N-decylidene-1-decanamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-decylidene-1-decanamine
• 英文别名: N-decyldecan-1-imine
• 化学式: C₂₀H₄₁N
• 分子量: 295.552
• InChiKey: WNRDUAZYWFBVIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  21
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-decylidene-1-decanamine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 二癸胺
  参考文献：
  名称：

  Anchor Dependency for Non-Glycerol Based Cationic Lipofectins: Mixed Bag of Regular and Anomalous Transfection Profiles

  摘要：

  Although detailed structure activity, physicochemical and biophysical investigations in probing the anchor influence in liposomal gene delivery have been reported for glycerol-based transfection lipids, the corresponding investigation for non-glycerol based simple monocationic transfection lipids have not yet been undertaken. Towards this end, herein, we delineate our structure - activity and physicochemical approach in deciphering the anchor dependency in liposomal gene delivery using fifteen new structural analogues (lipids 1 - 15) of recently reported nonglycerol based monocationic transfection lipids. The C-14 analogues in both series 1 (lipids 1 - 6) and series 2 (lipids 7-15) showed maximum efficiency in transfecting COS-1 and CHO cells. However, the C-12 analogue of the ether series (lipid 3) exhibited a seemingly anomalous behavior compared with its transfection efficient C-10 and C-14 analogues (lipids 2 and 4) in being completely inefficient to transfect both COS-1 and CHO cells. The present structure - activity investigation also convincingly demonstrates that enhancement of transfection efficiencies through incorporation of membrane reorganizing unsaturation elements in the hydrophobic anchor of cationic lipids is not universal but cell dependent. The strength of the interaction of lipids 1 - 15 with DNA was assessed by their ability to exclude ethidium bromide bound to the DNA. Cationic lipids with long hydrophobic tails were found, in general, to be efficient in excluding EtBr from DNA. Gel to liquid crystalline transition temperatures of the lipids was measured by fluorescence anisotropy measurement technique. In general (lipid 2 being an exception), transfection efficient lipids were found to have their mid transition temperatures at or below physiological temperatures (37degreesC).

  DOI：

  10.1002/1521-3765(20020215)8:4<900::aid-chem900>3.0.co;2-x
• 作为产物：
  描述：

  癸醛 、 1-氨基癸烷 以 甲醇 为溶剂， 反应 8.0h， 生成 N-decylidene-1-decanamine
  参考文献：
  名称：

  设计简单的脂质赖氨酸：分叉影响选择性的抗菌活性。

  摘要：

  在阻止抗菌素耐药性的全球努力中，脂肽是一类重要的抗菌剂，尤其是针对革兰氏阴性感染的抗菌剂。为了避免其合成复杂性，我们设计了仅涉及一个氨基酸和两个脂质尾巴的简单膜活性剂。在本文中，我们显示使用两个短脂质尾而不是单个长脂质尾显着增加了选择性抗菌活性。这项研究产生了几种选择性的抗菌化合物，并使用活性最高的化合物对此类化合物的性质进行了研究。荧光光谱研究揭示了代表性化合物引起细菌细胞膜去极化和透化的能力。化合物的这种膜活性性质赋予其对持久性细胞，生物膜和浮游细胞的优异活性。局部应用该化合物可减轻小鼠因烧伤引起的细菌负担鲍曼不动杆菌。我们期望本文所述的设计原理将指导几种具有临床重要性的抗微生物剂的开发。

  DOI：

  10.1002/cmdc.201600400

文献信息

• Designing Simple Lipidated Lysines: Bifurcation Imparts Selective Antibacterial Activity
  作者：Chandradhish Ghosh、Mohini Mohan Konai、Paramita Sarkar、Sandip Samaddar、Jayanta Haldar

  DOI：10.1002/cmdc.201600400

  日期：2016.11.7

  increases selective antibacterial activity. This study yielded several selective antibacterial compounds, and investigations into the properties of this compound class were conducted with the most active compound. Fluorescence spectroscopic studies revealed the capacity of the representative compound to cause depolarization and permeabilization of bacterial cell membranes. This membrane‐active nature

  在阻止抗菌素耐药性的全球努力中，脂肽是一类重要的抗菌剂，尤其是针对革兰氏阴性感染的抗菌剂。为了避免其合成复杂性，我们设计了仅涉及一个氨基酸和两个脂质尾巴的简单膜活性剂。在本文中，我们显示使用两个短脂质尾而不是单个长脂质尾显着增加了选择性抗菌活性。这项研究产生了几种选择性的抗菌化合物，并使用活性最高的化合物对此类化合物的性质进行了研究。荧光光谱研究揭示了代表性化合物引起细菌细胞膜去极化和透化的能力。化合物的这种膜活性性质赋予其对持久性细胞，生物膜和浮游细胞的优异活性。局部应用该化合物可减轻小鼠因烧伤引起的细菌负担鲍曼不动杆菌。我们期望本文所述的设计原理将指导几种具有临床重要性的抗微生物剂的开发。
• Anchor Dependency for Non-Glycerol Based Cationic Lipofectins: Mixed Bag of Regular and Anomalous Transfection Profiles
  作者：Rajkumar Sunil Singh、Koushik Mukherjee、Rajkumar Banerjee、Arabinda Chaudhuri、Samik Kumar Hait、Satya Priya Moulik、Yerramsetti Ramadas、Amash Vijayalakshmi、Nalam Madhusudhana Rao

  DOI：10.1002/1521-3765(20020215)8:4<900::aid-chem900>3.0.co;2-x

  日期：2002.2.15

  Although detailed structure activity, physicochemical and biophysical investigations in probing the anchor influence in liposomal gene delivery have been reported for glycerol-based transfection lipids, the corresponding investigation for non-glycerol based simple monocationic transfection lipids have not yet been undertaken. Towards this end, herein, we delineate our structure - activity and physicochemical approach in deciphering the anchor dependency in liposomal gene delivery using fifteen new structural analogues (lipids 1 - 15) of recently reported nonglycerol based monocationic transfection lipids. The C-14 analogues in both series 1 (lipids 1 - 6) and series 2 (lipids 7-15) showed maximum efficiency in transfecting COS-1 and CHO cells. However, the C-12 analogue of the ether series (lipid 3) exhibited a seemingly anomalous behavior compared with its transfection efficient C-10 and C-14 analogues (lipids 2 and 4) in being completely inefficient to transfect both COS-1 and CHO cells. The present structure - activity investigation also convincingly demonstrates that enhancement of transfection efficiencies through incorporation of membrane reorganizing unsaturation elements in the hydrophobic anchor of cationic lipids is not universal but cell dependent. The strength of the interaction of lipids 1 - 15 with DNA was assessed by their ability to exclude ethidium bromide bound to the DNA. Cationic lipids with long hydrophobic tails were found, in general, to be efficient in excluding EtBr from DNA. Gel to liquid crystalline transition temperatures of the lipids was measured by fluorescence anisotropy measurement technique. In general (lipid 2 being an exception), transfection efficient lipids were found to have their mid transition temperatures at or below physiological temperatures (37degreesC).