S-nitroso-N-acetyl cysteine

• 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-N-acetyl cysteine
• 英文别名: S-nitroso-N-acetylcysteine；nitroso-N-acetylcysteine；2-Acetamido-3-nitrososulfanylpropanoic acid
• 化学式: C₅H₈N₂O₄S
• 分子量: 192.196
• InChiKey: QTJKCQPXTOYYHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-nitroso-N-acetyl cysteine 在 乙二胺四乙酸 、 sodium hydrogensulfite 作用下， 以 phosphate buffer 为溶剂， 生成 N-乙酰基-L-半胱氨酸
  参考文献：
  名称：

  Munro, Andrew P.; Williams, D. Lyn H., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 9, p. 1794 - 1797

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙酰基-L-半胱氨酸 在 乙二胺四乙酸 、 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 S-nitroso-N-acetyl cysteine
  参考文献：
  名称：

  Direct Detection of S-Nitrosothiols Using Planar Amperometric Nitric Oxide Sensor Modified with Polymeric Films Containing Catalytic Copper Species

  摘要：

  通过对之前报道过的安培法一氧化氮气体传感器进行改良，使其具有含催化 Cu(II)/(I) 位点的亲水聚氨酯薄膜，从而实现了对 S-亚硝硫醇物种（RSNOs）的直接安培检测。催化 Cu(II)/(I)介导的 S-亚硝硫醇分解会在氮氧化物传感器远端聚合物薄膜中生成 NO(g)。我们研究了生成催化层的三种不同物质：(1) 亲脂性 Cu(II)-ligand 复合物；(2) Cu(II)-phosphate 盐；(3) 金属 Cu0 小颗粒（3-μm）。所有三个催化层都能产生可逆的安培反应，与水性测试溶液中的 S-亚硝硫醇（如亚硝基半胱氨酸、亚硝基谷胱甘肽、S-亚硝基-N-乙酰半胱氨酸、S-亚硝基白蛋白）浓度成比例。对不同 RSNO 物种的敏感性取决于活性 Cu(I)对 RSNO 物种各自的催化分解率、RSNO 物种进入含有催化剂的聚氨酯层的可及性、溶液中用于帮助生成活性 Cu(I) 物种的还原剂（抗坏血酸盐）的含量以及测试溶液中存在的金属离子络合剂（如 EDTA）的浓度。在优化条件下，所有 RSNO 物种的检测浓度均≤1 μM，基于磷酸铜（II）和 Cu0 粒子的传感器寿命至少为 10 天。研究进一步表明，新的 RSNO 传感器可用于评估新鲜血液样本的 "NO 生成 "能力，有效检测这些样本中存在的活性 RSNO 物种的总水平。

  DOI：

  10.1021/ac048192u

文献信息

• Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols
  作者：Kun Wang、Zhong Wen、Wei Zhang、Ming Xian、Jin-Pei Cheng、Peng George Wang

  DOI：10.1016/s0960-894x(00)00688-0

  日期：2001.2

  Using UV-vis spectrometrical measurements, equilibrium constants for NO transfer between S-nitroso-N-acetyl-penicillamine (SNAP) and different thiols as well as kinetic data for NO transfer from S-nitroso bovine serum albumin (BSANO) to thiols have been obtained, NO transfer from SNAP to other primary/secondary thiols are thermodynamically favorable, whereas other S-nitrosothiols exhibit similar NO transfer potential. The obtained Gibbs free energy, enthalpy and entropy data indicated that NO transfer reactions from SNAP to four thiols are exothermic with entropy loss. The kinetic behavior of BSANO/RSH transfer can be related to both the acidity of sulfhydryl group and the electronic structure in thiol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Holmes, Anthony J.; Williams, D. Lyn H., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 8, p. 1639 - 1644
  作者：Holmes, Anthony J.、Williams, D. Lyn H.

  DOI：——

  日期：——
• Barnett, D.Jonathan; Rios, Ana; Williams, D. Lyn H., Journal of the Chemical Society. Perkin transactions II, 1995, # 7, p. 1279 - 1282
  作者：Barnett, D.Jonathan、Rios, Ana、Williams, D. Lyn H.

  DOI：——

  日期：——
• S,S′-dinitrosobucillamine, a new nitric oxide donor, induces a better vasorelaxation than other S-nitrosothiols
  作者：Fatima Dahboul、Caroline Perrin-Sarrado、Ariane Boudier、Isabelle Lartaud、Raphaël Schneider、Pierre Leroy

  DOI：10.1016/j.ejphar.2014.02.034

  日期：2014.5

  S-nitrosothiols (RSNO) are considered as potential drugs for delivering nitric oxide ((NO)-N-center dot) or related species in cardiovascular disorders associated with decrease in NO bioavailability. We have synthesized a new RSNO, i.e. S,S'-dinitrosobucillamine (BUC(NO)(2)), which combines in its structure two S-mononitrosothiols, S-nitroso-N-acetylpenicillamine (SNAP) and S-nitroso-N-acetylcysteine (NACNO). Synthesized BUC(NO)(2) was structurally characterized using high-performance liquid chromatography/mass spectrometry (HPLC/MS), H-1 nuclear magnetic resonance (H-1 NMR), infrared (IR) and UV-visible spectroscopies, and thermal analysis; resulting data are consistent with the expected structure. The vasorelaxant effect of BUC(NO)(2) was evaluated using isolated rat aortic rings and compared to SNAP, NACNO, and to an equimolar mixture of NACNO plus SNAP in order to mimic the number of (NO)-N-center dot contained in a BUC(NO)(2) molecule. BUC(NO)(2) (pD(2)=7.8 +/- 0.1) was more potent in vasorelaxation than NACNO (pD(2)=6.4 +/- 0.2), SNAP (pD(2)=6.7 +/- 0.1) and the mixture of SNAP plus NACNO (pD(2)=6.7 +/- 0.2). The release of (NO)-N-center dot from BUC(NO)(2) was 6-fold that of the basal value and significantly higher than the release of NO from the SNAP plus NACNO mixture (4-fold increase versus basal value). Finally, the role of protein disulfide isomerase (PDI) in BUC(NO)(2) metabolism was investigated. Vasorelaxant effect (pD(2)=6.8 +/- 0.2) and (NO)-N-center dot release decreased in the presence of a PDI inhibitor (both P<0.05 versus BUC(NO)(2)). In conclusion, BUC(NO)(2) releases a larger amount of (NO)-N-center dot into the aorta, partially through PDI activation, and induces vasorelaxation at lower concentrations than other RSNO previously reported. (C) 2014 Elsevier B.V. All rights reserved.
• SHAW, ANDREW J.;GESCHER, ANDREAS;TOOTH, DAVID;LINHART, IGOR;FARMER, PETER+, CHEM. RES. TOXICOL., 3,(1990) N, C. 27-32
  作者：SHAW, ANDREW J.、GESCHER, ANDREAS、TOOTH, DAVID、LINHART, IGOR、FARMER, PETER+

  DOI：——

  日期：——