2-chloropalmitaldehyde

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 2-chloropalmitaldehyde
• 英文别名: 2-chlorohexadecanal
• 化学式: C₁₆H₃₁ClO
• 分子量: 274.875
• InChiKey: AUGQGGLBBDGNTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloropalmitaldehyde 在 sodium cyanoborohydride 作用下， 以 乙醚 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  源自髓过氧化物酶的2-氯十六烷与乙醇胺甘油磷脂和赖氨酸的伯胺形成席夫碱。

  摘要：

  大量研究表明，髓过氧化物酶，炎症和动脉粥样硬化之间存在相关性。MPO衍生的反应性氯化物（RCS）攻击膜缩醛磷脂，释放出包括2-氯十六醛（2-ClHDA）的α-氯脂肪醛（alpha-Cl-FALD）。α-Cl-FALD的分子靶标是未知的。目前的研究表明2-ClHDA与乙醇胺甘油磷脂和Fmoc-赖氨酸的加合物。利用电喷雾电离质谱法，观察到氯化加合物是明显的席夫碱加合物。用氰基硼氢化钠还原这些席夫碱加合物会产生一种新的稳定的加合物，该加合物通过消除HCl生成。NMR进一步证实了该结构。乙醇胺甘油磷脂的2-ClHDA加合物也是磷脂酶D（PLD）的底物。将水解产物衍生为五氟苯甲酸酯，并通过GC-MS进一步结构确认。在用2-ClHDA处理的内皮细胞中观察到2-ClHDA-N-修饰的乙醇胺甘油磷脂的多种分子种类。这些结果显示了α-Cl-FALD与伯胺的新型席夫碱加合物，这可能代表了α-Cl-FALD的重要命运。

  DOI：

  10.1016/j.chemphyslip.2005.12.003

文献信息

• Diagnosis of leukocyte-mediated disease and halogen gas exposure
  申请人：Saint Louis University

  公开号：US10983137B2

  公开（公告）日：2021-04-20

  Described are glutathione adducts of fatty aldehydes (FALD-GSH) and methods useful in the detection of FALD-GSH in the identification of pathologies associated with leukocyte-mediated disease conditions, including eosinophil and neutrophil activation. Thus, the present disclosure provides methods of diagnosing a subject as having or being at risk of developing a leukocyte-mediated disease (LMD) comprising (a) detecting the level of glutathione adducts of 2-halofatty aldehydes (FALD-GSH) in a sample; (b) comparing the amount of FALD-GSH with a control or standard reflective of diseased and/or healthy levels of FALD-GSH; and (c) diagnosing the subject as having or being at risk of developing LMD if the level of FALD-GSH in the sample is higher than the control or standard.

  本发明描述了脂肪醛的谷胱甘肽加合物（FALD-GSH）和检测 FALD-GSH 的方法，这些方法可用于鉴定与白细胞介导的疾病（包括嗜酸性粒细胞和中性粒细胞活化）相关的病理学。因此，本公开提供了诊断受试者患有白细胞介导的疾病（LMD）或有患该病风险的方法，包括 (a) 检测样本中 2-脂肪醛的谷胱甘肽加合物（FALD-GSH）的水平；(b) 将 FALD-GSH 的含量与反映 FALD-GSH 患病和/或健康水平的对照或标准进行比较；以及 (c) 如果样本中的 FALD-GSH 水平高于对照或标准，则诊断受试者患有 LMD 或有患 LMD 的风险。
• Strategies for the analysis of chlorinated lipids in biological systems
  作者：Bradley K. Wacker、Carolyn J. Albert、Benjamin A. Ford、David A. Ford

  DOI：10.1016/j.freeradbiomed.2012.06.013

  日期：2013.6

  Myeloperoxidase-derived HOCl reacts with the vinyl ether bond of plasmalogens yielding alpha-chlorofatty aldehydes. These chlorinated aldehydes can be purified using thin-layer chromatography, which is essential for subsequent analysis of extracts from some tissues such as myocardium. The alpha-chlorofatty aldehyde 2-chlorohexadecanal (2-ClHDA) is quantified after conversion to its pentafluorobenzyl oxime derivative using gas chromatography-mass spectrometry and negative-ion chemical ionization detection. 2-ClHDA accumulates in activated human neutrophils and monocytes, as well as in atherosclerotic lesions and infarcted myocardium. Metabolites of 2-ClHDA have also been identified, including the oxidation product, 2-chlorohexadecanoic acid (2-ClHA), and the reduction product, 2-chlorohexadecanol. 2-ClHA can be quantified using LC-MS with selected reaction monitoring (SRM) detection. 2-ClHA can be omega-oxidized by hepatocytes and subsequently beta-oxidized from the omega-end, leading to the production of the dicarboxylic acid, 2-chloroadipic acid. This dicarboxylic acid is excreted in the urine and can also be quantified using LC-MS methods with SRM detection. Quantitative analyses of these novel chlorinated lipids are essential to identify the role of these lipids in leukocyte-mediated injury and disease. (c) 2012 Elsevier Inc. All rights reserved.
• Identification of glutathione adducts of α-chlorofatty aldehydes produced in activated neutrophils
  作者：Mark A. Duerr、Rajeev Aurora、David A. Ford

  DOI：10.1194/jlr.m058636

  日期：2015.5

  alpha-Chlorofatty aldehydes (alpha-ClFALDs) are produced by hypochlorous acid targeting plasmalogens during neutrophil activation. This study investigated the reaction of the alpha-chlorinated carbon of alpha-ClFALD with the nucleophile, GSH. Utilizing ESI/MS/MS, the reaction product of GSH and the 16-carbon alpha-ClFALD, 2-chlorohexadecanal (2-ClHDA), was characterized. The resulting conjugate of 2-ClHDA and GSH (HDA-GSH) has an intact free aldehyde, and the chlorine at the alpha-carbon is ejected. Stable isotope-labeled [d(4)] HDA-GSH was synthesized, which further confirmed the structure, and was used to quantify natural alpha-ClFALD conjugates of GSH (FALD-GSH) using reverse-phase LC with detection by ESI/MS/MS using selected reaction monitoring. HDA-GSH is elevated in RAW 264.7 cells treated with physiologically relevant concentrations of exogenous 2-ClHDA. Furthermore, PMA-treated primary human neutrophils have elevated levels of HDA-GSH and the conjugate of 2-chlorooctadecanal (2-ClODA) and GSH (ODA-GSH), as well as elevated levels of 2-ClHDA and 2-ClODA. Production of both conjugates in PMA-stimulated neutrophils was reduced by 3-aminotriazole pretreatment, which also blocks endogenous alpha-ClFALD production. Additionally, plasma FALD-GSH levels were elevated in the K/BxN mouse arthritis model. Taken together, these studies demonstrate novel peptidoaldehydes derived from GSH and alpha-ClFALD in activated human neutrophils and in vivo in K/BxN mice.
• DIAGNOSTIC METHOD FOR BIOMARKERS OF ADVERSE CORONARY EVENTS
  申请人：Ford David A.

  公开号：US20110091980A1

  公开（公告）日：2011-04-21

  A diagnostic method using biomarkers to predict future adverse coronary events is provided. More particularly, the present invention is directed to diagnostic tests for characterizing an individual's risk of developing or having cardiovascular disease. In certain embodiments, the method of the present invention quantitates the presence of elevated levels of chlorinated lipids derived from myeloperoxidase as a prognostic indicator of future adverse coronary events.
• ASSAYS FOR HDL BIOMOLECULAR INTERACTIONS
  申请人：Pritchard Jr., JR. Kirkwood A.

  公开号：US20130017556A1

  公开（公告）日：2013-01-17

  The invention relates to methods, compositions and kits for detecting molecular interactions. In one embodiment, the invention relates to methods for quantifying HDL interactions with biomolecules. In still another embodiment, the invention relates to methods for determining HDL function.