6-bromomethyl-4'-N,N-dimethylamino-3-hydroxyflavone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-bromomethyl-4'-N,N-dimethylamino-3-hydroxyflavone
• 英文别名: 6-(bromomethyl)-2-(4-(diethylamino)phenyl)-3-hydroxy-4H-chromen-4-one；6-bromomethyl-4'-N,N-diethylamino-3-hydroxyflavone；6-Bromomethyl-4'-diethylamino-3-hydroxyflavone；6-(bromomethyl)-2-[4-(diethylamino)phenyl]-3-hydroxychromen-4-one
• 化学式: C₂₀H₂₀BrNO₃
• 分子量: 402.288
• InChiKey: VWBJPFUHQZWZMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromomethyl-4'-N,N-dimethylamino-3-hydroxyflavone 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 6-(azidomethyl)-2-(4-(diethylamino)phenyl)-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  一种用于 DNA 检测的水溶性和光稳定荧光色素的合成和应用的快速方法

  摘要：

  基于具有荧光特性的有机分子的杂交探针的深入研究目前正引起特别的关注，因为它们具有有效识别不同 DNA 构象和局部环境的潜力。然而，大多数已建立的有机发色团不满足这项任务的要求，因为它们在水性缓冲介质中没有表现出良好的亮度，发展聚集和/或不容易与寡脱氧核苷酸 (ODN) 结合，同时保持其光物理完整性。在此，对众所周知的荧光团 2-(4-(二乙基氨基)苯基)-3-羟基色酮 ( dEAF ) 采用了一种重要的修饰策略。）。尽管这种推拉染料在可见光范围内强烈吸收，并在所有有机溶剂中显示出具有大斯托克斯位移的发射，但它在水中会强烈淬火。这一致命弱点促使我们实施了一项新策略，以获取一系列染料，这些染料在水中保留了dEAF的所有光物理特性，易于与寡核苷酸结合，此外还表现出对水合的敏感性，从而为高性能荧光剂铺平了道路DNA杂交探针。

  DOI：

  10.3390/molecules27072267
• 作为产物：
  描述：

  2-[4-(diethylamino)phenyl]-6-(ethoxymethyl)-3-hydroxy-4H-chromen-4-one 在 氢溴酸 、 碳酸氢钠 作用下， 反应 3.0h， 生成 6-bromomethyl-4'-N,N-dimethylamino-3-hydroxyflavone
  参考文献：
  名称：

  Synthesis of 3-hydroxyflavone fluorescent probes and study of their fluorescence properties

  摘要：

  Direct measurement of dipole potential in biological membranes has been impossible and 3-hydroxyflavones (3HFs) have allowed detection of changes in dipole potential in biological systems. In the present study, sixteen derivatives of 3HF with aliphatic hydrocarbon chains of different lengths at 4'-position and 6-position were synthesized The basic fluorescence properties of 3HFs are maintained in all the probes in terms of strong blue shift in maximum fluorescence emission wavelength and >100 fold increase in quantum yield in organic solvents and in dioleoylphosphatidylcholine (DOPC) small unilamellar vesicles (SUV) in comparison to in aqueous Hepes buffer (15 mmol/L, pH 7.4). More importantly, the ability of the new compounds to report dipole potential changes in biological systems are also maintained, since all the new probes showed spectrum properties that are similar to yet different from that of F4N1. which potentially may allow more sensitive measurement of the dipole potential change in membranes. (C) 2009 Wen Bao Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2009.12.003

文献信息

• Compounds and kits for the detection and the quantification of cell apoptosis
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US07880021B2

  公开（公告）日：2011-02-01

  3-hydroxyflavone derivatives are useful in the detection and the quantification of cell apoptosis. Such derivatives are also useful as fluorescent probes in studying lipid asymmetry of cell plasma membrane and in detecting apopoptic cells. The derivatives can be used to monitor the evolution of diseases involving cell apoptosis.

  3-羟基黄酮衍生物在细胞凋亡的检测和定量方面非常有用。这些衍生物也可作为荧光探针用于研究细胞质膜的脂质不对称性和检测凋亡细胞。这些衍生物可用于监测涉及细胞凋亡的疾病的进展。
• Fluorescent Biomembrane Probe for Ratiometric Detection of Apoptosis
  作者：Vasyl V. Shynkar、Andrey S. Klymchenko、Corinne Kunzelmann、Guy Duportail、Christian D. Muller、Alexander P. Demchenko、Jean-Marie Freyssinet、Yves Mely

  DOI：10.1021/ja068008h

  日期：2007.2.1

  Herein, we developed the first ratiometric fluorescent probe for apoptosis detection. This probe incorporates selectively into the outer leaflet of the cell plasma membrane and senses the loss of the plasma membrane asymmetry occurring during the early steps of apoptosis. The high specificity to the plasma membranes was achieved by introduction into the probe of a membrane anchor, composed of a zwitterionic

  在此，我们开发了第一个用于细胞凋亡检测的比率荧光探针。该探针选择性地结合到细胞质膜的外小叶中，并感知细胞凋亡早期阶段发生的质膜不对称性的丧失。对质膜的高度特异性是通过将膜锚引入探针实现的，膜锚由两性离子基团和长（十二烷基）疏水尾组成。该探针的荧光报告分子是 4'-(二乙氨基)-3-羟基黄酮，它表现出激发态分子内质子转移 (ESIPT)，导致双波段发射对生物膜的脂质成分高度敏感。荧光光谱、流式细胞术、显微镜测量表明，探针的两个发射带的比率会随着细胞凋亡而发生显着变化。这种反应反映了细胞质膜外小叶脂质组成的变化，因为在细胞凋亡的早期阶段，内小叶的阴离子磷脂暴露。由于是比例式的，新探头的响应可以很容易地在绝对尺度上量化。这允许通过激光扫描共聚焦显微镜监测细胞质膜凋亡变化的程度和空间分布，这是常用的荧光标记膜联蛋白 V 测定法难以实现的特征。这种反应反映了细胞质膜外小叶脂质组成的变化，因为在细胞凋
• 3 -HYDROXYFLAVONE DERIVATIVES FOR THE DETECTION AND THE QUANTIFICATION OF CELL APOPTOSIS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：EP1948633A2

  公开（公告）日：2008-07-30
• JP2009511566A
  申请人：——

  公开号：JP2009511566A

  公开（公告）日：2009-03-19
• Compounds and Kits for the Detection and the Quantification of Cell Apoptosis
  申请人：Mely Yves

  公开号：US20090269793A1

  公开（公告）日：2009-10-29

  The present invention relates a compound of formula (1) wherein: —R1 represents a linear alkyl group of 4 to 20 carbon atoms; —Y represents a linear alkyl group of 1 to 5 carbon atoms or a group of formula —R—O—R′—, —R—CO—R′— or —R—CO—NH—R′—, in which R represents a linear alkyl group of 1 to 3 carbon atoms, R′ represents a linear alkylene group of 0-3 carbon atoms, Y being linked to the bicycle in position 6 or 7; -Z represents a linear alkyl chain of 3 or 4 carbon atoms; -A represents an oxygen atom, a sulphur atom, or a —NH group, or an amminoalkyl group —NR″ in which R″ represents an alkyl group of 1 to 20 carbon atoms; —Ar represents an aromatic cycle or polycycle consisting of 6 to 14 carbon atoms, or an aromatic heterocycle, said heterocycle containing 4, 5 or 6 carbon atoms and at least one heteroatom selected in the group consisting of N, S, and O, or a condensed aromatic heterobicycle, said heterobicycle consisting of 6 to 9 carbon atoms and at least one heteroatom selected in the group consisting of N, S, and O; —R2 and R3, which are identical or different, each representing a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, R2 and R3 optionally forming a 5- to 7-membered ring with the nitrogen atom; —R4, R5 and R6, identical or different, represent an hydrogen, a linear alkyl group or a linear oxyalkyl group of 1 to 4 carbon atoms.