16-HETE | 128914-46-5

• 物质功能分类: 生物化工 - 生化试剂
• 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: 16-HETE
• 英文别名: 16-hydroxyeicosatetraenoic acid；(±)16-HETE；(5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acid
• CAS: 128914-46-5
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: JEKNPVYFNMZRJG-UFINWASNSA-N

物化性质

• 溶解度：
  0.1 M Na2CO3：2 mg/mL； DMF：可混溶； DMSO：可混溶；乙醇：可混溶； PBS（pH 7.2）：0.8 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

16-羟基二十烷酸是花生酸的一种已知人类代谢物。

16-HETE is a known human metabolite of arachidonic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 16-HETE 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到16-HETE N-hydroxysuccinimide ester
  参考文献：
  名称：

  Methods and products related to 16-HETE analogs

  摘要：

  本发明包括16-HETE类似物，其是16-HETE的激动剂和拮抗剂。这些组合物可以制成药学上可接受的制剂。该发明还包括使用16-HETE激动剂抑制中性粒细胞黏附和中性粒细胞聚集的方法和产品。本发明的一种方法涉及将16-HETE激动剂与溶栓剂联合给患有血栓栓塞性卒中的患者进行治疗。

  公开号：

  US06359158B1
• 作为产物：
  描述：

  花生四烯酸 在 还原型辅酶II(NADPH)四钠盐 作用下， 以 水 为溶剂， 反应 0.5h， 生成 18-hydroxyeicosatetraenoic acid 、 16-HETE
  参考文献：
  名称：

  LC–MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22

  摘要：

  CYP4F22 and CYP4F8 are expressed in epidermis, and mutations of CYP4F22 are associated with lamellar ichthyosis. Epoxyalcohols (HEETs) and epoxides (EETs) of 20:4n-6 appear to be important for the water permeability barrier of skin. Our aim was to study the MS/MS spectra and fragmentation of these compounds and to determine whether they were oxidized by CYP4F22 or CYP4F8 expressed in yeast. HEETs were prepared from 1 5-hydroperoxyeicosatetraenoic acid (15-HPETE), 12-HPETE, and their- [H-2(8)]labeled isotopomers, and separated by normal phase-HPLC with MS/MS analysis. CYP4F22 oxygenated 20:4n-6 at C-I 8, whereas metabolites of HEETs could not be identified. CYP4F8 formed omega 3 hydroxy metabolites of HEETs derived from 12R-HPETE with 11,12-epoxy-10-hydroxy configuration, but not HEETs derived from 15S-HPETE. 8,9-EET and 11,12-EET were also subject to omega 3 hydroxylation by CYP4F8. We conclude that CYP4F8 and CYP4F22 oxidize 20:4n-6 and that CYP4F8 selectively oxidizes 8,9-EET, 11,12-EET, and 10, 11R, 12R-HEET at the omega 3 position. (C) 2010 Published by Elsevier Inc.

  DOI：

  10.1016/j.abb.2009.11.013

文献信息

• Repurposing Resveratrol and Fluconazole To Modulate Human Cytochrome P450-Mediated Arachidonic Acid Metabolism
  作者：Ahmed A. El-Sherbeni、Ayman O. S. El-Kadi

  DOI：10.1021/acs.molpharmaceut.5b00873

  日期：2016.4.4

  Cytochrome P450 (P450) enzymes metabolize arachidonic acid (AA) to several biologically active epoxyeicosatrienoic acids (EETs) and hydroxyeicosatetraenoic acids (HETEs). Repurposing clinically-approved drugs could provide safe and readily available means to control EETs and HETEs levels in humans. Our aim was to determine how to significantly and selectively modulate P450-AA metabolism in humans by

  细胞色素P450（P450）酶将花生四烯酸（AA）代谢为几种具有生物活性的环氧二十碳三烯酸（EET）和羟基二十碳四烯酸（HETE）。重新使用经过临床批准的药物可以为控制人类中的EET和HETE水平提供安全且容易获得的手段。我们的目标是确定如何通过临床批准的药物显着和选择性地调节人体内的P450-AA代谢。液相色谱-质谱法用于测定人重组P450酶以及人肝和肾微粒体形成的15种AA代谢产物。CYP2C19显示最高的EET形成活性，而CYP1B1和CYP2C8显示最高的中链HETE形成活性。CYP1A1和CYP4分别显示出最高的亚末端和20-HETE形成活性。与研究药物相比，白藜芦醇和氟康唑对肝P450-AA代谢产生了最有选择性和最显着的调节作用。蒙特卡洛模拟显示，每天服用2.5克后，有90％的人口在16-，18-和20-HETE形成中分别减少6-22％，16-39％和16-35％。白藜芦醇，氟康唑50
• A simple method for the preparation of (5 Z ,8 Z ,11 Z ,14 Z )-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid enantiomers and the corresponding 14,15-Dehydro analogues: role of the 16-Hydroxy group for the lipoxygenase reaction
  作者：Igor V Ivanov、Stepan G Romanov、Nataliya V Groza、Santosh Nigam、Hartmut Kuhn、Galina I Myagkova

  DOI：10.1016/s0968-0896(02)00024-x

  日期：2002.7

  was tested as lipoxygenase substrate, we found that it is well oxygenated by the soybean 15-lipoxygenase and by the recombinant human 5-lipoxygenase. Analysis of the reaction products suggested an arachidonic acid-like alignment at the active site of the two enzymes. In contrast, the product pattern of 16-HETE methyl ester oxygenation by the soybean lipoxygenase (5-lipoxygenation) may be explained

  （5Z，8Z，11Z，13E）-15-羟基-5,8,11,13-二十碳四烯酸（15-HETE）不能被花生四烯酸15-脂氧合酶氧化，原因有两个：（i）它包含一个靠近其甲基末端的亲水性OH-基团；（ii）在C（13）处缺少双烯丙基亚甲基。我们合成了外消旋（5Z，8Z，11Z，14Z）-16-羟基-5,8,11,14-二十碳四烯酸（16-HETE），其中仍然含有双烯丙基C（13），分离出对映异构体，光学纯度为> 99％并测试它们作为5-和15-脂氧合酶的底物。我们的合成途径基于聚乙炔前体的立体定向加氢，除16-HETE外，还产生了大量（30％）14,15-dehydro-16-HETE。当测试16-HETE作为脂氧合酶底物时，我们发现大豆15-脂氧合酶和重组人5-脂氧合酶能很好地氧合。反应产物的分析表明在两种酶的活性位点上类似花生四烯酸的排列。相比之下，大豆脂氧合酶的16-HETE甲酯氧合的产物
• Arachidonic acid metabolite, 16-hete
  申请人：University of Vermont

  公开号：US05753702A1

  公开（公告）日：1998-05-19

  The present invention provides methods and products for inhibiting neutrophil adhesion and neutrophil aggregation. The invention includes a method for treating a subject to inhibit neutrophil adhesion and neutrophil aggregation by administering 16-hydroxyeicosatetraenoic acid (16-HETE) to the subject. 16-HETE is an arachidonic acid metabolite. The invention also includes a pharmaceutical preparation of 16-HETE.

  本发明提供了一种抑制中性粒细胞粘附和聚集的方法和产品。该发明包括一种通过向受试者注射16-羟基二十四碳六烯酸（16-HETE）来抑制中性粒细胞粘附和聚集的治疗方法。16-HETE是一种花生四烯酸代谢产物。该发明还包括16-HETE的制药制剂。
• Methods and products relating to 16-HETE analogs
  申请人：University of Vermont and State Agricultural College

  公开号：US20020165262A1

  公开（公告）日：2002-11-07

  The present invention includes 16-HETE analogs which are agonists and antagonists of 16-HETE. The compositions may be formulated in pharmaceutically acceptable formulations. The invention also includes methods and products for inhibiting neutrophil adhesion and neutrophil aggregation using the 16-HETE agonists. One method of the invention involves the administration of a 16-HETE agonist in combination with a thrombolytic agent to a patient suffering from thromboembolic stroke.

  本发明涉及16-HETE类似物，其是16-HETE的激动剂和拮抗剂。这些组合物可以制成药学上可接受的制剂。本发明还包括使用16-HETE激动剂抑制中性粒细胞粘附和中性粒细胞聚集的方法和产品。本发明的一种方法涉及将16-HETE激动剂与溶栓剂联合给患有血栓栓塞性中风的患者治疗。
• Arachidonic acid metabolite, 16-HETE
  申请人：The University of Vermont and State Agricultural College

  公开号：US06140364A1

  公开（公告）日：2000-10-31

  The present invention provides methods and products for inhibiting neutrophil adhesion and neutrophil aggregation. The invention includes a method for treating a subject to inhibit neutrophil adhesion and neutrophil aggregation by administering 16-hydroxyeicosatetraenoic acid (16-HETE) to the subject. 16-HETE is an arachidonic acid metabolite. The invention also includes a pharmaceutical preparation of 16-HETE. Methods and products are also provided for treating thromboembolic stroke. The method involves the administration of 16-HETE in combination with a thrombolytic agent to a patient suffering from thromboembolic stroke. Preferably, the 16-HETE is 16(R)-HETE and the thrombolytic agent is tPA. The product is a pharmaceutical preparation of 16-HETE and a thrombolytic agent and a pharmaceutically acceptable carrier.

  本发明提供了抑制中性粒细胞粘附和聚集的方法和产品。该发明包括通过向受试者投予16-羟基二十四碳六烯酸（16-HETE）来治疗受试者以抑制中性粒细胞粘附和聚集的方法。16-HETE是花生四烯酸代谢产物。本发明还包括16-HETE的药物制剂。还提供了治疗血栓栓塞性中风的方法和产品。该方法涉及向患有血栓栓塞性中风的患者投予16-HETE和溶栓剂的组合物。优选地，16-HETE是16（R）-HETE，而溶栓剂是tPA。该产品是16-HETE和溶栓剂以及药学上可接受的载体的药物制剂。