2-[2-[Bis(carboxymethyl)amino]ethyl-[(1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]-8-yl)methyl]amino]acetic acid | 1006591-02-1

• 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-[Bis(carboxymethyl)amino]ethyl-[(1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]-8-yl)methyl]amino]acetic acid
• CAS: 1006591-02-1
• 化学式: C₂₈H₃₂N₄O₉
• 分子量: 568.583
• InChiKey: ZDLKLMCUITYBHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  177
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-[2-[Bis(carboxymethyl)amino]ethyl-[(1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]-8-yl)methyl]amino]acetic acid 、 溴甲基乙酸酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以2.4 mg的产率得到bis(acetoxymethyl) 2,2'-((2-((2-(acetoxymethoxy)-2-oxoethyl)((1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indolin]-8-yl)methyl)amino)ethyl)azanediyl)diacetate
  参考文献：
  名称：

  Optically Switchable Chelates:  Optical Control and Sensing of Metal Ions

  摘要：

  [GRAPHICS]This study introduces new concepts in the design, synthesis, and in vitro and in vivo characterization, manipulation, and imaging of organic chelates whose association with metal ions is rapidly and reversibly controlled by using light. Di- and tricarboxylic group bearing photochromes, nitrobenzospiropyran (nitroBIPS), undergo rapid and reversible, optically driven transitions between their spiro (SP) and fluorescent merocyanine (MC) states. The MC state of nitroBIPS-8-DA binds tightly to various metal ions resulting in specific shifts in absorption and fluorescence, and the dissociation constant for its Gadolinium complex in water is measured at similar to 5 mu M. The metal-bound MC state is converted to the weaker-binding, SP state with use of 543 nm light, while the SP to MC transition is complete with use of 365 or 720 nm (2-photon) light within several microseconds. Fluorescence imaging of the MC state of nitroBIPS-8-TriA was used to quantify the rate and efficiency of optical switching and to provide a real-time readout of the state of the optically switchable chelate within living cells.

  DOI：

  10.1021/jo7019898
• 作为产物：
  描述：

  C₄₀H₅₆N₄O₉ 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-[2-[Bis(carboxymethyl)amino]ethyl-[(1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]-8-yl)methyl]amino]acetic acid
  参考文献：
  名称：

  Optically Switchable Chelates:  Optical Control and Sensing of Metal Ions

  摘要：

  [GRAPHICS]This study introduces new concepts in the design, synthesis, and in vitro and in vivo characterization, manipulation, and imaging of organic chelates whose association with metal ions is rapidly and reversibly controlled by using light. Di- and tricarboxylic group bearing photochromes, nitrobenzospiropyran (nitroBIPS), undergo rapid and reversible, optically driven transitions between their spiro (SP) and fluorescent merocyanine (MC) states. The MC state of nitroBIPS-8-DA binds tightly to various metal ions resulting in specific shifts in absorption and fluorescence, and the dissociation constant for its Gadolinium complex in water is measured at similar to 5 mu M. The metal-bound MC state is converted to the weaker-binding, SP state with use of 543 nm light, while the SP to MC transition is complete with use of 365 or 720 nm (2-photon) light within several microseconds. Fluorescence imaging of the MC state of nitroBIPS-8-TriA was used to quantify the rate and efficiency of optical switching and to provide a real-time readout of the state of the optically switchable chelate within living cells.

  DOI：

  10.1021/jo7019898