2-(3-chloropropoxy)-9-(diethylamino)-5H-benzo[a]phenoxazin-5-one | 1220995-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(3-chloropropoxy)-9-(diethylamino)-5H-benzo[a]phenoxazin-5-one
• 英文别名: 9-(diethylamino)-2-(3-chloropropoxy)-5H-benzo[a]phenoxazin-5-one
• CAS: 1220995-10-7
• 化学式: C₂₃H₂₃ClN₂O₃
• 分子量: 410.9
• InChiKey: IBWHNZMDFXYTLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.57
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-甲基-1-十八胺 、 2-(3-chloropropoxy)-9-(diethylamino)-5H-benzo[a]phenoxazin-5-one 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以60%的产率得到9-(diethylamino)-2-(3-(methyl(octadecyl)amino)propoxy)-5H-benzo[a]phenoxazin-5-one
  参考文献：
  名称：

  A selective Nile Red based solvatochromic probe: A study of fluorescence in LUVs and GUVs model membranes

  摘要：

  DOI：

  10.1016/j.dyepig.2021.109759
• 作为产物：
  描述：

  5-(二乙氨基)-2-(亚硝基苯酚) 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(3-chloropropoxy)-9-(diethylamino)-5H-benzo[a]phenoxazin-5-one
  参考文献：
  名称：

  A selective Nile Red based solvatochromic probe: A study of fluorescence in LUVs and GUVs model membranes

  摘要：

  DOI：

  10.1016/j.dyepig.2021.109759

文献信息

• Disassembly-Driven Fluorescence Turn-on of Polymerized Micelles by Reductive Stimuli in Living Cells
  作者：Yosuke Niko、Youri Arntz、Yves Mely、Gen-ichi Konishi、Andrey S. Klymchenko

  DOI：10.1002/chem.201405040

  日期：2014.12.8

  imaging and therapeutic applications. Ideally, they should be assembled from biodegradable materials featuring small size and cooperative response to biological stimuli that trigger particle disassembly and release of an active molecule that could be readily monitored in situ. A concept is developed that consists of organic nanoparticles, assembled from fluorescent amphiphiles and polymerized with a redox‐cleavable

  刺激反应纳米颗粒已成为用于成像和治疗应用的强大工具。理想情况下，它们应由可生物降解的材料组装而成，这些材料的尺寸小且对生物刺激具有协同反应，从而触发颗粒的分解和活性分子的释放，可以很容易地就地对其进行监测。提出了一种由有机纳米颗粒组成的概念，该纳米颗粒由荧光两亲物组装而成，并与可氧化还原裂解的交联剂聚合。我们获得了带有自猝灭尼罗红染料残基的20 nm纳米颗粒，由于外部或内部还原刺激，这些残基可在活细胞中分解为高度荧光的分子单元。获得的结果为新的刺激响应性纳米材料铺平了道路，这些材料可用于无背景成像以及药物递送，
• Switchable Nile Red-Based Probe for Cholesterol and Lipid Order at the Outer Leaflet of Biomembranes
  作者：Oleksandr A. Kucherak、Sule Oncul、Zeinab Darwich、Dmytro A. Yushchenko、Youri Arntz、Pascal Didier、Yves Mély、Andrey S. Klymchenko

  DOI：10.1021/ja100351w

  日期：2010.4.7

  Cholesterol and sphingomyelin form together a highly ordered membrane phase, which is believed to play important biological functions in plasma membranes of mammalian cells. Since sphingomyelin is present mainly at the outer leaflet of cell membranes, monitoring its lipid order requires molecular probes capable to bind specifically at this leaflet and exhibit negligibly slow flip-flop. In the present work, such a probe was developed by modifying the solvatochromic fluorescent dye Nile Red with an amphiphilic anchor group. To evaluate the flip-flop of the obtained probe (NR12S), we developed a methodology of reversible redox switching of its fluorescence at one leaflet using sodium dithionite. This method shows that NR12S, in contrast to parent Nile Red, binds exclusively the outer membrane leaflet of model lipid vesicles and living cells with negligible flip-flop in the time scale of hours. Moreover, the emission maximum of NR12S in model vesicles exhibits a significant blue shift in liquid ordered phase (sphingomyelin-cholesterol) as compared to liquid disordered phase (unsaturated phospholipids). As a consequence, these two phases could be clearly distinguished in NR12S-stained giant vesicles by fluorescence microscopy imaging of intensity ratio between the blue and red parts of the probe emission spectrum. Being added to living cells, NR12S binds predominantly, if not exclusively, their plasma membranes and shows an emission spectrum intermediate between those in liquid ordered and disordered phases of model membranes. Importantly, the emission color of NR12S correlates well with the cholesterol content in cell membranes, which allows monitoring the cholesterol depletion process with methyl-beta-cyclodextrin by fluorescence spectroscopy and microscopy. The attractive photophysical and switching properties of NR12S, together with its selective outer leaflet staining and sensitivity to cholesterol and lipid order, make it a new powerful tool for studying model and cell membranes.