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 POW 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.