N-(5-aminopentyl)-12-[(6-chloro-2-methoxyacridin-9-yl)amino]dodecanamide | 872854-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(5-aminopentyl)-12-[(6-chloro-2-methoxyacridin-9-yl)amino]dodecanamide
• CAS: 872854-03-0
• 化学式: C₃₁H₄₅ClN₄O₂
• 分子量: 541.177
• InChiKey: GDSAZUPGTVJBHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  38
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  89.3
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(5-aminopentyl)-12-[(6-chloro-2-methoxyacridin-9-yl)amino]dodecanamide 、 4-(N-马来酰亚胺基甲基)环己烷-1-羧酸琥珀酰亚胺酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl-methyl)-cyclohexanecarboxylic acid {5-[12-(6-chloro-2-methoxy-acridin-9-ylamino)-dodecanoylamino]-pentyl}-amide
  参考文献：
  名称：

  Synthesis of acridine-nuclear localization signal (NLS) conjugates and evaluation of their impact on lipoplex and polyplex-based transfection

  摘要：

  We report on the synthesis of various acridine(Acr)-spacer-nuclear localization signal (NLS) peptide conjugates and explore whether their use as NLS-labeling agent of plasmidic DNA could improve gene nuclear import and expression into cells when mediated by synthetic DNA complexes. As the conditions of successful use of the NLS properties to enhance gene transfer are not clear, and with the aim of detecting and defining the requirements of NLS-enhanced transfection, we investigated gene delivery and expression into various cell lines with various DNA complexes (lipoplexes or polyplexes) that were formulated for various N/P ratios from various preformed Acr-spacer-NLS/DNA complexes (1: 1, 5:1 and 10: 1 molar ratio). For the in vitro transfection assays, the lipoplexes and polyplexes were formulated from the preformed Acr-spacer-NLS/DNA complexes and dioctadecylamidoglycylspermine (DOGS)/dioleylphosphatidylethanolamine (DOPE) 1:1 mol and branched polyethyleneimine (PEI) 25 kDa, respectively, which are very efficient in vitro gene transfer systems. We show by fluorescence experiments that part of the acridine-NLS-conjugates remains intercalated within the plasmid for most of the N/P lipoplexes and polyplexes investigated. We show that, as several other studies performed with NLS-conjugates that are not covalently linked to DNA, the expression of the transgene is in most cases not improved upon complexation of plasmidic DNA with NLS-intercalating conjugates prior to its formulation as lipoplexes or polyplexes. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.015
• 作为产物：
  描述：

  12-氨基十二酸 在 N-甲基吗啉 、 sodium hydroxide 、 四(三苯基膦)钯 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 二乙胺 、 三乙胺 、 三氟乙酸 、 苯酚 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 N-(5-aminopentyl)-12-[(6-chloro-2-methoxyacridin-9-yl)amino]dodecanamide
  参考文献：
  名称：

  Synthesis of acridine-nuclear localization signal (NLS) conjugates and evaluation of their impact on lipoplex and polyplex-based transfection

  摘要：

  We report on the synthesis of various acridine(Acr)-spacer-nuclear localization signal (NLS) peptide conjugates and explore whether their use as NLS-labeling agent of plasmidic DNA could improve gene nuclear import and expression into cells when mediated by synthetic DNA complexes. As the conditions of successful use of the NLS properties to enhance gene transfer are not clear, and with the aim of detecting and defining the requirements of NLS-enhanced transfection, we investigated gene delivery and expression into various cell lines with various DNA complexes (lipoplexes or polyplexes) that were formulated for various N/P ratios from various preformed Acr-spacer-NLS/DNA complexes (1: 1, 5:1 and 10: 1 molar ratio). For the in vitro transfection assays, the lipoplexes and polyplexes were formulated from the preformed Acr-spacer-NLS/DNA complexes and dioctadecylamidoglycylspermine (DOGS)/dioleylphosphatidylethanolamine (DOPE) 1:1 mol and branched polyethyleneimine (PEI) 25 kDa, respectively, which are very efficient in vitro gene transfer systems. We show by fluorescence experiments that part of the acridine-NLS-conjugates remains intercalated within the plasmid for most of the N/P lipoplexes and polyplexes investigated. We show that, as several other studies performed with NLS-conjugates that are not covalently linked to DNA, the expression of the transgene is in most cases not improved upon complexation of plasmidic DNA with NLS-intercalating conjugates prior to its formulation as lipoplexes or polyplexes. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.015