S-nitroso-L-glutathione

• 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-nitroso-L-glutathione
• 英文别名: Tocris-0603；(2R)-2-amino-5-[[(2S)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• 化学式: C₁₀H₁₆N₄O₇S
• 分子量: 336.326
• InChiKey: HYHSBSXUHZOYLX-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  22
• 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：
  214
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  S-nitroso-L-glutathione 在 盐酸 、 sodium sulfide 、 三羟甲基氨基甲烷 作用下， 以 水 为溶剂， 生成 perthionitrite
  参考文献：
  名称：

  Nitrosopersulfide (SSNO⁻) Is a Unique Cysteine Polysulfidating Agent with Reduction-Resistant Bioactivity

  摘要：

  Aims: The aim of the present study was to investigate the biochemical properties of nitrosopersulfide (SSNO-), a key intermediate of the nitric oxide (NO)/sulfide cross talk.Results: We obtained corroborating evidence that SSNO- is indeed a major product of the reaction of S-nitrosothiols with hydrogen sulfide (H2S). It was found to be relatively stable (t(1/2) similar to 1 h at room temperature) in aqueous solution of physiological pH, stabilized by the presence of excess sulfide and resistant toward reduction by other thiols. Furthermore, we here show that SSNO- escapes the reducing power of the NADPH-driven biological reducing machineries, the thioredoxin and glutathione reductase systems. The slow decomposition of SSNO- produces inorganic polysulfide species, which effectively induce per/polysulfidation on glutathione or protein cysteine (Cys) residues. Our data also demonstrate that, in contrast to the transient activation by inorganic polysulfides, SSNO- induces long-term potentiation of TRPA1 (transient receptor potential ankyrin 1) channels, which may be due to its propensity to generate a slow flux of polysulfide in situ.Innovation: The characterized properties of SSNO- would seem to represent unique features in cell signaling by enabling sulfur and nitrogen trafficking within the reducing environment of the cytosol, with targeted release of both NO and polysulfide equivalents.Conclusion: SSNO- is a surprisingly stable bioactive product of the chemical interaction of S-nitrosothiol species and H2S that is resistant to reduction by the thioredoxin and glutathione systems. As well as generating NO, it releases inorganic polysulfides, enabling transfer of sulfane sulfur species to peptide/protein Cys residues. The sustained activation of TRPA1 channels by SSNO- is most likely linked to all these properties.

  DOI：

  10.1089/ars.2020.8049
• 作为产物：
  描述：

  Cbz-反式-4-羟基-L-脯氨醇 在 sodium nitrite 作用下， 生成 S-nitroso-L-glutathione
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiopure thionitrites: The solid-phase synthesis and nitrosation of d -glutathione as a molecular probe

  摘要：

  The D-isomer of the naturally-occurring tripeptide glulathione (gamma-L-Glu-L-Cys-Gly, L-GSH) has been synthesised using the Fmoc solid phase peptide synthesis strategy. The D-GSH obtained has been nitrosated to give the D-isomer of the bioactive thionitrite, S-nitroso-L-glutathione. The biological activity of both enantiomers of S-nitrosoglutathione has been studied and compared to the activity of the D- and L-isomers of N-acetyl-S-nitrosopenicillamine (SNAP) and S-nitrosocysteine (CysNO). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00060-3

文献信息

• COMPOSITION FOR INCREASING PERMEABILITY OF BLOOD-BRAIN BARRIER COMPRISING NITRIC OXIDE DONOR AND USE THEREOF
  申请人：POSTECH Research and Business Development Foundation

  公开号：US20210244750A1

  公开（公告）日：2021-08-12

  The present invention relates to a composition to be used for increasing the blood-brain barrier permeability, the composition including a nitric oxide donor, and a use of the composition. More particularly, the invention relates to a composition to be used for increasing the blood-brain barrier permeability, the composition including a nitric oxide donor capable of carrying nitric oxide (NO), wherein the nitric oxide delivered to a site adjacent to the blood-brain barrier by the nitric oxide donor activates matrix metallopeptidase-9 (MMP-9), and the activated MMP-9 weakens a tight junction between a cerebrovascular endothelial cell and a cerebrovascular endothelial cell to increase the blood-brain barrier permeability, and to a use of the composition.

  本发明涉及一种用于增加血脑屏障通透性的组合物，该组合物包括一种一氧化氮供体，以及该组合物的用途。更具体地，本发明涉及一种用于增加血脑屏障通透性的组合物，该组合物包括一种能够携带一氧化氮（NO）的一氧化氮供体，其中通过一氧化氮供体将一氧化氮输送到血脑屏障相邻位置，激活基质金属蛋白酶-9（MMP-9），激活的MMP-9削弱脑血管内皮细胞之间的紧密连接，以增加血脑屏障通透性，并且用于该组合物的用途。
• S-nitroso- and S-nitro-N-acyl-L-cysteine ester derivatives as pharmalogically active agents and pharmaceutical compositions containing said compounds
  申请人：——

  公开号：US20020091102A1

  公开（公告）日：2002-07-11

  SNACE derivatives as pharmacological active agents and pharmacological compositions containing these compounds, in particular for transdermal, oral, rectal and inhalational application, are described.

  本文描述了作为药理活性剂的蛇皮酸衍生物及含有这些化合物的药物组合物，特别是用于经皮、口服、直肠和吸入应用。
• Use of nitric oxide mimetics in cancer treatment
  申请人：Cellegy Pharmaceuticals, Inc

  公开号：EP1502604A1

  公开（公告）日：2005-02-02

  Methods and formulations for inhibiting and preventing a malignant cell phenotype by administering to cells a low dose of a nitric oxide mimetic are provided

  提供了通过向细胞施用低剂量一氧化氮模拟物来抑制和预防恶性细胞表型的方法和制剂
• Methods and compositions for regulating biofilm development
  申请人：Environmental Biotechnology CRC Pty Limited

  公开号：EP2351828A1

  公开（公告）日：2011-08-03

  The present invention relates to methods for promoting dispersal of, or preventing formation of microbial biofilms, comprising: exposing a biofilm to an effective amount of nitric oxide or at least one nitric oxide generating or releasing agent; treating a surface or medium susceptible to biofilm formation with an effective amount of nitric oxide or at least one nitric oxide generating or releasing agent; incorporating an effective amount of nitric oxide or at least one nitric oxide generating or releasing agent in a surface or medium susceptible to biofilm formation; or inducing the accumulation of one or more reactive oxygen or nitrogen species within microorganisms within said biofilm or capable of forming a biofilm. The invention also relates to methods for maintaining or enhancing or maintaining and enhancing the functioning of a biofilm, comprising exposing a biofilm to at least one nitric oxide scavenger, at least one antioxidant or at least one nitric oxide scavenger and at least one antioxidant. The invention also relates to compositions for promoting dispersal of, or preventing formation of microbial biofilms, or for maintaining or enhancing or maintaining and enhancing the functioning of microbial biofilms.

  本发明涉及促进微生物生物膜的分散或防止其形成的方法，包括将生物膜暴露于有效量的一氧化氮或至少一种一氧化氮产生剂或释放剂；用有效量的一氧化氮或至少一种一氧化氮产生剂或释放剂处理易形成生物膜的表面或介质；在易形成生物膜的表面或介质中加入有效量的一氧化氮或至少一种一氧化氮产生剂或释放剂；或诱导所述生物膜内或能形成生物膜的微生物体内一种或多种活性氧或氮物种的积累。本发明还涉及维持或增强或维持和增强生物膜功能的方法，包括将生物膜暴露于至少一种一氧化氮清除剂、至少一种抗氧化剂或至少一种一氧化氮清除剂和至少一种抗氧化剂。本发明还涉及用于促进微生物生物膜的分散或防止微生物生物膜的形成，或用于维持或增强或维持和增强微生物生物膜功能的组合物。
• Formulations and methods of using nitric oxide mimetics against a malignant cell phenotype
  申请人：——

  公开号：US20020040059A1

  公开（公告）日：2002-04-04

  Methods and formulations for inhibiting and preventing a malignant cell phenotype by administering to cells a low dose of a nitric oxide mimetic are provided.

  本研究提供了通过向细胞施用低剂量一氧化氮模拟物来抑制和预防恶性细胞表型的方法和制剂。