2,3-bis(dodecyloxy)propan-1-amine | 396727-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-bis(dodecyloxy)propan-1-amine
• 英文别名: 2,3-Didodecoxypropan-1-amine
• CAS: 396727-95-0
• 化学式: C₂₇H₅₇NO₂
• 分子量: 427.755
• InChiKey: RHRQNMDWDVLSMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  30
• 可旋转键数：
  26
• 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(dodecyloxy)propan-1-amine 在 95percent aq. TFA 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 N-[2,3-Bis(dodecyloxy)propyl]-L-lysinamide
  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
• 作为产物：
  描述：

  N-(2-hydroxy-3-lauryloxypropyl)phthalimide 在 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 96.0h， 生成 2,3-bis(dodecyloxy)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

• CATIONIC AMPHIPHILE COMPOSITIONS FOR INTRACELLULAR DELIVERY OF THERAPEUTIC MOLECULES
  申请人：Genzyme Corporation

  公开号：EP0954339A2

  公开（公告）日：1999-11-10
• [EN] CATIONIC AMPHIPHILE COMPOSITIONS FOR INTRACELLULAR DELIVERY OF THERAPEUTIC MOLECULES<br/>[FR] COMPOSITIONS CATIONIQUES AMPHIPHILES POUR LA DISTRIBUTION INTRACELLULAIRE DE MOLECULES THERAPEUTIQUES
  申请人：——

  公开号：WO1998002191A2

  公开（公告）日：1998-01-22

  [EN] Novel cationic amphiphiles are provided that facilitate transport of biologically active (therapeutic) molecules into cells. By this invention, such cationic amphiphile is used in a state in which it is capable of accepting additional protons, i.e., it is not fully protonated. For purposes of this invention, cationic amphiphiles may be considered to encompass four general categories: (A) T-shaped/steroid-based amphiphiles; (B) T-shaped/non steroid-based amphiphiles; (C) non T-shaped/steroid based amphiphiles and (D) non T-shaped/non steroid-based amphiphiles.
  [FR] L'invention concerne de nouveaux amphiphiles cationiques facilitant l'introduction de molécules biologiquement actives (thérapeutiques) dans les cellules. Selon l'invention, l'amphiphile cationique est utilisé dans un état où il est capable d'accepter des protons supplémentaires, c'est-à-dire où sa protonation n'est pas totale. Pour l'objectif de l'invention, on peut considérer que les amphiphiles cationiques sont divisés en quatre catégories: (A) en forme de T/à base de stéroïdes; (B) en forme de T/pas à base de stéroïde; (C) pas en forme de T/à base de stéroïdes; et (D) pas en forme de T/pas à base de stéroïde.
• [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.
• [EN] RNA PARTICLES COMPRISING POLYSARCOSINE<br/>[FR] PARTICULES D'ARN COMPRENANT DE LA POLYSARCOSINE
  申请人：BIONTECH RNA PHARMACEUTICALS GMBH

  公开号：WO2021191265A1

  公开（公告）日：2021-09-30

  The present disclosure relates to RNA particles for delivery of RNA to target tissues after administration, in particular after parenteral administration such as intravenous, intramuscular, subcutaneous or intratumoral administration, and compositions comprising such RNA particles. The RNA particles in one embodiment comprise single-stranded RNA such as mRNA which encodes a peptide or protein of interest, such as a pharmaceutically active peptide or protein. The RNA is taken up by cells of a target tissue and the RNA is translated into the encoded peptide or protein, which may exhibit its physiological activity.
• [EN] ANTIGEN-SPECIFIC T CELL RECEPTORS AND T CELL EPITOPES<br/>[FR] RÉCEPTEURS DE LYMPHOCYTES T SPÉCIFIQUES À UN ANTIGÈNE ET ÉPITOPES DE LYMPHOCYTES T
  申请人：BIONTECH CELL & GENE THERAPIES GMBH

  公开号：WO2021185775A1

  公开（公告）日：2021-09-23

  The present invention relates to the provision of clinically relevant T cell receptors and T cell epitopes which are useful for immunotherapy. The present invention also relates to therapies involving immune effector cells such as T cells expressing a T cell receptor disclosed herein and/or being specific for a T cell epitope disclosed herein.