angiotensin III | 13602-53-4

• 物质功能分类: 生物化工 - 多肽
• 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: angiotensin III
• 英文别名: Arg-Val-Tyr-Ile-His-Pro-Phe；human angiotensin III；angiotensin-(1-7)；angiotensin-III；angotensin-III；angiotensin 3；(2S)-2-[[(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid
• CAS: 13602-53-4；32738-16-2；82043-65-0
• 化学式: C₄₆H₆₆N₁₂O₉
• 分子量: 931.105
• InChiKey: QMMRCKSBBNJCMR-KMZPNFOHSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)
• 溶解度：
  H2O：1.0 mg/mL，澄清，无色
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  67
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  342
• 氢给体数：
  11
• 氢受体数：
  12

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Angiotensin III（人源、小鼠）是一种七肽，为血管紧张素 2 型受体 (AT2R) 激动剂。其对 AT2R 和 AT1R 的 IC50 分别为 0.648 nM 和 21.1 nM。

靶点

• IC50: 0.648 nM（AT2R），21.1 nM（AT1R）

体外研究

Angiotensin III（人源、小鼠）是一种七肽，作为内源性血管紧张素 2 型受体 (AT2R) 激动剂。其对 AT2R 和 AT1R 的 IC50 分别为 0.648 nM 和 21.1 nM。

体内研究

在 SD 大鼠中，Angiotensin III（7、14 和 28 nmol/kg/min）可增加尿钠排泄 (U_Na)、钠的分数排泄 (FE_Na) 和锂的分数排泄 (FE_Li)。在肾素-血管紧张素系统 (RAS) 中，Angiotensin III 增加交感神经活动和抗利尿激素释放，并降低压力感受性反射，从而导致大鼠血压升高。

反应信息

• 作为反应物：
  描述：

  angiotensin III 在 ferrous ammonium sulphate 、 双氧水 、 disodium ethylenediaminetetraacetic acid 、 碳酸氢铵 、 硫脲 、 DL-蛋氨酸 作用下， 以 水 为溶剂， 反应 0.27h， 生成
  参考文献：
  名称：

  A new biomarker of protein oxidation degree and site using angiotensin as the target by MS

  摘要：

  Hydroxyl radicals generated from Fenton reaction were used to damage the angiotensin. The oxidative damage degree and sites of peptides were measured by HPLC-MS and MS/MS. Experimental results proved that the oxidative damage degree increased with longer reaction time. The results also showed that the side chains of phenylalanine and tyrosine in angiotension can be attacked by hydroxyl radicals to form the oxidative products. A new strategy was established to monitor the oxidative degree and sites of peptides and laid the foundation for protein oxidation. This method can be used to investigate the mechanism of protein oxidative damage caused by oxidative stress which is induced by environmental pollutants and physiological activities. There will also be a wide application in the research of pathogenesis of some disease related to oxidative stress. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2009.12.034
• 作为产物：
  描述：

  血管紧张素II 在 aspartyl aminopeptidase 、 水 作用下， 以 二甲基亚砜 为溶剂， 生成 L-天门冬氨酸 、 angiotensin III
  参考文献：
  名称：

  哺乳动物天冬氨酰氨肽酶新型抑制剂的鉴定和表征。

  摘要：

  天冬氨酰氨肽酶 (DNPEP) 与血管紧张素信号传导和内体运输的控制有关，但其精确的生物学作用仍未完全确定。我们对约 25,000 个小分子进行了高通量筛选，以鉴定 DNPEP 抑制剂，用作研究其生物学功能的工具。23 次确认的命中抑制了 DNPEP 催化的血管紧张素 II 水解，具有微摩尔效力。谷氨酰氨肽酶 (ENPEP) 是一种底物特异性与 DNPEP 相似的酶，通过反筛选确定了八种 DNPEP 选择性抑制剂。构效关系和建模研究揭示了已鉴定抑制剂共有的结构特征，包括金属螯合基团和可与酶活性位点部分相互作用的带电或极性部分。

  DOI：

  10.1124/mol.114.093070

文献信息

• 5(4H)-Oxazolinones as acyl donors in papain-catalyzed peptide fragment condensations
  作者：Byung Keun Hwang、Qu-Ming Gu、Charles J. Sih

  DOI：10.1016/0040-4039(94)85208-1

  日期：1994.4

  Papain, a thiol protease was shown to utilize 5(4H)-oxazolinones of peptides as acyl donors in peptide segment condensations. The effectiveness of this methodology is illustrated by the successful coupling of oxidized insulin B chain (30 residues) to angiotensin III (7 residues) in 59% yield.

  木瓜蛋白酶，一种硫醇蛋白酶，在肽段缩合中显示出利用5（4H）-恶唑啉酮作为酰基供体。该方法的有效性通过氧化胰岛素B链（30个残基）与血管紧张素III（7个残基）的成功偶联以59％的产率得以说明。
• Improving fragmentation of poorly fragmenting peptides and phosphopeptides during collision-induced dissociation by malondialdehyde modification of arginine residues
  作者：Alexander Leitner、Alexandra Foettinger、Wolfgang Lindner

  DOI：10.1002/jms.1233

  日期：2007.7

  Despite significant technological and methodological advancements in peptide sequencing by mass spectrometry, analyzing peptides that exhibit only poor fragmentation upon collision-induced dissociation (CID) remains a challenge. A major cause for unfavorable fragmentation is insufficient proton ‘mobility’ due to charge localization at strongly basic sites, in particular, the guanidine group of arginine. We have recently demonstrated that the conversion of the guanidine group of the arginine side chain by malondialdehyde (MDA) is a convenient tool to reduce the basicity of arginine residues and can have beneficial effects for peptide fragmentation. In the present work, we have focused on peptides that typically yield incomplete sequence information in CID-MS/MS experiments. Energy-resolved tandem MS experiments were carried out on angiotensins and arginine-containing phosphopeptides to study in detail the influence of the modification step on the fragmentation process. MDA modification dramatically improved the fragmentation behavior of peptides that exhibited only one or two dominant cleavages in their unmodified form. Neutral loss of phosphoric acid from phosphopeptides carrying phosphoserine and threonine residues was significantly reduced in favor of a higher abundance of fragment ions. Complementary experiments were carried out on three different instrumental platforms (triple-quadrupole, 3D ion trap, quadrupole–linear ion trap hybrid) to ascertain that the observation is a general effect. Copyright © 2007 John Wiley & Sons, Ltd.

  尽管质谱技术在肽测序方面取得了重大的技术和方法进步，但分析碰撞诱导解离（CID）后碎片不佳的肽仍然是一项挑战。造成碎片不佳的一个主要原因是质子在强碱性位点（尤其是精氨酸的胍基）的电荷定位导致质子 "流动性 "不足。我们最近证明，用丙二醛（MDA）转换精氨酸侧链的胍基是降低精氨酸残基碱性的一种便捷工具，对肽的破碎有好处。在本研究中，我们重点研究了在 CID-MS/MS 实验中通常会产生不完整序列信息的肽段。我们对血管紧张素和含精氨酸的磷酸肽进行了能量分辨串联质谱实验，以详细研究修饰步骤对碎裂过程的影响。MDA 修饰极大地改善了肽的碎裂行为，这些肽在未修饰状态下只有一到两种主要裂解。携带磷酸丝氨酸和苏氨酸残基的磷酸肽的磷酸中性损失显著减少，碎片离子的丰度更高。在三种不同的仪器平台（三重四极杆、三维离子阱、四极杆线性离子阱混合型）上进行了补充实验，以确定该观察结果是一种普遍效应。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.
• HOMOGENEOUS IMMUNOASSAYS AND ENZYME BASED ASSAYS OF ANALYTES USING CAPILLARY ELECTROPHORESIS
  申请人：BECKMAN INSTRUMENTS, INC.

  公开号：EP0740790A1

  公开（公告）日：1996-11-06
• [EN] HOMOGENEOUS IMMUNOASSAYS AND ENZYME BASED ASSAYS OF ANALYTES USING CAPILLARY ELECTROPHORESIS<br/>[FR] IMMUNODOSAGES HOMOGENES ET DOSAGES ENZYMATIQUES D'ANALYTES PAR ELECTROPHORESE CAPILLAIRE
  申请人：BECKMAN INSTRUMENTS, INC.

  公开号：WO1995020161A1

  公开（公告）日：1995-07-27

  (EN) Homogeneous immunoassays and enzyme-substrate assays which use capillary electrophoresis and fluorescent detection systems are described. The method is useful for detecting and/or quantitating the concentration of analytes in a sample.(FR) La présente invention concerne des immunodosages homogènes et des dosages à substrats enzymatiques par électrophorèse capillaire et des systèmes de détection par fluorescence. Le procédé convient particulièrement à la détection et/ou à la quantification de la concentration d'analytes dans un échantillon.
• A new biomarker of protein oxidation degree and site using angiotensin as the target by MS
  作者：Yanmin Tian、Rutao Liu、Wansong Zong、Feng Sun、Meijie Wang、Pengjun Zhang

  DOI：10.1016/j.saa.2009.12.034

  日期：2010.2

  Hydroxyl radicals generated from Fenton reaction were used to damage the angiotensin. The oxidative damage degree and sites of peptides were measured by HPLC-MS and MS/MS. Experimental results proved that the oxidative damage degree increased with longer reaction time. The results also showed that the side chains of phenylalanine and tyrosine in angiotension can be attacked by hydroxyl radicals to form the oxidative products. A new strategy was established to monitor the oxidative degree and sites of peptides and laid the foundation for protein oxidation. This method can be used to investigate the mechanism of protein oxidative damage caused by oxidative stress which is induced by environmental pollutants and physiological activities. There will also be a wide application in the research of pathogenesis of some disease related to oxidative stress. (C) 2010 Elsevier B.V. All rights reserved.