1-(β-carboxyethyl)-2,3,3-trimethylindolenium-5-sulfonate | 398459-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(β-carboxyethyl)-2,3,3-trimethylindolenium-5-sulfonate
• 英文别名: 1-(2-Carboxyethyl)-2,3,3-trimethylindol-1-ium-5-sulfonate
• CAS: 398459-23-9
• 化学式: C₁₄H₁₇NO₅S
• 分子量: 311.359
• InChiKey: QDLVXYCJIRUSET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(β-carboxyethyl)-2,3,3-trimethylindolenium-5-sulfonate 在 sodium acetate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Supramolecular Assembly of an Evolved Miniprotein Host and Fluorogenic Guest Pair

  摘要：

  Small-molecule-induced assembly of defined protein structures could have broad implications for the fabrication of new materials as well as biological signaling pathways. However, the design of new hostguest pairs capable of small-molecule-induced assembly in a biologically relevant context remains a significant challenge. Herein, we report a series of miniprotein hosts, evolved from the tenth type III domain of fibronectin (Fn3), that display remarkable binding affinity toward a red-shifted environment-sensitive merocyanine derivative, termed sI-Pht. Importantly, the consensus binder isolated from directed evolution experiments (6.2.18) forms a higher order assembly in response to addition of sI-Pht, as assessed by analytical ultracentrifugation. sI-Pht-induced assembly of 6.2.18 results in a 570-fold increase in fluorescence compared to free dye. This property enables the direct visualization of hostguest assemblies by fluorescence microscopy. As a demonstration, we show that supramolecular assembly of the 6.2.18-sI-Pht system can be visualized on the surface of living yeast cells. This new hostguest pair provides a tool for the potential development of new materials as well as pathway engineering. In a broader context, this work details a new design paradigm for the discovery of hostguest systems that function in the context of living cells.

  DOI：

  10.1021/jacs.5b09494
• 作为产物：
  描述：

  2,3,3-trimethyl-3H-indole-5-sulfonate 、 3-碘丙酸 以 邻二氯苯 为溶剂， 反应 19.0h， 以0.91 g的产率得到1-(β-carboxyethyl)-2,3,3-trimethylindolenium-5-sulfonate
  参考文献：
  名称：

  Unsymmetrical pentamethine cyanines for visualizing physiological acidities from the whole-animal to the cellular scale with pH-responsive deep-red fluorescence

  摘要：

  非对称五甲基吲哚氰染料被开发并用于通过pH响应性深红荧光从整体动物到细胞尺度可视化生理酸度。

  DOI：

  10.1039/d1ra02217b

文献信息

• Development and Application of a Near-Infrared Fluorescence Probe for Oxidative Stress Based on Differential Reactivity of Linked Cyanine Dyes
  作者：Daihi Oushiki、Hirotatsu Kojima、Takuya Terai、Makoto Arita、Kenjiro Hanaoka、Yasuteru Urano、Tetsuo Nagano

  DOI：10.1021/ja910090v

  日期：2010.3.3

  Reactive oxygen species (ROS) operate as signaling molecules under various physiological conditions, and overproduction of ROS is involved in the pathogenesis of many diseases. Therefore, fluorescent probes for visualizing ROS are promising tools with which to uncover the molecular mechanisms of physiological and pathological processes and might also be useful for diagnosis. Here we describe a novel fluorescence probe, FOSCY-1, operating in the physiologically favorable near-infrared region. The probe consists of two differentially ROS-reactive cyanine dyes connected by a linker; reaction of the more susceptible dye with ROS releases intramolecular fluorescence quenching of the less susceptible dye. We successfully applied this probe to detect ROS produced by HL60 cells and porcine neutrophils and for imaging oxidative stress in a mouse model of peritonitis.