N-acetyl cysteine trisuifide | 244173-27-1

• 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-acetyl cysteine trisuifide
• 英文别名: N,N'-diacetyl-L-cysteine trisulfide；N,N′-diacetyl-L-cysteine trisulfide；(R,R')-3,3'-trithiobis(2-acetamidopropanoic acid)；(2R)-2-acetamido-3-[[(2R)-2-acetamido-2-carboxyethyl]trisulfanyl]propanoic acid
• CAS: 244173-27-1
• 化学式: C₁₀H₁₆N₂O₆S₃
• 分子量: 356.445
• InChiKey: AFZFDUSMFAIGNE-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  209
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 在 sodium hydrogen sulfide 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 N-acetyl cysteine trisuifide
  参考文献：
  名称：

  Enhanced Cellular Polysulfides Negatively Regulate TLR4 Signaling and Mitigate Lethal Endotoxin Shock

  摘要：

  Cysteine persulfide and cysteine polysulfides are cysteine derivatives having sulfane sulfur atoms bound to cysteine thiol. Accumulating evidence has suggested that cysteine persulfides/polysulfides are abundant in prokaryotes and eukaryotes and play important roles in diverse biological processes such as antioxidant host defense and redox-dependent signal transduction. Here, we show that enhancement of cellular polysulfides by using polysulfide donors developed in this study resulted in marked inhibition of lipopolysaccharide (LPS)-initiated macrophage activation. Polysulfide donor treatment strongly suppressed LPS-induced pro-inflammatory responses in macrophages by inhibiting Toll-like receptor 4 (TLR4) signaling. Other TLR signaling stimulants-including zymosan A-TLR2 and poly(I:C)-TLR3-were also significantly suppressed by polysulfur donor treatment. Administration of polysulfide donors protected mice from lethal endotoxin shock. These data indicate that cellular polysulfides negatively regulate TLR4-mediated pro-inflammatory signaling and hence constitute a potential target for inflammatory disorders.

  DOI：

  10.1016/j.chembiol.2019.02.003

文献信息

• Development of <i>S</i>-Substituted Thioisothioureas as Efficient Hydropersulfide Precursors
  作者：Vinayak S. Khodade、John P. Toscano

  DOI：10.1021/jacs.8b08469

  日期：2018.12.19

  must be generated in situ using precursors, but very few physiologically useful RSSH precursors have been developed to date. In this work, we report the design, synthesis, and evaluation of novel S-substituted thiosiothioureas as RSSH precursors. These water-soluble precursors show efficient and controllable release of RSSH under physiological conditions.

  由于其固有的不稳定性，氢过硫化物 (RSSH) 必须使用前体原位生成，但迄今为止开发的生理学上有用的 RSSH 前体很少。在这项工作中，我们报告了作为 RSSH 前体的新型 S 取代硫代硫脲的设计、合成和评估。这些水溶性前体在生理条件下显示出有效且可控的 RSSH 释放。
• Compounds, Compositions and Methods for Treating or Preventing Hypoxic or Ischemic Injury
  申请人：Ruan Fuqiang

  公开号：US20110195945A1

  公开（公告）日：2011-08-11

  Compositions and methods of treating or preventing disease or injury to a human patient or biological material undergoing ischemic or hypoxic conditions.

  治疗或预防人类患者或生物材料在缺血或低氧条件下遭受疾病或损伤的组合物和方法。
• COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING OR PREVENTING HYPOXIC OR ISCHEMIC INJURY
  申请人：FRED HUTCHINSON CANCER RESEARCH CENTER

  公开号：US20140228302A1

  公开（公告）日：2014-08-14

  Compositions and methods of treating or preventing disease or injury to a human patient or biological material undergoing ischemic or hypoxic conditions.
• US8680151B2
  申请人：——

  公开号：US8680151B2

  公开（公告）日：2014-03-25
• METHOD FOR PRODUCING TRISULFIDE COMPOUND OR SELENOTRISULFIDE COMPOUND
  申请人：Kyowa Pharma Chemical Co., Ltd.

  公开号：US20230192604A1

  公开（公告）日：2023-06-22

  Disclosed is a method for producing a trisulfide compound or a selenotrisulfide compound. This production method includes: a step for oxidizing a disulfide compound with an oxidizing agent to obtain a sulfoxide compound; and a step for reacting the sulfoxide compound that has been obtained with a source of sulfur or a source of selenium to obtain a trisulfide compound or a selenotrisulfide compound.