(Z)-18-bromo-9-octadecenoic acid | 885022-72-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-18-bromo-9-octadecenoic acid
• 英文别名: (Z)-18-bromooctadec-9-enoic acid
• CAS: 885022-72-0
• 化学式: C₁₈H₃₃BrO₂
• 分子量: 361.363
• InChiKey: LNQJNMXSLKVPRD-UPHRSURJSA-N

物化性质

• 沸点：
  429.0±28.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-18-bromo-9-octadecenoic acid 在 N,N'-二环己基碳二亚胺 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 生成 (Z)-18-Iodo-octadec-9-enoic acid [(S)-1-hydroxymethyl-2-(4-hydroxy-phenyl)-ethyl]-amide
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l
• 作为产物：
  描述：

  1-溴-8-(四氢吡喃氧基)辛烷 在 lithium hydroxide 、 sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 乙醇 、 四溴化碳 、 四丁基氟化铵 、 nickel diacetate 、 4-甲基苯磺酸吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 93.59h， 生成 (Z)-18-bromo-9-octadecenoic acid
  参考文献：
  名称：

  Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake

  摘要：

  On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [C-14]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8 (Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [C-14]anandamide hydrolysis with IC50 < 50 mu M, except for 1b.

  DOI：

  10.1021/jm051226l

文献信息

• BIODEGRADABLE LIPIDS FOR THE DELIVERY OF ACTIVE AGENTS
  申请人：ALNYLAM PHARMACEUTICALS, INC.

  公开号：US20160009637A1

  公开（公告）日：2016-01-14

  The present invention relates to a cationic lipid having one or more biodegradable groups located in the mid- or distal section of a lipidic moiety (e.g., a hydrophobic chain) of the cationic lipid. These cationic lipids may be incorporated into a lipid particle for delivering an active agent, such as a nucleic acid. The invention also relates to lipid particles comprising a neutral lipid, a lipid capable of reducing aggregation, a cationic lipid of the present invention, and optionally, a sterol. The lipid particle may further include a therapeutic agent such as a nucleic acid.

  本发明涉及一种阳离子脂质，其具有位于脂质基团（例如，疏水链）的中部或远端部位的一个或多个可生物降解的基团。这些阳离子脂质可以被纳入脂质颗粒中，用于传递活性剂，例如核酸。该发明还涉及包括中性脂质、能够减少聚集的脂质、本发明的阳离子脂质以及可选地固醇的脂质颗粒。脂质颗粒还可以进一步包含治疗剂，如核酸。
• Synthesis of biotinylated-LPG as a chemical biology tool enabling discovery of ALCAT1 modulators
  作者：Hui Huang、Renmei Zhou、He Wen、Zhixiang Xu、Shengmei Zhang、Weixue Wang、Daniel Krosky、Robyn Miller

  DOI：10.1016/j.bmcl.2022.128861

  日期：2022.9

  lysocardiolipin acyltransferase-1) facilitates the conversion of CL by incorporating polyunsaturated fatty acids into lysocardiolipin. Accumulating evidence suggests that overexpression of ALCAT1 is involved in pathological cardiolipin remodeling and mitochondrial bioenergetics. Few ALCAT1 modulators are reported in the literature, and the enzymatic activity was tested via a low-throughput TLC (thin

  作为线粒体特征磷脂，心磷脂 (CL) 是膜结构、呼吸、动力学、碎片化和线粒体自噬所必需的。活性氧 (ROS) 改变 CL 可导致线粒体功能障碍，这与许多疾病的发病机制有关。酶 ALCAT1（酰基辅酶A：溶心磷脂酰基转移酶-1）通过将多不饱和脂肪酸掺入溶心磷脂中来促进 CL 的转化。越来越多的证据表明 ALCAT1 的过表达与病理性心磷脂重塑和线粒体生物能量学有关。文献中报道的 ALCAT1 调节剂很少，酶活性通过低通量 TLC（薄层色谱）测定进行测试。为了鉴定小分子 ALCAT1 抑制剂，需要一个强大的分析来实现全甲板高通量筛选。闪烁邻近分析 (SPA) 是首选方法，因为它允许在均质系统中快速和灵敏地测量广泛的生物过程。开发 SPA 需要生物素化的 ALCAT1 底物作为化学生物学工具。在一组磷脂中，溶血磷脂酰甘油 (LPG) 被确定为 ALCAT1 的最佳底物。在这里，我们报告了具有不同接头长度的生物素化
• US9012498B2
  申请人：——

  公开号：US9012498B2

  公开（公告）日：2015-04-21
• US9061063B2
  申请人：——

  公开号：US9061063B2

  公开（公告）日：2015-06-23
• US9682922B2
  申请人：——

  公开号：US9682922B2

  公开（公告）日：2017-06-20