[5,6,8,9,11,12,14,15-3H(N)]-花生四烯酸 | 66753-05-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: [5,6,8,9,11,12,14,15-3H(N)]-花生四烯酸
• 英文名称: <5,6,8,9,11,12,14,15-3H8>arachidonic acid
• 英文别名: [5,6,8,9,11,12,14,15(n)-(3)H]-arachidonic acid；[5,6,8,9,11,12,14,15-3H(N)]arachidonic acid；[5,6,8,9,11,12,14,15-3H8]arachidonic acid；[5,6,8,9,11,12,14,15-3H(N)] archidonic acid；[5,6,8,9,11,12,14,15-3H]arachidonic acid；(5,6,8,9,11,12,14,15-3H)Arachidonic acid；(5Z,8Z,11Z,14Z)-5,6,8,9,11,12,14,15-octatritioicosa-5,8,11,14-tetraenoic acid
• CAS: 66753-05-7
• 化学式: C₂₀H₃₂O₂
• 分子量: 320.409
• InChiKey: YZXBAPSDXZZRGB-CRJVGOJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  F,Xi,R
• 危险品运输编号：
  UN 2910 7

反应信息

• 作为反应物：
  描述：

  [5,6,8,9,11,12,14,15-3H(N)]-花生四烯酸 在 4(3H)-喹唑啉酮,6-氨基-3-(3-氯-2-甲基苯基)-2-甲基- hemin 、 肾上腺素 、 Lubrol PX 作用下， 以 乙醇 为溶剂， 反应 0.11h， 以63%的产率得到[5,6,8,9,11,12,14,15-(3)H]-prostaglandin F_2α
  参考文献：
  名称：

  Enzymatic synthesis of tritium labelled eicosanoids

  摘要：

  Methods for the synthesis of tritium labelled prostaglandins, thromboxanes, and hydroxy-derivatives of eicosapolyenoic acids using mono-, two-, and three-enzyme systems have been developed. Optimization of the eicosanoid syntheses with respect to the concentrations of enzymes and eicosapolyenoic acid. time, and temperature of incubation are reported. It is demonstrated that a number of compounds can be produced by enzymatic modifications of prostaglandins and thromboxane. Procedures for the preparation of twenty tritium labelled compounds are described.

  DOI：

  10.1002/(sici)1099-1344(1998080)41:8<741::aid-jlcr123>3.0.co;2-w
• 作为产物：
  描述：

  5,8,11,14-花生四烯酸 在 Lindlar's catalyst 超重氢 作用下， 以 1,4-二氧六环 为溶剂， 20.0 ℃ 、40.0 kPa 条件下， 反应 2.0h， 生成 [5,6,8,9,11,12,14,15-3H(N)]-花生四烯酸
  参考文献：
  名称：

  Synthesis of tritium labelled arachidonic acid amide and ester derivatives with dopamine, serotonin, vanillylamine, and ethyleneglycol moieties

  摘要：

  通过混合酸酐或酰氟与相应的胺和醇缩合，从三价花生四烯酸制备出了具有多巴胺、血清素、香草醛胺和乙二醇酯分子的氚标记花生四烯酸酰胺，其比活度（120 Ci/mmol）和收率（70-90%）都很高。标记的化合物被用于研究小鼠脾脏淋巴细胞对它们的吸收。从获得的数据来看，花生四烯酸酰胺是通过被动扩散的方式渗透膜的，而花生四烯酸乙二醇的跨膜运输似乎是由浓度梯度驱动的，由水解酶维持。用上述方法合成的化合物还可用于受体结合研究以及脂肪酸酰胺和酯的氧化代谢研究。Copyright © 2002 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.663

文献信息

• Simplified chemical and radiochemical synthesis of 2-arachidonoyl-glycerol, an endogenous ligand of cannabinoid receptors
  作者：Antonella Cartoni、Andrea Margonelli、Giancarlo Angelini、Alessandro Finazzi-Agrò、Mauro Maccarrone

  DOI：10.1016/j.tetlet.2004.02.045

  日期：2004.3

  emerged as a new class of lipid mediators, with manifold roles in the central nervous system and in the periphery. Several studies have identified 2-arachidonoyl-glycerol (2-AG) as a major endogenous agonist of cannabinoid receptors. Here, the chemical synthesis of 2-AG is reported, along with the synthesis of its tritium-labeled derivative. These unlabeled and radiolabeled compounds are suitable tools for

  内源性大麻素已成为一类新型的脂质介体，在中枢神经系统和周围神经系统中起着多种作用。几项研究已确定2-花生四烯酰基甘油（2-AG）是大麻素受体的主要内源性激动剂。在此，报告了2-AG的化学合成及其tri标记衍生物的合成。这些未标记和放射性标记的化合物是揭示2-AG在各种细胞和组织中的某些代谢途径和生物活性的合适工具。
• Preparation of high specific activity tritium-labelled leukotriene B4 suitable for radioligand binding assay
  作者：Stanislav I. Schramm、Igor Yu. Nagaev、Alan Sabirsh、Valeriy P. Shevchenko、Anastasiya S. Arkhipova、Jesper Z. Haeggström、Nikolay F. Myasoedov

  DOI：10.1002/jlcr.1488

  日期：2008.2

  We describe a method of preparation of high specific activity tritium-labelled leukotriene (LT) B4 from [5,6,8,9,11,12,14,15-3H] arachidonic acid (AA; 6.66 TBq/mmol) utilizing a LTB4-synthesizing enzyme system from rat basophilic leukemia (RBL-1) cells. It was shown that both cyclooxygenase inhibitor indomethacin and adenosine 5′-triphosphate induced [3H] AA transformation to [3H] LTB4. In optimized conditions up to 15% of total radioactivity of the incubation mixture was present in [3H] LTB4. A separation of [3H] LTB4 from other labelled C20:4 products was achieved by a three-step reverse phase-high-performance liquid chromatography in methanol- and acetonitrile-based solvent systems. [3H] LTB4 was confirmed to be identical to the naturally occurring LTB4 by a radioligand binding assay using a culture of HF1 cells that express a BLT1 receptor. Copyright © 2008 John Wiley & Sons, Ltd.

  我们描述了一种利用大鼠嗜碱性白血病（RBL-1）细胞中的 LTB4 合成酶系统，从[5,6,8,9,11,12,14,15-3H] 花生四烯酸（AA；6.66 TBq/mmol）制备高特异性氚标记的白三烯（LT）B4 的方法。研究表明，环氧化酶抑制剂吲哚美辛和腺苷 5′-三磷酸都能诱导[3H] AA 转化为[3H] LTB4。在优化条件下，[3H] LTB4 的放射性占到孵育混合物总放射性的 15%。在甲醇和乙腈溶剂系统中，通过三步反相高效液相色谱法将[3H] LTB4 从其他标记的 C20:4 产物中分离出来。通过使用表达 BLT1 受体的 HF1 细胞培养物进行放射性配体结合试验，证实[3H] LTB4 与天然存在的 LTB4 相同。Copyright © 2008 John Wiley & Sons, Ltd. All Rights Reserved.
• A Methodology for Radiolabeling of the Endocannabinoid 2-Arachidonoylglycerol (2-AG)
  作者：Richard I. Duclos、Meghan Johnston、Subramanian K. Vadivel、Alexandros Makriyannis、Sherrye T. Glaser、S. John Gatley

  DOI：10.1021/jo102277q

  日期：2011.4.1

  The metabolic intermediate and endocannabinoid signaling lipid 2-arachidonoylglycerol (2-AG) has not been readily labeled, primarily because of its instability toward rearrangement. We now detail a synthetic method that easily gives tritiated 2-AG from [5,6,8,9,11,12,14,15-H-3(N)]arachidonic acid in two steps. We utilized a short chain 1,3-diacylglycerol and proceeded through the "structured lipid" [5 '',6 '',8 '',9 '',11 '',12 '', 14 '',15 ''-H-3(N)]2-arachidonoyl-1,3-dibutyrylglycerol, a triacylglycerol that was conveniently deprotected in ethanol with acrylic beads containing Candida antarctica lipase B to give [5 '',6 '',8 '',9 '',11 '',12 '',14 '',15 ''-H-3(N)]2-arachidonoylglycerol ([H-3]2-AG). The flash chromatographic separation necessary to isolate the labeled 2'-acylglycerol [H-3]2-AG resulted in only 4% of the rearrangement byproducts that have been a particular problem with previous methodologies. This reliable "kit" method to prepare the radiolabeled endocannabinoid as needed gave tritiated 2-arachidonoylglycerol [H-3](2)-AG with a specific activity of 200 Ci/mmol for enzyme assays, metabolic studies, and tissue imaging. It has been run on unlabeled materials on over 10 mg scales and should be generally applicable to other 2-acylglycerols.
• Intermediacy of 8-(R)-HPETE in the conversion of arachidonic acid to pre-clavulone a by Clavularia viridis. Implications for the biosynthesis of marine prostanoids
  作者：E. J. Corey、Marc D'Alarcao、Seiichi P. T. Matsuda、Peter T. Lansbury、Yasuji Yamada

  DOI：10.1021/ja00235a053

  日期：1987.1
• Margonelli; Angelini; Attina, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S787-S789
  作者：Margonelli、Angelini、Attina、Cartoni、Finazzi Agro、Maccarrone

  DOI：——

  日期：——