2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl trifluoromethanesulfonate | 155863-37-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl trifluoromethanesulfonate
• 英文别名: 2-(2,5-Dioxopyrrol-1-yl)ethyl trifluoromethanesulfonate
• CAS: 155863-37-9
• 化学式: C₇H₆F₃NO₅S
• 分子量: 273.19
• InChiKey: JIUYDXPCRYKTOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl trifluoromethanesulfonate 以 乙醚 、 水 、 乙腈 为溶剂， 生成 1-<2-<3-propylthio-1-(2,5-dioxpyrrolidinyl)>ethyl>-4-<2-<6-(3,4-dihydro-2H-1-benzopyranyl)>-5-oxazolyl>pyridinium trifluoromethanesulfonate
  参考文献：
  名称：

  Litak, Peter T.; Kauffman, Joel M., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 457 - 480

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-羟乙基)马来酰亚胺 、 三氟甲磺酸酐 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(2,5-dioxo-1H-pyrrol-1-yl)ethyl trifluoromethanesulfonate
  参考文献：
  名称：

  Maleimidoethyl 3-(Tri-n-butylstannyl)hippurate: A Useful Radioiodination Reagent for Protein Radiopharmaceuticals To Enhance Target Selective Radioactivity Localization

  摘要：

  In pursuit of radiolabeled monoclonal antibodies (mAbs) with rapid urinary excretion of radioactivity from nontarget tissues, radioiodinated mAbs releasing a m-iodohippuric acid from the mAbs in nontarget tissues were designed. A novel reagent, maleimidoethyl 3-(tri-n-butylstannyl)hippurate (MIH), was synthesized by reacting N-(hydroxyethyl)maleimide with N-Boc-glycine before coupling with N-succinimidyl 3-(tri-n-butylstannyl)benzoate (ATE). MIH possessed a maleimide group for mAb conjugation and a butylstannyl moiety for high-yield and site-specific radioiodination, and the two functional groups were linked via an ester bond to release m-iodohippuric acid. To investigate the fate of radiolabels after lysosomal proteolysis, hepatic parenchymal cells were used as a model nontarget tissue and I-131-labeled MIH was conjugated with galactosyl-neoglycoalbumin (NGA). Further conjugation of[I-131]MIH with a mAb against osteogenic sarcoma (OST7) after reduction of its disulfide bonds was followed up. In murine biodistribution studies, [I-131]MIH-NGA exhibited rapid accumulation in the liver followed by radioactivity elimination from the liver at a rate that was identical to and faster than those of I-131-labeled NGA via direct iodination ([I-131]NGA) and [I-131]ATE-labeled NGA, respectively. While [I-131]NGA indicated high radioactivity levels in the murine neck, stomach, and blood, such increases in the radioactivity count were not detectable by the administration of either [I-131]MIH-NGA or [I-131]ATE-NGA. At 6 h postinjection of [I-131]MIH-NGA, 80% of the injected radioactivity was recovered in the urine. Analyses of urine samples indicated that m-iodohippuric acid was the sole radiolabeled metabolite. In biodistribution studies using [I-131]MIH-OST7 and [I-131]ATE-OST7, while both I-131-labeled OST7s registered almost identical radioactivity levels in the blood up to 6 h postinjection, the former demonstrated a lower radioactivity level than [I-131]ATE-OST7 in nontarget tissues throughout the experiment. Such chemical and biological characteristics of MIH would enable high target/nontarget ratios in diagnostic and therapeutic nuclear medicine using mAbs and other polypeptides.

  DOI：

  10.1021/jm00042a014

文献信息

• Synthesis and Photochemistry of a New Class of Photocleavable Protein Cross-linking Reagents
  作者：Lilia Milanesi、Gavin D. Reid、Godfrey S. Beddard、Christopher A. Hunter、Jonathan P. Waltho

  DOI：10.1002/chem.200305405

  日期：2004.4.2

  A new series of photocleavable protein cross-linking reagents based on bis(maleimide) derivatives of diaryl disulfides have been synthesised. They have been functionalised with cysteine and transient absorption spectra for the photolysis reaction have been recorded by using the pump-probe technique with a time resolution of 100 femtoseconds. Photolysis of the disulfide bond yields the corresponding

  合成了一系列基于二芳基二硫化物的双(马来酰亚胺)衍生物的新型光裂解蛋白交联剂。它们已经用半胱氨酸功能化，并且已经通过使用时间分辨率为 100 飞秒的泵探针技术记录了光解反应的瞬态吸收光谱。二硫键的光解在不到一皮秒的时间内产生相应的硫基自由基。有大量的双子重组，但一些自由基逃离溶剂笼，光裂解的量子产率为 30% 在水中。
• Maleimidoethyl 3-(Tri-n-butylstannyl)hippurate: A Useful Radioiodination Reagent for Protein Radiopharmaceuticals To Enhance Target Selective Radioactivity Localization
  作者：Yasushi Arano、Kouji Wakisaka、Yoshiro Ohmomo、Takashi Uezono、Takahiro Mukai、Hiroshi Motonari、Hiromitsu Shiono、Harumi Sakahara、Junji Konishi

  DOI：10.1021/jm00042a014

  日期：1994.8

  In pursuit of radiolabeled monoclonal antibodies (mAbs) with rapid urinary excretion of radioactivity from nontarget tissues, radioiodinated mAbs releasing a m-iodohippuric acid from the mAbs in nontarget tissues were designed. A novel reagent, maleimidoethyl 3-(tri-n-butylstannyl)hippurate (MIH), was synthesized by reacting N-(hydroxyethyl)maleimide with N-Boc-glycine before coupling with N-succinimidyl 3-(tri-n-butylstannyl)benzoate (ATE). MIH possessed a maleimide group for mAb conjugation and a butylstannyl moiety for high-yield and site-specific radioiodination, and the two functional groups were linked via an ester bond to release m-iodohippuric acid. To investigate the fate of radiolabels after lysosomal proteolysis, hepatic parenchymal cells were used as a model nontarget tissue and I-131-labeled MIH was conjugated with galactosyl-neoglycoalbumin (NGA). Further conjugation of[I-131]MIH with a mAb against osteogenic sarcoma (OST7) after reduction of its disulfide bonds was followed up. In murine biodistribution studies, [I-131]MIH-NGA exhibited rapid accumulation in the liver followed by radioactivity elimination from the liver at a rate that was identical to and faster than those of I-131-labeled NGA via direct iodination ([I-131]NGA) and [I-131]ATE-labeled NGA, respectively. While [I-131]NGA indicated high radioactivity levels in the murine neck, stomach, and blood, such increases in the radioactivity count were not detectable by the administration of either [I-131]MIH-NGA or [I-131]ATE-NGA. At 6 h postinjection of [I-131]MIH-NGA, 80% of the injected radioactivity was recovered in the urine. Analyses of urine samples indicated that m-iodohippuric acid was the sole radiolabeled metabolite. In biodistribution studies using [I-131]MIH-OST7 and [I-131]ATE-OST7, while both I-131-labeled OST7s registered almost identical radioactivity levels in the blood up to 6 h postinjection, the former demonstrated a lower radioactivity level than [I-131]ATE-OST7 in nontarget tissues throughout the experiment. Such chemical and biological characteristics of MIH would enable high target/nontarget ratios in diagnostic and therapeutic nuclear medicine using mAbs and other polypeptides.
• Litak, Peter T.; Kauffman, Joel M., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 457 - 480
  作者：Litak, Peter T.、Kauffman, Joel M.

  DOI：——

  日期：——