O-(四癸酰磷酰)胆碱 | 77733-28-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: O-(四癸酰磷酰)胆碱
• 英文名称: Tetradecylphosphocholine
• 英文别名: tetradecylphosphorylcholine；n-tetradecylphosphocholine；C₁₄PC；tetradecyl-PC；MAPCHO-14；tetradecyl 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 77733-28-9
• 化学式: C₁₉H₄₂NO₄P
• 分子量: 379.521
• InChiKey: BETUMLXGYDBOLV-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226 °C
• 溶解度：
  DMF：16mg/mL； DMSO：16mg/mL；乙醇：15mg/mL； PBS（pH 7.2）：25 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2923900090
• WGK Germany：
  3
• 储存条件：
  -20℃

反应信息

• 作为反应物：
  描述：

  O-(四癸酰磷酰)胆碱 、 胞苷 在 phospholipase D from Streptomyces sp. AA 586 作用下， 以 氯仿 、 水 为溶剂， 反应 6.0h， 以77%的产率得到[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl tetradecyl hydrogen phosphate
  参考文献：
  名称：

  Shuto, Satoshi; Imamura, Shigeyuki; Fukukawa, Kiyofumi, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 12, p. 5020 - 5023

  摘要：

  DOI：
• 作为产物：
  描述：

  十四醇 在 二异丙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 14.0h， 生成 O-(四癸酰磷酰)胆碱
  参考文献：
  名称：

  Synthesis and Properties of Alkyl Phosphorylcholine Amphiphiles with a Linear and an Asymmetrically Branched Alkyl Chain

  摘要：

  成功合成了具有一条直链和一条不对称支链烷基链的烷基膦酰胆碱两亲物，使用2-氯-2-氧代-1,3,2-二氧磷环在四氢呋喃或乙酸乙酯中进行合成。1H和31P核磁共振研究表明，直链烷基膦酰胆碱（Cn-PC）在D2O中提供水溶胶束，在CDCl3中提供反向胶束，而支链烷基膦酰胆碱（ISOFOLn-PC）在D2O中形成囊泡。通过荧光染料溶解方法测定了Cn-PC的临界胶束浓度（CMCs）：在25°C的水中，C12-PC、C14-PC、C16-PC和C18-PC的CMCs分别为1.6、0.38、0.16和0.11 mM。在25°C的水中，ISOFOL16-PC、ISOFOL20-PC和ISOFOL24-PC的临界缔合浓度（CACs）分别为0.068、0.005和0.077 mM。通过动态光散射方法测量了ISOFOLn-PC在水溶液中的囊泡大小。ISOFOLn-PC囊泡的平均直径约为30 nm，尺寸分布相对单一。ISOFOLn-PC囊泡在水溶液中形成，具有几周时间的胶体稳定性。

  DOI：

  10.1246/bcsj.78.1558

文献信息

• Mucosal formulation
  申请人：Boga Rameshbabu

  公开号：US20070264206A1

  公开（公告）日：2007-11-15

  A mucosal formulation for administration to mucosal membranes, such as in the mouth, nasal passage, stomach, vagina, etc., is disclosed. The mucosal formulation contains a lipid-pharmaceutical agent complex formed from phospholipids possessing a hydrophobic moiety that orients into a hydrophobic phase and a polar head moiety that orients towards the aqueous phase (i.e., “amphipathic” lipids). When placed in an aqueous medium (e.g., vaginal fluid), the phospholipids form liposomes or other small lipid vesicles (e.g., micelles) that may then be used to deliver pharmaceutical agents into a living organism.

  揭示了一种用于给粘膜膜的制剂，例如口腔、鼻腔、胃、阴道等。这种粘膜制剂包含从磷脂中形成的含有疏水部分的脂质-药物复合物，该疏水部分朝向疏水相，极性头部分朝向水相（即“两性”脂质）。当置于水性介质中（例如阴道液），磷脂形成脂质体或其他小的脂质囊泡（例如胶束），然后可用于将药物输送到活体内。
• Phospholipids, their production and use thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0108565A2

  公开（公告）日：1984-05-16

  Phospholipids, inclusive of pharmaceutically acceptable salts thereof, of the formula wherein R' is a C8.30 aliphatic hydrocarbon residue, R2, R3 and R4 are independently hydrogen or lower alky or represents cyclic ammonio and n is 0 or 1, exhibit inhibitory activity to multiplication of tumor cells and antimycotic (antifungal) and antiprotozoal activities, and are useful for inhibiting multiplication of tumor cells and prolonging the survival time of tumor-bearing warm-blooded animals, for treating or preventing a disease in an animal caused by a mycete (fungus) and for treating or preventing a plant disease.

  磷脂，包括其药学上可接受的盐，其式为 其中 R' 为 C8.30 脂肪族烃残基，R2、R3 和 R4 独立地为氢或低级烷基或 代表环氨，n 为 0 或 1，具有抑制肿瘤细胞增殖的活性以及抗真菌和抗原虫活性，可用于抑制肿瘤细胞的增殖，延长患肿瘤的温血动物的存活时间，治疗或预防由真菌引起的动物疾病，以及治疗或预防植物疾病。
• Nuhn; Kertscher; Dobner, Pharmazie, 1982, vol. 37, # 10, p. 706 - 708
  作者：Nuhn、Kertscher、Dobner、Braune、Kluge

  DOI：——

  日期：——
• Autotaxin structure–activity relationships revealed through lysophosphatidylcholine analogs
  作者：E. Jeffrey North、Daniel A. Osborne、Peter K. Bridson、Daniel L. Baker、Abby L. Parrill

  DOI：10.1016/j.bmc.2009.03.030

  日期：2009.5

  Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) to form the bioactive lipid lysophosphatidic acid (LPA). LPA stimulates cell proliferation, cell survival, and cell migration and is involved in obesity, rheumatoid arthritis, neuropathic pain, atherosclerosis and various cancers, suggesting that ATX inhibitors have broad therapeutic potential. Product feedback inhibition of ATX by LPA has stimulated structure-activity studies focused on LPA analogs. However, LPA displays mixed mode inhibition, indicating that it can bind to both the enzyme and the enzyme-substrate complex. This suggests that LPA may not interact solely with the catalytic site. In this report we have prepared LPC analogs to help map out substrate structure-activity relationships. The structural variances include length and unsaturation of the fatty tail, choline and polar linker presence, acyl versus ether linkage of the hydrocarbon chain, and methylene and nitrogen replacement of the choline oxygen. All LPC analogs were assayed in competition with the synthetic substrate, FS-3, to show the preference ATX has for each alteration. Choline presence and methylene replacement of the choline oxygen were detrimental to ATX recognition. These findings provide insights into the structure of the enzyme in the vicinity of the catalytic site as well as suggesting that ATX produces rate enhancement, at least in part, by substrate destabilization. (C) 2009 Elsevier Ltd. All rights reserved.
• NOJIMA, SHOSHICHI;NOMURA, HIROAKI
  作者：NOJIMA, SHOSHICHI、NOMURA, HIROAKI

  DOI：——

  日期：——