亚硝酸氧盐 | 19059-14-4

• 分子结构分类: 无机化合物 - 均质非金属化合物 - 非金属氧阴离子化合物
• 中文名称: 亚硝酸氧盐
• 英文名称: peroxynitrite
• 英文别名: peroxynitrite anion；ONOO-；peroxynitrite ion；Oxido nitrite
• CAS: 19059-14-4
• 化学式: NO₃
• 分子量: 62.0049
• InChiKey: CMFNMSMUKZHDEY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  亚硝酸氧盐 在 [Mn(III)(TMpyP)(H2O)OH](4+) 作用下， 以 水 为溶剂， 生成 二氧化氮
  参考文献：
  名称：

  Manganese Porphyrins as Redox-Coupled Peroxynitrite Reductases

  摘要：

  Superoxide (O-2.(-)) and peroxynitrite (ONOO-) have been implicated in many pathophysiological conditions. To develop novel catalysts that have both ONOO- decomposition and O-2.(-) dismutase activity, and to understand the mechanisms of these processes, we have explored the reactivity of 5,10, 15,20-tetrakis(N-methyl-4'-pyridyl)porphinatomanganese [Mn(III)TMPyP] toward ONOO- and O-2.(-). The reaction of Mn(III)TMPyP with ONOO- to generate an oxomanganese(IV) porphyrin species [(oxoMn(IV)] is fast, but Mn(III)TMPyP is not catalytic for ONOO- decomposition because of the slow reduction of oxoMn(IV) back to the Mn(III) oxidation state. However, biological antioxidants such as ascorbate, glutathione, and Trolox rapidly turn over the catalytic cycle by reducing oxoMn(IV). Thus, Mn(III)TMPyP becomes an efficient peroxynitrite reductase when coupled with ascorbate, glutathione, and Trolox (k(c) approximate to 2 x 10(6) M-1 s(-1)), though the direct reactions of ONOO- with these biological antioxidants are slow (88 M-1 s(-1), 5.8 x 10(2) M-1 s(-1) and 33 M-1 s(-1), respectively). Mn(In)TMPyP is known to catalyze the dismutation of O-2.(-), and using stopped-flow spectrophotometry, the rate of Mn(III)TMPyP-catalyzed dismutation has been measured directly (k(c)= 1.1 x 10(7) M-1 s(-1)). Further, O-2.(-), like the biological antioxidants, rapidly reduces oxoMn(IV) to the Mn(III) oxidation state (k approximate to 10(8) M-1 s(-1)), transforming Mn(III)TMPyP into a O-2.(-)-coupled ONOO- reductase. Under conditions of oxidative stress and reduced antioxidant levels, Mn(III)TMPyP may deplete O-2.(-) primarily as a function of its ONOO- reductase activity, and not through its O-2.(-) dismutase activity.

  DOI：

  10.1021/ja9801036
• 作为产物：
  描述：

  sodium nitrite 在 盐酸 、 双氧水 、 sodium hydroxide 作用下， 生成 亚硝酸氧盐
  参考文献：
  名称：

  An uncommon redox behavior sheds light on the cellular antioxidant properties of ergothioneine

  摘要：

  Ergothioneine (ESH), an aromatic thiol occurring in the human diet and which accumulates in particular cells, is believed to act as an antioxidant. However, its redox mechanism remains unclear and it does not seem to provide any advantage compared to other antioxidants, such as alkylthiols, which are better reducing agents and generally present in cells at higher levels. Here, we investigated by ESI-MS the products of ESH oxidation produced by neutrophils during oxidative burst and, to further elucidate ESH redox behavior, we also analyzed the oxidation products of the reaction of ESH with hypochlorite in cell-free solutions. Indeed, neutrophils are the main source of hypochlorite in humans. Furthermore, we also tested other biologically relevant oxidants, such as peroxynitrite and hydrogen peroxide. Our results indicate that treatment of human neutrophils with phorbol 12-myristate 13-acetate in the presence of ESH leads to a remarkable production of the sulfonated form (ESO3H), a compound never described before, and hercynine (EH), the desulfurated form of ESH. Similar results were obtained when ESH was subjected to cell-free oxidation in the presence of hypochlorite, as well as hydrogen peroxide or peroxynitrite. Furthermore, when the disulfide of ESH was reacted with those oxidants, we found that it was also oxidized, with production of EH and ESO3H, whose amount was dependent on the oxidant strength. These data reveal a unique ESH redox behavior, entirely different from that of alkylthiols, and suggest a mechanism, so far overlooked, through which ESH performs its antioxidant action in cells. (C) 2015 Published by Elsevier Inc.

  DOI：

  10.1016/j.freeradbiomed.2014.11.017
• 作为试剂：
  描述：

  卡托普利二硫化物 在 亚硝酸氧盐 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 10.33h， 生成
  参考文献：
  名称：

  基于肽的卡托普利类似物对血管紧张素转化酶活性和过氧亚硝酸盐介导的酪氨酸硝化作用的影响†

  摘要：

  血管紧张素 转换酶（ACE）通过转换来调节血压 血管紧张素 我来 血管紧张素II 和 缓激肽 到 缓激肽1–7。这两个反应使血压升高血管紧张素II 和 缓激肽分别是血管收缩激素和血管舒张激素。因此，抑制ACE是治疗高血压的重要策略。ACE的天然底物，即，血管紧张素II 和 缓激肽在水解位点附近含有Pro-Phe基序。因此，在ACE的活性位点可能存在Pro-Phe结合口袋，这可能有助于底物结合。有鉴于此，我们合成了一系列含巯基和硒醇的二肽和卡托普利类似物并研究了它们的ACE抑制活性。这项研究表明硒醇或巯基部分和脯氨酸残基对于ACE抑制都是必不可少的。虽然引入了苯丙氨酸残基卡托普利 并且它的硒类似物大大降低了抑制作用，在ACE的活性位点似乎有一个Phe结合口袋。

  DOI：

  10.1039/c1ob05148b

文献信息

• Alleviating Cellular Oxidative Stress through Treatment with Superoxide‐Triggered Persulfide Prodrugs
  作者：Yin Wang、Kearsley M. Dillon、Zhao Li、Ethan W. Winckler、John B. Matson

  DOI：10.1002/anie.202006656

  日期：2020.9.14

  specifically with O2.−, decomposing to generate N‐acetyl cysteine (NAC) persulfide. To enhance persulfide delivery to cells, we conjugated the SOPD motif to a short, self‐assembling peptide (Bz‐CFFE‐NH2) to make a superoxide‐responsive, persulfide‐donating peptide (SOPD‐Pep). Both SOPD‐NAC and SOPD‐Pep delivered persulfides/H2S to H9C2 cardiomyocytes and lowered ROS levels as confirmed by quantitative in vitro

  超氧阴离子 (O 2 .− )（主要细胞活性氧 (ROS)）的过量产生与多种人类疾病有关。为了减少超氧化物过量产生的细胞氧化应激，我们开发了一种与 O 2 .−反应释放过硫化物 (RSSH) 的化合物，过硫化物是一种与气体递质硫化氢 (H 2 S) 相关的活性硫物质。这种过硫化物供体被称为SOPD-NAC ，与 O 2 .−发生特异性反应，分解生成N-乙酰半胱氨酸 (NAC) 过硫化物。为了增强过硫化物向细胞的输送，我们将 SOPD 基序与短的自组装肽 (Bz-CFFE-NH 2 ) 结合，形成超氧化物响应性过硫化物供给肽 ( SOPD-Pep )。定量体外荧光成像研究证实，SOPD-NAC和SOPD-Pep均将过硫化物/H 2 S 递送至 H9C2 心肌细胞并降低 ROS 水平。对 RAW 264.7 巨噬细胞的其他体外研究表明，SOPD-Pep比SOPD-NAC和几种对照化合物（包括常见的
• Functional hybrids of layered double hydroxides with hemin: synergistic effect for peroxynitrite-scavenging activity
  作者：Fengmin Qiao、Weijie Shi、Jing Dong、Wei Lv、Shiyun Ai

  DOI：10.1039/c4ra08200a

  日期：——

  Hemin has been successfully modified onto the surface of CuAl layered double hydroxide nanosheets by a simple coprecipitation process, which afforded a hemin modified CuAl layered double hydroxide (H-LDH) hybrid functional material that exhibited protective effects against the harmful ONOO−. The obtained products were characterized by X-ray powder diffraction, scanning electron microscopy, transmission

  氯高铁血红素已经成功修改到的CuAl的表面层状双氢氧化物纳米片通过简单的共沉淀法，得到改性的CuAl一氯高铁血红素层状双氢氧化物（H-LDH）混合功能的材料，其表现出对有害ONOO保护作用- 。通过X射线粉末衍射，扫描电子显微镜，透射电子显微镜和傅里叶变换红外光谱对所得产物进行表征，结果表明样品具有六边形对称结构，平均横向尺寸为1μm，表面被吸附。直径约300 nm的圆形颗粒。对ONOO的详细抑制研究-介导的硝化反应表明，在有协同作用氯高铁血红素和水滑石的结果之间的相互作用，这导致有效地降低ONOO的-为硝酸盐。目前的研究表明，H-水滑石有一个高效的ONOO -清除能力，也不失为一种有效的ONOO -清除剂对ONOO细胞防御活动的保护-相关的疾病。
• pH‐Dependent Nitrotyrosine Formation in Ribonuclease A is Enhanced in the Presence of Polyethylene Glycol (PEG)
  作者：Pritam Roy、Atashi Panda、Sumon Hati、Swagata Dasgupta

  DOI：10.1002/asia.201901225

  日期：2019.12.13

  crowded medium. The degree of nitration is higher at pH 7.4 (physiological pH) compared to pH 6.0 (tumor cell pH). The extent of nitration increases significantly when PN is added to RNase A in the presence of crowding agents PEG 400 and PEG 6000. PEG has been found to stabilize PN over a prolonged period, thereby increasing the degree of nitration. NT formation in RNase A also results in a significant

  过氧亚硝酸盐介导的氧化应激可能导致蛋白质硝化。细胞培养基中过亚硝酸盐（PN）的过量产生会导致生物分子的氧化损伤。核糖核酸酶A（RNase A）的体外硝化导致硝基酪氨酸（NT）的形成，强烈依赖于培养基的pH。为了模拟本研究中的细胞环境，已经在拥挤的培养基中进行了PN介导的RNase A硝化作用。与pH 6.0（肿瘤细胞pH）相比，pH 7.4（生理pH）下的硝化度更高。当在拥挤剂PEG 400和PEG 6000存在下将PN添加到RNase A中时，硝化程度会显着增加。已发现PEG可长时间稳定PN，从而增加硝化度。
• Pulse-radiolysis study of the reaction of nitric oxide with superoxide
  作者：Kazuo Kobayashi、Miyako Miki、Seiichi Tagawa

  DOI：10.1039/dt9950002885

  日期：——

  Using the pulse-radiolysis technique, nitric oxide (NO) was produced by the reaction of an hydrated electron with NO2–. This was verified by the formation of the NO complex of iron(II) myoglobin (Mb) after pulse radiolysis of iron(III) myoglobin in the presence of NO2– under anaerobic conditions. By employing this technique, the reaction of superoxide (O2–) with NO was followed directly in an oxygen-saturated

  使用脉冲辐解技术，一氧化氮（NO）通过用一个NO水合电子反应生成2 - 。这通过的NO络合铁的形成验证（II）的肌红蛋白（MB）铁（的脉冲辐解后III在NO存在下）肌红蛋白2 -在厌氧条件下。通过采用这种技术，反应超氧化物（O 2 - ）与NO在含有NO的氧饱和溶液之后直接跟随2 - 。发现O 2 –与NO反应的二级速率常数为3.8×10 9 dm 3 mol –1s –1在pH 7.5下形成氧过氧膦酸酯（III）[NO（O 2）– ]，其最大吸收在300 nm附近。由此形成的过氧过氧酸（III）在pH 7.5时的一级速率常数为0.8 s –1分解。通过监控的停止流，在O 2 –与NO的反应中观察到了类似的衰减过程，其中将二甲基亚砜中的一部分KO 2与9份的NO饱和水溶液混合。在停止流系统的停滞时间内，过氧肟酸（III）的形成完成。
• Direct evidence of singlet molecular oxygen generation from peroxynitrate, a decomposition product of peroxynitrite
  作者：Sayuri Miyamoto、Graziella E. Ronsein、Thaís C. Corrêa、Glaucia R. Martinez、Marisa H. G. Medeiros、Paolo Di Mascio

  DOI：10.1039/b905560f

  日期：——

  The decomposition of peroxynitrite to nitrite and dioxygen at neutral pH follows complex kinetics, compared to its isomerization to nitrate at low pH. Decomposition may involve radicals or proceed by way of the classical peracid decomposition mechanism. Peroxynitrite (ONOOH/ONOO(-)) decomposition has been proposed to involve formation of peroxynitrate (O(2)NOOH/O(2)NOO(-)) at neutral pH (D. Gupta,

  与在低pH下异构化为硝酸盐相比，在中性pH下过氧化亚硝酸盐分解为亚硝酸盐和双氧具有复杂的动力学。分解可能涉及自由基或通过经典的过酸分解机理进行。已提出过氧亚硝酸盐（ONOOH / ONOO（-））分解涉及在中性pH值下形成过氧硝酸盐（O（2）NOOH / O（2）NOO（-））（D. Gupta，B.Harish，R.Kissner和WH Koppenol，Dalton Trans。，2009，DOI：10.1039 / b905535e，请参阅本期随附的论文）。过氧硝酸盐不稳定并分解为亚硝酸盐和双氧。这项研究旨在调查是否ONOOH / ONOO（-）分解形成O（2）NOO（-）生成单线态分子氧[O（2）（（1）Delta（g））]。正如通过在1270 nm处的近红外区域中测量单摩尔发光以及通过化学捕集实验所明确揭示的那样，在中性至碱性pH值下ONOO（-）或O（2）NOOH的分解生成O（2）（（1