2,3-bis(tetradecyloxy)propan-1-amine | 396727-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-bis(tetradecyloxy)propan-1-amine
• 英文别名: 3,2-dimyristyloxypropylamine；2,3-dimyristyloxyproylamine；DMA；1,2-dimyristyloxypropylamine；1-Propanamine, 2,3-bis(tetradecyloxy)-；2,3-di(tetradecoxy)propan-1-amine
• CAS: 396727-98-3
• 化学式: C₃₁H₆₅NO₂
• 分子量: 483.863
• InChiKey: DPVZNLNBPGLMRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  558.8±30.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  34
• 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：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-bis(tetradecyloxy)propan-1-amine 在 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 生成 3-[bis(4-methoxyphenyl)(phenyl)methoxy]-2-hydroxypropyl N-[2,3-di(tetradecyloxy)propyl]carbamate
  参考文献：
  名称：

  脂质修饰的寡核苷酸偶联物：深入了解基因沉默，与模型膜的相互作用和细胞摄取机制。

  摘要：

  寡核苷酸沉默特定基因或抑制特定蛋白质的生物学活性的能力引起了人们对其使用作为研究工具和治疗剂的极大兴趣。不幸的是，它们的生物学应用遇到了细胞可及性差的局限性。开发合适的寡核苷酸递送系统对于实现其有效的细胞摄取至关重要。在本工作中，合成了一系列硫代磷酸酯脂质-寡核苷酸杂合体，在反义寡核苷酸的3'-和5'-末端同时引入了共价的单或双脂质尾巴。培养细胞中的基因转染显示反义荧光素酶抑制作用，而未使用在5'-末端双脂质尾修饰的偶联物转染剂。在几种模型膜系统以及细胞摄取实验中进一步详细研究了双脂尾修饰的效果。在这些研究中，可以清楚地观察到自组装微结构的自发形成。脂质化允许通过巨胞饮作用机制将寡核苷酸有效地掺入HeLa细胞，而不会引起细胞的细胞毒性或改变寡核苷酸缀合物的结合特性。此外，单尾和双尾化合物在脂质模型膜中均表现出相似的行为，使其可用于基于核苷酸的技术。在这些研究中，可以清楚地观察到自组装微结构

  DOI：

  10.1016/j.bmc.2016.10.024
• 作为产物：
  描述：

  十四醇 在 吡啶 、 1,8-双二甲氨基萘 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 98.0h， 生成 2,3-bis(tetradecyloxy)propan-1-amine
  参考文献：
  名称：

  Synthesis of Novel Cationic Lipids:  Effect of Structural Modification on the Efficiency of Gene Transfer

  摘要：

  A series of novel cationic lipids was designed and synthesized in an effort to understand the importance of the various structural features with respect to transfection efficiency. Particular attention has been paid to the hydrophobic domain and the cationic headgroup. An efficient method of synthesizing asymmetric diether lipids is described, using alkyl chains ranging from C-12 to C-18 and the unsaturated oleyl group. The ternary formulations including the diether lipid 3beta-[N-(N',N'-dimethylaminoethyl)carbamoyl]cholesterol (DC-Chol) and dioleoyl phosphatidylethanolamine (DOPE) were up to 10-fold more efficacious in in vitro assays than the DC-Chol/DOPE control. The shorter and most asymmetric diether lipids performed the best. The chemical nature and basicity of the headgroups have been varied by the coupling of the four naturally occurring amino acids with cationic side chains-arginine, histidine, lysine, and tryptophan. Transfection efficiency was highest for arginine/lysine derivatives, with binary formulations containing the amino acid derivative alone and,DOPE proving superior.

  DOI：

  10.1021/jm010918g

文献信息

• LIPIDOSOME PREPARATION, PREPARATION METHOD AND APPLICATION THEREOF
  申请人：BIOMICS BIOTECHNOLOGIES CO., LTD.

  公开号：US20150272886A1

  公开（公告）日：2015-10-01

  The present invention discloses a liposome formulation, its preparation method, and its application in the treatment of diseases caused by abnormal gene expression. The liposome formulation comprises complementary cationic lipid pairs, phospholipids, and long-circulating lipids. The method of preparing the liposome formulation comprises: mixing the complementary cationic lipid pairs with the phospholipid and the long-circulating lipid to generate pre-formed vesicles; and then mixing the pre-formed vesicles with the nucleic acid solution to generate the liposome-nucleic acid formulation. This liposome formulation provided by the present invention is easily prepared; and in the treatment of diseases caused by abnormal gene expression, the liposome formulation can be used to deliver in vivo therapeutic agents, including nucleic acids.

  本发明公开了一种脂质体配方，其制备方法以及在治疗由异常基因表达引起的疾病中的应用。该脂质体配方包括互补的阳离子脂质对、磷脂和长循环脂质。制备该脂质体配方的方法包括：将互补的阳离子脂质对与磷脂和长循环脂质混合以生成预形成的囊泡；然后将预形成的囊泡与核酸溶液混合以生成脂质体-核酸配方。本发明提供的这种脂质体配方易于制备；在治疗由异常基因表达引起的疾病中，可以使用该脂质体配方来输送体内治疗剂，包括核酸。
• FORMULATION AND DELIVERY OF MODIFIED NUCLEOSIDE, NUCLEOTIDE, AND NUCLEIC ACID COMPOSITIONS
  申请人：MODERNA THERAPEUTICS, INC.

  公开号：US20160038612A1

  公开（公告）日：2016-02-11

  The present disclosure provides, inter alia, formulation compositions comprising modified nucleic acid molecules which may encode a protein, a protein precursor, or a partially or fully processed form of the protein or a protein precursor. The formulation composition may further include a modified nucleic acid molecule and a delivery agent. The present invention further provides nucleic acids useful for encoding polypeptides capable of modulating a cell's function and/or activity.

  本公开提供了包含修饰核酸分子的配方组合，该核酸分子可以编码蛋白质、蛋白质前体或蛋白质或蛋白质前体的部分或完全加工形式的组合物。该配方组合还可以包括一种修饰核酸分子和一种传递剂。本发明还提供了用于编码能够调节细胞功能和/或活性的多肽的核酸。
• SNALP FORMULATIONS CONTAINING POLYOXAZOLINE-DIALKYLOXYPROPYL CONJUGATES
  申请人：Heyes James

  公开号：US20110313017A1

  公开（公告）日：2011-12-22

  The present invention provides polyoxaline-dialkyloxypropyl conjugates (POZ-DAA), SNALP compositions comprising POZ-DAA conjugates and methods of using such SNALP compositions to introduce a therapeutic agent, such as a nucleic acid, into a cell (e.g., for the treatment of a disease or disorder).

  本发明提供了聚草酸二烷氧基丙基共轭物（POZ-DAA），包括POZ-DAA共轭物的SNALP组合物以及使用这种SNALP组合物将治疗剂（例如核酸）引入细胞（例如治疗疾病或障碍）的方法。
• LIPID ENCAPSULATING INTERFERING RNA
  申请人：Protiva Biotherapeutics, Inc.

  公开号：US20160115477A1

  公开（公告）日：2016-04-28

  Rich tooling is provided for REST application development that integrates the exploration of a REST API, modeling of data types and the REST API, and the generation of artifacts using the modeled REST API and data types.

  为REST应用程序开发提供了丰富的工具，包括探索REST API、建模数据类型和REST API，以及使用建模的REST API和数据类型生成工件。
• [EN] AMINOACID LIPIDS<br/>[FR] LIPIDES D'ACIDES AMINÉS
  申请人：MERCK PATENT GMBH

  公开号：WO2013135360A1

  公开（公告）日：2013-09-19

  The present invention is directed to a new class of lipids, more specifically ether-lipids having a polar headgroup, as well as vesicles comprising these lipids, methods of their preparation as well as their uses in medical applications, wherein the ether-lipids are represented by general formula (I) wherein Y represents O, N, S or a covalent bond; P1 represents H, an Y- protecting group or an Y-activating group or a spacer group; P2, P3 represent independently of each other H, an amino-protecting group or a spacer group, or P2 and P3 form together with the N to which they are bound a ring structure; L is a group of formula (a) wherein the dashed line represents the linkage to N; R1 represents H or a group of formula -(CH2)2-ORb1; R1 represents H or a group of formula - (CH2)2-ORb2, R2 represents H or a group of formula -CH2-ORc; R2 Represents H or a group of formula -ORd or -CH2-ORc,' R2 represents H or a group of formula -(CH2)2-ORe or -(CH2)3-ORe; Ra, Rb1, Rb2, Rc, Rd,Re represent independently of each other a saturated or unsaturated, straight or branched hydrocarbon chain, and m is 1, 2 or 3; with the proviso that at least one of R1, R1', R2, R2', R3 is not H.

  本发明涉及一种新型脂类，更具体地说是具有极性头基团的醚脂类，以及包含这些脂类的囊泡、它们的制备方法以及它们在医学应用中的用途，其中醚脂类由通式（I）表示，其中Y代表O、N、S或共价键；P1表示H、一个Y-保护基或Y-活化基或空间基；P2、P3独立地表示H、氨基保护基或空间基，或者P2和P3与它们所结合的N一起形成一个环状结构；L是一个式子（a）的基团，其中虚线表示与N的连接；R1表示H或一个式子-(CH2)2-ORb1的基团；R1表示H或一个式子-(CH2)2-ORb2的基团，R2表示H或一个式子-CH2-ORc的基团；R2表示H或一个式子-ORd或-CH2-ORc的基团，R2表示H或一个式子-(CH2)2-ORe或-(CH2)3-ORe的基团；Ra、Rb1、Rb2、Rc、Rd、Re独立地表示饱和或不饱和的直链或支链烃链，m为1、2或3；但至少有一个R1、R1'、R2、R2'、R3不是H。