(2R)-3-(十六烷氧基)-2-(棕榈酰氧基)丙基2-(三甲基铵基)乙基磷酸酯 | 88587-94-4

• 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: (2R)-3-(十六烷氧基)-2-(棕榈酰氧基)丙基2-(三甲基铵基)乙基磷酸酯
• 中文别名: 2H-吡咯并[3,4-c]吡啶-1-甲醛,4,5,6,7-四氢-4-羰基-
• 英文名称: L-1-hexadecyl-2-palmitoyl-phosphatidylcholine
• 英文别名: 1-O-hexadecyl-2-O-palmitoyl-sn-glycero-3-phosphocholine；(R)-1-O-hexadecyl-2-palmitoyl-sn-glycero-3-phosphocholine；(R)-1-O-hexadecyl-2-palmitoyl-glycero-3-phosphocholine；1-Hexadecyl-2-hexadecanoyl-sn-glycero-3-phosphocholine；[(2R)-2-hexadecanoyloxy-3-hexadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 88587-94-4
• 化学式: C₄₀H₈₂NO₇P
• 分子量: 720.067
• InChiKey: WOTHHEHCEYHCFE-LDLOPFEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  49
• 可旋转键数：
  40
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-十六烷醇 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 Petroleum ether 为溶剂， 反应 35.0h， 生成 (2R)-3-(十六烷氧基)-2-(棕榈酰氧基)丙基2-(三甲基铵基)乙基磷酸酯
  参考文献：
  名称：

  通过特定的磷脂酶A2激活脂质体形成前药的酶促释放抗肿瘤醚脂质。

  摘要：

  已经研究了涉及被掩盖的抗肿瘤醚脂质（AEL）的基于酶活化脂质体的药物递送概念。该概念利用了AEL药物的细胞毒性特性以及这些分子的膜通透性增强特性，这可以导致增强的药物扩散进入细胞。合成了三种AEL的前药（proAELs），并研究了由这些proAELs组成的四个脂质体系统对分泌型磷脂酶A（2）（sPLA（2））的酶促降解作用，从而导致了AELs的释放。三种合成的proAEL是（R）-1-O-十六烷基-2-棕榈酰基-sn-甘油-3-磷酸胆碱（1-O-DPPC），（R）-1-O-十六烷基-2-棕榈酰-sn-甘油-3-磷酸乙醇胺聚乙二醇（350）（1-O-DPPE-PEG（350））和1-O-DPPE-PEG（2000），其中1-O-DPPC是主要脂质体组分。从通用原料（R）-O-苄基缩水甘油合成所有三种磷脂。开发了一种使用二氯甲基磷酸酯的磷酸化方法，并将其应用于（R）-1-O-十六烷基-2-棕榈

  DOI：

  10.1021/jm031029r

文献信息

• Lipid-based drug delivery system for administration of a drug substance
  申请人：Liplasome Pharma A/S

  公开号：EP1484332A2

  公开（公告）日：2004-12-08

  The present invention relates to a lipid based drug delivery system for administration of a drug substance, wherein the drug substance is incorporated in the system, said system including lipid derivatives which has (a) an aliphatic group of a length of at least 7 carbon atoms and an organic radical having at least 7 carbon atoms, and (b) a hydrophilic moiety, where the lipid derivative furthermore is a substrate for extracellular phospholipase A2 to the extent that the organic radical can be hydrolytically cleaved off, said system having included therein lipopolymers or glycolipids so as to present hydrophilic chains on the surface of the system.

  本发明涉及一种用于给药的基于脂质的给药系统，其中药物掺入该系统中，所述系统包括脂质衍生物，该脂质衍生物具有(a) 长度至少为 7 个碳原子的脂肪族基团和至少为 7 个碳原子的有机基、(b) 亲水性分子，其中脂质衍生物还是细胞外磷脂酶 A2 的底物，以至于有机基可以被水解，所述系统中还包括脂聚合物或糖脂，以便在系统表面形成亲水链。
• Lipid-based drug delivery systems containing phospholipase A2 degradable lipid derivatives and the therapeutic uses thereof
  申请人：——

  公开号：US20020001614A1

  公开（公告）日：2002-01-03

  The present invention relates to a lipid-based drug delivery system for administration of a lysolipid derivative present in prodrug from, said prodrug furthermore being a substrate for extracellular phospholipase A 2 to the extent that an organic radical can be hydrolytically cleaved off, whereas the aliphatic group of the lysolipid derivative remains substantially unaffected, said system having included therein lipopolymers or glycolipids so as to present hydrophilic chains on the surface of the system. Particularly interesting lipid derivatives are ether lipids and ether lipids in which drug substance is covalently attached in the sn-2-position. Pharmaceutical compositions comprising the drug delivery system can be used in the targeted treatment of various disorders, e.g. cancer, infectious, and inflammatory conditions, etc., i.e. disorders and diseases associated with or resulting from increased levels of extracellular PLA 2 activity in the diseased tissue.

  本发明涉及一种基于脂质的给药系统，用于给药原药中的溶血磷脂衍生物，所述原药是细胞外磷脂酶 A 2 有机自由基可被水解，而溶血磷脂衍生物的脂肪基基本不受影响，所述系统包含脂聚物或糖脂，以便在系统表面形成亲水链。特别有趣的脂质衍生物是醚脂和药物物质在 sn-2 位上共价连接的醚脂。包含该给药系统的药物组合物可用于各种疾病的靶向治疗，如癌症、感染性疾病和炎症等，即与细胞外聚乳酸（PLA）水平升高有关或因细胞外聚乳酸（PLA）水平升高导致的疾病。 2 活性增高有关或导致的紊乱和疾病。
• Lipid-based drug delivery systems containing phospholipase a2 degradable lipid derivatives for topical application to the skin
  申请人：——

  公开号：US20030170297A1

  公开（公告）日：2003-09-11

  The invention relates to lipid-based pharmaceutical or cosmetic compositions for use in the treatment prevention or alleviation of diseases or conditions in skin or mucous membranes of mammals that are associated with or resulting from increased levels of extracellular phospholipase A 2 (PLA 2 ) activity in the tissue.

  本发明涉及基于脂质的药物或化妆品组合物，用于治疗、预防或减轻与细胞外磷脂酶 A 2 （PLA 2 ）在组织中的活性增加有关或导致的疾病或病症。
• Lipid-based systems for targeting diagnostic agents
  申请人：——

  公开号：US20030175205A1

  公开（公告）日：2003-09-18

  The invention relates to targeting of diagnostic agents by use of lipid-based compositions. The invention is useful in the diagnosis of various disorders which are associated with or resulting from increased levels of extracellular PLA 2 activity in the diseased tissue, e.g. cancer, infectious, and inflammatory conditions.

  本发明涉及通过使用脂基组合物来靶向诊断制剂。本发明可用于诊断与细胞外 PLA 2 活性增高有关或导致的各种疾病，如癌症、感染性疾病和炎症。
• An efficient stereocontrolled route to both enantiomers of platelet activating factor and analogs with long-chain esters at C-2: saturated and unsaturated ether glycerolipids by opening of glycidyl arenesulfonates
  作者：Pedro N. Guivisdalsky、Robert Bittman

  DOI：10.1021/jo00280a035

  日期：1989.9