A series of multifunctional compounds (MFCs) 1a-1e based on 1,8-naphthalimide and [12]aneN3 building blocks were designed and synthesized. They were used as not only fluorescent probes for recognition of Cu2+ ions but also as non-viral gene vectors for DNA and RNA delivery. Furthermore, their complexes with Cu2+ (1-Cu) could also selectively stain lysosome in HeLa cells. In order to achieve high performance multifunctional materials, structure-performance relationship of MFCs 1a-1e was studied. It was found that MFCs 1a-1e exhibited highly selective fluorescence turn-off for Cu2+, without interference by other metal ions in aqueous solution. The fluorescence emission of 1a-1e was quenched by a factor of 10-fold, 47-fold, 6-fold, 64-fold, and 15-fold respectively in the presence of Cu2+ ions. Due to high sensitivity, good water solubility, and low cytotoxicity, MFCs 1a-1d were successfully applied in the recognition of Cu2+ and selectively staining lysosome in HeLa cells. Most importantly, MFCs 1a and 1b had excellent HeLa cell selectivity in RNA delivery, and their performances were far better than lipofectamine 2000 and 25 kDa PEI.

中文翻译：

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[12]aneN3基多功能化合物作为荧光探针和核酸递送剂。


设计并合成了一系列基于1,8-萘二甲酰亚胺和[12]aneN3结构单元的多功能化合物（MFC）1a-1e。它们不仅用作识别 Cu2+ 离子的荧光探针，还用作 DNA 和 RNA 传递的非病毒基因载体。此外，它们与 Cu2+ (1-Cu) 的复合物还可以选择性地对 HeLa 细胞中的溶酶体进行染色。为了获得高性能多功能材料，对MFCs 1a-1e的结构-性能关系进行了研究。研究发现MFCs 1a-1e对Cu2+表现出高度选择性的荧光关闭，且不受水溶液中其他金属离子的干扰。在Cu2+离子存在下，1a-1e的荧光发射分别被猝灭10倍、47倍、6倍、64倍和15倍。由于MFCs 1a-1d具有灵敏度高、水溶性好、细胞毒性低等优点，成功应用于HeLa细胞中Cu2+的识别和溶酶体的选择性染色。最重要的是，MFC 1a和1b在RNA递送方面具有优异的HeLa细胞选择性，其性能远优于lipofectamine 2000和25 kDa PEI。