Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Street, 41-819 Zabrze, Poland; Silesian University of Technology, Faculty of Chemistry, Department of Physical Chemistry and Technology of Polymers, Strzody 9 44-100, Gliwice, Poland.
J Photochem Photobiol B. 2020 Nov;212:112020. doi: 10.1016/j.jphotobiol.2020.112020. Epub 2020 Sep 11.
A series of new Schiff bases containing the phenyl-ethynyl-phenyl system was synthesized and their thermal stability, photophysical and electrochemical properties were investigated. Moreover, DFT calculations were performed to obtain the optimized ground-state geometry and distribution of the HOMO and LUMO levels as well as IR spectra of the prepared compounds. It was found that, the photoluminescence of synthesized imines was negligible in all investigated organic solvents except for the PBS/ACN mixture. As was proved in further studies, this phenomenon was related to the partial hydrolysis of imines, which is the source of the fluorogenic aldehyde causing the aggreggacion incrased-emision effect. In further research, due to the susceptibility of the azomethines to partial hydrolysis, the biological activity of 2-{(E)-[4-(phenylethynyl) phenyl]imino}phenol (1b), substrate (2-aminophenol) and Cu(II)-1b complex was analyzed. The biological tests showed, that 1b (as example of imine resveratrol analogue), demonstrated its increased cytostatic activity in prostate cancer cellular system. It was proved that the non-hydrolyzed imine was crucial for the cytotoxic effect. This activity could be ascribed to its Cu(II) complexing capability as showed in our previous research.
一系列含有苯乙炔基-苯系统的新型希夫碱被合成，并研究了它们的热稳定性、光物理和电化学性质。此外，还进行了 DFT 计算，以获得所制备化合物的优化基态几何形状、HOMO 和 LUMO 能级的分布以及 IR 光谱。结果发现，除了 PBS/ACN 混合物外，合成的亚胺在所有研究的有机溶剂中的荧光都可以忽略不计。进一步的研究证明，这种现象与亚胺的部分水解有关，这是产生荧光醛的原因，导致聚集增强发射效应。在进一步的研究中，由于亚甲胺对部分水解的敏感性，分析了 2-{(E)-[4-(苯乙炔基)苯基]亚氨基}苯酚（1b）、底物（2-氨基酚）和 Cu(II)-1b 配合物的生物活性。生物测试表明，1b（作为亚胺白藜芦醇类似物的例子）在前列腺癌细胞系统中表现出增加的细胞抑制活性。证明未水解的亚胺对于细胞毒性作用是至关重要的。这种活性可以归因于其如我们之前的研究所示的 Cu(II) 络合能力。
