7-Hydroxy-3H-phenoxazine-3-one anion | 23209-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-Hydroxy-3H-phenoxazine-3-one anion
• 英文别名: 7-hydroxy-3H-phenoxazin-3-one anion；Resorufin anion；resorufin；7-hydroxy-phenoxazin-3-one; deprotonated form；resorufin; deprotonated form；7-Hydroxyphenoxazin-3-one, sodium salt；7-oxophenoxazin-3-olate
• CAS: 23209-94-1
• 化学式: C₁₂H₆NO₃
• 分子量: 212.185
• InChiKey: HSSLDCABUXLXKM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• 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：

  7-Hydroxy-3H-phenoxazine-3-one anion 在 羟胺 作用下， 以 水 为溶剂， 生成 7-Oxido-3H-phenoxazon-(3)-N-oxid
  参考文献：
  名称：

  Size-Dependent Catalytic Activity and Dynamics of Gold Nanoparticles at the Single-Molecule Level

  摘要：

  Nanoparticles are important catalysts for petroleum processing, energy conversion, and pollutant removal. As compared to their bulk counterparts, their often superior or new catalytic properties result from their nanometer size, which gives them increased surface-to-volume ratios and chemical potentials. The size of nanoparticles is thus pivotal for their catalytic properties. Here, we use single-molecule fluorescence microscopy to study the size-dependent catalytic activity and dynamics of spherical Au-nanoparticles under ambient solution conditions. By monitoring the catalysis of individual Au-nanoparticles of three different sizes in real time with single-turnover resolution, we observe clear size-dependent activities in both the catalytic product formation reaction and the product dissociation reaction. Within a model of classical thermodynamics, these size-dependent activities of Au-nanoparticles can be accounted for by the changes in the adsorption free energies of the substrate resazurin and the product resorufin because of the nanosize effect. We also observe size-dependent differential selectivity of the Au-nanoparticles between two parallel product dissociation pathways, with larger nanoparticles less selective between the two pathways. The particle size also strongly influences the surface-restructuring-coupled catalytic dynamics; both the catalysis-induced and the spontaneous dynamic surface restructuring occur more readily for smaller Au-nanoparticles due to their higher surface energies. Using a simple thermodynamic model, we analyze the catalysis- and size-dependent dynamic surface restructuring quantitatively; the results provide estimates on the activation energies and time scales of spontaneous dynamic surface restructuring that are fundamental to heterogeneous catalysis in both the nano- and the macro-scale. This study further exemplifies the power of the single-molecule approach in probing the intricate workings of nanoscale catalysts.

  DOI：

  10.1021/ja904307n
• 作为产物：
  描述：

  resazurin sodium salt 在 diaphorase 、 Nicotinamidadenenindinucleotid 、 L-乳酸阴离子 、 sodium chloride 作用下， 以 aq. buffer 为溶剂， 生成 7-Hydroxy-3H-phenoxazine-3-one anion
  参考文献：
  名称：

  面向无细胞固定化酶系统的分层工程介孔金属有机框架

  摘要：

  由于缺乏对酶定位，底物和产物扩散以及酶和辅酶可及性的最佳空间控制，在传统的固定化酶系统中通常很难实现高效的无细胞酶系统。在这里，我们报告了一种策略，用于扩展一系列基于Zr的金属有机骨架（MOF）（称为NU-100x，x  = 3、4、5、6、7）的孔径（从3.3到6.7 nm ）通过保持对与连接子相关的扭转角的精确控制，使层状结构具有相互连接的分层孔。作为概念验证，我们使用扩展的NU-100xMOF结构封装了乳酸脱氢酶（LDH），并证明了捕获的蛋白质在无细胞生物合成催化系统中的用途。值得注意的是，固定在MOF大孔中的LDH可以通过烟酰胺腺嘌呤二核苷酸辅酶（NAD和NADH）获得，从而可实现原位辅酶再生，从而产生比游离酶更高的活性。

  DOI：

  10.1016/j.chempr.2018.03.001

文献信息

• An intramolecular crossed-benzoin reaction based KCN fluorescent probe in aqueous and biological environments
  作者：Jae Hong Lee、Joo Hee Jang、Nithya Velusamy、Hyo Sung Jung、Sankarprasad Bhuniya、Jong Seung Kim

  DOI：10.1039/c5cc02234g

  日期：——

  A turn-on fluorescent probe IND-1 was designed for selective cyanide anion sensing in aqueous and biological environments.

  设计了一种开启式荧光探针IND-1，用于在水性和生物环境中进行选择性氰化物阴离子感测。
• Resorufin based fluorescence ‘turn-on’ chemodosimeter probe for nitroxyl (HNO)
  作者：Kondapa Naidu Bobba、Ying Zhou、Lin E. Guo、Tie Nan Zang、Jun Feng Zhang、Sankarprasad Bhuniya

  DOI：10.1039/c5ra17837a

  日期：——

  A cellular responsive, highly selective fluorogenic and chromogenic chemodosimeter probe for HNO is developed. This new probe showed ∼30 fold fluorescence enhancement in the presence of HNO and is sensitive to HNO at concentrations as low as 0.02 μM. Further, it is capable of detecting HNO levels in cellular milieus as well as in live specimens e.g. C. elegans.

  开发了一种用于HNO的细胞响应型，高度选择性的荧光和发色化学计量仪探针。这种新的探针在HNO存在下显示约30倍的荧光增强，并且在低至0.02μM的浓度下对HNO敏感。此外，它能够检测细胞环境以及诸如秀丽隐杆线虫的活样品中的HNO水平。
• Development of an effective fluorescence probe for discovery of aminopeptidase inhibitors to suppress biofilm formation
  作者：Tianhu Zhao、Jian Zhang、Maomao Tang、Luyan Z. Ma、Xiaoguang Lei

  DOI：10.1038/s41429-019-0166-z

  日期：2019.6

  The human pathogen Pseudomonas aeruginosa can easily form biofilms. The extracellular matrix produced by the bacterial cells acts as a physical barrier to hinder the antibiotics treatment. It is necessary to destroy the biofilm in order to improve the efficacy of antibiotics. However, it has been a significant challenge to develop effective small molecules targeting the components of biofilm matrix. In this study, we report the development of a new effective fluorescence probe that could be used in the high throughput screening to identify novel small molecule inhibitors targeting the most abundant component in the biofilm formation: P. aeruginosa aminopeptidase (PaAP). Through screening of an in-house chemical library, a commercially available drug, balsalazide, has been identified as a novel PaAP inhibitor, which exhibited remarkable anti-biofilm effect. Our study indicated that the newly developed fluorescence probe is applicable in exploring new aminopeptidase inhibitors, and it also warrants further investigation of balsalazide as a new anti-biofilm agent to treat P. aeruginosa infection in combination with known antibiotics.

  人类病原体铜绿假单胞菌很容易形成生物膜。细菌细胞产生的细胞外基质会形成物理屏障，阻碍抗生素的治疗效果。为了提高抗生素的疗效，必须破坏生物膜。然而，开发针对生物膜基质成分的有效小分子药物一直是一项重大挑战。在这项研究中，我们报告了一种新型有效荧光探针的开发，该探针可用于高通量筛选，以鉴定针对生物膜形成中最丰富成分的新型小分子抑制剂：铜绿假单胞菌氨基肽酶（PaAP）。通过对内部化学库的筛选，一种市售药物——巴柳氮被鉴定为一种新型PaAP抑制剂，该抑制剂表现出显著的抗生物膜作用。我们的研究表明，新开发的荧光探针适用于探索新的氨基肽酶抑制剂，并且还证明了巴柳氮作为新的抗生物膜剂与已知抗生素联合治疗铜绿假单胞菌感染的进一步研究价值。
• Fluorometric study on the amine-catalysed Suzuki–Miyaura coupling
  作者：Jincy K. Vinod、Annelise K. Wanner、Elizabeth I. James、Kazunori Koide

  DOI：10.1038/s41929-021-00711-0

  日期：——

  Suzuki–Miyaura coupling is one of the most frequently used reactions in organic synthesis1. However, owing to toxicity and cost, there have been attempts to develop palladium-free Suzuki–Miyaura and related methods2–4. In several cases, trace palladium was present in the reagents and catalysed the reactions5–7. In 2021, Xu et al. reported an amine-catalysed Suzuki– Miyaura-type coupling of aryl halides

  匹兹堡大学化学系，宾夕法尼亚州匹兹堡，美国。✉电子邮件：[e-mail] 钯催化的 Suzuki-Miyaura 偶联是有机合成中最常用的反应之一。然而，由于毒性和成本，已经尝试开发无钯的 Suzuki-Miyaura 和相关方法 2-4。在一些情况下，试剂中存在痕量钯并催化反应 5-7。2021年，徐等人。报道了芳基卤化物和芳基硼​​酸的胺催化 Suzuki-Miyaura 型偶联。他们在三环己基膦（PCy3）存在下通过钯催化的1-溴-2-甲基苯和2-甲基苯1,3-二胺之间的反应制备芳胺1，并通过标准柱色谱法纯化胺（图1a）8。在 5 mol% 这种胺的存在下，Suzuki-Miyaura 联轴器的产量很高8。他们的电感耦合等离子体质谱分析表明反应混合物中含有 0.32 ppb 的钯。然而，尚不清楚痕量钯是否解释了明显的胺催化。因此，我们决定使用我们的痕量钯检测方法 6,9-13
• Colorimetric screening of elevated urinary mercury levels by a novel Hg²⁺-selective probe of resorufin phosphinothioate
  作者：Myung Gil Choi、Byung Hoon Yun、Hyeong Min Kim、Sangdoo Ahn、Suk-Kyu Chang

  DOI：10.1039/d2ra04093j

  日期：——

  Urinary mercury levels are the most reliable indicators of mercury exposure but identifying them requires complex techniques and heavy instruments. In this research, we reported a simple and convenient urinary mercury analysis method using a readily available office scanner. Probe MP-1 synthesized by the reaction of resorufin and dimethylthiophosphinoyl chloride revealed Hg2+-selective chromogenic

  尿汞含量是汞暴露最可靠的指标，但识别它们需要复杂的技术和重型仪器。在这项研究中，我们报告了一种使用现成的办公室扫描仪的简单方便的尿汞分析方法。试卤灵和二甲基硫代膦酰氯反应合成的探针MP-1揭示了 Hg 2+选择性显色和荧光信号传导行为。信号传导是通过 Hg 2+诱导的基于试卤灵的探针MP-1中的硫代膦保护基的脱保护实现的以产生母体荧光染料。从浅黄色到粉红色的颜色变化的显着比色响应以及开启型荧光增强被认为是专门针对 Hg 2+离子而不是其他金属离子和阴离子。比色法提供了一种比简单的荧光分析更有利的比率分析方法，它表现出关-开型响应，检测限为 12 nM (2.4 ppb)。MP-1探针的Hg 2+信号传导不受共存金属离子和阴离子的干扰。使用标准办公室扫描仪成功地证明了对临床上重要的神经系统症状和尿液中致命的无机汞水平的敏感和方便的诊断。