20:4 LPA | 65446-08-4

• 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: 20:4 LPA
• 英文别名: 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate；[(2R)-2-hydroxy-3-phosphonooxypropyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 65446-08-4
• 化学式: C₂₃H₃₉O₇P
• 分子量: 458.532
• InChiKey: XBFQFMCUPHZKTI-NZRYSPDRSA-N

物化性质

• 碰撞截面：
  202.71 Ų [M-H]- [CCS Type: TIMS, Method: single field calibrated]

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [1-¹⁴C]-oleoyl CoA 、 20:4 LPA 在 recombinant mouse His₁₂-CGI-58 fusion protein 作用下， 反应 0.17h， 生成
  参考文献：
  名称：

  CGI-58/ABHD5 is a coenzyme A-dependent lysophosphatidic acid acyltransferase

  摘要：

  Mutations in human CGI-58/ABHD5 cause Chanarin-Dorfman syndrome (CDS), characterized by excessive storage of triacylglycerol in tissues. CGI-58 is an alpha/beta-hydrolase fold enzyme expressed in all vertebrates. The carboxyl terminus includes a highly conserved consensus sequence (HXXXXD) for acyltransferase activity. Mouse CGI-58 was expressed in Escherichia coli as a fusion protein with two amino terminal 6-histidine tags. Recombinant CGI-58 displayed acyl-CoA-dependent acyltransferase activity to lysophosphatidic acid, but not to other lysophospholipid or neutral glycerolipid acceptors. Production of phosphatidic acid increased with time and increasing concentrations of recombinant CGI-58 and was optimal between pH 7.0 and 8.5. The enzyme showed saturation kinetics with respect to 1-oleoyl-lysophosphatidic acid and oleoyl-CoA and preference for arachidonoyl-CoA and oleoyl-CoA. The enzyme showed slight preference for 1-oleoyl lysophosphatidic acid over 1-palmitoyl, 1-stearoyl, or 1-arachidonoyl lysophosphatidic acid. Recombinant CGI-58 showed intrinsic fluorescence for tryptophan that was quenched by the addition of 1-oleoyl-lysophosphatidic acid, oleoyl-CoA, arachidonoyl-CoA, and palmitoyl-CoA, but not by lysophosphatidyl choline. Expression of CGI-58 in fibroblasts from humans with CDS increased the incorporation of radiolabeled fatty acids released from the lipolysis of stored triacylglycerols into phospholipids. CGI-58 is a CoA-dependent lysophosphatidic acid acyltransferase that channels fatty acids released from the hydrolysis of stored triacylglycerols into phospholipids.-Montero-Moran, G., J. M. Caviglia, D. McMahon, A. Rothenberg, V. Suramanian, Z. Xu, S. Lara-Gonzalez, J. Storch, G. M. Carman, and D. L. Brasaemle. CGI-58/ABHD5 is a coenzyme A-dependent lysophosphatidic acid acyltransferase. J. Lipid Res. 2010. 51: 709-719.

  DOI：

  10.1194/jlr.m001917
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以92 %的产率得到20:4 LPA
  参考文献：
  名称：

  甘油磷脂的简明合成

  摘要：

  甘油磷脂是细胞膜的主要成分，并提供重要的信号分子。除了塑造膜特性外，有些还与特定受体结合以激活生物途径。阐明单个甘油磷脂的作用需要明确定义的分子种类，这一挑战最好通过化学合成来解决。然而，由于这些脂质中存在相反的极性，甘油磷脂的合成通常很漫长。我们现在报告了一种通过雅各布森 Co(salen) 络合物催化的羧酸与磷酸三酯环氧化物的打开来快速获得甘油磷脂的一般策略。我们表明，该方法可以应用于多种市售脂肪酸、光可切换脂肪酸和其他羧酸，以提供相应的甘油磷酸衍生物。

  DOI：

  10.1021/acs.joc.2c02096

文献信息

• Compositions and methods for the treatment and prevention of fibrotic, inflammatory and neovascularization conditions
  申请人：Sabbadini A. Roger

  公开号：US20070148168A1

  公开（公告）日：2007-06-28

  The present invention relates to compositions and methods for prevention and treatment of diseases and conditions, including ocular diseases and conditions, characterized by aberrant fibrogenesis or scarring, inflammation and/or aberrant neovascularization or angiogenesis. The compositions and methods of the invention utilize immune-derived moieties that are specifically reactive against bioactive lipids and which are capable of decreasing the effective concentration of said bioactive lipid. In some embodiments, the immune-derived moiety is a monoclonal antibody that is reactive against sphingosine-1-phosphate (S1P) or lysophosphatidic acid (LPA).
• Methods for decreasing immune response and treating immune conditions
  申请人：Sabbadini Roger A.

  公开号：US20070280933A1

  公开（公告）日：2007-12-06

  The present invention relates to compositions and methods for decreasing an immune response in an animal comprising administering to said animal an agent that binds a bioactive lipid and reduces the effective concentration of said bioactive lipid. Also provided are methods for treating diseases or conditions, including autoimmune disorders, which are characterized by an aberrant, excessive or undesired immune response. The methods of the invention utilize agents that bind bioactive lipids and are capable of decreasing the effective concentration of the bioactive lipid. In some embodiments, the agent is a monoclonal antibody that is reactive against sphingosine-1-phosphate (S1P) or lysophosphatidic acid (LPA).
• Novel Bioactive Lipid Derivatives, and Methods of Making and Using Same
  申请人：SABBADINI A. Roger

  公开号：US20070281320A1

  公开（公告）日：2007-12-06

  Compositions and methods for producing monoclonal antibodies and their derivatives reactive against bioactive lipid targets are described. These compositions include derivatized lipids, each of which comprises a bioactive lipid that having a polar head group and at least one hydrocarbon chain (e.g., a lysolipid such as lysophosphatidic acid or sphingosine-1-phosphate) in which a carbon atom has been derivatized with a pendant reactive group; immunogens made by linking a derivatized lipid to a carrier moiety (e.g., a carrier protein, polyethylene glycol, colloidal gold, alginate, or a silicone bead); monoclonal antibodies and derivatives produced by immunizing an animal with such an immunogen; and therapeutic and diagnostic compositions containing such antibodies and antibody derivatives. Methods for making such derivatized lipids, immunogens, and monoclonal antibodies and derivatives, methods for detecting such antibodies once generated, and therapeutic and diagnostic methods for using such antibodies and derivatives, are also described.
• Immune-Derived Moieties Reactive Against Lysophosphatidic Acid
  申请人：SABBADINI Roger A.

  公开号：US20080145360A1

  公开（公告）日：2008-06-19

  Compositions and methods for producing monoclonal antibodies and their derivatives reactive against bioactive lipid targets are described. These compositions include derivatized lipids, each of which comprises a bioactive lipid that having a polar head group and at least one hydrocarbon chain (e.g., a lysolipid such as lysophosphatidic acid or sphingosine-1-phosphate) in which a carbon atom has been derivatized with a pendant reactive group; immunogens made by linking a derivatized lipid to a carrier moiety (e.g., a carrier protein, polyethylene glycol, colloidal gold, alginate, or a silicone bead); monoclonal antibodies and derivatives produced by immunizing an animal with such an immunogen; and therapeutic and diagnostic compositions containing such antibodies and antibody derivatives. Methods for making such derivatized lipids, immunogens, and monoclonal antibodies and derivatives, methods for detecting such antibodies once generated, and therapeutic and diagnostic methods for using such antibodies and derivatives, are also described.
• Methods and Reagents for Detecting Bioactive Lipids
  申请人：SABBADINI A. Roger

  公开号：US20080090303A1

  公开（公告）日：2008-04-17

  Compositions and methods for producing monoclonal antibodies and their derivatives reactive against bioactive lipid targets are described. These compositions include derivatized lipids, each of which comprises a bioactive lipid that having a polar head group and at least one hydrocarbon chain (e.g., a lysolipid such as lysophosphatidic acid or sphingosine-1-phosphate) in which a carbon atom has been derivatized with a pendant reactive group; immunogens made by linking a derivatized lipid to a carrier moiety (e.g., a carrier protein, polyethylene glycol, colloidal gold, alginate, or a silicone bead); monoclonal antibodies and derivatives produced by immunizing an animal with such an immunogen; and therapeutic and diagnostic compositions containing such antibodies and antibody derivatives. Methods for making such derivatized lipids, immunogens, and monoclonal antibodies and derivatives, methods for detecting such antibodies once generated, and therapeutic and diagnostic methods for using such antibodies and derivatives, are also described.