N-甲基-1,2-二油酰基磷脂酰乙醇胺 | 96687-23-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: N-甲基-1,2-二油酰基磷脂酰乙醇胺
• 英文名称: 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine-N-methyl
• 英文别名: [(2R)-2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl] 2-(methylazaniumyl)ethyl phosphate
• CAS: 96687-23-9
• 化学式: C42H80NO8P
• 分子量: 758.1
• InChiKey: LPXFOQGBESUDAX-NLEYBKGJSA-N

物化性质

• 沸点：
  760.2±70.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  52
• 可旋转键数：
  42
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-甲基-1,2-二油酰基磷脂酰乙醇胺 、 S-腺苷蛋氨酸 生成 1,2-二油酰基-sn-甘油-3-磷酸乙醇胺-N,N-二甲基 、 氢(+1)阳离子 、 S-(5'-腺苷)-L-高半胱氨酸
  参考文献：
  名称：

  Membrane Topography of Human Phosphatidylethanolamine N-Methyltransferase

  摘要：

  In liver, phosphatidylethanolamine is converted to phosphatidylcholine through a series of three sequential methylation reactions. Phosphatidylethanolamine N-methyltransferase (PEMT) catalyzes each transmethylation reaction, and S-adenosylmethionine is the methyl group donor. Biochemical analysis of human liver revealed that the methyltransferase activity is primarily localized to the endoplasmic reticulum and mitochondria-associated membranes. Bioinformatic analysis of the predicted amino acid sequence suggested that the enzyme adopts a polytopic conformation in those membranes. To elucidate the precise membrane topography of PEMT and thereby provide the basis for in-depth functional characterization of the enzyme, we performed endoproteinase-protection analysis of epitope-tagged, recombinant protein. Our data suggest a topographical model of PEMT in which four transmembrane regions span the membrane such that both the N and C termini of the enzyme are localized external to the ER. Two hydrophilic connecting loops protrude into the luminal space of the microsomes whereas a corresponding loop on the cytosolic side remains proximate to the membrane. Further support for this model was obtained following endoproteinase-protection analysis of mutant recombinant PEMT derivatives in which specific protease cleavage sites had been genetically engineered or ablated.

  DOI：

  10.1074/jbc.m210904200

文献信息

• Phospholipid-analogous compounds
  申请人：——

  公开号：US20030198663A1

  公开（公告）日：2003-10-23

  Phospholipid-analogous compounds of the general formula (I) 1 in which A 2 where R 1 and R 2 are, independently of one another, hydrogen, a saturated or unsaturated acyl or alkyl radical which can optionally be branched or/and substituted, where the total of the carbon atoms in the acyl and alkyl is 16 to 44 C atoms, s is an integer from 0 to 8, c is a radical of a primary or secondary alcohol of the formula RO—, where R is a saturated or unsaturated alkyl radical, mainly with cis double bond, of from 12 to 30 carbon atoms, n is an integer from 2 to 8, R 3 a can be 1,2-dihydroxypropyl or b can be alkyl with 1 to 3 C atoms when z is >0 or c can be alkyl with 1 to 3 carbon atoms when n≠2 and z=0, m is 1 or 2, x is an integer from 0 to 8, y is 1 for z=1 to 5 or is 1 to 4 for z=1 z is an integer from 0 to 5, are novel and are suitable as liposome constituents, solubilizers and pharmaceuticals.

  通式（I）的类磷脂类似化合物，其中A是一个基团，R1和R2独立地是氢、饱和或不饱和的酰基或烷基基团，可以是支链的和/或取代的，酰基和烷基中的碳原子总数为16到44个，s是从0到8的整数，c是具有RO—式的一级或二级醇基团，其中R是饱和或不饱和的烷基基团，主要带有顺式双键，碳原子数为12到30个，n是从2到8的整数，R3a可以是1,2-二羟基丙基或者当z>0时可以是碳原子数为1到3的烷基，或者当n≠2且z=0时可以是碳原子数为1到3的烷基，m为1或2，x是从0到8的整数，y对于z=1到5时为1，对于z=1时为1到4，z是从0到5的整数。这些化合物是新颖的，适用于脂质体成分、溶剂和药物。
• PHOSPHOLIPID-ANALOGOUS COMPOUNDS
  申请人：EIBL Hans-Jörg

  公开号：US20100183705A1

  公开（公告）日：2010-07-22

  Phospholipid-analogous compounds of the general formula (I) in which A where R 1 and R 2 are, independently of one another, hydrogen, a saturated or unsaturated acyl or alkyl radical which can optionally be branched or/and substituted, where the total of the carbon atoms in the acyl and alkyl is 16 to 44 C atoms, s is an integer from 0 to 8, c is a radical of a primary or secondary alcohol of the formula RO—, where R is a saturated or unsaturated alkyl radical, mainly with cis double bond, of from 12 to 30 carbon atoms, n is an integer from 2 to 8, R 3 a can be 1,2-dihydroxypropyl or b can be alkyl with 1 to 3 C atoms when z is >0 or c can be alkyl with 1 to 3 carbon atoms when n≠2 and z=0, m is 1 or 2, x is an integer from 0 to 8, y is 1 for z=1 to S′ or is 1 to 4 for z=1 z is an integer from 0 to 5, are novel and are suitable as liposome constituents, solubilizers and pharmaceuticals.

  通式（I）的类磷脂衍生物，其中A是，R1和R2分别是氢，饱和或不饱和的脂肪酰基或烷基，可以选择支链或/和取代，其中酰基和烷基中的碳原子总数为16到44个碳原子，s是0到8的整数，c是RO—的主要为顺式双键的一级或二级醇的基团，其中R是饱和或不饱和的烷基基团，其碳原子数为12到30个，n是2到8的整数，R3a可以是1,2-二羟基丙基或当z>0时可以是1到3个C原子的烷基，或当n≠2且z=0时可以是1到3个碳原子的烷基，m为1或2，x是0到8的整数，y为z=1到S'时为1或z=1z时为1到4，z是0到5的整数，这些化合物是新的，并适用于作为脂质体成分，溶解剂和药物。
• TARGETING AGENT FOR CANCER CELL OR CANCER-ASSOCIATED FIBROBLAST
  申请人：Nitto Denko Corporation

  公开号：US20130210744A1

  公开（公告）日：2013-08-15

  Disclosed are a novel therapeutic agent and a novel treatment method for cancer. Specifically disclosed are: a targeting agent for a cell selected from the group consisting of a cancer cell and a cancer-associated fibroblast, which comprises a retinoid and/or derivative thereof; a substance delivery carrier for the cell, which comprises the targeting agent; an anti-cancer composition utilizing the targeting agent or the carrier; an anticancer-associated fibroblast composition; and a method for treatment of cancer.

  本发明涉及一种新的治疗剂和癌症的新治疗方法。具体涉及的是：一种针对癌细胞和癌相关成纤维细胞中所选细胞的靶向剂，包括维甲酸和/或其衍生物；一种用于该细胞的物质传递载体，包括靶向剂；一种利用靶向剂或载体的抗癌组合物；一种抗癌相关成纤维细胞组合物；以及一种癌症治疗方法。
• Membrane Topography of Human Phosphatidylethanolamine N-Methyltransferase
  作者：David J. Shields、Richard Lehner、Luis B. Agellon、Dennis E. Vance

  DOI：10.1074/jbc.m210904200

  日期：2003.1

  In liver, phosphatidylethanolamine is converted to phosphatidylcholine through a series of three sequential methylation reactions. Phosphatidylethanolamine N-methyltransferase (PEMT) catalyzes each transmethylation reaction, and S-adenosylmethionine is the methyl group donor. Biochemical analysis of human liver revealed that the methyltransferase activity is primarily localized to the endoplasmic reticulum and mitochondria-associated membranes. Bioinformatic analysis of the predicted amino acid sequence suggested that the enzyme adopts a polytopic conformation in those membranes. To elucidate the precise membrane topography of PEMT and thereby provide the basis for in-depth functional characterization of the enzyme, we performed endoproteinase-protection analysis of epitope-tagged, recombinant protein. Our data suggest a topographical model of PEMT in which four transmembrane regions span the membrane such that both the N and C termini of the enzyme are localized external to the ER. Two hydrophilic connecting loops protrude into the luminal space of the microsomes whereas a corresponding loop on the cytosolic side remains proximate to the membrane. Further support for this model was obtained following endoproteinase-protection analysis of mutant recombinant PEMT derivatives in which specific protease cleavage sites had been genetically engineered or ablated.
• US6344576B1
  申请人：——

  公开号：US6344576B1

  公开（公告）日：2002-02-05