Indian Journal of Advances in Chemical Science, Volume: 9, Issue : 4, December 2021

ISSN No.: 2320-0898 (Print); 2320-0928 (Electronic)

DOI: 10.22607/IJACS.2021.904001

Review Article

Computational Models: A Sustainable Approach to Reveal the Inhibitory Potential of Benzo(a)anthracene and its Monohydroxy Derivatives Against Human Sex Hormone-Binding Globulin

Nikita Tiwari, Anil Mishra
 

ABSTRACT

Benzo(a)anthracene (BaA), a major environmental pollutant, is metabolized in vivo and produces many hydroxy derivatives. The density functional theory calculations were performed to investigate the frontier molecular orbitals as well as the chemical reactivity descriptors of BaA and its monohydroxy derivatives using B3LYP/3-21G basis set. Using in silico tools of AutoDock 1.5.6, these compounds were docked into the active site cavity of human sex hormone-binding globulin (hSHBG) to evaluate their binding affinity. Docking results showed that the binding affinities of BaA and its monohydroxy derivatives lie in the comparable range (−8.5 kcal/mol to −9.04 kcal/mol) with dihydrotestosterone (DHT) (−10.94 kcal/mol), a known ligand of hSHBG. The combined results from both the computational models emphasized that BaA and its metabolites can structurally mimic the binding pattern of DHT, a known inhibitor to hSHBG.

Key words:  Benzo(a)anthracene, Human sex hormone-binding globulin, Density functional theory calculations, Docking.
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