Meso-functionalized BODIPYs: Synthesis, molecular docking and photodynamic efficiency on breast cancer cells

The synthesis and biological studies of meso-functionalized BODIPYs (BD-1 and BD-2) are reported. A pharmacophoric group (2-methyl-4-nitro-N-phenylaniline) was introduced at the meso-position of the BODIPYs. The substitution resulted in the red-shifted emission from BD-1 and BD-2as compared to the parent meso-Aryl BODIPY. Molecular docking studies on PARP (Poly ADP-Ribose Polymerase) protein indicated efficient binding affinity of BD-2(-5.287) compared to BD-1. The cytotoxicity studies on triple-negative breast cancer cell line (MDA-MB-231) showed excellent photodynamic behavior of both compounds. Compound BD-2 showed excellent anti-proliferative activity in light with an IC50 value of 38 nm. However, in the dark condition both the compounds exhibited non-Toxic behavior with 75-80% cell viability. The bioimaging studies indicated the cytoplasmic distribution of BD-1 and BD-2in the breast cancer cells.