Bis(D-penicillamine)selenide | 104407-36-5

• 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: Bis(D-penicillamine)selenide
• 英文别名: L-penicillamine selenotrisulfide；(2R)-2-amino-3-[(1R)-1-amino-1-carboxy-2-methylpropan-2-yl]sulfanylselanylsulfanyl-3-methylbutanoic acid
• CAS: 104407-36-5
• 化学式: C₁₀H₂₀N₂O₄S₂Se
• 分子量: 375.372
• InChiKey: DWBDHLPCMJJWGP-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  L-青霉胺 在 硒脲酸 作用下， 反应 3.0h， 生成 Bis(D-penicillamine)selenide
  参考文献：
  名称：

  肽基脯氨酰顺反异构酶 A 参与硒转运到大鼠脑中

  摘要：

  硒是一种必需的微量营养素，在大脑中起着至关重要的作用。硒蛋白 P (SELENOP) 是一种主要的血浆硒蛋白，被认为可将硒转运至大脑。然而，喂食含有足量硒的饮食的 Selenop 基因敲除小鼠没有表现出客观的神经功能障碍，这在喂食硒缺乏饮食的 Selenop 中观察到。- 淘汰老鼠。这一事实表明，来自低质量硒源化合物的硒可以通过与 SELENOP 无关的替代途径转运到大脑。在这项研究中，为了获得关于 SELENOP 非依赖性转运途径的基本信息，我们进行了离体实验，其中分析大鼠脑细胞膜部分以使用其反应性代谢中间体三硫化硒找到硒结合和/或相互作用蛋白(STS) 和 MALDI TOF 质谱。发现几种具有半胱氨酸 (C) 硫醇的膜蛋白通过硫醇交换反应与 STS 发生反应。脑细胞膜部分中的一种含 C 蛋白被鉴定为肽基-脯氨酰顺式-反式异构酶 (PPIase) A 来自胰蛋白酶片段化实验和数据库搜索。在大鼠

  DOI：

  10.1007/s00775-021-01903-6

文献信息

• A Comprehensive Analysis of Selenium-Binding Proteins in the Brain Using Its Reactive Metabolite
  作者：Sakura Yoshida、Eriko Hori、Sakiko Ura、Mamoru Haratake、Takeshi Fuchigami、Morio Nakayama

  DOI：10.1248/cpb.c15-00689

  日期：——

  The intracellular metabolism of selenium in the brain currently remains unknown, although the antioxidant activity of this element is widely acknowledged to be important in maintaining brain functions. In this study, a comprehensive method for identifying the selenium-binding proteins using PenSSeSPen as a model of the selenium metabolite, selenotrisulfide (RSSeSR, STS), was applied to a complex cell lysate generated from the rat brain. Most of the selenium from L-penicillamine selenotrisulfide (PenSSeSPen) was captured by the cytosolic protein thiols in the form of STS through the thiol-exchange reaction (R-SH+PenSSeSPen→R-SSeSPen+PenSH). The cytosolic protein species, which reacted with the PenSSeSPen mainly had a molecular mass of less than 20 kDa. A thiol-containing protein at m/z 15155 in the brain cell lysate was identified as the cystatin-12 precursor (CST12) from a rat protein database search and a tryptic fragmentation experiment. CST12 belongs to the cysteine proteinase inhibitors of the cystatin superfamily that are of interest in mechanisms regulating the protein turnover and polypeptide production in the central nervous system and other tissues. Consequently, CST12 is suggested to be one of the cytosolic proteins responsible for the selenium metabolism in the brain.

  尽管人们普遍认为硒元素的抗氧化活性对于维持大脑功能非常重要，但硒在大脑中的细胞内代谢目前仍不清楚。在本研究中，使用 PenSSeSPen 作为硒代谢物三硫化硒 (RSSeSR、STS) 的模型来鉴定硒结合蛋白的综合方法，应用于大鼠大脑产生的复杂细胞裂解物。 L-青霉胺硒代三硫化物 (PenSSeSPen) 中的大部分硒通过硫醇交换反应 (R-SH+PenSSeSPen→R-SSeSPen+PenSH) 以 STS 的形式被胞质蛋白硫醇捕获。与PenSSeSPen反应的胞质蛋白种类主要具有小于20kDa的分子量。通过大鼠蛋白质数据库搜索和胰蛋白酶裂解实验，脑细胞裂解物中 m/z 15155 的含硫醇蛋白质被鉴定为胱抑素 12 前体 (CST12)。 CST12 属于半胱氨酸蛋白酶抑制剂超家族的半胱氨酸蛋白酶抑制剂，其对调节中枢神经系统和其他组织中蛋白质周转和多肽产生的机制感兴趣。因此，CST12 被认为是负责大脑中硒代谢的胞质蛋白之一。
• An effective method for profiling the selenium-binding proteins using its reactive metabolic intermediate
  作者：Eriko Hori、Sakura Yoshida、Mamoru Haratake、Sakiko Ura、Takeshi Fuchigami、Morio Nakayama

  DOI：10.1007/s00775-015-1265-3

  日期：2015.7

  Currently, the intracellular reduction and/or transport of selenium still remain unknown. Certain reduced forms of selenium species are thought to be reactive with various endogenous molecules, particularly thiol-containing proteins. In this study, a profiling method for identifying the selenium-binding proteins using l-penicillamine selenotrisulfide (PenSSeSPen) as a model of the selenium metabolic intermediate was applied to the cell lysate generated from the rat liver. Several proteins with cysteine thiol were found to be reactive with PenSSeSPen through the thiol-exchange reaction by MALDI TOF-MS analysis. The most distinctive cysteine-containing protein at m/z 14,313 in the liver cell lysate was identified as the liver fatty acid-binding protein based on a rat protein database search and a tryptic fragmentation experiment. This methodology could be used for determining the selenium-binding proteins and/or selenium-interactive species and provide a better understanding of the selenium metabolism and utilization in biological systems.
• Peptidyl-prolyl cis–trans isomerase A participates in the selenium transport into the rat brain
  作者：Sakura Yoshida、Akinori Yamamoto、Hiroshi Masumoto、Takeshi Fuchigami、Akira Toriba、Mamoru Haratake、Morio Nakayama

  DOI：10.1007/s00775-021-01903-6

  日期：2021.12

  the cysteine (C) thiol were found to be reactive with STS through the thiol-exchange reaction. One of the C-containing proteins in the brain cell membrane fraction was identified as peptidyl-prolyl cis–trans isomerase (PPIase) A from tryptic fragmentation experiments and database search. Among the 4 C residues in rat PPIase A, 21st C was proved to react with STS by assessment using C mutated recombinant

  硒是一种必需的微量营养素，在大脑中起着至关重要的作用。硒蛋白 P (SELENOP) 是一种主要的血浆硒蛋白，被认为可将硒转运至大脑。然而，喂食含有足量硒的饮食的 Selenop 基因敲除小鼠没有表现出客观的神经功能障碍，这在喂食硒缺乏饮食的 Selenop 中观察到。- 淘汰老鼠。这一事实表明，来自低质量硒源化合物的硒可以通过与 SELENOP 无关的替代途径转运到大脑。在这项研究中，为了获得关于 SELENOP 非依赖性转运途径的基本信息，我们进行了离体实验，其中分析大鼠脑细胞膜部分以使用其反应性代谢中间体三硫化硒找到硒结合和/或相互作用蛋白(STS) 和 MALDI TOF 质谱。发现几种具有半胱氨酸 (C) 硫醇的膜蛋白通过硫醇交换反应与 STS 发生反应。脑细胞膜部分中的一种含 C 蛋白被鉴定为肽基-脯氨酰顺式-反式异构酶 (PPIase) A 来自胰蛋白酶片段化实验和数据库搜索。在大鼠