Synthesis of novel BODIPY chromophores for biomedical imaging

Merkes, Jean Michel; Rüping, Magnus (Thesis advisor); Albrecht, Markus (Thesis advisor)

Aachen (2021)
Dissertation / PhD Thesis

Dissertation, RWTH Aachen University, 2020


Chromophores are an essential tool in modern biological and medical imaging systems. In this thesis, four new dyes based on difluoroboron dipyrromethene (BODIPY) were developed and tested for specific imaging applications. For photoacoustic imaging two dyes, a NIR quencher based on pyrrolyl BODIPY (PyBODIPY) and a ROS sensing phenolic BODIPY (ROS-BODIPY), were prepared. Both dyes showed excellent photoacoustic properties during phantom and cell studies and, in case of PyBODIPY, also in vivo. In a third project amino-BODIPY (ABDP) was synthesized and tested for application in the superresolution microscopy method STED, with a focus on the 660 nm depletion laser. Stability of the dye was tested in unspecific labeling experiments and showed very low photobleaching for the target dye ABDP520. Further labeling of fixed cells for actin was possible and life cell imaging and showed good uptake of dye. In the last project a novel time-temperature-indicator (TTI) based on here, developed oxadiazaborinin was prepared. This dye showed interesting color changes in organic solvent and water depending on temperature. Potential applications for this dye are in the area of cold chain management, but also in the area of magnetic fluid hyperthermia treatment for the investigation of nanoheating in iron-nanoparticles.