[(2-{2-[6-bis(methoxycarbonylmethyl)amino-3-fluorophenoxy]ethoxy}-4-formyl-5-hydroxyphenyl)methoxycarbonylmethylamino]acetic acid methyl ester | 299172-14-8

• 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: [(2-{2-[6-bis(methoxycarbonylmethyl)amino-3-fluorophenoxy]ethoxy}-4-formyl-5-hydroxyphenyl)methoxycarbonylmethylamino]acetic acid methyl ester
• 英文别名: 5'-fluoro-5-formyl-4-hydroxy-BAPTA tetramethyl ester；methyl 2-[2-[2-[2-[bis(2-methoxy-2-oxoethyl)amino]-5-formyl-4-hydroxyphenoxy]ethoxy]-4-fluoro-N-(2-methoxy-2-oxoethyl)anilino]acetate
• CAS: 299172-14-8
• 化学式: C₂₇H₃₁FN₂O₁₂
• 分子量: 594.548
• InChiKey: AQZQSRDVCFFAPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2-{2-[6-bis(methoxycarbonylmethyl)amino-3-fluorophenoxy]ethoxy}-4-formyl-5-hydroxyphenyl)methoxycarbonylmethylamino]acetic acid methyl ester 在 盐酸 、 氢氧化钾 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetyloxymethyl 2-[6-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-5-[2-[2-[bis(acetyloxymethyl)amino]-5-fluorophenoxy]ethoxy]-1-benzofuran-2-yl]-1,3-oxazole-5-carboxylate
  参考文献：
  名称：

  New ratiometric fluorescent calcium indicators with moderately attenuated binding affinities

  摘要：

  Mono-halogenated derivatives of the calcium indicators fura-2 and indo-1 were synthesized and their spectroscopic properties evaluated. Halogenation ortho or para to the bridging oxygen in the BAPTA nucleus had a more pronounced weakening effect on binding affinity than in the meta position in the fura derivatives. Two new excitation ratioable fluorescent calcium indicators, benzothiaza-1 and 2, were also synthesized. K-d values of 400 nM to 5.3 mu M [Ca2+] were observed in these families of new probes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00280-8
• 作为产物：
  描述：

  5-氟-2-硝基苯酚 在 palladium on activated charcoal 、 platinum on activated charcoal 氢气 、 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(2-{2-[6-bis(methoxycarbonylmethyl)amino-3-fluorophenoxy]ethoxy}-4-formyl-5-hydroxyphenyl)methoxycarbonylmethylamino]acetic acid methyl ester
  参考文献：
  名称：

  New ratiometric fluorescent calcium indicators with moderately attenuated binding affinities

  摘要：

  Mono-halogenated derivatives of the calcium indicators fura-2 and indo-1 were synthesized and their spectroscopic properties evaluated. Halogenation ortho or para to the bridging oxygen in the BAPTA nucleus had a more pronounced weakening effect on binding affinity than in the meta position in the fura derivatives. Two new excitation ratioable fluorescent calcium indicators, benzothiaza-1 and 2, were also synthesized. K-d values of 400 nM to 5.3 mu M [Ca2+] were observed in these families of new probes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00280-8

文献信息

• Compositions and methods for detection and isolation of phosphorylated molecules
  申请人：Molecular Probes, Inc.

  公开号：US07102005B2

  公开（公告）日：2006-09-05

  The present invention relates to phosphate-binding compounds that find use in binding, detecting and isolating phosphorylated target molecules including the subsequent identification of target molecules that interact with phosphorylated target molecules or molecules capable of being phosphorylated. A binding solution is provide that comprises a phosphate-binding compound, an acid and a metal ion wherein the metal ion simultaneously interacts with an exposed phosphate group on a target molecule and the metal chelating moiety of the phosphate-binding compound forming a bridge between the phosphate-binding compound and a phosphorylated target molecule resulting in a ternary complex. The binding solution of the present invention finds use in binding and detecting immobilized and solubilized phosphorylated target molecules, isolation of phosphorylated target molecules from a complex mixture and aiding in proteomic analysis wherein kinase and phosphatase substrates and enzymes can be identified.

  本发明涉及磷酸结合化合物，用于结合、检测和分离包括随后鉴定与磷酸化靶分子相互作用或能够被磷酸化的分子的靶分子。提供一种包含磷酸结合化合物、酸和金属离子的结合溶液，其中金属离子同时与靶分子上的暴露的磷酸基团以及磷酸结合化合物的金属螯合基团相互作用，形成将磷酸结合化合物与磷酸化靶分子之间形成桥梁的三元复合物。本发明的结合溶液用于结合和检测固定和溶解的磷酸化靶分子，从复杂混合物中分离磷酸化的靶分子，并有助于蛋白质组学分析，其中激酶和磷酸酶底物和酶可被鉴定。
• Single Molecular Multianalyte (Ca²⁺, Mg²⁺) Fluorescent Probe and Applications to Bioimaging
  作者：Hirokazu Komatsu、Takahiro Miki、Daniel Citterio、Takeshi Kubota、Yutaka Shindo、Yoshiichiro Kitamura、Kotaro Oka、Koji Suzuki

  DOI：10.1021/ja0528228

  日期：2005.8.1

  Intracellular signal transduction relies on spatial and temporal signal transmitter dynamics. To clarify the correlations of these transmitter molecules, multicolor-imaging has been widely used. However, in the case of applying multiple indicators in a cell, spectral overlap of the indicators prevents accurate quantitative analysis. Moreover, the invasive (toxic) effect, the localization, the metabolism, as well as photobleaching of these indicators complicate the situation. Here, we show that single-molecular multifluorescent probes can overcome these problems. While intracellular calcium plays a critical role as a signal transmitter and magnesium acts as a cofactor in many situations, the correlations between the two cations are now the main issue. We designed and synthesized a Ca2+-Mg2+ responsive multifluorescent probe, KCM-1. KCM-1 shows a spectral blue shift upon complexation to Ca2+ and a red shift to the presence of Mg2+. With data analyzed at different excitation wavelengths, the concentrations of Ca2+ and Mg2+ are simultaneously quantified. Furthermore, by using the AM-ester method, intracellular Ca2+ and Mg2+ concentrations are simultaneously imaged. Such a type of intracellular multiple analyte imaging by a single-molecular multifluorescent probe is successfully demonstrated for the first time.
• New ratiometric fluorescent calcium indicators with moderately attenuated binding affinities
  作者：Kyle R. Gee、Eric A. Archer、Laura A. Lapham、Mary E. Leonard、Zhang-Lin Zhou、John Bingham、Zhenjun Diwu

  DOI：10.1016/s0960-894x(00)00280-8

  日期：2000.7

  Mono-halogenated derivatives of the calcium indicators fura-2 and indo-1 were synthesized and their spectroscopic properties evaluated. Halogenation ortho or para to the bridging oxygen in the BAPTA nucleus had a more pronounced weakening effect on binding affinity than in the meta position in the fura derivatives. Two new excitation ratioable fluorescent calcium indicators, benzothiaza-1 and 2, were also synthesized. K-d values of 400 nM to 5.3 mu M [Ca2+] were observed in these families of new probes. (C) 2000 Elsevier Science Ltd. All rights reserved.