Abstract
A series of multifunctional compounds (MFCs) 1a–1d based on 1,8-naphthalimide moiety were designed and synthesized. Due to the good fluorescence property and nucleic acid binding ability of 1,8-naphthalimide, these MFCs were applied in Cu2+ ion recognition, lysosome staining as well as RNA delivery. It was found that these MFCs exhibited highly selective fluorescence turn-off for Cu2+ in aqueous solution. The fluorescence emission of 1a−1d was quenched by a factor of 116-, 20-, 12-, and 14-fold in the presence of Cu2+ ions, respectively. Most importantly, 1a-Cu and 1b-Cu could be used as imaging reagents for detection of lysosome in live human cervical cancer cells (HeLa) using fluorescence microscopy. Furthermore, in order to evaluate the RNA delivery ability of 1a−1d, cellular uptake experiments were performed in HeLa, HepG2, U2Os, and MC3T3-E1 cell lines. The results showed that all the materials could deliver Cy5-labled RNA into the targeted cells. Among them, compound 1d modified with long hydrophobic chain exhibited the best RNA delivery efficiency in the four tested cell lines, and the performance was far better than lipofectamine 2000 and 25 kDa PEI, indicating the potential application in non-viral vectors.
Highlights
The results showed that the structure of these materials has significant impact on both probe performance and RNA delivery ability, which may give us clues for further design of high-performance multifunctional compounds
The localization of 1a-Cu and 1b-Cu in the cells was almost identical to that of Lyso-Tracker Red. These results suggested that 1a-Cu and 1b-Cu complexes can be used as fluorescence probes to label lysosomes in human cervical cancer cells (HeLa) cells
Due to high sensitivity toward pH value ranging from 4.5 to 5.5, 1a-Cu and 1b-Cu were successfully used as fluorescence probes to stain lysosomes in HeLa cells
Summary
Considerable efforts have been paid to develop 1,8-naphthalimide derivatives as fluorescent probes, fluorescent dyes, gene vectors, and anticancer agents (Xu, 2008; Duke et al, 2010; Banerjee et al, 2014; Gao et al, 2018; Xie et al, 2018). 1,8-Naphthalimide-based fluorescence probes have been widely used for sensing cations (Cu2+, Zn2+, Hg2+, Ag+, and Pb2+) (Grabchev et al, 2003; Bojinov et al, 2009; Aderinto and Imhanria, 2018), anions (F−, CN−, AcO−, and PO34−) (Jun Feng et al, 2011; Ren et al, 2011; Hao et al, 2018), and biomolecules (ATP, ADP, amino acid, and protein) (Huo et al, 2018; Seraj et al, 2018; Shahid et al, 2018). Considerable efforts have been paid to develop 1,8-naphthalimide derivatives as fluorescent probes, fluorescent dyes, gene vectors, and anticancer agents (Xu, 2008; Duke et al, 2010; Banerjee et al, 2014; Gao et al, 2018; Xie et al, 2018). Many excellent examples of 1,8-naphthalimide-based probes have been reported, and some of them have been successfully applied in live-cell imaging research (Dai et al, 2018; Zhu et al, 2018). It is well-known that development of safe and efficient gene vectors is important to gene therapy (Behr, 1993; Verma et al, 1997; Niidome and Huang, 2002). There is huge potential to develop 1,8-naphthalimide derivatives as multifunctional compounds
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