petroselinic acid potassium sal | 50614-01-2

• 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: petroselinic acid potassium sal
• 英文别名: potassium petroselinate；potassium;(Z)-octadec-6-enoate
• CAS: 50614-01-2
• 化学式: C₁₈H₃₃O₂*K
• 分子量: 320.557
• InChiKey: CAIAQDIOUWAZIY-USGGBSEESA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  十八碳6烯酸 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 petroselinic acid potassium sal
  参考文献：
  名称：

  Interaction kinetics of liposome-incorporated unsaturated fatty acids with fatty acid-binding protein 3 by surface plasmon resonance

  摘要：

  The role of heart-type fatty acid-binding protein (FABP3) in human physiology as an intracellular carrier of fatty acids (FAs) has been well-documented. In this study, we aimed to develop an analytical method to study real-time interaction kinetics between FABP3 immobilized on the sensor surface and unsaturated C18 FAs using surface plasmon resonance (SPR). To establish the conditions for SPR experiments, we used an FABP3-selective inhibitor 4-(2-(1-(4-bromophenyl)-5-phenyl-1H-pyrazol-3-yl)-phenoxy)-butyric acid. The affinity index thus obtained was comparable to that reported previously, further supporting the usefulness of the SPR-based approach for evaluating interactions between FABPs and hydrophobic ligands. A pseudo-first-order affinity of FABP3 to K+ petroselinate (C18:1 Delta 61 cis), K+ elaidate (C18:1 Delta 9 trans), and K+ oleate (C18:1 Delta 9 cis) was characterized by the dissociation constant (K-d) near micromolar ranges, whereas K+ linoleate (C18:2 Delta 9,12 cis/cis) and K+ alpha-linolenate (C18:3 Delta 9,12,15 cis/cis/cis) showed a higher affinity to FABP3 with K-d around 1 x 10 (6) M. Interactions between FAPB3 and C18 FAs incorporated in large unilamellar vesicles consisting of 1,2-dimyristoyl-sn-glycero-3-phosphocholine and FAs (5:1 molar ratio) were also analysed. Control DMPC liposomes without FA showed only marginal binding to FABP3 immobilized on a sensor chip while liposome-incorporated FA revealed significant responses in sensorgrams, demonstrating that the affinity of FAs to FABP3 could be evaluated by using the liposome-incorporated analytes. Significant affinity to FABP3 was observed for monounsaturated fatty acids (K-d in the range of 1 x 10 (7) M). These experiments demonstrated that highly hydrophobic compounds in a liposome-incorporated form could be subjected to SPR experiments for kinetic analysis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.001

文献信息

• Interaction kinetics of liposome-incorporated unsaturated fatty acids with fatty acid-binding protein 3 by surface plasmon resonance
  作者：Maria Carmen Tan、Shigeru Matsuoka、Hikaru Ano、Hanako Ishida、Mika Hirose、Fuminori Sato、Shigeru Sugiyama、Michio Murata

  DOI：10.1016/j.bmc.2014.02.001

  日期：2014.3

  The role of heart-type fatty acid-binding protein (FABP3) in human physiology as an intracellular carrier of fatty acids (FAs) has been well-documented. In this study, we aimed to develop an analytical method to study real-time interaction kinetics between FABP3 immobilized on the sensor surface and unsaturated C18 FAs using surface plasmon resonance (SPR). To establish the conditions for SPR experiments, we used an FABP3-selective inhibitor 4-(2-(1-(4-bromophenyl)-5-phenyl-1H-pyrazol-3-yl)-phenoxy)-butyric acid. The affinity index thus obtained was comparable to that reported previously, further supporting the usefulness of the SPR-based approach for evaluating interactions between FABPs and hydrophobic ligands. A pseudo-first-order affinity of FABP3 to K+ petroselinate (C18:1 Delta 61 cis), K+ elaidate (C18:1 Delta 9 trans), and K+ oleate (C18:1 Delta 9 cis) was characterized by the dissociation constant (K-d) near micromolar ranges, whereas K+ linoleate (C18:2 Delta 9,12 cis/cis) and K+ alpha-linolenate (C18:3 Delta 9,12,15 cis/cis/cis) showed a higher affinity to FABP3 with K-d around 1 x 10 (6) M. Interactions between FAPB3 and C18 FAs incorporated in large unilamellar vesicles consisting of 1,2-dimyristoyl-sn-glycero-3-phosphocholine and FAs (5:1 molar ratio) were also analysed. Control DMPC liposomes without FA showed only marginal binding to FABP3 immobilized on a sensor chip while liposome-incorporated FA revealed significant responses in sensorgrams, demonstrating that the affinity of FAs to FABP3 could be evaluated by using the liposome-incorporated analytes. Significant affinity to FABP3 was observed for monounsaturated fatty acids (K-d in the range of 1 x 10 (7) M). These experiments demonstrated that highly hydrophobic compounds in a liposome-incorporated form could be subjected to SPR experiments for kinetic analysis. (C) 2014 Elsevier Ltd. All rights reserved.