Department of Chemistry, The Center for Diagnostics and Therapeutics, The Center for Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30302-3965, USA.
Bioorg Med Chem Lett. 2014 Jan 1;24(1):214-9. doi: 10.1016/j.bmcl.2013.11.035. Epub 2013 Nov 25.
Here we report the synthesis of seven symmetrical carbocyanine dyes in which two nitrogen-substituted benz[e]indolium rings are joined by a pentamethine bridge that is meso-substituted with chlorine or bromine versus hydrogen. The heteroatom of benz[e]indolium is modified with a phenylpropyl, methyl, or cationic quaternary ammonium group. In reactions containing micro molar concentrations of halogenated dye, irradiation at 575, 588, 623, or 700nm produces good photocleavage of plasmid DNA. UV-visible spectra show that the carbocyanines are in their H-aggregated and monomeric forms. Scavenger experiments point to the involvement of singlet oxygen and hydroxyl radicals in DNA photocleavage.
在这里，我们报告了七种对称碳菁染料的合成，其中两个氮取代苯并[e]吲哚环由一个五甲川桥连接，该桥的中位取代基为氯或溴而不是氢。苯并[e]吲哚的杂原子用苯基丙基、甲基或阳离子季铵基团修饰。在含有微摩尔浓度卤化染料的反应中，在 575、588、623 或 700nm 处照射会导致质粒 DNA 产生良好的光解。紫外可见光谱表明碳菁染料处于其 H 聚集态和单体形式。清除剂实验表明，单线态氧和羟基自由基参与了 DNA 的光解。
