1‐palmitoyl‐2‐(5‐oxovaleroyl)‐sn‐glycero‐3‐phosphocholine | 121324-31-0

• 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‐palmitoyl‐2‐(5‐oxovaleroyl)‐sn‐glycero‐3‐phosphocholine
• 英文别名: [(2R)-3-hexadecanoyloxy-2-(5-oxopentanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate；1-palmitoyl-2-(5′-oxo-valeroyl)-sn-glycero-3-phosphocholine；1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine；1-palmitoyl-2-(5'-oxo-valeroyl)-sn-glycero-3-phosphocholine；1-palmitoyl-2-(5'-oxovaleroyl)-sn-glycero-3-phosphocholine；1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphocholine；Povpc
• CAS: 121324-31-0
• 化学式: C₂₉H₅₆NO₉P
• 分子量: 593.739
• InChiKey: RKIDALSACBQVTN-HHHXNRCGSA-N

物化性质

• 溶解度：
  DMF：15 mg/ml； DMSO：10 mg/ml；乙醇：30 mg/ml； PBS（pH 7.2）：10 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1‐palmitoyl‐2‐(5‐oxovaleroyl)‐sn‐glycero‐3‐phosphocholine 、 4-mercapto-benzoic acid hydrazide 以 甲醇 为溶剂， 反应 1.0h， 生成 POVPC-PACa
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS FOR IDENTIFYING AND/OR QUANTIFYING CARBONYLATED BIOMOLECULES
  [FR] COMPOSÉS ET PROCÉDÉS POUR L'IDENTIFICATION ET/OU LA QUANTIFICATION DE BIOMOLÉCULES CARBONYLÉES

  摘要：

  本发明提供了一种利用本发明化合物对羰基化生物分子进行衍生化、鉴定和/或定量的方法。本发明提供了一种利用这些化合物分析氧化生物分子物种（如肽、蛋白质和脂质）的方法。这种方法有利地实现了羰基化样品的同时衍生化、定量和富集，并且完全适用于质谱分析。

  公开号：

  WO2012152943A1
• 作为产物：
  描述：

  2-花生四烯酰-1-棕榈酰-sn-甘油-3-磷酸胆碱 在 氧气 作用下， 反应 72.0h， 生成 1‐palmitoyl‐2‐(5‐oxovaleroyl)‐sn‐glycero‐3‐phosphocholine 、 [(2R)-3-hexadecanoyloxy-2-[4-[3-[(E)-[(2S)-2-[(Z)-oct-2-enyl]-5-oxocyclopent-3-en-1-ylidene]methyl]oxiran-2-yl]butanoyloxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate 、 1-palmitoyl-2-(5,6)-epoxyisoprostane E2-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Catalytic reduction of carbonyl groups in oxidized PAPC by Kvβ2 (AKR6)

  摘要：

  The beta-subunits of the voltage-gated potassium channel (Kv beta) belong to the aldo-keto reductase superfamily. The Kv beta-subunits dock with the pore-forming Kv alpha-subunits and impart or accelerate the rate of inactivation in Kv channels. Inactivation of Kv currents by Kv beta is differentially regulated by oxidized and reduced pyridine nucleotides. In mammals, AKR6 family is comprised of 3 different genes Kv beta 1-3. We have shown previously that Kv beta 2 catalyzes the reduction of a broad range of carbonyls including aromatic carbonyls, electrophilic aldehydes and prostaglandins. However, the endogenous substrates for Kv beta have not been identified. To determine whether products of lipid oxidation are substrates of Kv beta s, we tested the enzymatic activity of Kv beta 2 with oxidized phospholipids generated during the oxidation of 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (PAPC). Electrospray ionization mass spectrometric analysis showed that Kv beta 2 catalyzed the NADPH-dependent reduction of several products of oxPAPC, including 1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine (POVPC), 1-palmitoyl-2-(epoxycyclopentenone)-sn-glycero-3-phosphorylcholine (PECPC), 1-palmitoyl-2-(5,6)- epoxyisoprostane E2-sn-glycero-3-phosphocholine (PEIPC). These results were validated using high resolution mass spectrometric analysis. Time course analysis revealed that the reduced products reached significant levels for ions at m/z 594/596 (POVPC/PHVPC), 810/812 (PECPC/2H-PECPC) and 828/830 (PEIPC/2H-PEIPC) in the oxPAPC + Kv beta 2 mixture (p < 0.01). These results suggest that Kv beta could serve as a sensor of lipid oxidation via its catalytic activity and thereby alter Kv currents under conditions of oxidative stress. (C) 2011 Published by Elsevier Ireland Ltd.

  DOI：

  10.1016/j.cbi.2011.01.032

文献信息

• Methods employing and compositions containing defined oxidized phospholipids for prevention and treatment of atherosclerosis
  申请人：Vascular Biogenics Ltd.

  公开号：US20030225035A1

  公开（公告）日：2003-12-04

  Novel synthetic forms of etherified oxidized phospholipids and methods of utilizing same for preventing and treating atherosclerosis and other related disorders, as well as inflammatory disorders, immune mediated diseases, autoimmune diseases and proliferative disorders, are provided. In addition, methods of synthesizing etherified and esterified oxidized phospholipids and of using same for preventing and treating atherosclerosis and other related disorders are also provided.

  提供了新型合成的醚化氧化磷脂和利用这些物质预防和治疗动脉粥样硬化和其他相关疾病，以及炎症性疾病、免疫介导性疾病、自身免疫疾病和增生性疾病的方法。此外，还提供了合成醚化和酯化氧化磷脂的方法，以及利用这些物质预防和治疗动脉粥样硬化和其他相关疾病的方法。
• Technology for the Preparation of Microparticles
  申请人：Malakhov Michael

  公开号：US20090098207A1

  公开（公告）日：2009-04-16

  Microspheres are produced by contacting a solution of a macromolecule or small molecule in a solvent with an antisolvent and a counterion, and chilling the solution. The microspheres are useful for preparing pharmaceuticals, nutraceuticals, cosmetic products and the like of defined dimensions.

  微球是通过将溶液中的大分子或小分子与抗溶剂和对离子接触，并冷却溶液而制备的。这些微球可用于制备具有明确定义尺寸的药物、营养保健品、化妆品等产品。
• PEPTIDOMIMETICS COMPRISING N-AMINO CYCLIC UREA RESIDUES AND USES THEREOF
  申请人：RSEM, LIMITED PARTNERSHIP

  公开号：US20140024606A1

  公开（公告）日：2014-01-23

  Novel peptidomimetics comprising N-amino cyclic urea residues are disclosed. Use of such peptidomimetics for modulating the activity of CD36 or IL-1 receptor in a cell, and for treating CD36- or IL-1-related disease, disorder or condition is also described

  本发明揭示了含有N-氨基环状脲残基的新型肽类似物。还描述了使用这种肽类似物来调节细胞中CD36或IL-1受体的活性，并用于治疗与CD36或IL-1相关的疾病、障碍或病况。
• Compositions and methods for treatment of neoplastic disease
  申请人：——

  公开号：US20020177551A1

  公开（公告）日：2002-11-28

  The present invention comprises compositions and methods for treating a tumor or neoplastic disease in a host, The methods employ conjugates comprising superantigen polypeptides, nucleic acids with other structures that preferentially bind to tumor cells and are capable of inducing apoptosis. Also provided are superantigen-glycolipid conjugates and vesicles that are loaded onto antigen presenting cells to activate both T cells and NKT cells. Cell-based vaccines comprise tumor cells engineered to express a superantigen along with glycolipids products which, when expressed, render the cells capable of eliciting an effective anti-tumor immune response in a mammal into which these cells are introduced. Included among these compositions are tumor cells, hybrid cells of tumor cells and accessory cells, preferably dendritic cells. Also provided are tumoricidal T cells and NKT cells devoid of inhitory receptors or inhibitory signaling motifs which are hyperresponsive to the the above compositions and lipid-based tumor associated antigens that can be administered for adoptive immunotherapy of cancer and infectious diseases.

  本发明涉及一种用于治疗宿主体内肿瘤或肿瘤性疾病的组合物和方法。该方法采用包含超抗原多肽、具有其他结构的核酸和优先结合于肿瘤细胞并能够诱导细胞凋亡的结构的共轭物。还提供了超抗原-糖脂共轭物和负载于抗原呈递细胞上的囊泡，以激活T细胞和NKT细胞。基于细胞的疫苗包括肿瘤细胞，这些肿瘤细胞被改造以表达超抗原和糖脂产物，当这些细胞被引入哺乳动物体内时，这些细胞能够引起有效的抗肿瘤免疫反应。这些组合物包括肿瘤细胞、肿瘤细胞和辅助细胞的杂交细胞，优选为树突状细胞。还提供了无抑制性受体或抑制性信号基序的肿瘤细胞杀伤T细胞和NKT细胞，这些细胞对上述组合物和基于脂质的肿瘤相关抗原具有高度反应性，可用于癌症和传染病的免疫治疗。
• Process for the preparation of oxidized phospholipids
  申请人：Halperin Gideon

  公开号：US20070112211A1

  公开（公告）日：2007-05-17

  Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.

  本发明揭示了一种新的合成路线，非常适用于工业制备具有治疗益处的氧化磷脂类化合物。特别是，本发明揭示了一种高效制备具有甘油骨架和一个或多个氧化基团连接到甘油骨架上的化合物的新方法，该方法不需要使用柱层析。此外，本发明还揭示了将含磷基团（如磷酸盐基团）引入具有甘油骨架和由此形成的中间体的化合物的新方法。