Computational and molecular docking approaches of a New axially chiral BODIPY fluorescent dye

Abstract

A new axially chiral BODIPY–based fluorescent dye, 4,4‒difluoro‒2,6‒bis(2‒methoxyphenyl)‒1,3,5,7‒tetramethyl‒8‒phenyl‒4‒bora‒3a,4a‒diaza‒s‒indacene, 3, has been synthesized. Its molecular structure confirmed by FT-IR, 1H-NMR, 13C-NMR, 19F-NMR, mass spectroscopy and elemental analysis. The 19F NMR spectrum is consistent with the presence of a 1:1 mixture of the chiral, anti-diastereoisomer and the meso, syn isomer which do not interconvert on heating to 100 °C in d8-toluene. Geometry minimization by density functional theory (DFT) calculations confirm the expected non-coplanarity caused by steric interactions between the 2-methoxyphenyl substituents and the methyl groups on the BODIPY core and predict a 7.46 Kcal mol−1 barrier to diastereomer conversion by rotation around the BODIPY-aryl bond. The syn isomer is predicted to be more stable than the anti-isomer by only 0.13931 Kcal mol−1. The theoretical potential of the present compound to act as an antibacterial agent has been explored by molecular docking studies. From the partition coefficient value, it can be inferred that the compound 3 could exhibit potential antibacterial activity. Furthermore, molecular docking results provided details of the binding site and the energy of the compound 3 with selected target molecules. The results of which revealed its potential to inhibit bacterial target enzymes viz., DNA gyrase, enzymes in the type II fatty acid synthesis and Ddl in peptidoglycan synthesis.