1-O-hexadecyl-2-(4-(4-(bis-(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phosphocholine | 1159279-46-5

• 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: 1-O-hexadecyl-2-(4-(4-(bis-(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phosphocholine
• 英文别名: [(2R)-2-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyloxy]-3-hexadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 1159279-46-5
• 化学式: C₃₈H₆₉Cl₂N₂O₇P
• 分子量: 767.855
• InChiKey: GJVKKBTXRSVSFL-DIPNUNPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  50
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-O-十六烷基-SN-甘油基-3-胆碱磷酸 、 苯丁酸氮芥 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 27.0h， 以75%的产率得到1-O-hexadecyl-2-(4-(4-(bis-(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Synthesis and Biophysical Characterization of Chlorambucil Anticancer Ether Lipid Prodrugs

  摘要：

  The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol headgroups. All four prodrugs have the ability to form unilamellar liposomes (86-125 nm) and are hydrolyzed by phospholipase A(2), resulting in chlorambucil release. Liposomal formulations of prodrug lipids displayed cytotoxicity toward HT-29, MT-3, and ES-2 cancer cell lines in the presence of phospholipase A(2), with IC50 values in the 8-36 mu M range.

  DOI：

  10.1021/jm900091h

文献信息

• Synthesis and Biophysical Characterization of Chlorambucil Anticancer Ether Lipid Prodrugs
  作者：Palle J. Pedersen、Mikkel S. Christensen、Tristan Ruysschaert、Lars Linderoth、Thomas L. Andresen、Fredrik Melander、Ole G. Mouritsen、Robert Madsen、Mads H. Clausen

  DOI：10.1021/jm900091h

  日期：2009.5.28

  The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol headgroups. All four prodrugs have the ability to form unilamellar liposomes (86-125 nm) and are hydrolyzed by phospholipase A(2), resulting in chlorambucil release. Liposomal formulations of prodrug lipids displayed cytotoxicity toward HT-29, MT-3, and ES-2 cancer cell lines in the presence of phospholipase A(2), with IC50 values in the 8-36 mu M range.