S-nitrosoacetylhomocysteine

• 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: S-nitrosoacetylhomocysteine
• 英文别名: 2-Acetamido-4-nitrososulfanylbutanoic acid
• 化学式: C₆H₁₀N₂O₄S
• 分子量: 206.222
• InChiKey: RDHIVJWARQYNEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-乙酰氨基-4-巯基丁酸γ-硫内酯 在 sodium hydroxide 、 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 4.17h， 生成 S-nitrosoacetylhomocysteine
  参考文献：
  名称：

  Mechanism-Based Triarylphosphine-Ester Probes for Capture of Endogenous RSNOs

  摘要：

  Nitrosothiols (RSNOs) have been proposed as important intermediates in nitric oxide (NO center dot) metabolism, storage, and transport as well as mediators in numerous NO. signaling pathways. RSNO levels are finely regulated, and dysregulation is associated with the etiology of several pathologies. Current methods for RSNO quantification depend on indirect assays that limit their overall specificity and reliability. Recent developments of phosphine-based chemical probes constitute a promising approach for the direct detection of RSNOs. We report here results from a detailed mechanistic and kinetic study for trapping RSNOs by three distinct phosphine probes, including structural identification of novel intermediates and stability studies under physiological conditions. We further show that a triarylphosphine-thiophenyl ester can be used in the absolute quantification of endogenous GSNO in several cancer cell lines, while retaining the elements of the SNO functional group, using an LC-MS-based assay. Finally, we demonstrate that a common product ion (m/z = 309.0), derived from phosphine RSNO adducts, can be used for the detection of other low-molecular weight nitrosothiols (LMW-RSNOs) in biological samples. Collectively, these findings establish a platform for the phosphine ligation-based, specific and direct detection of RSNOs in biological samples, a powerful tool for expanding the knowledge of the biology and chemistry of NO center dot-mediated phenomena.

  DOI：

  10.1021/ja401565w

文献信息

• [EN] S-NITROSOMERCAPTO COMPOUNDS AND RELATED DERIVATIVES<br/>[FR] COMPOSÉS DE S-NITROSOMERCAPTO ET DÉRIVÉS APPARENTÉS
  申请人：GALLEON PHARMACEUTICALS INC

  公开号：WO2009151744A1

  公开（公告）日：2009-12-17

  The present invention is directed to mercapto-based and S- nitrosomercapto-based SNO compounds and their derivatives, and their use in treating a lack of normal breathing control, including the treatment of apnea and hypoventilation associated with sleep, obesity, certain medicines and other medical conditions.

  本发明涉及基于巯基和S-亚硝基巯基的SNO化合物及其衍生物，以及它们在治疗正常呼吸控制缺失方面的用途，包括治疗与睡眠、肥胖、某些药物和其他医疗状况相关的呼吸暂停和低通气。
• SENSOR FOR DETECTING NITROSOTHIOLS
  申请人：Meyerhoff Mark E.

  公开号：US20100276284A1

  公开（公告）日：2010-11-04

  A device for detecting nitrosothiol content in a solution includes at least two electrodes disposed in a housing, wherein one of the at least two electrodes is a working electrode having a platinized tip and the other of the at least two electrodes is a counter electrode. A filter membrane is disposed at an end of the housing and is configured to come in contact with the solution. The filter membrane and at least a portion of the working electrode have a material coated thereon. The material includes a polymer and a source of copper dispersed within the material. The material and the platinized tip are configured to come into contact with the solution containing nitrosothiols to convert the nitrosothiols to nitric oxide in order to detect the nitrosothiol content.