4-nitrobenzyl N-(tert-butoxycarbonyl)glycylglycinate | 1350885-61-8

• 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 N-(tert-butoxycarbonyl)glycylglycinate
• CAS: 1350885-61-8
• 化学式: C₁₆H₂₁N₃O₇
• 分子量: 367.359
• InChiKey: OBHOVYJYGQYSGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  136.87
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-nitrobenzyl N-(tert-butoxycarbonyl)glycylglycinate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-nitrobenzyl N-(tert-butoxycarbonyl)glycylglycylglycinate
  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
• 作为产物：
  描述：

  Boc-Gly-ONb 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-nitrobenzyl N-(tert-butoxycarbonyl)glycylglycinate
  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

• 放射性テクネチウムの結合部位を有する化合物、及び、その放射性テクネチウム錯体
  申请人：独立行政法人国立がん研究センター

  公开号：JP2015063503A

  公开（公告）日：2015-04-09

  【課題】生体内の低酸素領域を可視化できる放射性テクネチウム錯体を提供する。【解決手段】所定の構造式で表され、放射性テクネチウムとの結合部位を有する化合物又はその塩、その放射性テクネチウム錯体、これを含む放射性医薬組成物、これを調製するために用いられるキットである。【選択図】なし

  提供一种能够可视化生物体内低氧区域的放射性锝配合物。该配合物或其盐以特定的结构式表示，具有与放射性锝结合位点，是放射性锝配合物、包含该配合物的放射性药物组合物以及用于制备该组合物的试剂盒。【选择图】无