Succinic acid mono-(2,3-bis-octadecanoyloxy-propyl) ester | 5512-60-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: Succinic acid mono-(2,3-bis-octadecanoyloxy-propyl) ester
• 英文别名: 4-[2,3-Di(octadecanoyloxy)propoxy]-4-oxobutanoic acid
• CAS: 5512-60-7
• 化学式: C₄₃H₈₀O₈
• 分子量: 725.103
• InChiKey: ABZNCHWVLIXLSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.2
• 重原子数：
  51
• 可旋转键数：
  43
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  季戊四醇 、 Succinic acid mono-(2,3-bis-octadecanoyloxy-propyl) ester 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以47%的产率得到Succinic acid 2,3-bis-octadecanoyloxy-propyl ester 3-hydroxy-2,2-bis-hydroxymethyl-propyl ester
  参考文献：
  名称：

  Pentaerythritol as the Core of Multivalent Glycolipids:  Synthesis of a Glycolipid with Three SO₃Le^a Ligands

  摘要：

  [GRAPHICS]A glycolipid containing three SO(3)Le(a) ligands was synthesized with pentaerythritol as the core. The glycolipid was used to prepare glycoliposomes that showed stability similar to that of DSPC liposomes without glycolipid. The easily prepared derivatives of pentaerythritol proved to be useful scaffolds for multivalent displaying of carbohydrates in the form of glycolipids and clustered glycoliposomes.

  DOI：

  10.1021/ol0514202
• 作为产物：
  描述：

  丁二酸酐 、 1,2-硬脂酸甘油酯 甘油硬脂酸 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 15.0h， 生成 Succinic acid mono-(2,3-bis-octadecanoyloxy-propyl) ester
  参考文献：
  名称：

  [EN] LIPID ASSEMBLIES AND USES THEREOF AND SOME pH AND ELECTROSTATIC MODULATING LIPIDS TO BE USED IN SAID ASSEMBLIES
  [FR] ASSEMBLAGES LIPIDIQUES ET LEURS UTILISATIONS ET QUELQUES LIPIDES DE MODULATION DE PH ET ÉLECTROSTATIQUE DESTINÉS À ÊTRE UTILISÉS DANS LESDITS ASSEMBLAGES

  摘要：

  本公开涉及改性脂质化合物及其在脂质组装中的应用。具体地，本公开揭示了包括（a）一种两性离子脂质，与之共价结合的包括（i）一个或多个酰基链；（ii）一个或多个弱碱基团；（iii）一个或多个弱酸基团；以及（b）一个或多个额外的脂质，其中至少一个是带电的两性离子脂质的脂质组装。在某些实施例中，两性离子脂质是一种化合物，包括（a）三官能团；（b）与三官能团中的两个官能团相关联的两个非磷脂质链；（c）可选地与三官能团中的第三个官能团相关联的间隔官能团；以及（d）一种聚烷基胺，可选地包括一个带有一到几个羧酸残基的短肽。本公开还揭示了脂质组装的用途，包括转染或癌症治疗等。

  公开号：

  WO2016125163A1

文献信息

• Lipid assemblies and uses thereof and some pH and electrostatic modulating lipids to be used in said assemblies
  申请人：Yissum Research Development Company of the Hebrew University of Jerusalem Ltd.

  公开号：US10722599B2

  公开（公告）日：2020-07-28

  Provided are modified lipid compounds and their use in the formation of lipid assemblies. Also provided are lipid assemblies including (a) an amphoteric lipid including in covalent association with (i) one or more acyl chains; (ii) one or more weak base moiety; (iii) one or more weak acid moiety; the lipid assembly also including (b) one or more additional lipids, at least one of which being a zwitterionic lipid. In some embodiments, the amphoteric lipid is a compound including (a) a tri-functional moiety; (b) two non-phosphate lipid chains associated with two of the functional moieties of said tri-functional moiety; (c) optionally a spacer moiety associated with the third of the functional moieties of said tri-functional moiety; and (d) a polyalkylamine optionally including a short peptide with one to several carboxylic acid residues. Further provided are the uses of the lipid assembly, inter alia, for transfection or cancer treatment.

  提供了改性脂质化合物及其在脂质组合物形成中的用途。还提供了脂质组合物，包括(a)与(i)一个或多个酰基链；(ii)一个或多个弱碱分子；(iii)一个或多个弱酸分子共价结合的两性脂质；脂质组合物还包括(b)一个或多个附加脂质，其中至少一个是齐聚物脂质。在某些实施方案中，两性脂质是一种化合物，包括：(a) 三官能团分子；(b) 与所述三官能团分子的两个官能团分子相关联的两条非磷酸脂质链；(c) 与所述三官能团分子的第三个官能团分子相关联的间隔分子；以及(d) 多烷基胺，可选地包括具有一至数个羧酸残基的短肽。此外，还提供了脂质组合物的用途，特别是用于转染或癌症治疗。
• LIPID ASSEMBLIES AND USES THEREOF AND SOME pH AND ELECTROSTATIC MODULATING LIPIDS TO BE USED IN SAID ASSEMBLIES
  申请人：Yissum Research Development Company of the Hebrew University of Jerusalem Ltd.

  公开号：US20180043036A1

  公开（公告）日：2018-02-15

  Provided are modified lipid compounds and their use in the formation of lipid assemblies. Also provided are lipid assemblies including (a) an amphoteric lipid including in covalent association with (i) one or more acyl chains; (ii) one or more weak base moiety; (iii) one or more weak acid moiety; the lipid assembly also including (b) one or more additional lipids, at least one of which being a zwitterionic lipid. In some embodiments, the amphoteric lipid is a compound including (a) a tri-functional moiety; (b) two non-phosphate lipid chains associated with two of the functional moieties of said tri-functional moiety; (c) optionally a spacer moiety associated with the third of the functional moieties of said tri-functional moiety; and (d) a polyalkylamine optionally including a short peptide with one to several carboxylic acid residues. Further provided are the uses of the lipid assembly, inter alia, for transfection or cancer treatment.
• Pentaerythritol as the Core of Multivalent Glycolipids:  Synthesis of a Glycolipid with Three SO₃Le^a Ligands
  作者：Jie Xue、Junmin Zhu、Roger E. Marchant、Zhongwu Guo

  DOI：10.1021/ol0514202

  日期：2005.8.1

  [GRAPHICS]A glycolipid containing three SO(3)Le(a) ligands was synthesized with pentaerythritol as the core. The glycolipid was used to prepare glycoliposomes that showed stability similar to that of DSPC liposomes without glycolipid. The easily prepared derivatives of pentaerythritol proved to be useful scaffolds for multivalent displaying of carbohydrates in the form of glycolipids and clustered glycoliposomes.
• [EN] LIPID ASSEMBLIES AND USES THEREOF AND SOME pH AND ELECTROSTATIC MODULATING LIPIDS TO BE USED IN SAID ASSEMBLIES<br/>[FR] ASSEMBLAGES LIPIDIQUES ET LEURS UTILISATIONS ET QUELQUES LIPIDES DE MODULATION DE PH ET ÉLECTROSTATIQUE DESTINÉS À ÊTRE UTILISÉS DANS LESDITS ASSEMBLAGES
  申请人：YISSUM RES DEV CO

  公开号：WO2016125163A1

  公开（公告）日：2016-08-11

  The present disclosure concerns modified lipid compounds and their use in the formation of lipid assemblies. Specifically are disclosed lipid assemblies comprising (a) an amphoteric lipid comprising in covalent association with (i) one or more acyl chains; (ii) one or more weak base moiety; (iii) one or more weak acid moiety; the lipid assembly also comprising (b) one or more additional lipids, at least one of which being a zwitterionic lipid. In some embodiments, the amphoteric lipid is a compound comprising (a) a tri-functional moiety; (b) two non-phosphate lipid chains associated with two of the functional moieties of said tri-functional moiety; (c) optionally a spacer moiety associated with the third of the functional moieties of said tri-functional moiety; and (d) a polyalkylamine optionally comprising a short peptide with one to several carboxylic acid residues. Also disclosed are the uses of the lipid assembly, inter alia, for transfection or cancer treatment.

  本公开涉及改性脂质化合物及其在脂质组装中的应用。具体地，本公开揭示了包括（a）一种两性离子脂质，与之共价结合的包括（i）一个或多个酰基链；（ii）一个或多个弱碱基团；（iii）一个或多个弱酸基团；以及（b）一个或多个额外的脂质，其中至少一个是带电的两性离子脂质的脂质组装。在某些实施例中，两性离子脂质是一种化合物，包括（a）三官能团；（b）与三官能团中的两个官能团相关联的两个非磷脂质链；（c）可选地与三官能团中的第三个官能团相关联的间隔官能团；以及（d）一种聚烷基胺，可选地包括一个带有一到几个羧酸残基的短肽。本公开还揭示了脂质组装的用途，包括转染或癌症治疗等。