Stasyuk Anton J, Smoleń Sabina, Glodkowska-Mrowka Eliza, Brutkowski Wojciech, Cyrański Michał K, Tkachenko Nikolai, Gryko Daniel T
Warsaw University of Technology Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw (Poland); Warsaw University, Department of Chemistry, Pasteura 1, 01-173 Warsaw (Poland).
Chem Asian J. 2015 Mar;10(3):553-8. doi: 10.1002/asia.201403339. Epub 2015 Jan 26.
The repertoire of synthetic methods leading to aza-analogues of polycyclic aromatic heterocycles has been enlarged by the discovery of the rearrangement of 10-substituted benzo[h]quinolines into compounds bearing an azonia-pyrene moiety. Acid-mediated intramolecular cyclization of derivatives bearing -CH2 CN and -CH2 CO2 Et groups led to compounds bearing a 5-substituted benzo[de]pyrido[3,2,1-ij]quinolinium core. Advanced photophysical studies including time-correlated single photon counting (TCSPC) and transient absorption spectroscopy of 5-aminobenzo[de]pyrido[3,2,1-ij]quinolin-4-ium salt and 5H-benzo[de]pyrido[3,2,1-ij]quinolin-5-one showed their promising optical properties such as high fluorescence quantum yields (37-59%), which was almost independent of the solvent, and high tenability of the absorption band position upon changing the solvent. The benzo[de]pyrido[3,2,1-ij]quinolinium salt selectively stains nucleic acids (in the nucleus and mitochondria) in eukaryotic cells.
10-取代苯并[h]喹啉重排为含氮杂蒽部分的化合物这一发现，扩大了合成多环芳香杂环氮类似物的方法库。含-CH2 CN和-CH2 CO2 Et基团的衍生物经酸介导的分子内环化反应，生成了含5-取代苯并[de]吡啶并[3,2,1-ij]喹啉鎓核心的化合物。对5-氨基苯并[de]吡啶并[3,2,1-ij]喹啉-4-鎓盐和5H-苯并[de]吡啶并[3,2,1-ij]喹啉-5-酮进行的包括时间相关单光子计数（TCSPC）和瞬态吸收光谱在内的高级光物理研究表明，它们具有良好的光学性质，如高荧光量子产率（37-59%），几乎与溶剂无关，并且在改变溶剂时吸收带位置具有高可调节性。苯并[de]吡啶并[3,2,1-ij]喹啉鎓盐可选择性地对真核细胞中的核酸（细胞核和线粒体中）进行染色。
