Effect of Acyclic and Cyclic Donor Groups in Boranil Partial J-Aggregations in Lipid Metabolism and Bio-Imaging.

Two new benzothiazole-based planar boranils (B1 and B2, with acyclic and cyclic donor groups, respectively) with typical π-π interactions showed aggregation-induced emission (AIE) due to integrated J-aggregate bending. During enhancement of water content in DMSO solution, the AIE for B2 was found slower in comparison to B1. The original green monomeric emission turned into red emission upon aggregation for both the probes. In the cell imaging studies with B1 in lung cancer NCIH460 cells, aggregated red emission was observed in hydrophilic cytoplasm and monomeric green emission in hydrophobic cell membrane. However, no red AIE was observed for B2, rather green emission was enhanced in the cytoplasm after prolong incubation. The difference in red emission among the cell lines in the presence of the probes motivated an examination of cellular metabolites via LCMS-MS studies. Careful analysis of the metabolic products suggested that cellular metabolism was significantly affected due to the probes. The major change in the cellular protein metabolism due to B1 probe could not restrict the AIE-based imaging. However, the change in lipid metabolism after B2 treatment did not allow the AIE-based imaging even after 6 h incubation. Cells after 48 h starvation period showed red emission from B2 probe.