dipalmitoylphosphatidyl-L-serine

• 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: dipalmitoylphosphatidyl-L-serine
• 英文别名: 1,2-dipalmitoyl-sn-glycero-3-phospho-L-serine；1,2-dipalmitoyl phosphatidylserine；1,2-dihexadecanoyl-sn-glycero-3-phospho-L-serine；L-α-dipalmitoylphosphatidyl-L-serine；1,2-di(O-palmitoyl)-sn-glycero-3-phosphoserine；1,2-dipalmitoyl-sn-glycero-3-phosphoserine；DPPS；[(2S)-2-azaniumyl-2-carboxyethyl] [(2R)-2,3-di(hexadecanoyloxy)propyl] phosphate
• 化学式: C₃₈H₇₄NO₁₀P
• 分子量: 735.98
• InChiKey: KLFKZIQAIPDJCW-GPOMZPHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  50
• 可旋转键数：
  40
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  172
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  dipalmitoylphosphatidyl-L-serine 在 次氯酸 、 sodium chloride 作用下， 反应 0.08h， 生成 1,2-dipalmitoyl-sn-glycero-3-phosphoacetaldehyde 、 1,2-dipalmitoyl-sn-glycero-3-phosphonitrile
  参考文献：
  名称：

  铵离子存在下次氯酸和髓过氧化物酶与磷脂酰丝氨酸的相互作用

  摘要：

  血红素酶髓过氧化物酶与非关键性多形核白细胞（PMN）和其他凋亡细胞在炎症部位的表面上的磷脂酰丝氨酸表位密切相关，这有助于髓过氧化物酶产物对该磷脂的修饰。如通过基质辅助激光解吸/电离飞行时间（MALDI-TOF）质谱检测到的，铵离子以浓度依赖的方式抑制次氯酸介导的由1,2-二棕榈酰-基形成的醛和腈产物的形成。Sn-甘油-3-磷酸丝氨酸（DPPS）。同时，一氯胺（NH 2 Cl）的形成随着NH 4 +浓度的增加而增加。从单氯化O-磷酸-1-丝氨酸向NH的转氯化作用4 +用NH的形成2氯只有当非常高的NH发生4 +浓度被应用。由于该过程的速率较低，为0.044 M -1  s -1，因此可以排除从丝氨酸部分的瞬时氯化中间体到NH 4 +的转卤代反应，这是促成HOCl介导的NH 2形成的重要过程。Cl。在铵离子存在下，髓过氧化物酶与DPPS相互作用会明显形成NH 2 Cl，仅在酸性pH值约为5时发

  DOI：

  10.1016/j.jinorgbio.2010.03.009
• 作为产物：
  描述：

  3-O-benzoyl-1,2-O-dipalmitoyl-sn-glycerol 在 platinum(IV) oxide 、 palladium on activated charcoal 、 钯 氢气 、 双氧水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.75h， 生成 dipalmitoylphosphatidyl-L-serine
  参考文献：
  名称：

  General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-Glycerols

  摘要：

  An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof. The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation this procedure is exemplified by the preparation of 10a,b. The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields. Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38. Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33. This phosphite coupling procedure was modified to assemble phospholipids bearing-polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26. The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues. For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48. Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates maybe prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.

  DOI：

  10.1021/jo00096a023

文献信息

• [EN] CATIONIC LIPIDS AND USES THEREOF<br/>[FR] LIPIDES CATIONIQUES ET UTILISATIONS DE CEUX-CI
  申请人：ABBOTT LAB

  公开号：WO2009129385A1

  公开（公告）日：2009-10-22

  Cationic lipids, cationic lipid based drug delivery systems, ways to make them and methods of treating diseases using them are disclosed.

  阳离子脂质、基于阳离子脂质的药物传递系统、制备它们的方法以及利用它们治疗疾病的方法被披露。
• FLUORESCENT ANTICANCER PLATINUM DRUGS
  申请人：INVICTUS ONCOLOGY PVT. LTD.

  公开号：US20180312534A1

  公开（公告）日：2018-11-01

  The present disclosure is in relation to the field of nanotechnology and cancer therapeutics. In particular, the present disclosure relates to fluorescent platinum based compounds. The disclosure further relates to synthesis of said fluorescent platinum based compounds, nanoparticles and compositions comprising said fluorescent platinum based compounds/nanoparticles. The disclosure also relates to methods of managing cancer by the fluorescence changes between aforesaid platinum based compounds and corresponding free ligands, nanoparticles and compositions.

  本公开涉及纳米技术和癌症治疗领域。具体而言，本公开涉及荧光铂基化合物。该公开进一步涉及合成所述荧光铂基化合物、纳米颗粒和包含所述荧光铂基化合物/纳米颗粒的组合物。该公开还涉及通过上述铂基化合物与相应的游离配体、纳米颗粒和组合物之间的荧光变化来管理癌症的方法。
• Structural Characterization of Oxidized Glycerophosphatidylserine: Evidence of Polar Head Oxidation
  作者：Elisabete Maciel、Raquel Nunes da Silva、Cláudia Simões、Pedro Domingues、M. Rosário M. Domingues

  DOI：10.1007/s13361-011-0194-9

  日期：2011.10.1

  Non-oxidized phosphatidylserine (PS) is known to play a key role in apoptosis but there is considerable research evidence suggesting that oxidized PS also plays a role in this event, leading to the increasing interest in studying PS oxidative modifications. In this work, different PS (1-palmitoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (PLPS), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS), and 1,2-dipalmitoyl-sn-glycero-3-phospho-L-serine (DPPS) were oxidized in vitro by hydroxyl radical, generated under Fenton reaction conditions, and the reactions were monitored by ESI-MS in negative mode. Oxidation products were then fractionated by thin layer chromatography (TLC) and characterized by tandem mass spectrometry (MS/MS). This approach allowed the identification of hydroxyl, peroxy, and keto derivatives due to oxidation of unsaturated fatty acyl chains. Oxidation products due to oxidation of serine polar head were also identified. These products, with lower molecular weight than the non-modified PS, were identified as [M – 29 – H]– (terminal acetic acid), [M – 30 – H]– (terminal acetamide), [M – 13 – H]– (terminal hydroperoxyacetaldehyde), and [M – 13 – H]– (terminal hydroxyacetaldehyde plus hydroxy fatty acyl chain). Phosphatidic acid was also formed in these conditions. These findings confirm the oxidation of the serine polar head induced by the hydroxyl radical. The identification of these modifications may be a valuable tool to evaluate phosphatidylserine alteration under physiopathologic conditions and also to help understand the biological role of phosphatidylserine oxidation in the apoptotic process and other biological functions.

  未氧化的磷脂酰丝氨酸（PS）已知在细胞凋亡中发挥关键作用，但大量研究证据表明，氧化的PS在这一事件中也起着作用，因此研究PS氧化修饰的兴趣日益增加。在本研究中，不同类型的PS（1-棕榈酰基-2-亚油酰基-sn-甘油-3-磷酸-L-丝氨酸（PLPS）、1-棕榈酰基-2-油酰基-sn-甘油-3-磷酸-L-丝氨酸（POPS）和1,2-二棕榈酰基-sn-甘油-3-磷酸-L-丝氨酸（DPPS））在体外通过在芬顿反应条件下产生的羟基自由基进行氧化，并通过负模式电子喷雾质谱（ESI-MS）监测反应。氧化产物随后通过薄层色谱（TLC）分离，并通过串联质谱（MS/MS）进行表征。这种方法使得能够鉴定由于不饱和脂肪酰链氧化而产生的羟基、过氧基和酮衍生物。同时，丝氨酸极性头部氧化产生的氧化产物也得到了鉴定。这些低于未修饰PS分子量的产物被鉴定为[M – 29 – H]–（末端乙酸）、[M – 30 – H]–（末端乙酰胺）、[M – 13 – H]–（末端过氧乙醛）和[M – 13 – H]–（末端羟基乙醛加羟基脂肪酰链）。在这些条件下，磷脂酸也被形成。这些发现确认了羟基自由基诱导的丝氨酸极性头部的氧化。这些修饰的鉴定可能是评估生理病理条件下磷脂酰丝氨酸改变的有价值工具，并有助于理解磷脂酰丝氨酸氧化在凋亡过程及其他生物功能中的生物学作用。
• [EN] LANGERIN+ CELL TARGETING<br/>[FR] CIBLAGE DE CELLULES DE LANGERINE+
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2019141731A1

  公开（公告）日：2019-07-25

  The present invention relates to the use of a vehicle for specific molecular targeting of Langerin+ cells, wherein the vehicle is capable of specifically binding to a Langerin+ cell, said vehicle comprising (a) at least one carrier and (b) at least one saccharide moiety-based conjugate for a targeted cargo delivery into a Langerin+ cell, as well as pharmaceutical compositions and uses comprising the inventive vehicle.

  本发明涉及使用一种车辆来针对Langerin+细胞进行特定分子靶向，其中该车辆能够特异性地结合到Langerin+细胞，所述车辆包括（a）至少一种载体和（b）至少一种基于糖苷基的共轭物，用于将目标载荷传递到Langerin+细胞内，以及包括该创新车辆的药物组合物和用途。
• Amine Cationic Lipids and Uses Thereof
  申请人：Dicerna Pharmaceuticals, Inc.

  公开号：US20140371293A1

  公开（公告）日：2014-12-18

  The present invention relates to lipid compounds and uses thereof. In particular, the compounds include a class of cationic lipids having an amine moiety, such as an amino-amine or an amino-amide moiety. The lipid compounds are useful for in vivo or in vitro delivery of one or more agents (e.g., a polyanionic payload or an antisense payload, such as an RNAi agent).

  本发明涉及脂质化合物及其用途。具体而言，这些化合物包括一类具有胺基团的阳离子脂质，例如氨基-胺或氨基-酰胺基团。这些脂质化合物可用于体内或体外传递一个或多个药物（例如，多聚阴离子荷载物或反义荷载物，如RNAi药物）。