2,3-bis(hexadecyloxy)propan-1-amine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-bis(hexadecyloxy)propan-1-amine
• 英文别名: 2,3-Dihexadecoxypropan-1-amine
• 化学式: C₃₅H₇₃NO₂
• 分子量: 539.97
• InChiKey: FEMSGAJBFJUPRG-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

• 作为反应物：
  描述：

  4-(4-nitro-phenoxycarbonyloxymethyl)phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 、 2,3-bis(hexadecyloxy)propan-1-amine 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((((2,3-bis(hexadecyloxy)propyl)carbamoyl)oxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  酶促脂质体的一般方法。

  摘要：

  脂质体是有效的纳米载体，因为它们能够将封装的药物递送到患病细胞。然而，脂质体的递送将通过增强控制靶部位内容物释放的能力而得到改善。虽然已经探索了各种刺激来触发脂质体释放，但由于它们在患病细胞中普遍过量表达，因此酶提供了出色的靶标。我们提出了一种利用酶促脂质体的通用方法，该酶体利用疾病中通常异常的靶标，包括酯酶，磷酸酶和β-半乳糖苷酶。设计并合成了与每个酶家族相关的响应性脂质，其带有通过自消灭性连接子连接至非双层脂质支架的酶底物部分，因此，酶促水解会触发脂质分解，破坏膜的完整性并释放内含物。脂质体染料泄漏测定表明，与对照中的最低释放量相比，酶处理后的每个酶促反应脂质体均产生大量的内容物释放。结果还表明，微调脂质体组成对于控制释放至关重要。DLS分析显示，在酯酶和β的情况下，粒径增加-半乳糖苷酶反应性脂质，支持膜特性的改变。这些结果展示了可以针对不同酶进行定制的有效模块化策略，为推进脂质体药物传递提供了有希望的新途径。

  DOI：

  10.1002/chem.202000529
• 作为产物：
  描述：

  1-十六烷醇 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(hexadecyloxy)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

• Phosphate bioisostere containing amphiphiles: a novel class of squaramide-based lipids
  作者：Abhishek Saha、Subhankar Panda、Saurav Paul、Debasis Manna

  DOI：10.1039/c6cc04089f

  日期：——

  We describe a novel class of amphiphiles with squaramide moiety as a phosphate bioisostere.

  我们描述了一类新颖的含有方酰胺基团的两性分子，作为磷酸生物同构体。
• Boronic acid liposomes for cellular delivery and content release driven by carbohydrate binding
  作者：Xiaoyu Zhang、Daiane S. Alves、Jinchao Lou、Shelby D. Hill、Francisco N. Barrera、Michael D. Best

  DOI：10.1039/c8cc00820e

  日期：——

  Boronic acid liposomes enable triggered content release and cell delivery driven by carbohydrate binding. Dye release assays using hydrophilic and hydrophobic fluorophores validate dose-dependent release upon carbohydrate treatment. Microscopy results indicate dramatic enhancements in cell delivery, showcasing the prospects of boronic acid lipids for drug delivery.

  硼酸脂质体能够使触发的内容释放和碳水化合物结合驱动的细胞递送。使用亲水性和疏水性荧光团的染料释放分析可验证碳水化合物处理后剂量依赖性的释放。显微镜检查结果表明细胞传递的显着增强，显示出硼酸脂质用于药物传递的前景。
• DE2835369
  申请人：——

  公开号：——

  公开（公告）日：——
• [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.