(2R)-3-((hydroxy(2-(3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamido)ethoxy)phosphoryl)oxy)propane-1,2-diyl dioleate | 1073588-75-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: (2R)-3-((hydroxy(2-(3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamido)ethoxy)phosphoryl)oxy)propane-1,2-diyl dioleate
• CAS: 1073588-75-6
• 化学式: C₅₅H₉₄NO₁₁P
• 分子量: 976.325
• InChiKey: MDYGXZPCUPCEOP-VFGPRJMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.99
• 重原子数：
  68.0
• 可旋转键数：
  43.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  171.6
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  二油酰基 L-α-磷脂酰乙醇胺 、 succinimidyl β,β,2,4,5-pentamethyl-3,6-dioxo-1,4-cyclohexadiene-1-propanoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(2R)-3-((hydroxy(2-(3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamido)ethoxy)phosphoryl)oxy)propane-1,2-diyl dioleate
  参考文献：
  名称：

  Redox-Triggered Contents Release from Liposomes

  摘要：

  An exciting new direction in responsive liposome research is endogenous triggering of liposomal payload release by overexpressed enzyme activity in affected tissues and offers the unique possibility of active and site-specific release. Bringing to fruition the fully expected capabilities of this new class of triggered liposomal delivery system requires a collection of liposome systems that respond to different upregulated enzymes; however, a relatively small number currently exist. Here we show that stable, similar to 100 nm diameter liposomes can be made from previously unreported quinone-dioleoyl phosphatidylethanolamine (Q-DOPE) lipids, and complete payload release (quenched fluorescent dye) from Q-DOPE liposomes occurs upon their redox activation when the quinone headgroup possesses specific substituents. The key component of the triggerable, contents-releasing Q-DOPE liposomes is a "trimethyl-locked" quinone redox switch attached to the N-terminus of DOPE lipids that undergoes a cleavage event upon two-electron reduction. Payload release by aggregation and leakage of "uncapped" Q-DOPE liposomes is supported by results from liposomes wherein deliberate alteration of the "trimethyl-locked" switch completely deactivates the redox-clestructible phenomena (liposome opening). We expect that Q-DOPE liposomes and their variants will be important in treatment of diseases with associated tissues that overexpress quinone reductases, such as cancers and inflammatory diseases, because the quinone redox switch is a known substrate for this group of reductases.

  DOI：

  10.1021/ja8050469