Computational Binding Analysis of Ethyl 3,3,5,5-Tetracyano-2-Hydroxy-2-Methyl-4,6-Diphenylcyclohexane-1-Carboxylate in Calf Thymus DNA.

Autor: Kurbanova M; Organic Chemistry Department, Baku State University, Z. Khalilov 23, Baku, AZ, 1148, Azerbaijan. mkurbanova72@mail.ru., Saravanan K; Faculty of Chemistry, University of Warsaw, Warsaw, Poland., Ahmad S; Department of Health and Biological Sciences, Abasyn University, Peshawar, 25000, Pakistan., Sadigova A; Organic Chemistry Department, Baku State University, Z. Khalilov 23, Baku, AZ, 1148, Azerbaijan., Askerov R; Organic Chemistry Department, Baku State University, Z. Khalilov 23, Baku, AZ, 1148, Azerbaijan., Magerramov A; Organic Chemistry Department, Baku State University, Z. Khalilov 23, Baku, AZ, 1148, Azerbaijan., Bakri YE; Department of Theoretical and Applied Chemistry, South Ural State University, Lenin prospect 76, Chelyabinsk, 454080, Russian Federation. yns.elbakri@gmail.com.
Jazyk: angličtina
Zdroj: Applied biochemistry and biotechnology [Appl Biochem Biotechnol] 2023 Sep; Vol. 195 (9), pp. 5338-5354. Date of Electronic Publication: 2022 Feb 23.
DOI: 10.1007/s12010-022-03849-0
Abstrakt: In the present paper, several computational binding analyses were performed on ethyl 3,3,5,5-tetracyano-2-hydroxy-2-methyl-4,6-diphenylcyclohexane-1-carboxylate which was newly synthesized by three-component condensation of benzaldehyde with ethyl acetoacetate and malononitrile in the presence of trichloroacetic acid, and the structure was finally proved by X-ray analysis. The visualization of molecular interaction was carried out through Hirshfeld surface analysis and ESP. The atomic charges, HOMO, LUMO, and electrostatic potential were also studied to explore the insight of the molecule deeper, and then, natural bonding orbitals (NBO) and non-linear optical properties (NLO) were calculated to reveal the interactions that happen to be between the filled and vacant orbitals. Afterwards, molecular docking studies predicted the compound binding mode fits in the minor groove of DNA and remained interacts via stable bonding as validated by molecular dynamics simulations. The binding energy estimation also affirmed domination van der Waals and electrostatic energies. Lastly, the compound was found as good drug-like molecule and had good pharmacokinetic profile with exception of toxic moieties.
(© 2022. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)
Databáze: MEDLINE
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