N-dodecanoyl-tryptophanethyl-ester | 261734-87-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-dodecanoyl-tryptophanethyl-ester
• 英文别名: ethyl (2S)-2-(dodecanoylamino)-3-(1H-indol-3-yl)propanoate
• CAS: 261734-87-6
• 化学式: C₂₅H₃₈N₂O₃
• 分子量: 414.588
• InChiKey: OLZJLFZAOWIZOS-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  D-色氨酸乙酯盐酸盐 、 alkaline earth salt of/the/ methylsulfuric acid 生成 N-dodecanoyl-tryptophanethyl-ester
  参考文献：
  名称：

  Membrane protein oxidation determines neuronal degeneration

  摘要：

  AbstractOxidative stress is an early hallmark in neurodegenerative disorders such as Alzheimer's and Parkinson's diseases. However, the critical biochemical effector mechanisms of oxidative neurotoxicity have remained surprisingly elusive. In screening various peroxides and potential substrates of oxidation for their effect on neuronal survival, we observed that intramembrane compounds were significantly more active than aqueous or amphiphilic compounds. To better understand this result, we synthesized a series of competitive and site‐specific membrane protein oxidation inhibitors termed aminoacyllipids, whose structures were designed on the basis of amino acids frequently found at the protein‐lipid interface of synaptic membrane proteins. Investigating the aminoacyllipids in primary neuronal culture, we found that the targeted protection of transmembrane tyrosine and tryptophan residues was sufficient to prevent neurotoxicity evoked by hydroperoxides, kainic acid, glutathione‐depleting drugs, and certain amyloidogenic peptides, but ineffective against non‐oxidative inducers of apoptosis such as sphingosine or Akt kinase inhibitors. Thus, the oxidative component of different neurotoxins appears to converge on neuronal membrane proteins, irrespective of the primary mechanism of cellular oxidant generation. Our results indicate the existence of a one‐electron redox cycle based on membrane protein aromatic surface amino acids, whose disturbance or overload leads to excessive membrane protein oxidation and neuronal death. image Membrane proteins have rarely been investigated as potential victims of oxidative stress in the context of neurodegeneration. This study provides evidence that excessive one‐electron oxidation of membrane proteins from within the lipid bilayer, depicted in the graphic, is a functionally decisive step toward neuronal cell death in response to different toxins.

  DOI：

  10.1111/jnc.12987

文献信息

• Tryptophanyl-esters and their n-acyl derivatives for preventing and treating diseases caused or aggravated by oxidation processes
  申请人：——

  公开号：US20010014695A1

  公开（公告）日：2001-08-16

  Use of a tryptophanyl-ester or an N-acyl derivative of a tryptophanyl-ester for the prophylaxis and therapy of oxidative pathologic processes in degenerative diseases and/or cancer diseases. Thereby, the tryptophanyl-ester or its N-acyl derivative is preferred to be tryptophanoctyl, N-oleoyl-tryptophanethyl-ester or N-dodecanoyl-tryptophanethyl-ester. Futhermore the tryptophanyl-esters and their N-acyl derivatives are preferred to be used for the treatment and/or prophylaxis of neurodegenerative diseases, cataracts,- neoplastic diseases and/or cardiovascular diseases. In particular, the invention relates to the use of the tryptophanyl-esters and their N-acyl derivatives for the treatment and/or prophylaxis of Alzheimer's disease, Parkinson's disease, apoplectic fit, amyotrophic lateral sclerosis, cancers, arteriosclerosis and/or myocardial infarction. In addition, the invention relates to a pharmaceutical composition comprising a tryptophanyl-ester or an N-acyl derivative of a tryptophanyl-ester.

  将色氨酸酯或色氨酸酯的 N-酰基衍生物用于预防和治疗退行性疾病和/或癌症中的氧化病理过程。因此，色氨酸酯或其 N-酰基衍生物最好是色氨酸辛酯、N-油酰-色氨酸乙酯或 N-十二酰-色氨酸乙酯。 此外，色氨酰酯及其 N-酰基衍生物最好用于治疗和/或预防神经退行性疾病、白内障、肿瘤性疾病和/或心血管疾病。特别是，本发明涉及色氨酸酯及其 N-酰基衍生物用于治疗和/或预防阿尔茨海默病、帕金森病、无痫症、肌萎缩性脊髓侧索硬化症、癌症、动脉硬化和/或心肌梗塞。 此外，本发明还涉及一种药物组合物，其中包含一种色氨酰酯或一种色氨酰酯的 N-酰基衍生物。
• TRYPTOPHANYLESTER UND DEREN N-ACYL-DERIVATE ZUR PRÄVENTION UND THERAPIE VON ERKRANKUNGEN, DIE DURCH OXIDATIONSPROZESSE VERURSACHT ODER VERSTÄRKT WERDEN
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP1113795B1

  公开（公告）日：2005-07-13
• Tryptophanyl-esters and their N-acyl derivatives for preventing and treating diseases caused or aggravated by oxidation processes
  申请人：——

  公开号：US20040176436A1

  公开（公告）日：2004-09-09

  Use of a tryptophanyl-ester or an N-acyl derivative of a tryptophanyl-ester for the prophylaxis and therapy of oxidative pathologic processes in degenerative diseases and/or cancer diseases. Thereby, the tryptophanyl-ester or its N-acyl derivative is preferred to be tryptophanoctyl, N-oleoyl-tryptophanethyl-ester or N-dodecanoyl-tryptophanethyl-ester. Furthermore the tryptophanyl-esters and their N-acyl derivatives are preferred to be used for the treatment and/or prophylaxis of neurodegenerative diseases, cataracts, neoplastic diseases and/or cardiovascular diseases. In particular, the invention relates to the use of the tryptophanyl-esters and their N-acyl derivatives for the treatment and/or prophylaxis of Alzheimer's disease, Parkinson's disease, apoplectic fit, amyotrophic lateral sclerosis, cancers, arteriosclerosis and/or myocardial infarction. In addition, the invention relates to a pharmaceutical composition comprising a tryptophanyl-ester or an N-acyl derivative of a tryptophanyl-ester.
• Dermatological compositions
  申请人：Stockel Richard F.

  公开号：US20090318557A1

  公开（公告）日：2009-12-24

  A dermatological composition comprising a salt of a cation and an anion. The cation is derived from a monomeric or polymeric molecule that will generate an amidine moieity, a guanidine moieity or a biguanide moieity. The anion is derived from a monomeric or polymeric molecule that will generate a carboxylic acid moieity. The composition may be prepared by a metathesis or acid-base reaction.
• US8212061B1
  申请人：——

  公开号：US8212061B1

  公开（公告）日：2012-07-03