DFT, Molecular Docking and ADME Studies of Thiazolidinones as Tyrosinase Inhibitors
Raqeeba Arshad, Muhammad Asim Khan, Sadaf Mutahir, Sufyan Hussain, Ghaferah H. Al‐Hazmi, Moamen S. Refat
Abstract
Thiazolidinones are pharmacologically active compounds, extensively used as a precursor for obtaining versatile molecules with several biological activities including anti-microbial, analgesic, antitumor, anti-inflammatory, anti-HIV, and antitubercular. In this study, various thiazolidinone scaffolds were selected for their virtual screening and DFT calculations to evaluate their inhibition potential against tyrosinase. In DFT calculations of selected compounds, numerous reactivity parameters like FMOs, HOMO–LUMO energy gap, electrophilicity index (ω), electron affinity (A), ionization energy (I), electronegativity (χ), chemical hardness (η) and chemical softness (σ) were examined and discussed. All these parameters can be related to different extents to prominently affect the binding affinity of selected thiazolidinones with active tyrosinase protein sites. DFT calculation confirmed that compound 12 revealed the lowest HUMO-LUMO energy gap of 0.01767 eV. Molecular docking study results exposed compounds 1 (−4.756) and 6 (4.576) have exhibited the highest docking scores. ADME study was also done to assess drug-likeness, which presents the potential of thiazolidinone moieties which could be expedient for several cosmetic formulations and could serve as effective and safe tyrosinase inhibitors.