1-[(1Z)-hexadecenyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine | 65877-71-6

• 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: 1-[(1Z)-hexadecenyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine
• 英文别名: [(2R)-3-[(Z)-hexadec-1-enoxy]-2-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 65877-71-6
• 化学式: C42H82NO7P
• 分子量: 744.1
• InChiKey: CRBBMHQTIAELIS-KQBBALDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  51
• 可旋转键数：
  40
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(1Z)-hexadecenyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine 、 水 生成 oleate 、 (R)-(-)-1-O-(1'-(Z)-hexadecenyl)glycero-3-phosphocholine 、 氢(+1)阳离子
  参考文献：
  名称：

  The Genomic Organization, Complete mRNA Sequence, Cloning, and Expression of a Novel Human Intracellular Membrane-associated Calcium-independent Phospholipase A2

  摘要：

  During the sequencing of the long arm of chromosome 7 in the Human Genome Project, a predicted protein product of 40 kDa was identified, which contained two similar to 10-amino acid segments homologous to the ATP and lipase consensus sequences present in the founding members of a family of calcium-independent phospholipases A(2). Detailed inspection of the identified sequence (residues 79,671-109,912 GenBank(TM) accession no. AC005058) demonstrated that it represented only a partial sequence of a larger undefined polypeptide product. Accordingly, we identified the complete genomic organization of this putative phospholipase A, through analyses of previously published expressed sequence tags, PCR of human heart cDNA, and 5'-rapid amplification of cDNA ends. Polymerase chain reaction and Northern blotting demonstrated a 3.4-kilobase message, which encoded a polypeptide with a maximum calculated molecular weight of 88476.9, This 3,4-kilobase message was present in multiple human parenchymal tissues including heart, skeletal muscle, placenta, brain, liver, and pancreas. Cloning and expression of the protein encoded by this message in Sf9 cells resulted in the production of two proteins of apparent molecular masses of 77 and 63 kDa as assessed by Western analyses utilizing immunoaffinity-purified antibody. Membranes from Sf9 cells expressing recombinant protein released fatty acid from sn-2-radiolabeled phosphatidylcholine and plasmenylcholine up to 10-fold more rapidly than controls. The initial rate of fatty acid release from the membrane fraction was 0.3 nmol/mg min. The recombinant protein was entirely calcium-independent, had a pH optimum of 8.0, was inhibited by (E)-6-(bromomethylene)-3-(1-naphthalenyl)-2H-tetrahydropyran (IC50 = 3 mu M), and was predominantly present in the membrane-associated fraction. Collectively, these results describe the genomic organization, complete mRNA sequence, and sn-a-lipase activity of a novel intracellular calcium-independent membrane-associated phospholipase A(2).

  DOI：

  10.1074/jbc.275.14.9937

文献信息

• Oxidized lipids and uses thereof in the treatment of inflammatory diseases and disorders
  申请人：Harats Dror

  公开号：US20100048515A1

  公开（公告）日：2010-02-25

  Novel synthetic oxidized lipids and methods utilizing oxidized lipids for treating and preventing an inflammation associated with an endogenous oxidized lipid are provided.

  提供了一种新型合成的氧化脂质以及利用氧化脂质用于治疗和预防与内源性氧化脂质相关的炎症的方法。
• NANOPARTICLE-BASED DELIVERY SYSTEM WITH OXIDIZED PHOSPHOLIPIDS AS TARGETING LIGANDS FOR THE PREVENTION, DIAGNOSIS AND TREATMENT OF ATHEROSCLEROSIS
  申请人：WANG Shu

  公开号：US20140287024A1

  公开（公告）日：2014-09-25

  Disclosed are nanoparticle-based medicine/nutrient delivery system that are coated or incorporated with oxidized phospholipids as targeting ligands. Such delivery systems can specifically target macrophages, which are determinant cells in the aortic wall for atherosclerotic lesion development, to significantly increase bioavailability and specificity for the prevention, diagnosis and treatment of atherosclerosis.

  揭示了一种基于纳米颗粒的医药/营养素传递系统，其涂有或包含氧化磷脂作为靶向配体。这样的传递系统可以特异性地靶向巨噬细胞，它们是动脉壁上动脉粥样硬化病变发展的决定性细胞，从而显着增加生物利用度和特异性，用于预防、诊断和治疗动脉粥样硬化。
• OXIDIZED LIPIDS AND USES THEREOF IN THE TREATMENT OF INFLAMMATORY DISEASES AND DISORDERS
  申请人：Vascular Biogenics Ltd.

  公开号：EP1626728A2

  公开（公告）日：2006-02-22
• EP1626728A4
  申请人：——

  公开号：EP1626728A4

  公开（公告）日：2009-09-02
• US7973023B2
  申请人：——

  公开号：US7973023B2

  公开（公告）日：2011-07-05