(9Z,12Z)-13-氢过氧基十八碳-9,12-二烯酸 | 34444-18-3

• 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: (9Z,12Z)-13-氢过氧基十八碳-9,12-二烯酸
• 英文名称: 13-hydroperoxylinoleic acid
• 英文别名: (9Z)-13-hydroperoxyoctadeca-9,12-dienoic acid
• CAS: 34444-18-3
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: ITZHGZMZQUJODL-MMDKRFMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium linoleate 在 soybean lipoxygenase 、 sodium chloride 作用下， 以 水 为溶剂， 反应 0.15h， 生成 (9Z,12Z)-13-氢过氧基十八碳-9,12-二烯酸
  参考文献：
  名称：

  Synthesis and biological evaluation of PEGylated CuO nanoparticles

  摘要：

  There is a growing field of research into the physicochemical properties of metal oxide nanoparticles (NPs) and their potential use against tumor formation, development and progression. Coated NPs with biocompatible surfactants can be incorporated into the natural metabolic pathway of the body and specifically favor delivery to the targeted cancerous cells versus normal cells. Polyethylene glycol (PEG) is an FDA approved, biocompatible synthetic polymer and PEGylated NPs are regarded as "stealth" nanoparticles, which are not recognized by the immune system. Herein, PEGylated cupric oxide nanoparticles (CuO NPs) with either PEG 1000 or PEG 8000 were hydrothermally prepared upon properly adjusting the reaction conditions. Depending on the reaction time CuO NPs in the range of core sizes 11-20 nm were formed, while hydrodynamic sizes substantially varied (330-1120 nm) with improved colloidal stability in PBS. The anticancer activity of the NPs was evaluated on human cervical carcinoma HeLa cells by using human immortalized embryonic kidney 293 FT cells as a control. Viability assays (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, MIT) revealed that CuO NPs could selectively reduce viability of tumor cells (IC50 values 11.91-25.78 mu g/mL). Reactive oxygen species (ROS) production, cell membrane damage and apoptotic DNA laddering were also evident by nitroblue tetrazolium (NBT) reduction, lactate dehydrogenase (LDH) release assays and DNA electrophoresis, respectively. CuO NPs strongly inhibited lipoxygenase (LOX) enzymatic activity with IC50 values 4-5.9 mu g/mL, highlighting in that manner their anti-inflammatory activity. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2016.09.003

文献信息

• Kinetic Properties of Lipoxygenase from Desert Truffle (<i>Terfezia claveryi </i>Chatin) Ascocarps:  Effect of Inhibitors and Activators
  作者：Manuela Pérez-Gilabert、Isabel Sánchez-Felipe、Asunción Morte、Francisco García-Carmona

  DOI：10.1021/jf050521b

  日期：2005.7.1

  There is very little information available on the kinetic characteristics of fungal lipoxygenases (LOXs) because most data on the mechanism of this enzyme concern soybean LOX. In this paper, the kinetic properties of LOX from Terfezia claveryi Chatin ascocarps were studied for the first time. The enzyme did not show the "substrate aggregation-dependent activity" described for other LOXs and presented a K, for linoleic acid of 41 mu M at pH 7.0. The effect of different inhibitors was also studied. The enzyme presented the characteristic lag phase of other LOXs, and the influence of different factors on its duration was analyzed. The lag period was reduced not only by the product of the reaction (13-HPOD) but also by 9-HPOD. Calculation of the activation constant is proposed for the first time as a useful tool for the characterization of LOX because this method makes it possible to quantify the effectiveness of different hydroperoxides as LOX activators. The activation constants obtained were 0.3 and 6.4 mu M for 13- and 9-HPOD, respectively; thus, the product of the reaction was similar to 21-fold more effective than 9-HPOD as a T. claveryi LOX activator.
• Synthesis and biological evaluation of PEGylated CuO nanoparticles
  作者：K. Giannousi、E. Hatzivassiliou、S. Mourdikoudis、G. Vourlias、A. Pantazaki、C. Dendrinou-Samara

  DOI：10.1016/j.jinorgbio.2016.09.003

  日期：2016.11

  There is a growing field of research into the physicochemical properties of metal oxide nanoparticles (NPs) and their potential use against tumor formation, development and progression. Coated NPs with biocompatible surfactants can be incorporated into the natural metabolic pathway of the body and specifically favor delivery to the targeted cancerous cells versus normal cells. Polyethylene glycol (PEG) is an FDA approved, biocompatible synthetic polymer and PEGylated NPs are regarded as "stealth" nanoparticles, which are not recognized by the immune system. Herein, PEGylated cupric oxide nanoparticles (CuO NPs) with either PEG 1000 or PEG 8000 were hydrothermally prepared upon properly adjusting the reaction conditions. Depending on the reaction time CuO NPs in the range of core sizes 11-20 nm were formed, while hydrodynamic sizes substantially varied (330-1120 nm) with improved colloidal stability in PBS. The anticancer activity of the NPs was evaluated on human cervical carcinoma HeLa cells by using human immortalized embryonic kidney 293 FT cells as a control. Viability assays (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, MIT) revealed that CuO NPs could selectively reduce viability of tumor cells (IC50 values 11.91-25.78 mu g/mL). Reactive oxygen species (ROS) production, cell membrane damage and apoptotic DNA laddering were also evident by nitroblue tetrazolium (NBT) reduction, lactate dehydrogenase (LDH) release assays and DNA electrophoresis, respectively. CuO NPs strongly inhibited lipoxygenase (LOX) enzymatic activity with IC50 values 4-5.9 mu g/mL, highlighting in that manner their anti-inflammatory activity. (C) 2016 Elsevier Inc. All rights reserved.