Near-infrared fluorescent probes based on naphthyridine derivatives for mitochondrial nucleic acid imaging.

Most current nucleic acid-responsive fluorescent probes are enhanced ones with short emission wavelengths. Therefore, the development of novel near-infrared, turn-on response nucleic acid fluorescent probes is of great significance. Herein, three cationic fluorescent dyes 1a-1c were synthesized by reacting naphthalidine salt with suitable aldehydes. These probes exhibited excellent photostability, maintaining over 95% of their absorption rate after 5 h of irradiation. Notably, probes 1a-1c exhibited an OFF-ON fluorescence response to DNA and RNA. The maximum emission wavelength could reach the near-infrared region (661-762 nm), with large Stokes shifts (153-222 nm) upon binding to DNA/RNA. The fluorescence intensity was enhanced 143 fold and 127 fold for 1b upon interaction with DNA and RNA, respectively. Co-staining and nucleic acid digestion assays showed that probes 1a-1c could target the mitochondria of fixed cells with low cytotoxicity. These findings may be useful for the early screening of genetic mutations related to mitochondrial diseases.