4-((e)-2-((e)-3-(1-(4-(1,3-Dioxoisoindolin-2-yl)butyl)-3,3-dimethyl-3h-indol-1-ium-2-yl)allylidene)-5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethylindolin-1-yl)butane-1-sulfonate | 1422978-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-((e)-2-((e)-3-(1-(4-(1,3-Dioxoisoindolin-2-yl)butyl)-3,3-dimethyl-3h-indol-1-ium-2-yl)allylidene)-5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethylindolin-1-yl)butane-1-sulfonate
• 英文别名: 4-[(2E)-2-[(E)-3-[1-[4-(1,3-dioxoisoindol-2-yl)butyl]-3,3-dimethylindol-1-ium-2-yl]prop-2-enylidene]-5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethylindol-1-yl]butane-1-sulfonate
• CAS: 1422978-58-2
• 化学式: C₄₁H₄₆AsN₃O₅S₃
• 分子量: 831.953
• InChiKey: CJORVPRDLKLMLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  53.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  100.83
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  4-(2-(3-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-3,3-dimethyl-3H-indol-1-ium-2-yl)allylidene)-3,3-dimethylindolin-1-yl)butane-1-sulfonate 、 三氯化砷 、 1,2-乙二硫醇 在 三氟乙酸 、 mercury(II) oxide 、 palladium diacetate 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 aq. phosphate buffer 为溶剂， 以5%的产率得到4-(2-(3-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethyl-3H-indol-1-ium-2-yl)allylidene)-5-(1,3,2-dithiarsolan-2-yl)-3,3-dimethylindolin-1-yl)butane-1-sulfonate
  参考文献：
  名称：

  Synthesis and Application of an Environmentally Insensitive Cy3-Based Arsenical Fluorescent Probe To Identify Adaptive Microbial Responses Involving Proximal Dithiol Oxidation

  摘要：

  Reversible disulfide oxidation between proximal cysteines in proteins represents a common regulatory control mechanism to modulate flux through metabolic pathways in response to changing environmental conditions. To enable in vivo measurements of cellular redox changes linked to disulfide bond formation, we have synthesized a cell-permeable thiol-reactive affinity probe (TRAP) consisting of a monosubstituted cyanine dye derivatized with arsenic (i.e., TRAP_Cy3) to trap and visualize dithiols in cytosolic proteins. Alkylation of reactive thiols prior to displacement of the bound TRAP_Cy3 by ethanedithiol permits facile protein capture and mass spectrometric identification of proximal reduced dithiols to the exclusion of individual cysteines. Applying TRAP_Cy3 to evaluate cellular responses to increases in oxygen and light levels in the photosynthetic microbe Synechococcus sp. PCC7002, we observe large decreases in the abundance of reduced dithiols in cellular proteins, which suggest redox-dependent mechanisms involving the oxidation of proximal disulfides. Under these same growth conditions that result in the oxidation of proximal thiols, there is a reduction in the abundance of post-translational oxidative protein modifications involving methionine sulfoxide and nitrotyrosine. These results suggest that the redox status of proximal cysteines responds to environmental conditions, acting to regulate metabolic flux and minimize the formation of reactive oxygen species to decrease oxidative protein damage.

  DOI：

  10.1021/ja3117284