[5-(12-aminododecanoyl)amino-pentyl]-carbamic acid tert-butyl ester | 872853-98-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [5-(12-aminododecanoyl)amino-pentyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[5-(12-aminododecanoylamino)pentyl]carbamate
• CAS: 872853-98-0
• 化学式: C₂₂H₄₅N₃O₃
• 分子量: 399.618
• InChiKey: JSMOEXSDRGHJOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  571.5±25.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [5-(12-aminododecanoyl)amino-pentyl]-carbamic acid tert-butyl ester 在 N-甲基吗啉 、 三氟乙酸 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 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
• 作为产物：
  描述：

  12-氨基十二酸 在 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 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 29.0h， 生成 [5-(12-aminododecanoyl)amino-pentyl]-carbamic acid tert-butyl ester
  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

文献信息

• Synthesis of acridine-nuclear localization signal (NLS) conjugates and evaluation of their impact on lipoplex and polyplex-based transfection
  作者：Caroline Boulanger、Christophe Di Giorgio、Pierre Vierling

  DOI：10.1016/j.ejmech.2005.07.015

  日期：2005.12

  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.