(1H-咪唑-4-基)-乙醛 | 645-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (1H-咪唑-4-基)-乙醛
• 英文名称: (3H-imidazol-4-yl)acetaldehyde
• 英文别名: 2-imidazoleacetaldehyde；imidazolylacetaldehyde；Imidazole-4-acetaldehyde；2-(1H-imidazol-5-yl)acetaldehyde
• CAS: 645-14-7
• 化学式: C₅H₆N₂O
• 分子量: 110.115
• InChiKey: MQSRGWNVEZRLDK-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  (1H-咪唑-4-基)-乙醛 在 histamine dehydrogenase from Rhizobium species 作用下， 生成 组胺
  参考文献：
  名称：

  Development of a novel l-histidine assay method using histamine dehydrogenase and a stable mutant of histidine decarboxylase

  摘要：

  L-Histidine analysis is essential in physiological research and clinical applications because L-histidine concentrations in biofluids are associated with various diseases. However, an enzymatic method for L-histidine quantitation has not yet been established. Here, we describe a novel L-histidine quantitation assay using a combination of histidine decarboxylase (HDC) and histamine dehydrogenase (HDH) enzymes. Wild-type HDC is unstable and completely lost its activity within 50 days of storage at 4 degrees C in solution. We rationally designed a HDC C57S mutant with markedly improved stability (storage at 4 degrees C for over 200 days) without altering the enzyme's substrate specificity. Together with HDH, the HDC C57S mutant was applied to quantify L-histidine concentrations in human plasma. The assay showed high precision (< 2.0% inter-assay variation) and high accuracy (< 5.8% deviation from the results of LC/MS).

  DOI：

  10.1016/j.ab.2018.12.017
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hypochlorite 、 水 作用下， 生成 (1H-咪唑-4-基)-乙醛
  参考文献：
  名称：

  Langheld, Chemische Berichte, 1909, vol. 42, p. 2372

  摘要：

  DOI：

文献信息

• Inhibitors of Tumor Progression Loci-2 (Tpl2) Kinase and Tumor Necrosis Factor α (TNF-α) Production:  Selectivity and in Vivo Antiinflammatory Activity of Novel 8-Substituted-4-anilino-6-aminoquinoline-3-carbonitriles
  作者：Neal Green、Yonghan Hu、Kristin Janz、Huan-Qiu Li、Neelu Kaila、Satenig Guler、Jennifer Thomason、Diane Joseph-McCarthy、Steve Y. Tam、Rajeev Hotchandani、Junjun Wu、Adrian Huang、Qin Wang、Louis Leung、Jefferey Pelker、Suzana Marusic、Sang Hsu、Jean-Baptiste Telliez、J. Perry Hall、John W. Cuozzo、Lih-Ling Lin

  DOI：10.1021/jm070436q

  日期：2007.9.1

  involved in diseases such as rheumatoid arthritis. Initial 4-anilino-6-aminoquinoline-3-carbonitrile leads showed poor selectivity for Tpl2 over epidermal growth factor receptor (EGFR) kinase. Using molecular modeling and crystallographic data of the EGFR kinase domain with and without an EGFR kinase-specific 4-anilinoquinazoline inhibitor (erlotinib, Tarceva), we hypothesized that we could diminish the

  肿瘤进展基因座2（Tpl2）（Cot / MAP3K8）是MAP3K家族中位于MEK上游的丝氨酸/苏氨酸激酶。最近使用Tpl2敲除小鼠的研究表明Tpl2在脂多糖（LPS）诱导的肿瘤坏死因子α（TNF-alpha）和其他与风湿性关节炎等疾病有关的促炎细胞因子的产生中具有重要作用。最初的4-苯胺基-6-氨基喹啉-3-甲腈导线显示出对Tpl2的选择性较表皮生长因子受体（EGFR）激酶差。使用和不使用EGFR激酶特异性4-苯胺基喹唑啉抑制剂（erlotinib，Tarceva）的EGFR激酶结构域的分子模型和晶体学数据，我们假设我们可以通过在C-8位置进行取代来减少对EGFR激酶的抑制作用4-苯胺基-6-氨基喹啉-3-腈引线。由适当的2-取代的4-硝基苯胺制备8-取代的4-苯胺基-6-氨基喹啉-3-甲腈。对C-6和C-8位置的修饰导致鉴定了对LPS刺激的大鼠和人类血液中TNF-α释放抑制作用增强的
• Site-directed mutation at residues near the catalytic site of histamine dehydrogenase from Nocardioides simplex and its effects on substrate inhibition
  作者：Maiko Tsutsumi、Noriaki Tsuse、Nobutaka Fujieda、Kenji Kano

  DOI：10.1093/jb/mvp162

  日期：2010.2

  Histamine dehydrogenase from Nocardioides simplex (nHmDH) is a homodimer containing one 6-S-cysteinyl FMN (CFMN) and one [4Fe–4S] cluster per monomer. nHmDH catalyses the oxidative deamination of histamine to ammonia and imidazole acetaldehyde, but histamine inhibits its catalytic activity at high concentrations. We mutated gene-encoded residues (Tyr180, Gly268 and Asp269) near CFMN to understand the biophysical meaning of the substrate inhibition. Three mutants Y180F, G268D/D269C and Y180F/G268D/D269C were expressed by considering the DNA sequence alignment of histamine dehydrogenase from Rhizobium sp. 4-9 (rHmDH), which does not suffer from the substrate inhibition. The Y180F/G268D/D269C mutation to mimic rHmDH successfully suppressed the inhibition, although the catalytic activity decreased. The substrate inhibition was weakened by the Y180F mutation, but G268D/D269C was still susceptible to the inhibition. It was found that it also causes changes in the UV-vis absorption spectra of the substrate-reduced form and the redox potential of the enzymes. The characterization suggests that the thermodynamic preference of the semiquinone form of CFMN in the two-electron-reduced subunit of the enzyme is responsible for the substrate inhibition. However, destabilization of the semiquinone form leads to kinetic hindrance due to the uphill single electron transfer from the fully reduced CFMN to the [4Fe–4S] cluster.

  来自Nocardioides simplex (nHmDH)的组胺脱氢酶是一种同型二聚体，每个单体含有一个6-S-半胱氨酰FMN (CFMN)和一个[4Fe-4S]簇。nHmDH催化组胺的氧化性脱氨作用生成氨和咪唑乙醛，但在高浓度下组胺会抑制其催化活性。我们突变了基因编码的残基（酪氨酸180、甘氨酸268和天冬氨酸269），以理解底物抑制的生物物理意义。根据来自根瘤菌4-9 (rHmDH)的组胺脱氢酶的DNA序列比对，该菌不受底物抑制的影响，我们表达了三种突变体Y180F、G268D/D269C和Y180F/G268D/D269C。Y180F/G268D/D269C突变成功地抑制了抑制作用，尽管催化活性有所下降。Y180F突变削弱了底物抑制，但G268D/D269C仍然容易受到抑制。研究发现，这还导致底物还原形式的紫外-可见吸收光谱和酶的氧化还原电位的变化。研究表明，酶的两电子还原单体中CFMN的半醌形式的能量偏好导致了底物抑制。然而，半醌形式的失稳导致由于从完全还原的CFMN向[4Fe-4S]簇的单电子转移的上坡动力学障碍。
• Magnetic nanoparticles loaded on mobile crystalline material-41: preparation, characterization and application as a novel material for the construction of an electrochemical nanosensor
  作者：Mohammad Hasanzadeh、Arash Bahrami、Mohammad Alizadeh、Nasrin Shadjou

  DOI：10.1039/c3ra42393j

  日期：——

  Herein, we envisage the possibility of preparing stable magnetic mobile crystalline material-41 using cetyltrimethylammonium bromide and Fe3O4 nanoparticles. The Fe3O4 nanoparticles are incorporated into mobile crystalline material-41 in hydrothermal conditions. The prepared mesoporous sample was characterized by Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy (SEM) and nitrogen adsorption–desorption techniques. The electrochemical behavior of cadaverine, histamine and putrescine was investigated on magnetic mobile crystalline material-41 (MCM-41-Fe2O3) modified carbon paste electrodes (CPEs). Due to the very large surface area (1213 m2 g−1) and the remarkable electrocatalytic properties of Fe2O3 nanoparticles, MCM-41-Fe2O3 exhibits potent electrocatalytic activity toward the electrooxidation of some selected biogenic amines. MCM-41-Fe2O3-CPEs provide new capabilities for electrochemical sensing by combining the advantages of Fe2O3 magnetic nanoparticles and MCM-41 with a very large surface area. The process of oxidation and its kinetics were established by using cyclic voltammetry, chronoamperometry techniques, and also, steady state polarization measurements. The apparent electron transfer rate constant (Ks) and transfer coefficient (α) were determined by cyclic voltammetry and were approximately 6.2 s−1 and 0.48, respectively. The linear concentration ranges of the proposed sensors for cadaverine, histamine and putrescine were 0.1–10, 0.01–0.5 and 0.9–35 μM, respectively. Finally, the applicability of the sensor to the determination of electroactive biogenic amine concentrations in fish samples has been successfully demonstrated.

  在此，我们设想利用十六烷基三甲基溴化铵和Fe3O4纳米颗粒制备稳定的磁性移动晶体材料41。Fe3O4纳米颗粒在水热条件下被纳入移动晶体材料41中。所制备的介孔样品通过傅里叶变换红外光谱（FTIR）、X射线衍射（XRD）、扫描电子显微镜（SEM）和氮气吸附-脱附技术进行了表征。我们在改性碳糊电极（CPEs）上研究了尸胺、组胺和腐胺的电化学行为。由于Fe2O3纳米颗粒具有非常大的表面积（1213 m² g⁻¹）和显著的电催化特性，MCM-41-Fe2O3对某些选定的生物胺的电氧化表现出强大的电催化活性。MCM-41-Fe2O3-CPEs通过结合Fe2O3磁性纳米颗粒和具有非常大表面积的MCM-41的优点，为电化学传感提供了新的能力。通过循环伏安法、计时安培法以及稳态极化测量确定了氧化过程及其动力学。表观电子转移速率常数（Ks）和转移系数（α）通过循环伏安法测定，分别约为6.2 s⁻¹和0.48。所提传感器对尸胺、组胺和腐胺的线性浓度范围分别为0.1–10、0.01–0.5和0.9–35 μM。最后，成功演示了传感器在鱼样品中测定电活性生物胺浓度的适用性。
• Influence of copper(II) catalyst on the oxidation of l-histidine by platinum(IV) in alkaline medium: a kinetic and mechanistic study
  作者：Ahmed Fawzy

  DOI：10.1007/s11243-014-9834-9

  日期：2014.8

  The kinetics of oxidation of l-histidine (His) by platinum(IV) in the absence and presence of copper(II) catalyst was studied using spectrophotometry in alkaline medium at a constant ionic strength of 0.1 mol dm−3 and at 25 °C. In both cases, the reactions exhibit a 1:1 stoichiometry ([His]:[PtIV]). The rate of the uncatalyzed reaction is dependent on the first power of each of the concentrations of

  使用分光光度法在碱性介质中以 0.1 mol dm-3 的恒定离子强度和 25 °C 研究了在不存在和存在铜 (II) 催化剂的情况下铂 (IV) 氧化 l-组氨酸 (His) 的动力学. 在这两种情况下，反应都表现出 1:1 的化学计量比 ([His]:[PtIV])。未催化反应的速率取决于氧化剂、底物和碱的每一种浓度的一次幂。催化路径显示出对 [PtIV] 和 [CuII] 的一级依赖性，但关于 [His] 和 [OH-] 的顺序小于统一。速率常数随着介质的离子强度和介电常数的增加而增加。已显示催化反应通过形成铜 (II)_组氨酸中间体复合物进行，它通过内球机制与氧化剂反应，导致复合物在速率决定步骤中分解。铂 (IV) 在一步两电子转移过程中被基板还原为铂 (II)。随后是其他快速步骤，产生氧化产物，经鉴定为 2-咪唑乙醛、氨和二氧化碳。提出了一种初步的反应机制，并推导出了相关的速率定
• Redox Hydrogel-Based Amperometric Bienzyme Electrodes for Fish Freshness Monitoring
  作者：Mihaela Niculescu、Catalin Nistor、Ivo Frébort、Pavel Peč、Bo Mattiasson、Elisabeth Csöregi

  DOI：10.1021/ac990848+

  日期：2000.4.1

  This work presents the design and optimization of amperometric biosensors for the determination of biogenic amines (e.g., histamine, putrescine, cadaverine, tyramine, cystamine, agmatine, spermidine), commonly present in food products, and their application for monitoring of freshness in fish samples. The biosensors were used as the working electrodes of a three-electrode electrochemical cell of wall-jet type, operated at −50 mV vs Ag/AgCl, in a flow injection system. Two different bienzyme electrode designs were considered, one based on the two enzymes [a newly isolated and purified amine oxidase (AO) and horseradish peroxidase (HRP)] simply adsorbed onto graphite electrodes, and one when they were cross-linked to an Os-based redox polymer. The redox hydrogel-based biosensors showed better biosensors characteristics, i.e., sensitivity of 0.194 A M-1 cm-2 for putrescine and 0.073 A M-1 cm-2 for histamine, and detection limits (calculated as three times the signal-to-noise ratio) of 0.17 μM for putrescine and 0.33 μM for histamine. The optimized redox hydrogel-based biosensors were evaluated in terms of stability and selectivity, and were used for the determination of total amine content in fish samples kept for 10 days in different conditions.

  本研究提出了用于测定食品中常见生物胺（如组胺、腐胺、尸胺、酪胺、半胱胺、阿根廷胺、丝氨酸）的安培生物传感器设计与优化，并应用于监测鱼样的鲜度。这些生物传感器作为一种墙射流型三电极电化学池的工作电极，在流动注射系统中以相对于Ag/AgCl的−50 mV进行操作。考虑了两种不同的双酶电极设计，一种是基于两种酶（新分离和纯化的胺氧化酶（AO）和辣根过氧化物酶（HRP））简单吸附在石墨电极上，另一种是将其交联到基于Os的红氧聚合物上。基于红氧水凝胶的生物传感器表现出更好的特性，即对腐胺的灵敏度为0.194 A M^-1 cm^-2，对组胺的灵敏度为0.073 A M^-1 cm^-2，检测限（计算为信噪比的三倍）为腐胺0.17 μM和组胺0.33 μM。优化后的基于红氧水凝胶的生物传感器在稳定性和选择性方面进行了评估，并用于测定在不同条件下保存10天的鱼样的总胺含量。