Naphthyridine-based neutral fluorescent probes for dynamic monitoring lipid droplet polarity

• Published in: Dyes and pigments 2023-12, Vol.220, p.111731, Article 111731
• Main Authors: Li, Meng-Nan, Zhao, Jing-Yu, Zhang, Gang, Xu, Yu-Jie, Ge, Jian-Feng, Sun, Ru
• Format: Article
• Language: English
• Subjects: Dynamic monitoring; Lipid droplets; Low concentration; Naphthyridine derivative; Polarity
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2023.111731

In this paper, several novel nitrogen-containing heterocycle dyes 1a-c with large conjugated planar structures based on naphthyridine derivatives were designed and synthesized, which had excellent optical properties and biological applications. Optical test showed the maximum absorption wavelengths of 1a-c were in the range of 443–485 nm, while the maximum emission wavelengths located at 523–610 nm in difference solvents. Furthermore, they exhibited polarity related fluorescence intensity changes with high fluorescence quantum yields, even up to 88% (1a in THF). Moreover, the transient absorption spectra revealed the excited-state lifetime of dye 1a became shorter with the increase of solvent polarity. Density functional theory calculations are also used to help explain the effect of the polarity of solvents on their fluorescence properties. Interestingly, the dyes 1a-c were somewhat toxic to cancer cells, while had an obvious growth-promoting effect on normal cells. Additionally, 1a-c with excellent lipid droplet (LD) targeting could be used for long-term observation of targeted cellular lis) hysiological activity and further applied to dynamic monitoring of changes in LDs polarity stimulated by TLR4 activator (LPS) in living cells. Overall, the excellent optical properties and biocompatibility of 1a-c indicate that they can serve as fluorescent probes for biological applications, and the results have important implications for understanding the physiological functions of LDs, especially in terms of morphological and polar changes. [Display omitted] •The dibenzo[c,f] [2,7]naphthyridine skeleton have been first applied in the field of cell imaging.•Dyes 1a-c possess high fluorescence quantum yield and excellent polarity response.•Dyes 1a-c are somewhat toxic to cancer cells, while have a growth-promoting effect on normal cells.•Dyes 1a-c can sensitively target lipid droplets with a low concentration, and dynamically monitor their polarity changes.