Fluorescent boron difluoride curcuminoides as perspective materials for bio-visualization

Curcuminoids of boron difluoride, 1-aryl(hetaryl)-5-phenylpenta-2,4-dien-1-onates of boron difluoride, have been synthesized. A comparative study of the electronic structure, luminescent properties and their potential for applications in bio-imaging has been carried out. The influence of the electronic structure of a-substituents on the luminescence of compounds was studied by the methods of stationary and time-resolved luminescence spectroscopy and DFT modeling. The introduction of rc-donor substituents leads to a noticeable bathochromic shift and an increase in the Stokes shift in the luminescence spectra. On going from a-donor substituents in the phenyl ring to rc-donor substituents, the luminescence quantum yield increases from 0.03 to 0.22. The maximum Stokes shift and high quantum yield of luminescence is exhibited by the complex with a stilbene substituent, which has the longest rc-system and the maximum efficiency of charge transfer. Dyes are able to penetrate into the cells of the model cell line and accumulate, moreover, accumulation occurs mainly in the cytoplasm of cells. The compounds penetrate into the cells by 12 h of incubation without damaging it's structure and without causing rapid cell death. The submicromolar range of non-toxic concentrations during long-term incubation for a model cell line was determined, which is a characteristic of fluorescent imaging. Due to uniform distribution in the cytoplasm of cells dye with naphtyl substituent is promising for visualization of the cell cytoplasm. This leader compound has the lowest cytotoxicity for cells from the synthesized series of dyes, which makes it promising for further studies as a fluorescent imaging agent.

Automated summary

Curcuminoids of boron difluoride, 1-aryl(hetaryl)-5-phenylpenta-2,4-dien-1-onates of boron difluoride, have been synthesized and their electronic structure, luminescent properties, and potential for bio-imaging applications have been studied. The effect of α-substituents on the luminescence of compounds was investigated using luminescence spectroscopy and DFT modeling. The introduction of rc-donor substituents resulted in a bathochromic shift and an increase in the Stokes shift in the luminescence spectra. The compounds showed promise for fluorescent imaging with low cytotoxicity.