1,2-di-[2-(tetradecylthio)acetyl]-sn-glycero-3-phosphocholine | 636589-28-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 1,2-di-[2-(tetradecylthio)acetyl]-sn-glycero-3-phosphocholine
• 英文别名: di-tetradecylthioacetyl-L-α-phosphatidylcholine；di-tetradecylthioacetyl-sn-glycero-3-phosphocholine；TTA-PC；1,2-ditetradecylthioacetyl-sn-glycero-3-phosphocholine；[(2R)-2,3-bis[(2-tetradecylsulfanylacetyl)oxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 636589-28-1
• 化学式: C₄₀H₈₀NO₈PS₂
• 分子量: 798.183
• InChiKey: ZZWQHNRGJQENEP-KXQOOQHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  52
• 可旋转键数：
  42
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-di-[2-(tetradecylthio)acetyl]-sn-glycero-3-phosphocholine 在 phospholipase A2 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 以70%的产率得到1-[2-(tetradecylthio)acetyl]-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Novel phospholipid analogues of pan-PPAR activator tetradecylthioacetic acid are more PPARα selective

  摘要：

  Tetradecylthioacetic acid (TTA) is a modified fatty acid that appears to improve insulin sensitivity, lower blood lipid levels, enhance fatty acid oxidation and promote anti-inflammatory action in vivo, through mechanisms partly dependent upon peroxisome proliferator-activated receptors (PPARs). In order to improve the biological efficacy of TTA as a PPAR agonist, two novel phospholipid analogue lyso tetradecylthioacetyl-L-alpha-phosphatidylcholine and di-tetradecylthioacetyl-L-alpha-phosphatidylglycerol have been developed. Here we report on the syntheses of these novel phospholipids and their relative potential to act as PPAR agonists in vitro, in comparison to TTA and other positive controls. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.115
• 作为产物：
  描述：

  、 甘磷酸胆碱 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 1,2-di-[2-(tetradecylthio)acetyl]-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Novel phospholipid analogues of pan-PPAR activator tetradecylthioacetic acid are more PPARα selective

  摘要：

  Tetradecylthioacetic acid (TTA) is a modified fatty acid that appears to improve insulin sensitivity, lower blood lipid levels, enhance fatty acid oxidation and promote anti-inflammatory action in vivo, through mechanisms partly dependent upon peroxisome proliferator-activated receptors (PPARs). In order to improve the biological efficacy of TTA as a PPAR agonist, two novel phospholipid analogue lyso tetradecylthioacetyl-L-alpha-phosphatidylcholine and di-tetradecylthioacetyl-L-alpha-phosphatidylglycerol have been developed. Here we report on the syntheses of these novel phospholipids and their relative potential to act as PPAR agonists in vitro, in comparison to TTA and other positive controls. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.115

文献信息

• [EN] SULFUR-CONTAINING PHOSPHOLIPID DERIVATIVES<br/>[FR] DERIVES PHOSPHOLIPIDIQUES CONTENANT DU SOUFRE
  申请人：IC VEC LTD

  公开号：WO2004000854A1

  公开（公告）日：2003-12-31

  The present invention provides a lipid compound comprising at least one non-polar moiety and a polar moiety, wherein each or at least one non-polar moiety is of the formula X-Y-Z-, wherein X is a hydrocarbyl chain, Y is selected from at least one of S, Se, SO2, SO, and O, and Z is an optional hydrocarbyl group, wherein the polar moiety is of the formula -[C(O)]mPHG, wherein PHG is a polar head group, and wherein m is the number of non-polar moieties.

  本发明提供了一种脂质化合物，包括至少一个非极性基团和一个极性基团，其中每个或至少一个非极性基团为X-Y-Z-式，其中X为烃基链，Y选自S、Se、SO2、SO和O中的至少一个，Z为可选的烃基团，其中极性基团为-[C(O)]mPHG，其中PHG为极性头基团，m为非极性基团的数量。
• The molecular structure of thio-ether fatty acids influences PPAR-dependent regulation of lipid metabolism
  作者：Jenny Lund、Camilla Stensrud、Rajender、Pavol Bohov、G. Hege Thoresen、Rolf K. Berge、Michael Wright、Ahmed Kamal、Arild C. Rustan、Andrew D. Miller、Jon Skorve

  DOI：10.1016/j.bmc.2016.01.045

  日期：2016.3

  Thio-ether fatty acids (THEFAs), including the parent 2-(tetradecylthio)acetic acid (TTA), are modified fatty acids (FAs) that have profound effects on lipid metabolism given that they are blocked for β-oxidation, and able to act as peroxisome proliferator-activated receptor (PPAR) agonists. Therefore, TTA in particular has been tested clinically for its therapeutic potential against metabolic syndrome

  硫醚脂肪酸（THEFAs），包括母体2-（十四烷基硫代）乙酸（TTA），是经过修饰的脂肪酸（FAs），对脂类代谢具有深远的影响，因为它们被β-氧化所阻断，并且能够充当过氧化物酶体增殖物激活受体（PPAR）激动剂。因此，特别是已经对TTA进行了针对代谢综合征相关疾病的治疗潜力的临床测试。在这里，我们描述了基于具有双键或三键的TTA支架的THEFAs的制备。它们在培养的人骨骼肌细胞（肌管）中以游离酸的形式或在酯化后以磷脂，溶血磷脂或单酰基甘油的形式进行测试。通过FA底物摄取和氧化研究，根据肌管中细胞的生物利用度评估代谢作用，以及选择的PPAR调控基因的基因调控研究。我们注意到，包含三键会促进THEFA介导的FA氧化。此外，THEFA作为溶血磷脂的酯化也促进了FA的氧化作用。鉴于剂量限制和不良的生物利用度抵消了TTA给药的明显临床益处，我们讨论了选择最新的THEFAs和含THEFA的脂质可能能够
• Synthesis and Analysis of Novel Glycerolipids for the Treatment of Metabolic Syndrome
  作者：Michael R. Jorgensen、Yushma Bhurruth-Alcor、Therese Røst、Pavol Bohov、Melanie Müller、Cristina Guisado、Kostas Kostarelos、Endre Dyrøy、Rolf K. Berge、Andrew D. Miller、Jon Skorve

  DOI：10.1021/jm801019s

  日期：2009.2.26

  Tetradecylthioacetic acid (TTA) 1 is a peroxisome proliferator-activated receptor (PPAR) agonist found to improve insulin sensitivity, lower blood lipid levels, enhance fatty acid oxidation, and promote anti-inflammation in vivo. In an attempt to enhance these properties, two key thioether fatty acid (Thefa) lipids, ditetradecylthioacetyl phosphatidylcholine 2 and tritetradecylthioacetyl glycerol 3, are synthesized and administered po to male Wistar rats at two different doses to study and compare metabolic outcomes relative to the administration of 1 alone after 6 days. Liposomal formulations of 1 and 2 are also prepared to evaluate acute metabolic responses (at 3 h) post iv injection. Across all metrics measured, 1-induced responses post po administration are in line with previous data. Responses induced from 3 are mostly equivalent to 1-induced responses. By contrast, 2-induced responses almost always outperform those of 1 and 3. Therefore, 2 may represent a new lead for the treatment of metabolic syndrome.
• Novel phospholipid analogues of pan-PPAR activator tetradecylthioacetic acid are more PPARα selective
  作者：Yushma Bhurruth-Alcor、Therese H. Rost、Michael R. Jorgensen、Rajender、Melanie Müller、Jon Skorve、Rolf K. Berge、Andrew D. Miller

  DOI：10.1016/j.bmcl.2009.11.115

  日期：2010.2

  Tetradecylthioacetic acid (TTA) is a modified fatty acid that appears to improve insulin sensitivity, lower blood lipid levels, enhance fatty acid oxidation and promote anti-inflammatory action in vivo, through mechanisms partly dependent upon peroxisome proliferator-activated receptors (PPARs). In order to improve the biological efficacy of TTA as a PPAR agonist, two novel phospholipid analogue lyso tetradecylthioacetyl-L-alpha-phosphatidylcholine and di-tetradecylthioacetyl-L-alpha-phosphatidylglycerol have been developed. Here we report on the syntheses of these novel phospholipids and their relative potential to act as PPAR agonists in vitro, in comparison to TTA and other positive controls. (C) 2009 Elsevier Ltd. All rights reserved.