2-((2-bromoethoxy)(hexadecyloxy)phosphoryloxy)ethoxy-β-apo-8‘-carotenoate | 1609100-69-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-((2-bromoethoxy)(hexadecyloxy)phosphoryloxy)ethoxy-β-apo-8‘-carotenoate
• CAS: 1609100-69-7
• 化学式: C₅₀H₈₀BrO₆P
• 分子量: 888.059
• InChiKey: GSWKWBSQUWLLKB-XXAUNDPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  58.0
• 可旋转键数：
  32.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-((2-bromoethoxy)(hexadecyloxy)phosphoryloxy)ethoxy-β-apo-8‘-carotenoate 、 三甲胺 以 氯仿 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 96.0h， 以72%的产率得到2-((choline)(hexadecyloxy)phosphoryloxy)ethoxy-β-apo-8‘-carotenoate
  参考文献：
  名称：

  Novel cationic polyene glycol phospholipids as DNA transfer reagents—Lack of a structure–activity relationship due to uncontrolled self-assembling processes

  摘要：

  Cationic glycol phospholipids were synthesized introducing chromophoric, rigid polyenoic C-20:5 and C-30:9 chains next to saturated flexible alkyl chains of variable lengths C6-20:0. Surface properties and liposome formation of the amphiphilic compounds were determined, the properties of liposome/DNA complexes (lipoplexes) were established using three formulations (no co-lipid, DOPE as a co-lipid, or cholesterol as a co-lipid), and the microstructure of the best transfecting compounds inspected using small angle X-ray diffraction to explore details of the partially ordered structures of the systems that constitute the series. Transfection and cytotoxicity of the lipoplexes were evaluated by DNA delivery to Chinese hamster ovary (CHO-K1) cells using the cationic glycerol phospholipid 1,2-dioleoyl-sn-glycero-3-ethylphosphocholine (EPC) as a reference compound.The uncontrollable self-association of the molecules in water resulted in aggregates and liposomes of quite different sizes without a structure-property relationship. Likewise, adding DNA to the liposomes gave rise to unpredictable sized lipoplexes, which, again, transfected without a structure-activity relationship. Nevertheless, one compound among the novel lipids (C-30:9 chain paired with a C-20:0 chain) exhibited comparable transfection efficiency and toxicity to the control cationic lipid EPC. Thus, the presence of a rigid polyene chain in this best performing achiral glycol lipid did not have an influence on transfection compared with the chiral glycerolipid reference ethyl phosphocholine EPC with two flexible saturated C-14 chains. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.04.006
• 作为产物：
  描述：

  β-apo-8'-carotenoic acid 、 (2-bromoethyl)(hexadecyl)(2-hydroxyethyl)phosphate 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到2-((2-bromoethoxy)(hexadecyloxy)phosphoryloxy)ethoxy-β-apo-8‘-carotenoate
  参考文献：
  名称：

  Novel cationic polyene glycol phospholipids as DNA transfer reagents—Lack of a structure–activity relationship due to uncontrolled self-assembling processes

  摘要：

  Cationic glycol phospholipids were synthesized introducing chromophoric, rigid polyenoic C-20:5 and C-30:9 chains next to saturated flexible alkyl chains of variable lengths C6-20:0. Surface properties and liposome formation of the amphiphilic compounds were determined, the properties of liposome/DNA complexes (lipoplexes) were established using three formulations (no co-lipid, DOPE as a co-lipid, or cholesterol as a co-lipid), and the microstructure of the best transfecting compounds inspected using small angle X-ray diffraction to explore details of the partially ordered structures of the systems that constitute the series. Transfection and cytotoxicity of the lipoplexes were evaluated by DNA delivery to Chinese hamster ovary (CHO-K1) cells using the cationic glycerol phospholipid 1,2-dioleoyl-sn-glycero-3-ethylphosphocholine (EPC) as a reference compound.The uncontrollable self-association of the molecules in water resulted in aggregates and liposomes of quite different sizes without a structure-property relationship. Likewise, adding DNA to the liposomes gave rise to unpredictable sized lipoplexes, which, again, transfected without a structure-activity relationship. Nevertheless, one compound among the novel lipids (C-30:9 chain paired with a C-20:0 chain) exhibited comparable transfection efficiency and toxicity to the control cationic lipid EPC. Thus, the presence of a rigid polyene chain in this best performing achiral glycol lipid did not have an influence on transfection compared with the chiral glycerolipid reference ethyl phosphocholine EPC with two flexible saturated C-14 chains. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.04.006