N,N'-bis(5-hydroxy-3-oxapentyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide | 1268493-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis(5-hydroxy-3-oxapentyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
• 英文别名: 11,22-Dibromo-7,18-bis[2-(2-hydroxyethoxy)ethyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• CAS: 1268493-76-0
• 化学式: C₃₂H₂₄Br₂N₂O₈
• 分子量: 724.359
• InChiKey: SJLLJZPSUKDPFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-bis(5-hydroxy-3-oxapentyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 N-2-[(2-O-4,4-dimethoxytrytilethoxy)ethyl]-N'-2-(2-ethoxy)ethyl-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q
• 作为产物：
  描述：

  (((5,12-dibromo-1,3,8,10-tetraoxo-1,3,8,10-tetrahydroanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-2,9-diyl)bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) diacetate 在 甲醇 、 氨 作用下， 以 水 为溶剂， 反应 2.0h， 生成 N,N'-bis(5-hydroxy-3-oxapentyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q

文献信息

• 一种苝酰亚胺衍生物荧光探针、制备方法及其应用
  申请人：扬州工业职业技术学院

  公开号：CN113831339B

  公开（公告）日：2022-05-20

  本案涉及一种苝酰亚胺衍生物荧光探针、制备方法及其应用，荧光探针分子的构筑主要是基于苝酰亚胺湾位进行共轭修饰，通过醛和活泼甲基的缩合反应制备具有近红外发射的长程共轭荧光给‑受体分子，湾位的另外一侧接具有给电子作用的发色团。本发明的荧光探针分子对氰基显示了优异的裸眼识别作用，探针分子具有近红外吸收和近红外发射荧光，其与氰基作用后其紫外光谱和荧光都发生了显著的蓝移，同时伴随从绿色到红色的颜色变化。探针分子对氰基具有快速的荧光响应、良好的抗干扰能力、较低的检测限，与已经报道的氰基荧光探针对比，其快速的荧光响应和裸眼识别效用和较低的检测限将为其在生物荧光示踪和环境中氰基化合物的检测创造了良好的条件。
• <i>N</i>-Cyclic Bay-Substituted Perylene G-Quadruplex Ligands Have Selective Antiproliferative Effects on Cancer Cells and Induce Telomere Damage
  作者：Valentina Casagrande、Erica Salvati、Antonello Alvino、Armandodoriano Bianco、Alina Ciammaichella、Carmen D’Angelo、Luca Ginnari-Satriani、Anna Maria Serrilli、Sara Iachettini、Carlo Leonetti、Stephen Neidle、Giancarlo Ortaggi、Manuela Porru、Angela Rizzo、Marco Franceschin、Annamaria Biroccio

  DOI：10.1021/jm1013665

  日期：2011.3.10

  A series of bay-substituted perylene derivatives is reported as a new class of G-quadruplex ligands. The synthesized compounds hive differing N-cyclic substituents on the bay area and differing side chains on the perylene major axis. ESI-MS and FEET measurements highlighted the strongest quadruplex binders in this series and those showing the highest quadruplex/duplex selectivity. Several biological assays were performed on these compounds, which showed that compound 5 (PPL3C) triggered a DNA damage response in transformed cells with the formation of telomeric foci containing phosphorylated gamma-H2AX and 53BP1. This effect mainly occurred in replicating cells and was consistent with Pod dissociation. Compound S does not induce telomere damage in normal cells, which are unaffected by treatment with the: compound, suggesting that this agent preferentially kills cancer cells. These results reinforce the notion that G-quadruplex binding compounds can act as broad inhibitors of telomere-related processes and have potential as selective antineoplastic drugs.
• Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate
  作者：Marco Franceschin、Nicola Borbone、Giorgia Oliviero、Valentina Casagrande、Maria Scuotto、Teresa Coppola、Silvia Borioni、Luciano Mayol、Giancarlo Ortaggi、Armandodoriano Bianco、Jussara Amato、Michela Varra

  DOI：10.1021/bc100526q

  日期：2011.7.20

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.