2-(dihexadecylamino)ethanol | 169250-31-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(dihexadecylamino)ethanol
• 英文别名: 2-(Dihexadecylamino)ethan-1-ol
• CAS: 169250-31-1
• 化学式: C₃₄H₇₁NO
• 分子量: 509.944
• InChiKey: BUVABRXBEWFAPX-UHFFFAOYSA-N

物化性质

• 沸点：
  585.8±23.0 °C(Predicted)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.1
• 重原子数：
  36
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(dihexadecylamino)ethanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以64.8%的产率得到2-N,N-di-n-hexadecylaminoacetaldehyde
  参考文献：
  名称：

  Synthesis of novel porphyrin-based lipids and their antibacterial activity

  摘要：

  The purpose of this study was to investigate the antibacterial activity of newly developed cationic amphiphilic lipids having porphyrin as head group against two types of gram-positive bacteria and three types of gram-negative bacteria. The antibacterial activity of quantitatively prepared porphyrin-based amphiphilic lipids is evaluated by the disc-diffusion method against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae and Proteus vulgaris. These results are compared with the standard antibacterial activity of chloramphenicol. Both lipids showed antibacterial behaviour against gram-positive and gram-negative bacteria.

  DOI：

  10.1007/s00044-010-9432-0
• 作为产物：
  描述：

  O-tert-butyldimethylsilyl N-2-hydroxyethyl-N,N-di-n-hexadecylamine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以50%的产率得到2-(dihexadecylamino)ethanol
  参考文献：
  名称：

  Distance of Hydroxyl Functionality from the Quaternized Center Influence DNA Binding and in Vitro Gene Delivery Efficacies of Cationic Lipids with Hydroxyalkyl Headgroups

  摘要：

  In vitro gene delivery efficacies of cationic amphiphiles 1-7 (Scheme 1) were measured by both the reporter gene expression assays in CHO, COS-1, HepG2, and MCF7 cells and by the whole cell histochemical X-gal staining of representative Chinese hamster ovary cells. Our results demonstrated that in vitro gene delivery efficiencies of cationic lipids with hydroxyalkyl headgroups are adversely affected by increased covalent distances between the hydroxyl functionality and the cationic centers. Findings in the DNase I protection experiments and transmission electron microscopic study support the notion that such compromised gene delivery efficacies may originate from poor lipid-DNA binding interactions and significantly increased lipoplex nanosizes.

  DOI：

  10.1021/jm049656j

文献信息

• Preparation and antitubercular activities of alkylated amino alcohols and their glycosylated derivatives
  作者：Aline F. Taveira、Mireille Le Hyaric、Elaine F.C. Reis、Débora P. Araújo、Ana Paula Ferreira、Maria Aparecida de Souza、Lívia L. Alves、Maria C.S. Lourenço、Felipe Rodrigues C. Vicente、Mauro V. de Almeida

  DOI：10.1016/j.bmc.2007.08.045

  日期：2007.12

  A series of N- and C-alkylated amino alcohols and of their protected galactopyranosyl derivatives was synthesized and evaluated for antitubercular activity. Five of these compounds displayed good activity, with a MIC below 12.5mug/mL. The presence of the carbohydrate slightly affected the antibacterial activity.

  合成了一系列的N-和C-烷基化的氨基醇及其受保护的吡喃半乳糖基衍生物，并评估了其抗结核活性。这些化合物中的五种显示出良好的活性，MIC低于12.5mug / mL。碳水化合物的存在对抗菌活性有轻微的影响。
• Combinatorial Synthesis and High-Throughput Screening of Alkyl Amines for Nonviral Gene Delivery
  作者：Linxian Li、Fengjian Wang、Yihang Wu、Gary Davidson、Pavel A. Levkin

  DOI：10.1021/bc400158w

  日期：2013.9.18

  method based on an alkylation of amines, allowing for the fast parallel synthesis of libraries of cationic lipid-like molecules (lipidoids). We exploited the method to synthesize 200 lipidoids, which were screened for their transfection efficiency in HEK293T cells. The screen resulted in about 2% of new lipidoids capable of efficient cell transfection similar or higher than the efficiency of Lipofectamine

  质粒DNA和siRNA高效传递到细胞中对于生物学和生物医学研究至关重要。尽管为开发有效的非病毒载体，例如阳离子脂质和聚合物，已经做出了巨大的努力，但是大多数载体需要多步合成，这使得这种载体的快速结构优化和组合合成变得复杂。在这里，我们提出了一种基于胺烷基化的简便，单步方法，可以快速并行合成阳离子脂质样分子（类脂质）的文库。我们利用该方法合成了200个类脂质，筛选了它们在HEK293T细胞中的转染效率。筛选后，大约有2％的新型脂质能够有效转染细胞，其效率与Lipofectamine 2000相似或更高。此外，
• Aggregation behaviour and copper-binding properties of surfactants containing imidazole and pyrazole ligands
  作者：J.H. van Esch、M. Damen、M.C. Feiters、R.J.M. Nolte

  DOI：10.1002/recl.19941130405

  日期：——

  precipitate. The pyrazole surfactants on the other hand do not form vesicles but give, with one molar equivalent of HCl, water-insoluble stacked bilayers. The pyrazole moieties in these stacked bilayers do not coordinate copper(II) ions. This behaviour is most probably due to the formation of an intramolecular hydrogen bond in the mono-protonated pyrazole surfactant molecule. The imidazole surfactants cannot

  描述了简单的二烷基胺-咪唑和二烷基胺-吡唑表面活性剂的合成和聚集行为。在一当量的HCl存在下，咪唑表面活性剂形成稳定的囊状分散体。向这些分散体中添加二氯化铜（II）导致形成金属囊泡，其中四个咪唑基团与一个铜（II）离子配位。这些金属囊泡是不稳定的，并缓慢地转变成堆叠的双层，其沉淀。另一方面，吡唑表面活性剂不形成囊泡，但以一摩尔当量的HCl给出不溶于水的堆叠双层。这些堆叠的双层中的吡唑部分不配位铜（II）离子。此行为很可能是由于在单质子化吡唑表面活性剂分子中形成了分子内氢键。
• Cationic Amphiphile with Shikimic Acid Headgroup Shows More Systemic Promise Than Its Mannosyl Analogue as DNA Vaccine Carrier in Dendritic Cell Based Genetic Immunization
  作者：Ramishetti Srinivas、Priya P. Karmali、Dipankar Pramanik、Arup Garu、Yenugonda Venkata Mahidhar、Bharat K. Majeti、Sistla Ramakrishna、Gunda Srinivas、Arabinda Chaudhuri

  DOI：10.1021/jm901295s

  日期：2010.2.11

  Mannosylated cationic vectors have been previously used for delivering DNA vaccines to antigen presenting cells (APCs) via mannose receptors expressed on the cell surface of APCs. Here we show that cationic amphiphiles containing mannose-mimicking quinic acid and shikimic acid headgroups deliver genes to APCs via mannose receptor. Cationic amphiphile with shikimic acid headgroup was more efficacious than its

  甘露糖基化的阳离子载体先前已用于通过在APC细胞表面表达的甘露糖受体将DNA疫苗递送至抗原呈递细胞（APC）。在这里，我们显示了包含模仿甘露糖的奎尼酸和sh草酸头基的阳离子两亲物通过甘露糖受体将基因传递给APC。通过基于树突状细胞（最专业的APC）的基因免疫，具有sh草酸头基的阳离子两亲物比其甘露糖基对应物更有效。
• Nicotinic acid-based cationic vectors for efficient gene delivery to glioblastoma cells
  作者：Shireesha Manturthi、Dwaipayan Bhattacharya、Kalyani Rajesh Sakhare、Kumar Pranav Narayan、Srilakshmi V. Patri

  DOI：10.1039/d2nj03207d

  日期：——

  The cytotoxicity of the liposomes and lipoplexes was examined and found to be minimal in multiple cell lines. Further, their transfection potentials were investigated, and U87 and GL261 cells showed superior transfection with the lipid NGT. In particular, cytoplasmic fluorescence cellular uptake assays with the two cationic lipid formulations showed effective uptake in U87 cells for the lipid NGT.

  高效载体的生产是基因治疗的一个重要方面，基因治疗是一种用于递送治疗性核酸的革命性方法。将核酸递送至各种人体细胞的靶向基因治疗是当前的一项具有挑战性的任务。使用新型合成的阳离子脂质进行脑靶向基因传递是正在发展的方法之一。为了建立向脑癌细胞的靶向基因递送，本研究开发并合成了两种具有不同疏水区域的烟酸阳离子脂质，一种具有α-生育酚 (NGT)，另一种具有长烃链 (NGC)。为了生产合成阳离子脂质的持续水性形式，它们与 DOPE (1,2-dioleoyl- sn-glycero-磷酸乙醇胺）作为辅助脂质。检查了这些制剂的物理化学性质，例如它们的流体动力学大小和 zeta 电位，发现它们显示出有利于测试转染的最佳结果。DNA 结合和肝素置换分析清楚地说明了脂质体与质粒 DNA 的相互作用。检查了脂质体和脂质复合物的细胞毒性，发现在多个细胞系中的细胞毒性最小。此外，研究了它们的转染潜力，U87 和 GL261