School of Pharmacy, Jiangsu University, Zhenjiang 212013, PR China.
The Key Laboratory of Biomedical Material, School of Life Science and Technology, Xinxiang Medical University, Xinxiang 453003, PR China.
Spectrochim Acta A Mol Biomol Spectrosc. 2024 Dec 15;323:124901. doi: 10.1016/j.saa.2024.124901. Epub 2024 Jul 29.
Fluorescent solvatochromic dyes that are sensitive to the nature of local microenvironmental, have been explored as probes in applications ranging from the imaging biomolecules to understanding of basic biomolecule functions. To expand the scope of fluorescent solvatochromic dyes for G-quadruplex (G4) DNA structures, and to illustrate the relationship between structure and properties, three newly designed D-π-A type fluorescent dyes were synthesized by introducing diarylimidazole to carbazole skeleton linked to benzene, furan or thiophene π-conjugated bridge and connected with pyridinium acceptor, respectively. Their structural characteristics, optical properties, and G4 DNA binding properties were discussed in detail. In general, the incorporation of furan and thiophene as π-conjugated bridges leads the better conjugation and molecular coplanarity with more efficient intramolecular charge transfer (ICT) effect compared with benzene bridge. The fluorescence intensities induced upon interaction were found that TP-6 with thiophene π-conjugated bridge had the strongest response toward G4 DNAs. In addition, the application of this dye as a fluorescent agent for living cell imaging was also demonstrated.
荧光溶剂变色染料对局部微观环境的性质敏感,已被探索作为探针应用于从成像生物分子到理解基本生物分子功能的各个领域。为了扩展用于 G-四链体 (G4) DNA 结构的荧光溶剂变色染料的范围,并说明结构与性质之间的关系,我们通过将二芳基咪唑引入咔唑骨架,连接苯、呋喃或噻吩π-共轭桥,并分别与吡啶鎓受体连接,合成了三种新型 D-π-A 型荧光染料。详细讨论了它们的结构特征、光学性质和与 G4 DNA 的结合性质。一般来说,与苯桥相比,呋喃和噻吩作为π-共轭桥的引入导致更好的共轭和分子共面性,具有更有效的分子内电荷转移 (ICT) 效应。发现相互作用诱导的荧光强度表明,具有噻吩π-共轭桥的 TP-6 对 G4 DNA 具有最强的响应。此外,还证明了该染料作为荧光试剂在活细胞成像中的应用。