N,N’-bis[[4-(3-aminopropyl)piperazinyl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide | 265323-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N’-bis[[4-(3-aminopropyl)piperazinyl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide
• 英文别名: N,N'-bis[3-(4-(3-aminopropyl)piperazin-1-yl)propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide；N,N'-bis[3-[4-(3-aminopropyl)piperazin-1-yl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide；N,N'-bis[[4-(3-aminopropyl)piperazinyl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide；6,13-Bis[3-[4-(3-aminopropyl)piperazin-1-yl]propyl]-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 265323-32-8
• 化学式: C₃₄H₄₈N₈O₄
• 分子量: 632.806
• InChiKey: LVEWUTUVXQRXAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  对苯二甲酸 、 N,N’-bis[[4-(3-aminopropyl)piperazinyl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以10%的产率得到1,5,18,22,25,29,36,40-Octazaoctacyclo[38.2.2.222,25.231,34.15,13.110,18.07,12.011,16]pentaconta-7,9,11(16),12,14,31(46),32,34(45)-octaene-6,17,30,35,49,50-hexone
  参考文献：
  名称：

  Thermodynamics and kinetic studies in the binding interaction of cyclic naphthalene diimide derivatives with double stranded DNAs

  摘要：

  Previously, we reported our investigations of the interaction between a cyclic naphthalene diimide derivative (cNDI 1) and double stranded DNA (dsDNA) (Bioorg. Med. Chem. 2014, 22, 2593). Here, we report the synthesis of the novel cNDI 2, which has shorter linker chains than cNDI 1. We performed comparative investigations of the interactions of both cNDI 1 and cNDI 2 with different types of dsDNA, including analysis of their thermodynamics and kinetics. Interactions between the cNDIs and calf thymus DNA (CT-DNA), poly[d(A-T)](2), or poly[d(G-C)](2) were explored by physicochemical and biochemical methods, including UV-Vis spectroscopy, circular dichroism (CD) spectroscopy, stopped-flow kinetics, and a topoisomerase I assay. Upon addition of cNDIs to CT-DNA, the existence of an induced CD signal at approximately the wavelength of the naphthalene diimide chromophore and unwinding of the DNA duplex, as detected by the topoisomerase I assay, revealed that cNDIs bound to the DNA duplex. As indicated by the steric constraint in the formation of the complex, bis-threading intercalation was the more favorable binding mode. UV-Vis spectroscopic titration of the cNDIs with DNA duplexes showed affinities on the order of 10(5)-10(6) M-1, with a stoichiometry of one cNDI molecule per four DNA base pairs. Thermodynamic parameters (Delta G, Delta H, and Delta S) based on the van't Hoff equation indicated that exothermic and entropy-dependent hydrophobic interactions played a major role in the reaction. Stopped-flow association and dissociation analysis showed that cNDI interactions with poly[d(G-C)](2) were more stable and had a slower dissociation rate than their interactions with poly[d(A-T)](2) and CT-DNA. Measurement of ionic strength indicated that electrostatic attraction is also an important component of the interaction between cNDIs and CT-DNA. Because of its longer linker chain, cNDI 1 showed higher binding selectivity, a more entropically favorable interaction, and much slower dissociation from dsDNA than cNDI 2. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.046
• 作为产物：
  描述：

  N,N'-bis[[3-(3-tert-butoxycarbonylaminopropyl)piperazin-1-yl]propyl]-naphthalene-1,4,5,8-tetracarboxylic acid diimide 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 N,N’-bis[[4-(3-aminopropyl)piperazinyl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide
  参考文献：
  名称：

  Synthesis and DNA binding behavior of a naphthalene diimide derivative carrying two dicobalt hexacarbonyl complexes as an infrared DNA probe

  摘要：

  Naphthalene diimide having two dicobalt hexacarbonyl complexes at its substituent termini 1 was designed and synthesized as an infrared probe for double stranded DNA. Spectrophotometric and viscometric DNA binding studies of 1 and naphthalene diimide having two acetylene moieties 2 as its precursor were carried out to prove their threading intercalation binding modes. Fourier Transform Infrared Reflection-Absorption Spectroscopy (FT-IR RAS) measurements were achieved for DNA-immobilized on a gold surface before and after hybridization with complementary DNA strand. Distinguished absorption peaks assigned to the dicobalt hexacarbonyl complexes were obtained in the case of the formation of double stranded DNA after treatment with 1. This result revealed that 1 can be used as an infrared probe for monitoring double stranded DNA. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.02.020

文献信息

• DNA Sensing on a DNA Probe-Modified Electrode Using Ferrocenylnaphthalene Diimide as the Electrochemically Active Ligand
  作者：Shigeori Takenaka、Kenichi Yamashita、Makoto Takagi、Yoshihiro Uto、Hiroki Kondo

  DOI：10.1021/ac991031j

  日期：2000.3.1

  Naphthalene diimide derivative 1 carrying ferrocenyl moieties at the termini of imide substituents binds intact calf thymus DNA 4 times more strongly than the denatured DNA, and its complex with the intact DNA dissociates 80 times more slowly than that with the denatured DNA. On the basis of these observations, ligand 1 was applied to a probe of electrochemical DNA sensing. A thiol-linked single-stranded DNA probe was immobilized through the S−Au bonding to 20−30 pmol/mm2 on a gold electrode. Following hybridization with the complementary DNA, the electrode was soaked in a solution containing 1 (intercalation step) and then washed with buffer for 5 s. The cyclic voltammogram and differential pulse voltammogram for this electrode gave an electrochemical signal due to the redox reaction of 1 that was bound to the double-stranded DNA on the electrode. Thus, dA20 and the yeast choline transport gene were quantitated at the subpicomole level. The sensitivity of DNA detection was improved to 10 zmol by reducing the amount of immobilized DNA probe and protecting the uncovered surface of the electrode with 2-mercaptoethanol.

  在亚胺取代基的末端含有二茂铁的萘二亚胺衍生物 1 与完整的小牛胸腺 DNA 的结合强度是变性 DNA 的 4 倍，其与完整 DNA 的复合物的解离速度是与变性 DNA 的复合物的 80 倍。根据这些观察结果，配体 1 被应用于电化学 DNA 传感探针。通过 S-Au 键将硫醇连接的单链 DNA 探针固定在金电极上，浓度为 20-30 pmol/mm2。与互补 DNA 杂交后，将电极浸泡在含有 1 的溶液中（插层步骤），然后用缓冲液洗涤 5 秒钟。该电极的循环伏安图和差分脉冲伏安图显示出电化学信号，这是由于 1 与电极上的双链 DNA 发生了氧化还原反应。因此，对 dA20 和酵母胆碱转运基因的定量达到了亚微量级。通过减少固定 DNA 探针的数量并用 2-巯基乙醇保护未覆盖的电极表面，DNA 检测的灵敏度提高到了 10 zmol。
• Design of tetraplex specific ligands: cyclic naphthalene diimide
  作者：Yugo Esaki、Md. Monirul Islam、Satoshi Fujii、Shinobu Sato、Shigeori Takenaka

  DOI：10.1039/c4cc01005a

  日期：——

  Cyclic naphthalene diimide 1 bound to hybrid-type tetraplex DNA from 5′-AGGG(TTAGGG)₃-3′ (K = 8.6 × 10⁶ M⁻¹) with 260-fold greater affinity than that when binding to double stranded oligonucleotide consisting of 5′-GGG AGG TTT CGC-3′ and 3′-CCC TCC AAA GCG-5′ (nK = 3.3 × 10⁴ M⁻¹) with 0.5 μM of IC₅₀ for telomerase activity.

  环状萘二酰亚胺1与5'-AGGG(TTAGGG)3'-3'的混合型四链体DNA结合的亲和力比与由5'-GGG AGG TTT CGC-3'和3'-CCC TCC AAA GCG-5'组成的双链寡核苷酸结合时高260倍（K = 8.6 × 10^6 M^-1），并且对端粒酶活性的IC50为0.5μM（nK = 3.3 × 10^4 M^-1）。
• Electrochemically active threading intercalator with high double stranded DNA selectivity
  作者：Shigeori Takenaka、Yoshihiro Uto、Hideki Saita、Makoto Yokoyama、Hiroki Kondo、W. David Wilson

  DOI：10.1039/a801539b

  日期：——

  A naphthalene diimide threading intercalator carrying ferrocenyl moieties as its termini can discriminate double stranded DNA from single stranded counterparts owing to a difference in their dissociation rates.

  一种以二茂铁为端基的萘二亚胺穿线插层剂可以区分双链 DNA 和单链 DNA，因为它们的解离率不同。
• Single-layer organic el device
  申请人：Isobe Shinichiro

  公开号：US20070116981A1

  公开（公告）日：2007-05-24

  Disclosed is an organic EL dye enabling to provide an organic EL device which is capable of emitting a light at a low voltage even when it has a single layer structure. Also disclosed is an organic EL device using such an organic EL dye. The organic EL dye is represented by the general formula (1): (Y—L)nXm wherein x is an n-valent charge-transporting group, Y is a light-emitting group, L is a linking group bonding the charge-transporting group and the light-emitting group, and m and n are respectively an integer not less than 1.

  本发明公开了一种有机EL染料，能够提供一种能够在低电压下发光的有机EL器件，即使该器件具有单层结构。还公开了使用这种有机EL染料的有机EL器件。该有机EL染料由通式（1）表示：（Y-L）nXm，其中X是n价输运基团，Y是发光基团，L是连接基团，连接输运基团和发光基团，m和n分别是不小于1的整数。
• US8048536B2
  申请人：——

  公开号：US8048536B2

  公开（公告）日：2011-11-01