Anti-inflammatory biomolecular activity of chlorinated-phenyldiazenyl-naphthalene-2- sulfonic acid derivatives: perception from DFT, molecular docking, and molecular dynamic simulation
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Taylor & Francis. online
Abstract
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In this study, two novel derivatives of naphthalene-2-sulfonic acid: 6-(((1S,5R)-3,5-
dichloro-2,4,6-triazabicyclo [z3.1.0]hex-3-en-1-yl)amino)-5-((E)-
phenyldiazenyl)naphthalene-2-sulfonic acid (DTPS1) and (E)-6-((4,6-dichloro-1,3,5-
triazine2-yl)amino)-4-hydroxy-3-(phenyldiazenyl)naphthalene-2-sulfonic acid (DTPS2)
have been synthesized and characterized using FT-IR, UV-vis, and NMR spectroscopic
techniques. Applying density functional theory (DFT) at the B3LYP, APFD, PBEPBE,
HCTH, TPSSTPSS, and ωB97XD/aug-cc-pVDZ level of theories for the electronic
structural properties. In-vitro analysis, molecular docking, molecular dynamic (MD)
simulation of the compounds was conducted to investigate the anti-inflammatory
potential using COXs enzymes. Docking indicates binding affinity of −9.57, −9.60, −6.77
and −7.37 kcal/mol for DTPS1, DTPS2, Ibuprofen and Diclofenac which agrees with invitro
assay. Results of MD simulation, indicates sulphonic group in DTPS1 has > 30%
interaction with the hydroxyl and oxygen atoms in amino acid residues, but > 35%
interaction with the DTPS2. It can be said that the DTPS1 and DTPS2 can induce
inhibitory effect on COXs to halt biosynthesis of prostaglandins (PGs), a chief mediator
of inflammation and pain in mammals.
Communicated by Ramaswamy H. Sarma
Keywords
QH Natural history, QH301 Biology, QR Microbiology