S-(2-phenyl carbamoyl benzeneselenenyl)-glutathione | 101562-89-4

• 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-(2-phenyl carbamoyl benzeneselenenyl)-glutathione
• 英文别名: ebselen-glutathione adduct；ebselen；GSH-ebselen；(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-[2-(phenylcarbamoyl)phenyl]selanylsulfanylpropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 101562-89-4
• 化学式: C₂₃H₂₆N₄O₇SSe
• 分子量: 581.508
• InChiKey: CBJJMECNRUUSMP-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  213
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  S-(2-phenyl carbamoyl benzeneselenenyl)-glutathione 在 双氧水 作用下， 以 氘代氯仿 为溶剂， 生成 N-苯基-2-[2-(苯基氨基甲酰)苯基]二硒基苯甲酰胺
  参考文献：
  名称：

  抗炎化合物依布硒啉的抗氧化活性：通过硒酸和硒酸中间体的可逆环化途径。

  摘要：

  描述了一种修正的机制，该机制解释了有机硒化合物依布硒啉的谷胱甘肽过氧化物酶（GPx）样催化活性。结果表明依布硒啉与H（2）O（2）的反应产生硒酸作为唯一的氧化产物。硒酸的X射线晶体结构表明，硒原子参与了与羰基氧原子的非共价相互作用。在过量硫醇的存在下，依布硒啉中的Se-N键很容易被硫醇裂解，生成相应的硒烯基硫化物。如此产生的亚硒基硫化物在H（2）O（2）存在下发生歧化反应，生成二硒化物，其与H（2）O（2）反应生成硒酸和硒酸的混合物。向包含硒酸和硒酸的混合物中添加硫醇会导致亚硒基硫化物的形成。当反应混合物中硫醇的浓度相对较低时，硒酸会快速环化生成依布硒啉。另一方面，硒酸与二硒化物反应生成依卜硒林作为最终产物。DFT计算表明，与亚磺酸到相应的亚磺酰基酰胺相比，硒酸对相应的亚硒基酰胺的环化更有利。这表明依卜硒仑在各种条件下的再生可保护硒部分免受不可逆的失活，这可能是依卜硒仑的生物学活性的原因。

  DOI：

  10.1002/chem.200801258
• 作为产物：
  描述：

  苯甲酰氯,2-(氯硒代)- 在 sodium hydroxide 作用下， 以 异丙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 S-(2-phenyl carbamoyl benzeneselenenyl)-glutathione
  参考文献：
  名称：

  Fisher, Hartmut; Dereu, Norbert, Bulletin des Societes Chimiques Belges, 1987, vol. 96, # 10, p. 757 - 768

  摘要：

  DOI：

文献信息

• Computer-assisted designed “selenoxy–chinolin”: a new catalytic mechanism of the GPx-like cycle and inhibition of metal-free and metal-associated Aβ aggregation
  作者：Zhiren Wang、Yali Wang、Wenrui Li、Zhihong Liu、Zonghua Luo、Yang Sun、Ruibo Wu、Ling Huang、Xingshu Li

  DOI：10.1039/c5dt02130h

  日期：——

  Using support from rational computer-assisted design, a novel series of hybrids designed by fusing the metal-chelating agent CQ and the antioxidant ebselen were synthesized and evaluated as multitarget-directed ligands.

  利用理性计算机辅助设计的支持，通过融合金属螯合剂CQ和抗氧化剂ebselen设计的新型混合物系列被合成并评估为多靶点定向配体。
• Chemistry Related to the Catalytic Cycle of the Antioxidant Ebselen
  作者：Kai N. Sands、Austin L. Burman、Esther Ansah-Asamoah、Thomas G. Back

  DOI：10.3390/molecules28093732

  日期：——

  formation of benzaldehyde. Oxidation of ebselen seleninic acid did not afford a selenonium seleninate salt as previously observed with benzene seleninic acid, but instead generated a mixture of the seleninic and selenonic acids. Thiolysis of ebselen with benzyl thiol was faster than oxidation by ca. an order of magnitude and produced a stable selenenyl sulfide. When glutathione was employed, the product

  抗氧化药物依布硒啉已在实验室和临床试验中得到广泛研究。它通过与谷胱甘肽或其他硫醇还原来破坏过氧化氢的催化机制很复杂，并且一直是争论不休的主题。在对几个关键步骤的重新研究过程中，我们发现构成依布硒啉第一个氧化产物的亚硒酰胺经历了容易的可逆甲醇分解，生成不稳定的亚硒酸酯和两种二聚产物。在与苯甲醇的反应中，亚硒酰胺产生了一种苯甲酯，该苯甲酯很容易通过硒氧化物消除反应，并形成苯甲醛。依布硒酸的氧化并没有像之前用苯硒酸观察到的那样得到硒酸盐，而是产生了硒酸和硒酸的混合物。依布硒啉与苄基硫醇的硫解比 ca 的氧化快。一个数量级并产生稳定的硒基硫化物。当使用谷胱甘肽时，产物迅速歧化为谷胱甘肽二硫化物和依布硒化物。S-苄基硒基硫化物的氧化，或亚硒酰胺与苄基硫醇的硫解作用，提供了一种瞬时硫醇亚硒酸盐，它也很容易经历硒氧化物消除。当同时存在硫醇和三乙胺催化时，S-苄基衍生物很容易歧化。当暴露于环境光或紫外线 (360
• Ebselen as a peroxynitrite scavenger in vitro and ex vivo
  作者：Andreas Daiber、Ming-Hui Zou、Markus Bachschmid、Volker Ullrich

  DOI：10.1016/s0006-2952(99)00309-3

  日期：2000.1

  We have previously shown that peroxynitrite (PN) selectively impaired prostacyclin (PGI,)dependent vasorelaxation by tyrosine nitration of PGI, synthase in an in situ model (Zou MH, Jendral M and Ullrich V, Br] Pharmacol 126: 1283-1292, 1999). By using this established model, we tested whether or not ebselen (2-phenyl-1,2-benzisoselenazol-3(2H)-one which reacts rapidly with the anionic form of PN, affected PN inhibition of PGI(2) synthase. Administration of ebselen (1 to 50 mu M) to bovine coronary strips 5 min Frier to PN (1 mu M) treatment neither prevented PN-triggered vasoconstriction nor the inhibition of PGI(2) release. In line with these results, ebselen affected neither PN inhibition of the conversion of [C-14]-PGH(2) into 6 keto PGF(1 alpha) nor the nitration of PGI(2) synthase in bovine aortic microsomes. Following the hypothesis that a reaction of ebselen with cellular thiols could have caused the inefficiency of ebselen, we observed that free ebselen quickly reacted with thiols in both coronary strips and in aortic microsomes to form two metabolites, one of which was identified as the ebselen-glutathione adduct, whereas the other had a similar retention time to that of the ebselen-cysteine adduct. The nitration of phenol by PN in a metal-free solution could be blocked more efficiently in the presence of ebselen or glutathione alone than in the presence of both, indicating that like selenomethionine and other selenocompounds, ebselen-thiol adducts were less reactive towards PN than ebselen itself. Further evidence came from the results that ebselen became effective in preventing the inhibition and nitration of PGI(2) synthase after thiol groups of microsomal proteins were previously oxidized with Ellman's reagent. We conclude that in cellular systems ebselen is present as thiol adducts and thus loses its high reactivity towards PN, which is required to compete with the nitration of PGI, synthase. BIOCHEM PHARMACOL 59;2: 153-160, 2000. (C) 1999 Elsevier Science Inc.
• Fisher, Hartmut; Dereu, Norbert, Bulletin des Societes Chimiques Belges, 1987, vol. 96, # 10, p. 757 - 768
  作者：Fisher, Hartmut、Dereu, Norbert

  DOI：——

  日期：——
• Antioxidant Activity of the Anti-Inflammatory Compound Ebselen: A Reversible Cyclization Pathway via Selenenic and Seleninic Acid Intermediates
  作者：Bani Kanta Sarma、Govindasamy Mugesh

  DOI：10.1002/chem.200801258

  日期：——

  A revised mechanism that accounts for the glutathione peroxidase (GPx)-like catalytic activity of the organoselenium compound ebselen is described. It is shown that the reaction of ebselen with H(2)O(2) yields seleninic acid as the only oxidized product. The X-ray crystal structure of the seleninic acid shows that the selenium atom is involved in a noncovalent interaction with the carbonyl oxygen atom

  描述了一种修正的机制，该机制解释了有机硒化合物依布硒啉的谷胱甘肽过氧化物酶（GPx）样催化活性。结果表明依布硒啉与H（2）O（2）的反应产生硒酸作为唯一的氧化产物。硒酸的X射线晶体结构表明，硒原子参与了与羰基氧原子的非共价相互作用。在过量硫醇的存在下，依布硒啉中的Se-N键很容易被硫醇裂解，生成相应的硒烯基硫化物。如此产生的亚硒基硫化物在H（2）O（2）存在下发生歧化反应，生成二硒化物，其与H（2）O（2）反应生成硒酸和硒酸的混合物。向包含硒酸和硒酸的混合物中添加硫醇会导致亚硒基硫化物的形成。当反应混合物中硫醇的浓度相对较低时，硒酸会快速环化生成依布硒啉。另一方面，硒酸与二硒化物反应生成依卜硒林作为最终产物。DFT计算表明，与亚磺酸到相应的亚磺酰基酰胺相比，硒酸对相应的亚硒基酰胺的环化更有利。这表明依卜硒仑在各种条件下的再生可保护硒部分免受不可逆的失活，这可能是依卜硒仑的生物学活性的原因。