7-amino-4-((6-aminohex-1-yl)carbamoylmethyl)quinolin-2(1H)-one | 1207862-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-amino-4-((6-aminohex-1-yl)carbamoylmethyl)quinolin-2(1H)-one
• 英文别名: 7-amino-4-carboxamido-(6-aminohexyl)methyl-2(1H)quinolone；7-amino-4-carboxamido(6-aminohexyl)methyl-2(1H)quinolone
• CAS: 1207862-72-3
• 化学式: C₁₇H₂₄N₄O₂
• 分子量: 316.403
• InChiKey: YESFYVYNYHTSOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  114.0
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-amino-4-((6-aminohex-1-yl)carbamoylmethyl)quinolin-2(1H)-one 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[[2-[[4-[2-[6-[(2-bromoacetyl)amino]hexylamino]-2-oxoethyl]-2-oxo-1H-quinolin-7-yl]amino]-2-oxoethyl]-(carboxymethyl)amino]ethyl]amino]acetic acid
  参考文献：
  名称：

  New quinolone-based thiol-reactive lanthanide luminescent probes

  摘要：

  Luminescent lanthanide ion complexes are distinguished by unique light emitting properties that enable both highly sensitive detection of lanthanide labels attached to biomolecules and contrast imaging of various micro objects (cells, nanoparticles, etc.). Previously, we synthesized amine-reactive cs124-based luminescent lanthanide chelates with improved brightness and metal retention. Here we report the synthesis of new thiol-reactive derivatives of the same compounds including bromoacetamido-, and maleimido-forms of cs124 and cs124CF(3) fluorophores. Maleimido-compounds displayed exceptional reactivity instantaneously coupling to thiols at physiological conditions at micromolar probes concentrations. Surprisingly, they displayed strong quenching by adjacent maleimido-group, which was completely eliminated after reaction with thiols, thereby enabling their simple detection by monitoring the light emission of the reaction mixture. This reaction can be used for hyper-sensitive determination of biologically important sulphydryl compounds (e.g. glutathione, co-enzyme A, etc.) in time-resolved mode. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.12.008
• 作为产物：
  描述：

  1,3-丙酮二羧酸二乙酯 在 zinc(II) chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 39.0h， 生成 7-amino-4-((6-aminohex-1-yl)carbamoylmethyl)quinolin-2(1H)-one
  参考文献：
  名称：

  FLUOROPHORE CHELATED LANTHANIDE LUMINESCENT PROBES WITH IMPROVED QUANTUM EFFICIENCY

  摘要：

  这项发明涉及含有荧光物质的新型发光组合物，制备这些组合物的合成方法，这些组合物的高分子共轭物，以及在各种检测方法中使用这些组合物的用途。该发明还提供了包含这些组合物及其共轭物的试剂盒，用于上述检测方法。

  公开号：

  US20130202536A1

文献信息

• Luminescent Probes for Ultrasensitive Detection of Nucleic Acids
  作者：Lev N. Krasnoperov、Salvatore A. E. Marras、Maxim Kozlov、Laura Wirpsza、Arkady Mustaev

  DOI：10.1021/bc900403n

  日期：2010.2.17

  Novel amino-reactive derivatives of lanthanide-based luminescent labels of enhanced brightness and metal retention were synthesized and used for the detection of cDNA oligonucleotides by molecular beacons. Time-resolved acquisition of the luminescent signal that occurs upon hybridization of the probe to the target enabled the avoidance of short-lived background fluorescence, markedly enhancing the sensitivity of detection, which was less than 1 pM. This value is about 50 to 100 times More sensitive than the level achieved with conventional fluorescence-based molecular beacons, and is 10 to 60 times more sensitive than previously reported for other lanthanide-based hybridization probes. These novel luminescent labels should significantly enhance the sensitivity of all type of nucleic acid hybridization probes, and could dramatically improve the detection limit of other biopolymers and small compounds that are used in a variety of biological applications.