N-丁基荧光素 | 335193-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: N-丁基荧光素
• 中文别名: 正丁基荧光素
• 英文名称: 3'-O-butylfluorescein
• 英文别名: N-Butylfluorescein；3'-butoxy-6'-hydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one
• CAS: 335193-91-4
• 化学式: C₂₄H₂₀O₅
• 分子量: 388.42
• InChiKey: UMLSFGLXYOSGJH-UHFFFAOYSA-N

物化性质

• 熔点：
  203-205°C
• 沸点：
  603.7±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿：微溶；甲醇：微溶

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

制备方法与用途

正丁基荧光素是一种烷基取代的荧光素，常用于合成荧光底物来测定磷脂酰肌醇特异性磷脂酶C。

反应信息

• 作为反应物：
  描述：

  3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoyl chloride 、 N-丁基荧光素 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以48 mg的产率得到6'-O-(N-maleimido-β-alanyl)-3'-O-butylfluorescein
  参考文献：
  名称：

  General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

  摘要：

  To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg(9). The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg(9)Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.016
• 作为产物：
  描述：

  fluorescein disodium salt 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 N-丁基荧光素
  参考文献：
  名称：

  General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

  摘要：

  To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg(9). The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg(9)Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.016

文献信息

• Optically-Detectable Enzyme Substrates and Their Method of Use
  申请人：Life Technologies Corporation

  公开号：US20160139135A1

  公开（公告）日：2016-05-19

  The present invention relates to compounds that are substrates for an enzyme, and upon reaction with the enzyme provide a detectable response, such as an optically detectable response. In particular, the compounds have utility in detecting the presence of a β-lactamase in a sample. In addition to the compounds, methods are disclosed for analyzing a sample for the presence of a β-lactmase, for example, as an indicator of expression of a nucleic acid sequence including a sequence coding for a β-lactmase. Kits are disclosed that include the disclosed compounds and additional components, for example, cells, antibodies, a β-lactmase or instructions for using the components in an assay.

  本发明涉及一种酶底物化合物，与酶反应后产生可检测的响应，例如光学可检测的响应。具体而言，这些化合物在检测样品中β-内酰胺酶的存在方面具有实用性。除了这些化合物外，还公开了用于分析样品中β-内酰胺酶存在的方法，例如，作为表达包括编码β-内酰胺酶序列的核酸序列的指示器。还公开了包括这些化合物和额外组分的试剂盒，例如细胞、抗体、β-内酰胺酶或使用这些组分进行检测的说明书。
• General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability
  作者：Xiaoxu Li、John Stephen Taylor

  DOI：10.1016/j.bmc.2003.11.016

  日期：2004.2

  To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg(9). The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg(9)Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described. (C) 2003 Elsevier Ltd. All rights reserved.