N,N'-bis[12-(diaza-18-crown-6)dodecyl]-18-crown-6 | 165191-72-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis[12-(diaza-18-crown-6)dodecyl]-18-crown-6
• 英文别名: 7,16-Bis[12-(1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl)dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane；7,16-bis[12-(1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl)dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 165191-72-0
• 化学式: C₆₀H₁₂₂N₆O₁₂
• 分子量: 1119.66
• InChiKey: BFYKRFWYRPZMBM-UHFFFAOYSA-N

物化性质

• 沸点：
  1030.1±60.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  78
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  月桂酰氯 、 N,N'-bis[12-(diaza-18-crown-6)dodecyl]-18-crown-6 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以78.4%的产率得到1-[16-[12-[16-[12-(16-Dodecanoyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl)dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]dodecan-1-one
  参考文献：
  名称：

  活细胞中电生理方法记录的合成离子通道活性

  摘要：

  Hydraphiles 是合成离子通道，使用冠醚作为入口并跨越磷脂双层膜。这些化合物的质子和钠阳离子传输已在脂质体和平面双层中得到证实。在目前的工作中，全细胞膜片钳实验表明亲水胶整合到人胚胎肾 (HEK 293) 细胞的膜中并显着增加膜电导。膜通透性的改变是可逆的，研究中的细胞在实验过程中仍然至关重要。太短（C(8)-苄基通道）无法跨越双层或由于中央继电器缺陷而处于非活动状态的对照化合物不会引起类似的电导增加。对照实验证实非活性通道类似物不显示非特异性效应，例如激活天然通道。

  DOI：

  10.1021/ja046626x
• 作为产物：
  描述：

  12-溴十二烷酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氯化亚砜 、 硼烷 、 氢气 、 sodium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 25.0~40.0 ℃ 、482.63 kPa 条件下， 反应 241.0h， 生成 N,N'-bis[12-(diaza-18-crown-6)dodecyl]-18-crown-6
  参考文献：
  名称：

  Synthetic Models for Transmembrane Channels: Structural Variations That Alter Cation Flux

  摘要：

  Twelve novel bis- or tris(macrocyclic) compounds have been designed as models for cation-conducting channels that function in phospholipid bilayer vesicle membranes. In general, the channel model systems have the structure ''sidearm-crown-spacer-crown-spacer-crown-sidearm'', although certain features have been altered from compound to compound to assess the structure-activity relationship. Two additional compounds have been prepared exclusively as controls. The ionophores have been incorporated into the membranes either by warming the compound with the preformed vesicle or by incorporation during vesicle formation. The two methods gave identical results within experimental error. Cation flux was assessed by two different analytical methods. In one case, the fluorescent dye pyranine was encapsulated within vesicles containing ionophore. Proton transport was then monitored by changes in dye fluorescence with time following an acid pulse. Ionophoretic activity far most of the compounds was studied using a dynamic NMR method in which the flux rate of Na-23(+) through the bilayer was monitored. All NMR studies were done in conjunction with gramicidin as a control to minimize experimental variations from run to run. Several of the synthetic ionophores showed cation conduction of as much as 40% of the activity of gramicidin. Apparently, small structural changes significantly altered flux rates and two known carriers closely related to the channel formers failed to exhibit measurable transport under comparable conditions.

  DOI：

  10.1021/ja00134a011

文献信息

• The influence of varied amide bond positions on hydraphile ion channel activity
  作者：Michelle E. Weber、Wei Wang、Sarah E. Steinhardt、Michael R. Gokel、W. Matthew Leevy、George W. Gokel

  DOI：10.1039/b510863m

  日期：——

  Hydraphile compounds have been prepared in which certain of the amine nitrogens have been replaced by amide residues. The amide bonds are present either in the sidearm, the side chain, or the central relay. Sodium cation transport through phospholipid vesicles mediated by each hydraphile was assessed. All of the amide-containing hydraphiles showed increased levels of Na(+) transport compared to the

  已经制备了亲水化合物，其中某些胺氮已被酰胺残基取代。酰胺键存在于侧臂、侧链或中央中继中。评估了由每个亲水物介导的通过磷脂囊泡的钠阳离子转运。与母体化合物相比，所有含酰胺的亲水物都显示出增加的 Na(+) 运输水平，但观察到侧臂胺到酰胺置换的速率增加最显着。我们将这种增强归因于双层中侧臂的稳定性，以实现更好的离子传导构象。用大肠杆菌和枯草芽孢杆菌对酰胺亲水菌进行的生物学研究表明，只有后者才具有显着的毒性。更远，
• Activity of synthetic ion channels is influenced by cation–π interactions with phospholipid headgroups
  作者：Michelle E. Weber、Elizabeth K. Elliott、George W. Gokel

  DOI：10.1039/b513179k

  日期：——

  A suite of synthetic hydraphile ion channels has been used to probe the possibility of cation-pi interactions between the channel and the phospholipid bilayer. The hydraphiles selected for this study contained either no sidearm, aliphatic sidearms or aromatic sidearms that varied in electron-richness. An ion selective electrode (ISE) method was used to evaluate the ion transport ability of these hydraphiles

  一套合成的亲水离子通道已用于探测通道与磷脂双层之间阳离子-pi相互作用的可能性。选择用于本研究的亲水物不包含侧基，脂肪族侧基或芳香族侧基，这些侧基的电子富集度不同。离子选择性电极（ISE）方法用于评估这些亲水物跨合成双层的离子迁移能力。运输取决于侧臂的身份。当侧臂富含电子并且从100％DOPC（三甲基铵阳离子头基，总体中性）制备囊泡时，芳族侧链化合物的离子迁移活性最大。当通过将组成从DOPC更改为70:30（w / w）DOPC：DOPA使脂质头基更加阴性时，芳香族侧链通道的运输减少。荧光研究表明，当脂质成分发生变化时，头基会经历不同的极性，这表明重新定位。数据与亲水通道的芳族侧臂和磷脂磷脂头基之间的稳定的阳离子-π相互作用相一致。
• Planar Bilayer Conductance and Fluorescence Studies Confirm the Function and Location of a Synthetic, Sodium-Ion-Conducting Channel in a Phospholipid Bilayer Membrane
  作者：Ernesto Abel、Glenn E. M. Maguire、Eric S. Meadows、Oscar Murillo、Takashi Jin、George W. Gokel

  DOI：10.1021/ja971098t

  日期：1997.9.1
• Hydraphile Channels:  Structural and Fluorescent Probes of Position and Function in a Phospholipid Bilayer
  作者：Ernesto Abel、Glenn E. M. Maguire、Oscar Murillo、Iwao Suzuki、Stephen L. De Wall、George W. Gokel

  DOI：10.1021/ja9909172

  日期：1999.10.1

  Three novel tris(macrocycle)s having fluorescent residues at their distal termini have been prepared and studied. The compounds are of the form R[N18N]C-12[N18N]C-12[N18N]R in which R is 2-(3-indolyl)ethyl (1), 2-(3-(N-methylindolyl))ethyl (2), and dansyl (3). Compounds 2 and 3 were found to transport Naf at rates similar to those of other tris(macrocyclic)s but 1 was not an ionophore in the bilayer as assessed by Na-23 NMR analysis. The latter failure may be due to a hydrogen-bond blockade leading to a globular conformation adopted by the hydraphile. The fluorescence maximum of 3 was determined in a variety of solvents and in a phospholipid bilayer. The polarity experienced by the dansyl group in the bilayer was intermediate between that observed in methanol and ethanol. Fluorescence depth quenching using doxyl-substituted lipids showed that the dansyl headgroups of 3 were 14 Angstrom from the bilayer's midplane or separated by about 28 Angstrom. Fluorescence energy transfer between 2 acid 3 showed that these two hydraphiles were not appreciably aggregated in the bilayer.
• The presence of cholestanyl substituents in hydraphile channels inhibits cation transport in the phospholipid bilayer
  作者：Eric S Meadows、Ernesto Abel-Santos、Daniel C Frankel、George W Gokel

  DOI：10.1016/s0040-4039(00)00068-x

  日期：2000.3

  The presence of steroids within a synthetic, cation channel model compound restricts or prevents the passage of Na+ through the phospholipid bilayer owing to collapse of the pore induced by hydraphobic contacts (C) 2000 Elsevier Science Ltd. All rights reserved.