N,N-di-n-tetradecyl-N,N-dihydroxyethylammonium chloride

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-di-n-tetradecyl-N,N-dihydroxyethylammonium chloride
• 英文别名: N,N-di-n-tetradecyl-N,N-dihyroxyethylammonium chloride；Bis(2-hydroxyethyl)-di(tetradecyl)azanium;chloride
• 化学式: C₃₂H₆₈NO₂*Cl
• 分子量: 534.35
• InChiKey: YBCBDEIUJOYHMY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  36
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  十四胺 在 sodium hydroxide 、 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 N,N-di-n-tetradecyl-N,N-dihydroxyethylammonium chloride
  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

• Methods and compositions for the efficient delivery of therapeutic agents to cells and animals
  申请人：Rana M. Tariq

  公开号：US20070260055A1

  公开（公告）日：2007-11-08

  The present invention provides methods of carrying out the safe and reliable preparation of lipids comprising quaternary amines. Such lipids are especially suited for introducing therapeutic agents into cells or organisms. In particular, the lipids of the invention are suitable for the efficient transfer of gene therapy agents into mammalian cells or organisms in a cell type specific or tissue specific manner.

  本发明提供了一种安全可靠的制备含季铵盐脂质的方法。这种脂质特别适合将治疗剂介入细胞或生物体中。特别是，本发明的脂质适用于以细胞类型特异性或组织特异性的方式高效地将基因治疗剂转移到哺乳动物细胞或生物体中。
• WO2007/22030
  申请人：——

  公开号：——

  公开（公告）日：——
• METHODS AND COMPOSITIONS FOR THE EFFICIENT DELIVERY OF THERAPEUTIC AGENTS TO CELLS AND ANIMALS
  申请人：University of Massachusetts

  公开号：EP1940775A2

  公开（公告）日：2008-07-09
• AMPHOTERIC LIPOSOMAL COMPOSITIONS FOR CELLULAR DELIVERY OF SMALL RNA MOLECULES FOR USE IN RNA INTERFERENCE
  申请人：Council of Scientific & Industrial Research

  公开号：EP2414519A1

  公开（公告）日：2012-02-08
• RICE BRAN-LIPIDS BASED FORMULATION AND PROCESS FOR PREPARATION THEREOF FOR SELECTIVE DELIVERY OF GENES TO CANCER CELLS
  申请人：Council Of Scientific And Industrial Research

  公开号：US20150164797A1

  公开（公告）日：2015-06-18

  The present invention relates to a formulation in which glycolipids and phospholipids, isolated from rice bran gum samples, were used in conjunction with gene carrying lipids to test its efficacy in delivering genes to cancer cells selectively. This formulation did not mediate efficient delivery of genes to non-cancerous cells, thus, showing potential use of this formulation to deliver anticancer therapeutics to cancer cells without eliciting treatment related toxicity to normal cells