2-(9,10-Dioxo-1-phenylmethoxyanthracen-2-yl)acetaldehyde | 1086461-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(9,10-Dioxo-1-phenylmethoxyanthracen-2-yl)acetaldehyde
• CAS: 1086461-14-4
• 化学式: C₂₃H₁₆O₄
• 分子量: 356.378
• InChiKey: KVLMOVDPTVXMOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(9,10-Dioxo-1-phenylmethoxyanthracen-2-yl)acetaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 以80 mg的产率得到2-(1-(benzyloxy)-9,10-anthraquinonyl)-acetic acid
  参考文献：
  名称：

  水溶性笼中的4-羟基-反式-2-壬烯醛的发展中重原子效应的观察。

  摘要：

  在我们研究1-烷氧基-9,10-蒽醌的光化学过程中，我们开发了第二代笼状的4-羟基-反式-2-壬烯醛（4-HNE）。当我们优化蒽醌基生色团以达到水溶性时，我们研究了各种取代基的光化学，以了解它们对光化学的影响。我们观察到了显着的重原子效应，该效应严重降低了烷氧基的氧化裂解速率。根据我们对取代基的研究结果，我们设计了一种新的笼状4-HNE，该笼在生理条件下可溶，并且可以高产率光化学释放4-HNE。

  DOI：

  10.1039/b810954k
• 作为产物：
  描述：

  1-hydroxy-2-(prop-2'-enyl)-9,10-anthraquinone 在 potassium carbonate 、 臭氧 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.25h， 生成 2-(9,10-Dioxo-1-phenylmethoxyanthracen-2-yl)acetaldehyde
  参考文献：
  名称：

  Temporally Controlled Targeting of 4-Hydroxynonenal to Specific Proteins in Living Cells

  摘要：

  In-depth chemical understanding of complex biological processes hinges upon the ability to systematically perturb individual systems. However, current approaches to study impacts of biologically relevant reactive small molecules involve bathing of the entire cell or isolated organelle with excess amounts, leading to off-target effects. The resultant lack of biochemical specificity has plagued our understanding of how biological electrophiles mediate signal transduction or regulate responses that confer defense mechanisms to cellular electrophilic stress Here we introduce a target specific electrophile delivery platform that will ultimately pave the way to interrogate effects of reactive electrophiles on specific target proteins in cells. The new methodology is demonstrated by photoinducible targeted delivery of 4-hydroxynonenal (HNE) to the proteins Keap1 and PTEN. Covalent conjugation of the HNE-precursor to HaloTag fused to the target proteins enables directed HNE delivery upon photoactivation. The strategy provides proof of concept of selective delivery of reactive electrophiles to individual electrophile-responsive proteins in mammalian cells. It opens a new avenue enabling more precise determination of the pathophysiological consequences of HNE-induced chemical modifications on specific target proteins in cells.

  DOI：

  10.1021/ja405400k

文献信息

• Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal
  作者：Paul B. Jones、Robert G. Brinson、Saurav J. Sarma、Salwa Elkazaz

  DOI：10.1039/b810954k

  日期：——

  anthraquinonyl chromophore to achieve water solubility, we studied the photochemistry of various substituents to understand their effect on the photochemistry. We observed a significant heavy atom effect that severely reduced the rate of oxidative cleavage of the alkoxy group. Based on the results of our substituent study, we designed a new caged 4-HNE that is soluble under physiological conditions, and

  在我们研究1-烷氧基-9,10-蒽醌的光化学过程中，我们开发了第二代笼状的4-羟基-反式-2-壬烯醛（4-HNE）。当我们优化蒽醌基生色团以达到水溶性时，我们研究了各种取代基的光化学，以了解它们对光化学的影响。我们观察到了显着的重原子效应，该效应严重降低了烷氧基的氧化裂解速率。根据我们对取代基的研究结果，我们设计了一种新的笼状4-HNE，该笼在生理条件下可溶，并且可以高产率光化学释放4-HNE。
• Temporally Controlled Targeting of 4-Hydroxynonenal to Specific Proteins in Living Cells
  作者：Xinqiang Fang、Yuan Fu、Marcus J. C. Long、Joseph A. Haegele、Eva J. Ge、Saba Parvez、Yimon Aye

  DOI：10.1021/ja405400k

  日期：2013.10.2

  In-depth chemical understanding of complex biological processes hinges upon the ability to systematically perturb individual systems. However, current approaches to study impacts of biologically relevant reactive small molecules involve bathing of the entire cell or isolated organelle with excess amounts, leading to off-target effects. The resultant lack of biochemical specificity has plagued our understanding of how biological electrophiles mediate signal transduction or regulate responses that confer defense mechanisms to cellular electrophilic stress Here we introduce a target specific electrophile delivery platform that will ultimately pave the way to interrogate effects of reactive electrophiles on specific target proteins in cells. The new methodology is demonstrated by photoinducible targeted delivery of 4-hydroxynonenal (HNE) to the proteins Keap1 and PTEN. Covalent conjugation of the HNE-precursor to HaloTag fused to the target proteins enables directed HNE delivery upon photoactivation. The strategy provides proof of concept of selective delivery of reactive electrophiles to individual electrophile-responsive proteins in mammalian cells. It opens a new avenue enabling more precise determination of the pathophysiological consequences of HNE-induced chemical modifications on specific target proteins in cells.