Fluorenyl-corroles: Characterization, photophysical, photobiological, and DNA/BSA-binding properties of novel examples

Abstract

In this study, it was evaluated the photophysical, electrochemical, photobiological, and DNA/BSA-binding properties of fluorenyl corrole derivatives H₃MFluCor and H₃TFluCor. Absorption and emission analyses were corroborated by theoretical calculations performed using time-dependent density functional theory, which revealed natural transition orbitals densities concentrated around the tetrapyrrolic macrocycle in all cases. The experimental studies indicated that the corroles H₃MFluCor and H₃TFluCor are stable in solution and exhibited photostability primarily in DMSO(5%)/Tris-HCl (pH 7.4) buffer. The generation of reactive oxygen species (ROS) and log P_OW values highlight their potential application in photobiological methods, as these corroles effectively generate ROS with more lipophilic characteristics. Furthermore, their binding capacity towards double-stranded DNA and bovine serum albumin (BSA) was also evaluated by spectroscopic techniques and molecular docking calculations. The interactive profile with biomolecules indicates that the corrole derivatives H₃MFluCor and H₃TFluCor tend to binding into the minor grooves of DNA through secondary forces, which are particularly pronounced at site III of the BSA, likely due to the static interactions.