N-oleyl-N-n-octadecylamine | 173790-60-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-oleyl-N-n-octadecylamine
• 英文别名: N-[(Z)-octadec-9-enyl]octadecan-1-amine
• CAS: 173790-60-8
• 化学式: C₃₆H₇₃N
• 分子量: 519.982
• InChiKey: MGCFWOXFBXVIGW-ZPHPHTNESA-N

物化性质

• 沸点：
  589.8±29.0 °C(Predicted)
• 密度：
  0.831±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  37
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-oleyl-N-n-octadecylamine 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 52.0h， 生成 N-oleyl-N-n-octadecyl-N-2-hydroxyethylamine
  参考文献：
  名称：

  Novel Series of Non-Glycerol-Based Cationic Transfection Lipids for Use in Liposomal Gene Delivery

  摘要：

  A novel series of nontoxic and non-glycerol-based simple monocationic transfection lipids containing one or two hydroxyethyl groups directly linked to the positively charged nitrogen atom were synthesized. The in vitro transfection efficiencies of these new liposomal gene delivery reagents were better than that of lipofectamine, a widely used transfection agent in cationic lipid-mediated gene transfer. The most efficient transfection formulation was observed to be a 1:1:0.3 mol ratio of DHDEAB (N,N-di-n-hexadecyl-N,N-dihydroxyethylammonium bromide): cholesterol:HDEAB (N-n-hexadecyl-N,N-dihydroxyethylammonium bromide) using a DHDEAB-to-DNA charge ratio (+/-) of 0.3:1. Observation of good transfection at charge ratios lower than 1 suggests that the amphiphile-DNA complex may have net negative charge. Our results reemphasize the important point that in cationic lipid-mediated gene delivery, the overall charge of the lipid-DNA complex need not always be positive. In addition, our transfection results also imply that favorable hydrogen-bonding interactions between the lipid headgroups and the cell surface of biological membranes may have some role for improving the transfection efficiency in cationic lipid-mediated gene delivery.

  DOI：

  10.1021/jm9806446
• 作为产物：
  描述：

  油醇 在 sodium tetrahydroborate 、 Celite 、 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-oleyl-N-n-octadecylamine
  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

文献信息

• Monitoring the Dynamics of Ligand−Receptor Complexes on Model Membranes
  作者：Suman Lata、Martynas Gavutis、Jacob Piehler

  DOI：10.1021/ja054700l

  日期：2006.1.1

  After ligand binding, the receptor complexes formed on the membrane are dynamically maintained by two-dimensional protein-protein interactions on the membrane. The biophysical principles governing the dynamics of such interactions have not been understood, mainly because the measurement of lateral interactions on membranes so far has not been experimentally addressed. Here, we describe a generic approach

  配体诱导的细胞表面受体交联是许多跨膜受体信号激活的基本范例。配体结合后，膜上形成的受体复合物通过膜上的二维蛋白质-蛋白质相互作用动态维持。控制这种相互作用动力学的生物物理原理尚未被理解，主要是因为迄今为止尚未通过实验解决膜上横向相互作用的测量。在这里，我们描述了一种在体外测量二维解离速率常数的通用方法，该方法使用新型高亲和力螯合剂脂质在固体支持的膜上重建三元细胞因子受体复合物。在通过荧光共振能量转移监测配体和膜上受体亚基之一之间的相互作用时，表面的平衡因快速束缚大量过量的未标记受体亚基而受到干扰。检测到三元复合物中未标记蛋白质标记的置换作为供体淬灭的恢复。由于在这些条件下配体-受体复合物在膜平面内的解离是限速步骤，因此确定了该过程的二维速率常数。引人注目的是，二维解离比配体解离到溶液中要慢得多，这表明膜束缚显着影响了解离过程。
• Stabilization of polynucleotide complexes
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP1491217A1

  公开（公告）日：2004-12-29

  Polynucleotide complexes are stabilized by adding a cryoprotectant compound and lyophilizing the resulting formulation. The lyophilized formulations are milled or sieved into a dry powder formulation which may be used to deliver the polynucleotide complex. Delivery of the polynucleotide to a desired cell tissue is accomplished by contacting the tissue with the powder to rehydrate it. In a preferred embodiment, a dry powder formulation is used to induce genetic modification of a patient's lung tissue.

  聚核苷酸复合物通过添加一种抗冻保护剂并对所得的配方进行冻干处理来稳定。冻干配方经过研磨或筛选成为干粉配方，可用于传递聚核苷酸复合物。将聚核苷酸传递到所需细胞组织的方法是通过将粉末与组织接触以重新水合。在一个首选实施例中，使用干粉配方来诱导患者肺组织的基因修饰。
• Asymmetric cationic lipid based non-viral vectors for an efficient nucleic acid delivery
  作者：Rakeshchandra R. Meka、Sudhakar Godeshala、Srujan Marepally、Ketan Thorat、Hari Krishna Reddy Rachamalla、Ashish Dhayani、Ankita Hiwale、Rajkumar Banerjee、Arabinda Chaudhuri、Praveen Kumar Vemula

  DOI：10.1039/c6ra07256a

  日期：——

  trend in the transfection profiles of linker-based lipids is different from linker-less lipids. Influence of unsaturation in the hydrophobic chains has been investigated in linker-based lipids. However, in linker-less lipids, it remains unexplored. Herein, we demonstrate that the designed cationic lipid Lipid S-U with an asymmetric hydrophobic core having one stearyl (18 : 0) and one oleyl chain (18 : 1)

  阳离子脂质已被广泛研究其与核酸复合的能力，以浓缩并因此将其递送至细胞中。然而，开发安全有效的阳离子脂质用于递送核酸仍然是未解决的挑战。先前的结构活性研究导致了解脂质结构及其转染效率的途径。基于接头的脂质的转染曲线的趋势不同于无接头的脂质。在基于连接基的脂质中已经研究了疏水链中不饱和的影响。但是，在无接头的脂质中，它仍未开发。在这里，我们证明了设计的阳离子脂质脂质SU具有一个硬脂基（18：0）和一个油基链（18：1）的不对称疏水核与其对称的对应物Lipid SS（包含两个硬脂链（18：0）的疏水核）相比，转染效率更高脂质UU（两条油基链（18：1）），在体外。涉及用FACS进行膜融合性的机理研究表明，脂类SU脂质体在B16F10细胞膜上的融合性（89％）高于饱和脂质SS（66％）和不饱和脂质UU（70％）。共聚焦显微镜检查HEK 293细胞内体逃逸研究表明脂质SU的脂质复合物与饱和脂质SS和
• High-Fidelity Protein Targeting into Membrane Lipid Microdomains in Living Cells
  作者：Oliver Beutel、Jörg Nikolaus、Oliver Birkholz、Changjiang You、Thomas Schmidt、Andreas Herrmann、Jacob Piehler

  DOI：10.1002/anie.201306328

  日期：2014.1.27

  phase. Interestingly, His‐tag‐mediated lipid crosslinking turned out to be required for efficient targeting into the lo phase by tris‐NTA DODA. Robust partitioning into lo phases was confirmed by using viral lipid mixtures and giant plasma membrane vesicles. Moreover, efficient protein targeting into lo and ld domains within the plasma membrane of living cells was demonstrated by single‐molecule tracking

  开发了带有三个次氮基三乙酸（tris-NTA）头基的脂质类似物，用于将His标记的蛋白选择性靶向到液体有序（l o）或液体无序（l d）脂质相。强分割成升Ò结合到三-NTA His-标记的蛋白的相缀合于饱和烷基链（三-NTA DODA）中实现，而三-NTA缀合的不饱和烷基链（三-NTA SOA）在主要是居住的升d相。有趣的是，tris-NTA DODA有效地靶向进入l o相是必需的His-tag介导的脂质交联。稳健地划分为l o通过使用病毒脂质混合物和巨大的质膜囊泡证实了肝癌的发生。此外，通过单分子跟踪证明了有效的蛋白质靶向活细胞质膜内的l o和d d结构域，从而建立了一种高度通用的原位探索脂质微结构域的方法。
• BLOCK COPOLYMER AND COMPOSITION THEREOF
  申请人：Asahi Kasei Chemicals Corporation

  公开号：EP1498438A1

  公开（公告）日：2005-01-19

  The present invention provides a block copolymer or a hydrogenated product thereof excellent in low-temperature shrinkability, natural shrinkability, rigidity and the like, excellent in a balance of physical properties such as blocking resistance, resistance to fusion bonding in hot water, impact resistance and the like, and having a few fish eyes (FE's) caused by gels. Further, the invention provides a heat shrinkable film and a heat shrinkable multilayer film suitable for drink container packaging, cap seals and the like, using such a block copolymer or the hydrogenated product thereof. The invention provides a block copolymer having a weight ratio of a vinyl aromatic hydrocarbon and a conjugated diene of 60/40 to 90/10 and a number average molecular weight measured by gel permeation chromatography (GPC) of 30,000 to 500,000, wherein the vinyl aromatic hydrocarbon constituting the block copolymer has a block rate of from 10 to 90% by weight, the vinyl aromatic hydrocarbon polymer blocks constituting the block copolymer have a peak molecular weight within the molecular weight range of 5,000 to 30,000, and 40 to 80% by weight of the vinyl aromatic hydrocarbon polymer blocks have a molecular weight of 35,000 or less.

  本发明提供了一种嵌段共聚物或其氢化产品，具有优异的低温收缩性、自然收缩性、刚性等性能，在耐阻塞性、耐热水熔融粘合性、耐冲击性等物理性能的平衡方面表现出色，并且很少出现由凝胶引起的鱼眼（FE）。此外，本发明还提供了一种热收缩薄膜和一种热收缩多层膜，使用这种嵌段共聚物或其氢化产物，适用于饮料容器包装、瓶盖密封等。本发明提供了一种嵌段共聚物，其乙烯基芳香烃和共轭二烯的重量比为 60/40 至 90/10，凝胶渗透色谱法（GPC）测得的平均分子量为 30,000 至 500,000，其中构成嵌段共聚物的乙烯基芳香烃的嵌段率为 10%至 90%（按重量计）、构成嵌段共聚物的乙烯基芳香烃聚合物嵌段的峰值分子量在 5,000 至 30,000 的分子量范围内，40%至 80%（按重量计）的乙烯基芳香烃聚合物嵌段的分子量在 35,000 或以下。