N^α-[4-(1',3'-dioxyl-4',4',5',5'-tetramethyldihydroimidazol-2'-yl)phenyloxyacetyl]-L-arginine | 943443-97-8

• 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: N^α-[4-(1',3'-dioxyl-4',4',5',5'-tetramethyldihydroimidazol-2'-yl)phenyloxyacetyl]-L-arginine
• CAS: 943443-97-8
• 化学式: C₂₁H₃₁N₆O₆
• 分子量: 463.514
• InChiKey: NOQYAEOVPIVXOB-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  173
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N^α-[4-(1',3'-dioxyl-4',4',5',5'-tetramethyldihydroimidazol-2'-yl)phenyloxyacetyl]-L-arginine methyl ester 在 sodium hydroxide 作用下， 以73%的产率得到N^α-[4-(1',3'-dioxyl-4',4',5',5'-tetramethyldihydroimidazol-2'-yl)phenyloxyacetyl]-L-arginine
  参考文献：
  名称：

  一类新型的可标记碱性和酸性氨基酸的硝酰基硝基氧：合成，用于制备ESR可选标记肽的应用以及生物活性研究。

  摘要：

  瞄准任选的ESR标记，将2-（4'-羟基）苯基-4,4,5,5-四甲基咪唑啉-3-氧化物-1-氧基引入到L-Arg-OH的胍基中，以甲基羧基为连接基的L-Lys-OH，和以乙氨基为连接基的L-Asp-OH的β-羧基和L-Glu-OH的γ-羧基。研究表明，合成的30种新型ESR标记氨基酸衍生物对肽合成的反应条件足够稳定。他们的加入导致了12种新颖的ESR，可选地标记了PAK，RGDS，RGDV和ECG。一系列与NO相关的化学测试，这些肽的体外和体内测定证实了该策略是可行的。

  DOI：

  10.1016/j.bmc.2008.01.022

文献信息

• A class of novel nitronyl nitroxide labeling basic and acidic amino acids: Synthesis, application for preparing ESR optionally labeling peptides, and bioactivity investigations
  作者：Jianwei Zhang、Ming Zhao、Guohui Cui、Shiqi Peng

  DOI：10.1016/j.bmc.2008.01.022

  日期：2008.4.1

  beta-carboxyl of L-Asp-OH and the gamma-carboxyl of L-Glu-OH with ethylamino as a linker. It was explored that the synthetic 30 novel ESR labeling amino acid derivatives were stable enough to the reaction conditions of peptide synthesis. Their incorporation led to 12 novel ESR optionally labeling PAK, RGDS, RGDV, and ECG. A series of NO related chemical tests, the in vitro and in vivo assays of these

  瞄准任选的ESR标记，将2-（4'-羟基）苯基-4,4,5,5-四甲基咪唑啉-3-氧化物-1-氧基引入到L-Arg-OH的胍基中，以甲基羧基为连接基的L-Lys-OH，和以乙氨基为连接基的L-Asp-OH的β-羧基和L-Glu-OH的γ-羧基。研究表明，合成的30种新型ESR标记氨基酸衍生物对肽合成的反应条件足够稳定。他们的加入导致了12种新颖的ESR，可选地标记了PAK，RGDS，RGDV和ECG。一系列与NO相关的化学测试，这些肽的体外和体内测定证实了该策略是可行的。
• Protective effect of nitronyl nitroxide–amino acid conjugates on liver ischemia–reperfusion induced injury in rats
  作者：Wei Bi、Jianhui Cai、Ping Xue、Yanrong Zhang、Sanguang Liu、Xiang Gao、Meng Li、Zhibo Wang、Michèle Baudy-Floc’h、Sarah A. Green、Lanrong Bi

  DOI：10.1016/j.bmcl.2008.02.030

  日期：2008.3

  Stable nitroxides are potential antioxidant drugs. In this study, we have linked nitroxide to natural amino acids with the aim to improve therapeutic activity. The radical scavenging activities of two nitronyl nitroxide - amino acid conjugates ( NNR and NNK) were evaluated in PC 12 cell survival assays. The NO scavenging activities of these compounds were confirmed in the acetylcholine-induced vasorelaxation assay. In addition, the protective effect of NNR was demonstrated in an in vivo rat model of hepatic ischemia - reperfusion ( I/ R) induced injury and oxidative change. Because NNR reduced hepatic I/ R injury by minimizing oxidative stress, it might be possible to develop it into a possible therapeutic agent for hepatic I/ R injury. (C) 2008 Elsevier Ltd. All rights reserved.