Spectroscopic and Biological Properties of the 3-Imino-1,8-naphthalimide Derivatives as Fluorophores for Cellular Imaging

This paper presents the photophysical and biological properties of eight 3-imino-1,8-naphthalimides. The optical properties of the compounds were investigated in the solvents that differed in their polarity (dichloromethane, acetonitrile, and methanol), including three methods of sample preparation using different pre-dissolving solvents such as dimethyl sulfoxide or chloroform. In the course of the research, it was found that there are strong interactions between the tested compounds and DMSO, which was visible as a change in the maximum emission band (& lambda;em) of the neat 3-imino-1,8-naphthalimides (& lambda;em = 470-480 nm) and between the compounds and DMSO (& lambda;em = 504-514 nm). The shift of the emission maximum that was associated with the presence of a small amount of DMSO in the sample was as much as 41 nm. In addition, the susceptibility of imines to hydrolysis in the methanol/water mixture with increasing water content and in the methanol/water mixture (v/v; 1:1) in the pH range from 1 to 12 was discussed. The studies showed that the compounds are hydrolysed in the CH3OH/H2O system in an acidic environment (pH in the range of 1 to 4). In addition, it was found that partial hydrolysis occurs in systems with an increased amount of water, and its degree may depend on the type of substituent on the imine bond. The compounds tended to quench the emission (ACQ) in the aggregated state and increase the emission related to the protonation of the imine bond. Moreover, it was found that the substituent in the imine bonds influenced a compound's individual photophysical properties. Biological tests, including cytotoxicity studies and cellular localisation, were also performed for all of the molecules. All of the tested compounds exhibited green fluorescence in the MCF-7 cells and showed co-localisation in the mitochondria, endoplasmic reticulum, and lysosome. The obtained photophysical and biological results indicate the promising potential use of the tested compounds as cellular dyes.

Automated summary

This paper presents the photophysical and biological properties of eight 3-imino-1,8-naphthalimides. It was found that the tested compounds exhibited strong interactions with DMSO, causing a shift in the emission maximum. The compounds also underwent hydrolysis in acidic environments and their photophysical properties were influenced by the substituents on the imine bonds. Biological tests showed that the compounds exhibited green fluorescence and co-localization in cells, indicating their potential as cellular dyes.