4-nitrobenzyl mercaptoacetylglycylglycylglycinate | 1350885-63-0

• 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: 4-nitrobenzyl mercaptoacetylglycylglycylglycinate
• 英文别名: (4-Nitrophenyl)methyl 2-[[2-[[2-[(2-sulfanylacetyl)amino]acetyl]amino]acetyl]amino]acetate
• CAS: 1350885-63-0
• 化学式: C₁₅H₁₈N₄O₇S
• 分子量: 398.397
• InChiKey: IAODAKFPGMMTEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-nitrobenzyl N-(tert-butoxycarbonyl)glycylglycinate 在 三异丙基硅烷 、 水 、 1-羟基苯并三唑 、 乙二醇 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 4-nitrobenzyl mercaptoacetylglycylglycylglycinate
  参考文献：
  名称：

  Synthesis and evaluation of a novel 99mTc-labeled bioreductive probe for tumor hypoxia imaging

  摘要：

  Tumor hypoxia is closely associated with the malignant progression and/or the high metastatic ability of tumors and often induces resistance to chemo- and/or radiotherapy. Thus, the detection and evaluation of hypoxia is important for the optimization of cancer therapy. We designed a novel Tc-99m-labeled probe for tumor hypoxia imaging that utilizes bioreductive reactions in hypoxic cells. This probe, which contains a 4-nitrobenzyl ester group, is reduced in hypoxic cells to produce a corresponding carboxylate anion that cannot penetrate cell membranes because of its hydrophilicity and negative charge; therefore, it is expected to be trapped inside hypoxic cells. Based on this unique strategy, we synthesized the Technetium-99m ( Tc-99m)-labeled probe Tc-99m-SD32. The uptake of Tc-99m-SD32 in tumor cells was investigated under normoxic and hypoxic conditions. Tc-99m-SD32 showed sufficient accumulation and good retention in hypoxic cells. In addition, we demonstrated that Tc-99m-SD32 was subjected to bioreduction in hypoxic cells and was trapped as the corresponding carboxylate anion. These results indicated that Tc-99m-SD32 would be a promising agent for in vivo hypoxia imaging. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.022

文献信息

• Synthesis and evaluation of a novel 99mTc-labeled bioreductive probe for tumor hypoxia imaging
  作者：Sadaaki Kimura、Izumi O. Umeda、Noriyuki Moriyama、Hirofumi Fujii

  DOI：10.1016/j.bmcl.2011.10.022

  日期：2011.12

  Tumor hypoxia is closely associated with the malignant progression and/or the high metastatic ability of tumors and often induces resistance to chemo- and/or radiotherapy. Thus, the detection and evaluation of hypoxia is important for the optimization of cancer therapy. We designed a novel Tc-99m-labeled probe for tumor hypoxia imaging that utilizes bioreductive reactions in hypoxic cells. This probe, which contains a 4-nitrobenzyl ester group, is reduced in hypoxic cells to produce a corresponding carboxylate anion that cannot penetrate cell membranes because of its hydrophilicity and negative charge; therefore, it is expected to be trapped inside hypoxic cells. Based on this unique strategy, we synthesized the Technetium-99m ( Tc-99m)-labeled probe Tc-99m-SD32. The uptake of Tc-99m-SD32 in tumor cells was investigated under normoxic and hypoxic conditions. Tc-99m-SD32 showed sufficient accumulation and good retention in hypoxic cells. In addition, we demonstrated that Tc-99m-SD32 was subjected to bioreduction in hypoxic cells and was trapped as the corresponding carboxylate anion. These results indicated that Tc-99m-SD32 would be a promising agent for in vivo hypoxia imaging. (C) 2011 Elsevier Ltd. All rights reserved.