoniaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-16-yl)anilino]acetate 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以96%的产率得到2-[2-[7-azido-2-[2-[bis(carboxymethyl)amino]-4-chlorophenoxy]octoxy]-N-(carboxymethyl)-4-(3-oxa-23-aza-9-azoniaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-16-yl)anilino]acetic acid
  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 、 sodium azide 、 tin(II) chloride dihdyrate 、 氢溴酸 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 丙酸 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 89.0h， 生成 methyl 2-[2-[7-azido-2-[2-[bis(2-methoxy-2-oxoethyl)amino]-4-chlorophenoxy]octoxy]-N-(2-methoxy-2-oxoethyl)-4-(3-oxa-23-aza-9-azoniaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-16-yl)anilino]acetate
  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

• 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.