N,N'-bis(5-methanesulfonyl-3-oxapentyl)-1,7-bis(1-piperidinyl)perylene-3,4,9,10-tetracarboxylic diimide | 1268493-82-8

• 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-methanesulfonyl-3-oxapentyl)-1,7-bis(1-piperidinyl)perylene-3,4,9,10-tetracarboxylic diimide
• 英文别名: 2-[2-[18-[2-(2-Methylsulfonyloxyethoxy)ethyl]-6,8,17,19-tetraoxo-11,22-di(piperidin-1-yl)-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-decaen-7-yl]ethoxy]ethyl methanesulfonate
• CAS: 1268493-82-8
• 化学式: C₄₄H₄₈N₄O₁₂S₂
• 分子量: 889.017
• InChiKey: ALRGEBOFSPOAQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  62
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  203
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  N,N'-bis(5-methanesulfonyl-3-oxapentyl)-1,7-bis(1-piperidinyl)perylene-3,4,9,10-tetracarboxylic diimide 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 18.0h， 生成 N,N'-bis(5-dimethylamino-3-oxapentyl)-1,7-bis(1-piperidinyl)perylene-3,4,9,10-tetracarboxylic diimide dihydrochloride
  参考文献：
  名称：

  N-Cyclic Bay-Substituted Perylene G-Quadruplex Ligands Have Selective Antiproliferative Effects on Cancer Cells and Induce Telomere Damage

  摘要：

  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.

  DOI：

  10.1021/jm1013665
• 作为产物：
  描述：

  N,N'-bis(5-hydroxy-3-oxapentyl)-1,7-bis(1-piperidinyl)perylene-3,4,9,10-tetracarboxylic diimide 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到N,N'-bis(5-methanesulfonyl-3-oxapentyl)-1,7-bis(1-piperidinyl)perylene-3,4,9,10-tetracarboxylic diimide
  参考文献：
  名称：

  N-Cyclic Bay-Substituted Perylene G-Quadruplex Ligands Have Selective Antiproliferative Effects on Cancer Cells and Induce Telomere Damage

  摘要：

  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.

  DOI：

  10.1021/jm1013665

文献信息

• <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.