N,N'-bis[3-[4-(3-(4-pentynamido)propyl)piperazin-1-yl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide | 1146670-11-2

• 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[3-[4-(3-(4-pentynamido)propyl)piperazin-1-yl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide
• 英文别名: N,N'-bis[(4-pentynamidopropyl)piperazin-1-yl]propylnaphthalene-1,4,5,8-tetracarboxylic acid diimide；N-[3-[4-[3-[5,7,12,14-tetraoxo-13-[3-[4-[3-(pent-4-ynoylamino)propyl]piperazin-1-yl]propyl]-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaen-6-yl]propyl]piperazin-1-yl]propyl]pent-4-ynamide
• CAS: 1146670-11-2
• 化学式: C₄₄H₅₆N₈O₆
• 分子量: 792.979
• InChiKey: OCSHRPRKGVEMHW-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  970.1±65.0 °C(predicted)
• 密度：
  1.239±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,N'-bis[3-[4-(3-(4-pentynamido)propyl)piperazin-1-yl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide 、 6-azido-6-deoxy-α-D-galactopyranose 在 copper(II) sulfate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 C₅₆H₇₈N₁₄O₁₆
  参考文献：
  名称：

  Metallization of Double-Stranded DNA Triggered by Bound Galactose-Modified Naphthalene Diimide

  摘要：

  Naphthalene diimide (NDI) derivatives bearing galactose moieties through different spacers, NDI-DS1 and NDI-DS2, were synthesized by the click reaction of the acetylene derivatives of NDI with galactose azide. They bound to double-stranded DNA with threading intercalation, as confirmed by the topoisomerase I assay and circular dichroism spectroscopy. The binding affinities of these ligands were on the order of 10(5) M-1 with several-fold higher affinity for double-stranded DNA than for single-stranded DNA. The silver mirror reaction on the double-stranded DNA bound to these ligands afforded silver nanowires that were converted to gold nanowires. In the atomic force microscopy measurements, the increased height of DNA areas on a mica plate was observed in the case of double-stranded DNA after NDI-DS2 treatment and subsequently silver mirror reaction, whereas the increased height of DNA areas was not observed in the case of single-stranded DNA after the same treatment.

  DOI：

  10.1021/bc500263b
• 作为产物：
  描述：

  炔丙基脲 、 N,N’-bis[[4-(3-aminopropyl)piperazinyl]propyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到N,N'-bis[3-[4-(3-(4-pentynamido)propyl)piperazin-1-yl]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

• Metallization of Double-Stranded DNA Triggered by Bound Galactose-Modified Naphthalene Diimide
  作者：Kohei Komizo、Hideyuki Ikedo、Shinobu Sato、Shigeori Takenaka

  DOI：10.1021/bc500263b

  日期：2014.8.20

  Naphthalene diimide (NDI) derivatives bearing galactose moieties through different spacers, NDI-DS1 and NDI-DS2, were synthesized by the click reaction of the acetylene derivatives of NDI with galactose azide. They bound to double-stranded DNA with threading intercalation, as confirmed by the topoisomerase I assay and circular dichroism spectroscopy. The binding affinities of these ligands were on the order of 10(5) M-1 with several-fold higher affinity for double-stranded DNA than for single-stranded DNA. The silver mirror reaction on the double-stranded DNA bound to these ligands afforded silver nanowires that were converted to gold nanowires. In the atomic force microscopy measurements, the increased height of DNA areas on a mica plate was observed in the case of double-stranded DNA after NDI-DS2 treatment and subsequently silver mirror reaction, whereas the increased height of DNA areas was not observed in the case of single-stranded DNA after the same treatment.
• Synthesis and DNA binding behavior of a naphthalene diimide derivative carrying two dicobalt hexacarbonyl complexes as an infrared DNA probe
  作者：Keiichi Ohtsuka、Kohei Komizo、Shigeori Takenaka

  DOI：10.1016/j.jorganchem.2010.02.020

  日期：2010.5

  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.