[(2-{(2-[2-bis(methoxycarbonylmethyl)amino-5-methylphenoxy]-7-azidooctan-2-yl)oxy}-4-formylphenyl)(methoxycarbonylmethyl)amino]acetic acid methyl ester | 1394052-24-4

• 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: [(2-{(2-[2-bis(methoxycarbonylmethyl)amino-5-methylphenoxy]-7-azidooctan-2-yl)oxy}-4-formylphenyl)(methoxycarbonylmethyl)amino]acetic acid methyl ester
• CAS: 1394052-24-4
• 化学式: C₃₄H₄₅N₅O₁₁
• 分子量: 699.758
• InChiKey: WZCCNMVAERWHCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  50.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  195.97
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  [(2-{(2-[2-bis(methoxycarbonylmethyl)amino-5-methylphenoxy]-7-azidooctan-2-yl)oxy}-4-formylphenyl)(methoxycarbonylmethyl)amino]acetic acid methyl ester 在 水 、 对甲苯磺酸 、 potassium hydroxide 作用下， 以 甲醇 、 丙酸 为溶剂， 反应 22.0h， 生成 2-[2-[7-azido-1-[2-[bis(carboxymethyl)amino]-5-(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)phenoxy]octan-2-yl]oxy-N-(carboxymethyl)-4-methylanilino]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：

  1,2-环氧-7-辛烯 在 盐酸 、 4-二甲氨基吡啶 、 sodium azide 、 tin(II) chloride dihdyrate 、 potassium tert-butylate 、 氢溴酸 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 141.0h， 生成 [(2-{(2-[2-bis(methoxycarbonylmethyl)amino-5-methylphenoxy]-7-azidooctan-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