glutathione disulfide | 464195-31-1

• 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: glutathione disulfide
• 英文别名: glutathione, oxidized；GSSG；H-gGlu-D-Cys(1)-Gly-OH.H-gGlu-D-Cys(1)-Gly-OH；(2S)-2-amino-5-[[(2S)-3-[[(2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]disulfanyl]-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 464195-31-1
• 化学式: C₂₀H₃₂N₆O₁₂S₂
• 分子量: 612.639
• InChiKey: YPZRWBKMTBYPTK-NNYUYHANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.1
• 重原子数：
  40
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  368
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  7-氟苯呋咱-4-磺酰胺 、 glutathione disulfide 生成 azanium;7-[(2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-2,1,3-benzoxadiazole-4-sulfonate
  参考文献：
  名称：

  TOYOOKA, TOSHIMASA;UCHIYAMA, SADAO;SAITO, YUKIO;IMAI, KAZUHIRO, ANAL. CHIM. ACTA, 205,(1988) N 1-2, 29-41

  摘要：

  DOI：
• 作为产物：
  描述：

  S-nitrosoglutathione 在 copper(II) sulfate 作用下， 生成 glutathione disulfide
  参考文献：
  名称：

  Controlled Nitric Oxide Delivery Platform Based on S-Nitrosothiol Conjugated Interpolymer Complexes for Diabetic Wound Healing

  摘要：

  Nitric oxide (NO) is known to play a critical role in enhancing wound healing as topical NO administration has demonstrated enhanced wound healing in diabetic animal models. However, this approach has been limited by the short duration of NO release, short half-life of NO, and instability of available NO donors. To overcome these deficiencies, we have developed a new NO delivery platform based on grafting S-nitrosothiols (RSNOs), derived from endogenous glutathione (GSH) or its oligomeric derivatives, phytochelatins (PCs), onto poly(vinyl methyl ether-co-maleic anhydride) (PVMMA), and their subsequent formation of interpolymer complexes with poly(vinyl pyrrolidone) (PVP). Such interpolymer complexes provide controlled release of NO for an extended duration (> 10 days) and exhibit enhanced stability in the solid state over that of free RSNOs. The existence of intermolecular hydrogen bonding in such complexes and the formation of disulfide bonds following the NO release have been confirmed by FTIR and Raman. Preliminary wound healing study in a diabetic rat model demonstrates that, with a single topical application, the present controlled release NO delivery system can effectively accelerate wound closure as compared with the control (p < 0.05). The results suggest that the present NO releasing interpolymer complexes could be potentially useful for diabetic wound healing.

  DOI：

  10.1021/mp900237f

文献信息

• Zn(II) Complexes of Glutathione Disulfide: Structural Basis of Elevated Stabilities
  作者：Artur Krȩżel、Jacek Wójcik、Maciej Maciejczyk、Wojciech Bal

  DOI：10.1021/ic101212y

  日期：2011.1.3

  (γECG-OEt)2, and (γEcG)2; dipeptide disulfides, (γEC)2 and (γEC-OEt)2; and mixed disulfides, γECG-γEC and γECG-γEC-OEt. The acid−base and Zn(II) complexation properties in this group of compounds are strictly correlated to average C-terminal electrostatic charges. In particular, it was demonstrated that GSSG assumes a bent (head-to-tail) conformation in solution at neutral pH, which is controlled by electrostatic

  谷胱甘肽二硫化物（GSSG）是谷胱甘肽（GSH）的长期被忽视的氧化还原伙伴，被认为参与细胞内锌稳态。我们对GSSG（（γECG）2）及其9个具有C末端修饰的类似物，三肽二硫化物：（γECS）2，（γECE）的一系列类似物的质子化和Zn（II）结合特性进行了协同的电位计和NMR光谱研究。2，（γECG-NH 2）2，（γECG-OET）2，和（γECGhref=https://www.molaid.com/MS_8376 target="_blank">ECG）2 ; 二肽二硫化物（γEC）2和（γEC-OEt）2; 以及混合的二硫化物γECG-γEC和γECG-γEC-OEt。这组化合物中的酸碱和Zn（II）络合特性与平均C端静电荷严格相关。特别地，已证明GSSG在中性pH下在溶液中呈弯曲（头对尾）构象，这由Glu残基的质子化γ-氨基与去质子化的C端Gly羧酸盐之间的静电吸引控制。这种相互作用通过影响氨基的碱度间接地和直接通过Gly羧酸盐参与Zn（II）离子的外部配位域的参与，间接调节GSSG配位
• Synthesis and reactions of nitroso sulphamethoxazole with biological nucleophiles: Implications for immune mediated toxicity
  作者：Dean J. Naisbitt、Paul M. O'Neill、Munir Pirmohamed、B. Kevin Park

  DOI：10.1016/s0960-894x(96)00260-0

  日期：1996.7

  Sulphamethoxazole hydroxylamine (SMX-NHOH) and nitroso sulphamethoxazole (SMX-NO) were prepared by a modified literature procedure. SMX-NO produced a complex set of unstable intermediates with sulphur nucleophiles, but did not react with amino containing compounds. No reactions were observed between sulphamethoxazole (SMX)/SMX-NHOH and the nucleophiles used in this study. Thus antigens formed from N-oxidation of SMX are likely to be unstable in vivo. Copyright (C) 1996 Elsevier Science Ltd
• Determination of selenols, diselenides, and selenenyl sulfides by reversed-phase liquid chromatography with electrochemical detection
  作者：Hamada M. A. Killa、Dallas L. Rabenstein

  DOI：10.1021/ac00171a025

  日期：1988.10.15
• Abedinzadeh, Z.; Gardes-Albert, M.; Ferradini, C., Canadian Journal of Chemistry, 1989, vol. 67, p. 1247 - 1256
  作者：Abedinzadeh, Z.、Gardes-Albert, M.、Ferradini, C.

  DOI：——

  日期：——
• ADAM, WALDEMAR;EPE, BERND;SCHIFFMANN, DIETMAR;VARGAS, FRANKLIN;WILD, DIET+, ANGEW. CHEM., 100,(1988) N, C. 443-445
  作者：ADAM, WALDEMAR、EPE, BERND、SCHIFFMANN, DIETMAR、VARGAS, FRANKLIN、WILD, DIET+

  DOI：——

  日期：——