Amphiphilic and Zwitterionic Multi Arylpyrroles with Near-Infrared Aggregation-Induced Emission for Cell Membrane Imaging

The cell membrane protects the cell stability and balance and participates in various physiological activities as an exchange channel. Therefore, the real-time monitoring of cell membrane biological dynamics can help us understand the physiological state of the current cell. Herein, a type of amphiphilic near infrared (NIR) aggregation-induced emission (AIE) molecules was designed and synthesized. Multiarylpyrroles (MAPs) with a dodecyl chain at the 1-position of the pyrrole ring, charged pyridinium sulfonate at the 2,5-position of the pyrrole ring and free rotating aryls at the 3-position of the pyrrole ring can target cell membranes. One of the MAPs, MAP22, had a maximum emission wavelength in the aggregation state of up to 721 nm with a large Stokes shift (similar to 280 nm). In addition, MAP22 nanoparticles can produce reactive oxygen species (ROS) with a quantum yield of 224%. Therefore, these AIE MAPs are promising candidates for theranostic nanoagents, including NIR fluorescence imaging to target cell membranes and ablate cancer cells by producing ROS.

Automated summary

Real-time monitoring of cell membrane biological dynamics is important for understanding the physiological state of cells. A type of amphiphilic near infrared (NIR) aggregation-induced emission (AIE) molecules, such as MAP22, has been found to have a large emission wavelength and Stokes shift in the aggregation state, and can generate reactive oxygen species. These AIE MAPs show potential as theranostic nanoagents for targeting cell membranes and ablating cancer cells.