Bithiophene-Cored, mono-, bis-, and tris-(Trimethylammonium)-Substituted, bis-Triarylborane Chromophores: Effect of the Number and Position of Charges on Cell Imaging and DNA/RNA Sensing

The synthesis, photophysical, and electrochemical properties of selectively mono-, bis- and tris-dimethylamino- and trimethylammonium-substituted bis-triarylborane bithiophene chromophores are presented along with the water solubility and singlet oxygen sensitizing efficiency of the cationic compounds Cat(1+), Cat(2+), Cat(i)(2+), and Cat(3+). Comparison with the mono-triarylboranes reveals the large influence of the bridging unit on the properties of the bis-triarylboranes, especially those of the cationic compounds. Based on these preliminary investigations, the interactions of Cat(1+), Cat(2+), Cat(i)(2+), and Cat(3+) with DNA, RNA, and DNApore were investigated in buffered solutions. The same compounds were investigated for their ability to enter and localize within organelles of human lung carcinoma (A549) and normal lung (WI38) cells showing that not only the number of charges but also their distribution over the chromophore influences interactions and staining properties.

Automated summary

This study presents the synthesis, photophysical, and electrochemical properties of selectively mono-, bis- and tris-dimethylamino- and trimethylammonium-substituted bis-triarylborane bithiophene chromophores, as well as the water solubility and singlet oxygen sensitizing efficiency of cationic compounds. The research highlights the significant influence of the bridging unit on the properties of bis-triarylboranes, especially the cationic compounds, and investigates their interactions with DNA, RNA, and DNApore in buffered solutions. Additionally, the study explores the compounds' ability to enter and localize within organelles of human lung carcinoma and normal lung cells, showing that both the number and distribution of charges on the chromophore affect interactions and staining properties.