(8Z,11Z,14Z)-octadeca-8,11,14-trienoic acid | 4906-91-6

• 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: (8Z,11Z,14Z)-octadeca-8,11,14-trienoic acid
• 英文别名: 8,11,14-Octadecatrienoic acid (Z,Z,Z)
• CAS: 4906-91-6
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: CTMZJQAVRYEWHS-YSTUJMKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (8Z,11Z,14Z)-octadeca-8,11,14-trienoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  刺激线粒体呼吸的抗水解异吲哚啉 N-酰基氨基酸类似物的发现

  摘要：

  N-酰基氨基酸直接结合线粒体并充当不依赖于 UCP1 的呼吸的内源解偶联剂。我们发现给小鼠施用N-酰基氨基酸可以改善葡萄糖稳态并增加能量消耗，表明该途径可能有助于治疗肥胖和相关疾病。我们报告了脂化N-酰基氨基酸及其非天然类似物的合成和线粒体解偶联生物活性的完整说明。中等长度的不饱和脂肪酸链和中性氨基酸头基是哺乳动物细胞上最佳解偶联活性所必需的。一类非天然N-酰基氨基酸类似物，其特征为异吲哚啉-1-羧酸酯头基（37），能够抵抗 PM20D1 的酶促降解，并在细胞和小鼠体内保持解偶联生物活性。

  DOI：

  10.1021/acs.jmedchem.8b00029

文献信息

• CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US20200317613A1

  公开（公告）日：2020-10-08

  Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).

  解耦呼吸是一个众所周知的过程，可以增加细胞的呼吸和产热。本文提供了化学解耦剂，这些解耦剂是化合物(I)的化合物。还提供了使用化合物(I)预防或治疗代谢性疾病和调节代谢过程的方法。
• Chemical uncouplers of respiration and methods of use thereof
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US11365177B2

  公开（公告）日：2022-06-21

  Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).

  呼吸解偶联是一个公认的过程，可增加细胞的呼吸和产热。本文提供的呼吸化学解偶联剂是式（I）化合物。还提供了使用式（I）化合物预防或治疗代谢紊乱和调节代谢过程的方法。
• Tripod-like Cationic Lipids as Novel Gene Carriers
  作者：Asier Unciti-Broceta、Emma Holder、Lisa J. Jones、Barbara Stevenson、Andrew R. Turner、David J. Porteous、A. Chris Boyd、Mark Bradley

  DOI：10.1021/jm701493f

  日期：2008.7.1

  An innovative family of tridentate-cationic "single-chained lipids" designed to enhance DNA compaction and to promote endosomal escape was synthesized by coupling various lipids to a multibranched scaffold. DNA retardation assays confirmed the ability of the most members of the library to complex DNA. Classical molecular dynamics simulations performed on the lauryl derivative, bound to a short strand of DNA in aqueous solution supported these observations. These showed that two "arms" of the tripodal molecule are ideally suited to forming strong Coulombic interactions with two contiguous phosphate groups from the DNA backbone while the lipophilic tail stays perpendicular to the DNA helix. Gene transfer abilities of the library were assessed in multiple cell lines (CHO, Cos7, and 16HBE14o-) with some library members giving excellent transfection abilities and low cytotoxicity, supporting the use of this tripodal approach for the development of efficient gene delivery agents.
• FATTY ACID DERIVATIVES FOR TREATING NON-ALCOHOLIC STEATOHEPATITIS
  申请人：BASF AS

  公开号：US20210177794A1

  公开（公告）日：2021-06-17

  The present disclosure provides a compound for use in therapeutic and/or prophylactic treatment of non-alcoholic steatohepatitis (NASH) and/or alcoholic steatohepatitis (ASH). The compound for use according to the invention, is an unsaturated fatty acid with an oxygen incorporated in the β-position, and further comprising an α-substituent. More particularly, the invention provides a compound for use in treatment of NASH and/or ASH, and a method using this, wherein the compound is of Formula (II), wherein RI, R2, R3, X, and Y are as defined in the specification; and wherein this compound may be administered alone or in combination with an additional active agent.