4,4'-((5-nitro-1,3-phenylene)bis(ethyne-2,1-diyl))bis(2,3,5,6-tetrafluoropyridine) | 1412499-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-((5-nitro-1,3-phenylene)bis(ethyne-2,1-diyl))bis(2,3,5,6-tetrafluoropyridine)
• 英文别名: 2,3,5,6-Tetrafluoro-4-[2-[3-nitro-5-[2-(2,3,5,6-tetrafluoropyridin-4-yl)ethynyl]phenyl]ethynyl]pyridine；2,3,5,6-tetrafluoro-4-[2-[3-nitro-5-[2-(2,3,5,6-tetrafluoropyridin-4-yl)ethynyl]phenyl]ethynyl]pyridine
• CAS: 1412499-28-5
• 化学式: C₂₀H₃F₈N₃O₂
• 分子量: 469.25
• InChiKey: ANTLFSRSLXRMDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4,4'-((5-nitro-1,3-phenylene)bis(ethyne-2,1-diyl))bis(2,3,5,6-tetrafluoropyridine) 在 tin(ll) chloride 、 三氯氧磷 作用下， 生成
  参考文献：
  名称：

  Opening Enediyne Scissors Wider: pH-Dependent DNA Photocleavage bymeta-Diyne Lysine Conjugates

  摘要：

  AbstractPhotochemical activation of meta‐diynes incapable of Bergman and C1–C5 cyclizations still leads to efficient double‐strand DNA cleavage. Spatial proximity of the two arylethynyl groups is not required for efficient DNA photocleavage by the enediyne‐lysine conjugates. Efficiency of the cleavage is a function of the external pH and DNA damage is strongly enhanced at pH < 7. The pH‐dependence of the DNA photocleavage activity stems from the protonation states of lysine amino groups, the internal electron donors responsible for intramolecular PET quenching and deactivation of the photoreactive excited states. DNA‐binding analysis suggests intercalative DNA binding for phenyl substituted conjugate and groove binding for TFP‐substituted conjugate. Additional insights in the possible mechanism for DNA damage from the ROS (Reactive Oxygen Species) scavenger experiments found that generation of singlet oxygen is partially involved in the DNA damage.

  DOI：

  10.1111/php.12412
• 作为产物：
  描述：

  1,3-二溴-5-硝基苯 在 cesium fluoride 作用下， 生成 4,4'-((5-nitro-1,3-phenylene)bis(ethyne-2,1-diyl))bis(2,3,5,6-tetrafluoropyridine)
  参考文献：
  名称：

  Opening Enediyne Scissors Wider: pH-Dependent DNA Photocleavage bymeta-Diyne Lysine Conjugates

  摘要：

  AbstractPhotochemical activation of meta‐diynes incapable of Bergman and C1–C5 cyclizations still leads to efficient double‐strand DNA cleavage. Spatial proximity of the two arylethynyl groups is not required for efficient DNA photocleavage by the enediyne‐lysine conjugates. Efficiency of the cleavage is a function of the external pH and DNA damage is strongly enhanced at pH < 7. The pH‐dependence of the DNA photocleavage activity stems from the protonation states of lysine amino groups, the internal electron donors responsible for intramolecular PET quenching and deactivation of the photoreactive excited states. DNA‐binding analysis suggests intercalative DNA binding for phenyl substituted conjugate and groove binding for TFP‐substituted conjugate. Additional insights in the possible mechanism for DNA damage from the ROS (Reactive Oxygen Species) scavenger experiments found that generation of singlet oxygen is partially involved in the DNA damage.

  DOI：

  10.1111/php.12412

文献信息

• DIPEPTIDE ACETYLENE CONJUGATES AND A METHOD FOR PHOTOCLEAVAGE OF DOUBLE STRAND DNA BY DIPEPTIDE ACETYLENE CONJUGATES
  申请人：Alabugin Igor

  公开号：US20120288940A1

  公开（公告）日：2012-11-15

  Photoreactive DNA cleaving conjugate compounds are provided comprising a DNA cleaving moiety which comprises an aryl alkyne group and a polyfunctional pH-regulated DNA-binding moiety which comprises at least one or two amino groups.

  提供了光反应性DNA切割共轭化合物，其中包含一个含有芳基炔基团的DNA切割部分和一个含有至少一个或两个氨基团的多功能pH调节DNA结合部分。
• US8927728B2
  申请人：——

  公开号：US8927728B2

  公开（公告）日：2015-01-06
• Opening Enediyne Scissors Wider: pH-Dependent DNA Photocleavage by<i>meta</i>-Diyne Lysine Conjugates
  作者：Kemal Kaya、Madeleine Johnson、Igor V. Alabugin

  DOI：10.1111/php.12412

  日期：2015.5

  AbstractPhotochemical activation of meta‐diynes incapable of Bergman and C1–C5 cyclizations still leads to efficient double‐strand DNA cleavage. Spatial proximity of the two arylethynyl groups is not required for efficient DNA photocleavage by the enediyne‐lysine conjugates. Efficiency of the cleavage is a function of the external pH and DNA damage is strongly enhanced at pH < 7. The pH‐dependence of the DNA photocleavage activity stems from the protonation states of lysine amino groups, the internal electron donors responsible for intramolecular PET quenching and deactivation of the photoreactive excited states. DNA‐binding analysis suggests intercalative DNA binding for phenyl substituted conjugate and groove binding for TFP‐substituted conjugate. Additional insights in the possible mechanism for DNA damage from the ROS (Reactive Oxygen Species) scavenger experiments found that generation of singlet oxygen is partially involved in the DNA damage.