Anti-inflammatory biomolecular activity of chlorinated-phenyldiazenyl-naphthalene-2-sulfonic acid derivatives: perception from DFT, molecular docking, and molecular dynamic simulation

Abstract

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 in-vitro 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:

• Anti-inflammation
• DFT
• in-vitro molecular docking
• MD simulation
• cyclooxygenases

Author contributions

Ernest C. Agwamba: Project administration, analysis, writing, and editing. Hitler Louis: Conceptualization, design, supervision, writing, and editing. Akaninyene D. Udoikono: Results analysis, writing, editing, and manuscript first draft. Innocent Benjamin: Analysis, writing and manuscript final draft. Eze F. Ahuekwe: Resources, analysis, writing, and editing. Kelechi Chukwuemeka and Emmanuel U. Ejiofor: Analysis, writing, and editing. validation, writing and editing. Adeyinka S. Adeyemi and Iqrar Ahmad: Methodology, Harun Patel, Amanda-Lee Manicum, and Moses M. Edim: analysis and discussion of molecular dynamics

Acknowledgements

The center for high performance computing (CHPC) South Africa is acknowledged for providing the computational resources utilized in this work.

Disclosure statement

No potential conflict of interest was reported by the authors.

Consent for publication

Not applicable.

Ethics approval and consent to participate

Not applicable.

Funding

No funding was received from any Government or Non-Government organization.

Availability of data and material

All data are contained within the manuscript and manuscript supporting information document (ESI).