2-stearyloxy-3-myristyloxypropylamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-stearyloxy-3-myristyloxypropylamine
• 英文别名: 2-Octadecoxy-3-tetradecoxypropan-1-amine
• 化学式: C₃₅H₇₃NO₂
• 分子量: 539.97
• InChiKey: LSDJCAKDISLSDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  38
• 可旋转键数：
  34
• 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

• 作为产物：
  描述：

  硬脂醇 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-stearyloxy-3-myristyloxypropylamine
  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

• [EN] LIPIDS, LIPID COMPOSITIONS, LIPOSOMES, AND LIPOPLEXES<br/>[FR] LIPIDES, COMPOSITIONS DE LIPIDES, LIPOSOMES ET LIPOPLEXES
  申请人：CANCER RES CAMPAIGN TECH

  公开号：WO2002072068A2

  公开（公告）日：2002-09-19

  This invention pertains to certain lipids and lipid compositions, liposomes and lipoplexes formed therefrom, methods for their synthesis and preparation, compositions and medicaments comprising such liposomes and lipoplexes, and methods of cellular delivery, transfection, and medical treatment employing such liposomes and lipoplexes. Preferred lipid compositions comprise: (a) a cationic lipid fraction; and, (b) a non-ionic lipid fraction; wherein said cationic lipid fraction comprises one of the following: (A) a mixture of different cationic lipids, and which mixture includes: (i) 3β-[N-(N',N'-dimethylaminoethyl)carbamoyl] cholesterol (DC-Chol); and, (ii) an amine diether lipid, or an amine diester lipid, or a mixture thereof; (B) an amino acid amide of an amine diether lipid, or an amino acid amide of an amine diester lipid, or a mixture thereof; (C) a mixture of different cationic lipids, and which mixture includes: (i) DC-Chol; and, (ii) an amino acid amide of an amine diether lipid, or an amino acid amide of an amine diester lipid, or a mixture thereof; (D) a mixture of different cationic lipids, and which mixture includes: (i) one or more of: (i-a) DC-Chol; (i-b) an amine diether lipid or an amine diester lipid, or a mixture thereof; and, (i-c) an amino acid amide of an amine diether lipid, or an amino acid amide of an amine diester lipid, or a mixture thereof; and, (ii) a peptide amide of an amine diether lipid, or a peptide amide of an amine diester lipid, or a mixture thereof.
• Synthesis of Novel Cationic Lipids:  Effect of Structural Modification on the Efficiency of Gene Transfer
  作者：James A. Heyes、Dan Niculescu-Duvaz、Robert G. Cooper、Caroline J. Springer

  DOI：10.1021/jm010918g

  日期：2002.1.1

  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.