methyl 6-(4-[(4-diethylaminophenyl)(4-diethylimino-2,5-cyclohexadien-1-ylidene)methyl]-3-sulfo-1-phenylsulfonamido)hexanoate | 872536-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 6-(4-[(4-diethylaminophenyl)(4-diethylimino-2,5-cyclohexadien-1-ylidene)methyl]-3-sulfo-1-phenylsulfonamido)hexanoate
• 英文别名: 2-[[4-(Diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]-5-[(6-methoxy-6-oxohexyl)sulfamoyl]benzenesulfonate
• CAS: 872536-99-7
• 化学式: C₃₄H₄₅N₃O₇S₂
• 分子量: 671.879
• InChiKey: MSPPGTHQSXXKSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 6-(4-[(4-diethylaminophenyl)(4-diethylimino-2,5-cyclohexadien-1-ylidene)methyl]-3-sulfo-1-phenylsulfonamido)hexanoate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以40%的产率得到{4-[[4-(5-Carboxy-pentylsulfamoyl)-2-sulfo-phenyl]-(4-diethylamino-phenyl)-methylene]-cyclohexa-2,5-dienylidene}-diethylammonium
  参考文献：
  名称：

  On the Use of Nonfluorescent Dye Labeled Ligands in FRET-Based Receptor Binding Studies

  摘要：

  The efficiency of fluorescence resonance energy transfer (FRET) is dependent upon donor-acceptor proximity and spectral overlap, whether the acceptor partner is fluorescent or not. We report here on the design, synthesis, and characterization of two novel pirenzepine derivatives that were coupled to patent blue VF and pinacyanol dyes. These nonfluorescent compounds, when added to cells stably expressing enhanced green fluorescent protein (EGFP)fused muscarinic M1 receptors, promote EGFP fluorescence extinction in a time-, concentration-, and atropine-dependent manner. They display nanomolar affinity for the muscarinic receptor, determined using either FRET or classical radioligand binding conditions. We provide evidence that these compounds behave as potent acceptors of energy from excited EGFP with quenching efficiencies comparable to those of analogous fluorescent bodipy or rhodamine red pirenzepine derivatives. The advantages they offer over fluorescent ligands are illustrated and discussed in terms of reliability, sensitivity, and wider applicability of FRET-based receptor binding assays.

  DOI：

  10.1021/jm050459+
• 作为产物：
  描述：

  酸性蓝 1 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 methyl 6-(4-[(4-diethylaminophenyl)(4-diethylimino-2,5-cyclohexadien-1-ylidene)methyl]-3-sulfo-1-phenylsulfonamido)hexanoate
  参考文献：
  名称：

  On the Use of Nonfluorescent Dye Labeled Ligands in FRET-Based Receptor Binding Studies

  摘要：

  The efficiency of fluorescence resonance energy transfer (FRET) is dependent upon donor-acceptor proximity and spectral overlap, whether the acceptor partner is fluorescent or not. We report here on the design, synthesis, and characterization of two novel pirenzepine derivatives that were coupled to patent blue VF and pinacyanol dyes. These nonfluorescent compounds, when added to cells stably expressing enhanced green fluorescent protein (EGFP)fused muscarinic M1 receptors, promote EGFP fluorescence extinction in a time-, concentration-, and atropine-dependent manner. They display nanomolar affinity for the muscarinic receptor, determined using either FRET or classical radioligand binding conditions. We provide evidence that these compounds behave as potent acceptors of energy from excited EGFP with quenching efficiencies comparable to those of analogous fluorescent bodipy or rhodamine red pirenzepine derivatives. The advantages they offer over fluorescent ligands are illustrated and discussed in terms of reliability, sensitivity, and wider applicability of FRET-based receptor binding assays.

  DOI：

  10.1021/jm050459+