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。
• Localization-independent Regulation of Homocysteine Secretion by Phosphatidylethanolamine N-Methyltransferase
  作者：David J. Shields、Susanne Lingrell、Luis B. Agellon、John T. Brosnan、Dennis E. Vance

  DOI：10.1074/jbc.m504658200

  日期：2005.7

  Genetic ablation of phosphatidylethanolamine N-methyltransferase (PEMT) in mice causes a 50% reduction in plasma homocysteine (Hcy) levels. Because hyperhomocysteinemia is an independent risk factor for cardiovascular disease, resolution of the molecular basis for this reduction is of significant clinical interest. The PEMT pathway is a metabolically channeled process localized to the endoplasmic reticulum ( ER). To assess the importance of PEMT localization for Hcy homeostasis, we identified and ablated the minimal ER targeting motif. Mutagenesis of a conserved, C-terminal lysine residue ( 197) relocalized the enzyme to the Golgi, demonstrating that Lys-197 is essential for targeting PEMT to the ER. To evaluate the functional significance of PEMT localization, hepatoma cell lines were generated that stably expressed either ER- or Golgi-localized PEMT only. Intriguingly, stable expression of PEMT in either the ER or the Golgi caused increased Hcy secretion. Moreover, PEMT-mediated Hcy secretion correlated with the methyltransferase activity of the enzyme, independently of subcellular localization. Thus, our data suggest that Hcy homeostasis is regulated concomitantly with PEMT activity but independently of PEMT localization.
• US6344576B1
  申请人：——

  公开号：US6344576B1

  公开（公告）日：2002-02-05