N,N-di-[O-tetradecanoyl-2-hydroxyethyl]-N-methylamine

• 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: N,N-di-[O-tetradecanoyl-2-hydroxyethyl]-N-methylamine
• 英文别名: 2-(2-(tetradecanoyloxy)ethyl(methyl)amino)ethyl tetradecanoate；2-[Methyl(2-tetradecanoyloxyethyl)amino]ethyl tetradecanoate；2-[methyl(2-tetradecanoyloxyethyl)amino]ethyl tetradecanoate
• 化学式: C₃₃H₆₅NO₄
• 分子量: 539.883
• InChiKey: CNWVZNDTDQXKHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  38
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-di-[O-tetradecanoyl-2-hydroxyethyl]-N-methylamine 、 碘甲烷 以 乙腈 为溶剂， 反应 1.0h， 生成 N,N-di(2-tetradecanoyloxyethyl)dimethylammonium iodide
  参考文献：
  名称：

  Preparation and Characterization of Phase-Segregated Vesicles of Photopolymerizable Diacetylene Mixed with Nonpolymerizable Amphiphiles

  摘要：

  将 1,2-二（十六烷氧基羰基）乙烷磺酸钠（2C16S）与可光聚合的 1,2-二（10,12-三缩水甘油酰）-sn-甘油 3-磷酸胆碱（DTPC）按 2:100 的比例混合，通过改良薄膜水合法处理，得到一种聚合体，在 254 纳米波长的照射下，聚合体变成了巨囊（GVs）。用激光共聚焦扫描显微镜分析了 GVs 横截面上的自发荧光，发现其呈直径为 3.8 微米的环形，环内存在约 1 微米的暗色部分。当十八烷基罗丹明 B（RhB）作为两亲性荧光探针加入龙胆紫时，RhB 的荧光从整个环中发射出来。因此，2C16S 与 DTPC 的相分离得到了证实。同样，在 N,N-二（2-十六碳酰氧基乙基）二甲基碘化铵与 DTPC 的混合囊泡中发现，相分离囊泡的直径为 3.7 微米，在横截面图像中，环上有约 1 微米的暗色部分。另一方面，与 1,2-二（十二烷氧基羰基）乙磺酸盐、N,N-二（2-十二烷酰氧乙基）二甲基碘化铵和 N,N-二（2-十四烷酰氧乙基）二甲基碘化铵混合的 DTPC 囊泡形成了球状结构，充满了囊泡内部。每种双亲化合物主要相变温度的差异解释了分离机制。

  DOI：

  10.1246/bcsj.20100192
• 作为产物：
  描述：

  N-甲基二乙醇胺 、 肉豆蔻酰氯 以 N,N-二甲基甲酰胺 为溶剂， 以1.55 g的产率得到N,N-di-[O-tetradecanoyl-2-hydroxyethyl]-N-methylamine
  参考文献：
  名称：

  Dramatic Influence of the Orientation of Linker between Hydrophilic and Hydrophobic Lipid Moiety in Liposomal Gene Delivery

  摘要：

  A number of prior studies have demonstrated that the DNA-binding and gene transfection efficacies of cationic amphiphiles crucially depend on their various structural parameters including hydrophobic chain lengths, headgroup functionalities, and the nature of the linker-functionality used in tethering the polar headgroup and hydrophobic tails. However, to date addressing the issue of linker orientation remains unexplored in liposomal gene delivery. Toward probing the influence of linker orientation in cationic lipid mediated gene delivery, we have designed and synthesized two structurally isomeric remarkably similar cationic amphiphiles 1 and 2 bearing the same hydrophobic tails and the same polar headgroups connected by the same ester linker group. The only structural difference between the cationic amphiphiles 1 and 2 is the orientation of their linker ester functionality. While lipid 1 showed high gene transfer efficacies in multiple cultured animal cells, lipid 2 was essentially transfection incompetent. Findings in both transmission electron microscopic and dynamic laser light scattering studies revealed no significant size difference between the lipoplexes of lipids 1 and 2. Findings in confocal microscopic and fluorescence resonance energy transfer (FRET) experiments, taken together, support the notion that the remarkably higher gene transfer efficacies of lipid 1 compared to those of lipid 2 presumably originate from higher biomembrane fusogenicity of lipid 1 liposomes. Differential scanning calorimetry (DSC) and fluorescence anisotropy studies revealed a significantly higher gel-to-liquid crystalline temperature for the lipid 2 liposomes than that for lipid 1 liposomes. Findings in the dye entrapment experiment were also consistent with the higher rigidity of lipid 2/cholesterol (1:1 mole ratio) liposomes. Thus, the higher biomembrane fusibility of lipid 1 liposomes than that of lipid 2 liposomes presumably originates from the more rigid nature of lipid 2 cationic liposomes. Taken together, the present findings demonstrate for the first time that even as minor a structural variation as linker orientation reversal in cationic amphiphiles can profoundly influence DNA-binding characteristics, membrane rigidity, membrane fusibility, cellular uptake, and consequently gene delivery efficacies of cationic liposomes.

  DOI：

  10.1021/ja0704683

文献信息

• [EN] POLYAMINE-FATTY ACID DERIVED LIPIDOIDS AND USES THEREOF<br/>[FR] LIPIDOÏDES DÉRIVÉS DE POLYAMINE-ACIDE GRAS ET LEURS UTILISATIONS
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2016004202A1

  公开（公告）日：2016-01-07

  The present disclosure provides polyamine-fatty acid derived lipidoids (e.g., compounds of Formula (I) or (II)) and methods of preparing the lipidoids. A described lipidoid includes R-C(=0)-0- moieties (where R is a lipid moiety), which may be hydrolyzed into non-toxic fatty acids. Also provided are compositions including a described lipidoid and an agent (e.g., polynucleotide, small molecule, peptide, or protein). The present disclosure also provides methods, kits, and uses that involve the lipidoids or compositions for delivering an agent to a subject, tissue, or cell and/or for treating and/or preventing a range of diseases, such as genetic diseases, proliferative diseases, hematological diseases, neurological diseases, immunological diseases, gastrointestinal diseases, respiratory diseases, painful conditions, psychiatric disorders, and metabolic disorders.

  本公开提供了聚胺脂肪酸衍生的脂质体（例如，化合物的化学式（I）或（II））以及制备脂质体的方法。所述脂质体包括R-C(=0)-0-基团（其中R是脂质基团），可以水解为无毒脂肪酸。还提供了包括所述脂质体和药剂（例如，多核苷酸、小分子、肽或蛋白质）的组合物。本公开还提供了涉及脂质体或组合物用于将药剂传递给受体、组织或细胞和/或用于治疗和/或预防一系列疾病的方法、试剂盒和用途，例如遗传疾病、增殖性疾病、血液疾病、神经系统疾病、免疫系统疾病、胃肠道疾病、呼吸系统疾病、疼痛症状、精神障碍和代谢性疾病。
• Synthesis, Surface Properties, and Antibacterial Activity of Novel Ester‐Containing Cationic Silicone Surfactants and Their Utilization as Fabric‐Finishing Agents
  作者：Yuan Wei、Cheng Zheng、Zhenqiang Zhang、Zhaowen Zeng、Taoyan Mao、Shikang Long、Hui Ling

  DOI：10.1002/jsde.12211

  日期：2019.3

  In this study, a series of cationic silicone surfactants SiQCnCl containing ester groups and double long‐chain alkyls (n = 9, 11, 13, 15, and 17) were synthesized by microwave irradiation and characterized using infrared Fourier transform (FTIR), 1H nuclear magnetic resonance (1H NMR), and thermogravimetric analysis (TGA). Surface activity and adsorption of these surfactants were investigated by measuring

  在这项研究中，通过微波辐射合成了一系列包含酯基和双长链烷基（n = 9、11、13、15和17）的阳离子硅表面活性剂SiQC n Cl ，并使用红外傅里叶变换（FTIR）进行了表征，1 H核磁共振（1 H NMR）和热重分析（TGA）。通过测量平衡表面张力来研究这些表面活性剂的表面活性和吸附。临界胶束浓度（CMC）随着SiQC的烷基长度减小Ñ在25℃Cl和所以没有在CMC中的对应的表面张力（γ CMC）。还通过透射电子显微镜（TEM）和动态光散射（DLS）系统研究了水溶液中的聚集行为。观察到直径为300至900 nm的球形或椭圆形聚集体。研究还表明，阳离子有机硅表面活性剂对金黄色葡萄球菌表现出一定的抗菌作用，但对大肠杆菌的作用稍差。SiQC 15的形态结构使用扫描电子显微镜（SEM）观察了用Cl处理过的棉织物，结果表明表面变得整洁光滑。而且，成品棉织物保持了一些抗菌性能并改善了柔软度，可以
• Compounds for targeting drug delivery and enhancing siRNA activity
  申请人：Nitto Denko Corporation

  公开号：US10000447B2

  公开（公告）日：2018-06-19

  Here described are compounds consisting of the structure (targeting molecule)m-linker-(targeting molecule)n, wherein the targeting molecule is a retinoid or a fat soluble vitamin having a specific receptor on the target cell; wherein m and n are independently 0, 1, 2 or 3; and wherein the linker comprises a polyethylene glycol (PEG) or PEG-like molecule, as well as compositions and pharmaceutical formulations including these compounds which are useful for the targeting and delivery of therapeutic agents; and methods of using these compositions and pharmaceutical formulations.

  这里描述的是由以下结构组成的化合物 (靶向分子）m-连接剂-（靶向分子）n、 其中，靶向分子是在靶细胞上具有特异性受体的视黄醇或脂溶性维生素；其中，m 和 n 独立地为 0、1、2 或 3；其中，连接剂包括聚乙二醇（PEG）或类 PEG 分子，以及包括这些化合物的组合物和药物制剂，这些组合物和药物制剂可用于治疗剂的靶向和递送；以及使用这些组合物和药物制剂的方法。
• [EN] COMPOUNDS FOR TARGETING DRUG DELIVERY AND ENHANCING SIRNA ACTIVITY<br/>[FR] COMPOSÉS POUR L'ADMINISTRATION DE MÉDICAMENT CIBLÉE ET L'AUGMENTATION DE L'ACTIVITÉ ARNSI
  申请人：NITTO DENKO CORP

  公开号：WO2012170952A9

  公开（公告）日：2013-02-21
• POLYAMINE-FATTY ACID DERIVED LIPIDOIDS AND USES THEREOF
  申请人：Massachusetts Institute of Technology

  公开号：US20160002178A1

  公开（公告）日：2016-01-07

  The present disclosure provides polyamine-fatty acid derived lipidoids (e.g., compounds of Formula (I) or (II)) and methods of preparing the lipidoids. A described lipidoid includes R—C(═O)—O— moieties (where R is a lipid moiety), which may be hydrolyzed into non-toxic fatty acids. Also provided are compositions including a described lipidoid and an agent (e.g., polynucleotide, small molecule, peptide, or protein). The present disclosure also provides methods, kits, and uses that involve the lipidoids or compositions for delivering an agent to a subject, tissue, or cell and/or for treating and/or preventing a range of diseases, such as genetic diseases, proliferative diseases, hematological diseases, neurological diseases, immunological diseases, gastrointestinal diseases, respiratory diseases, painful conditions, psychiatric disorders, and metabolic disorders.