BETWEEN ARTEMISININ AND DERIVATIVES WITH NEURAMINIDASE: A DOCKING STUDY INSIGHT
Objectives: This study aims to find the relationship between artemisinins and neuraminidase (NA) with molecular docking study and also to determine the most potent NA inhibitor from artemisinin and derivatives.
Methods: All ligands were sketched and optimized using Gaussian 03W with Hartree-Fock method basis sets 6-311G. Molecular docking was performed using AutoDock 4.2.3 toward NA in complexes with oseltamivir as co-crystal ligand. The main parameters used were the free energy of binding (Î”G) and dissociation constant (Ki) as affinity marker.
Results: Artesunate provided most negative free Î”G and lowest Ki toward NA with âˆ’9.55 kcal/mol and 100.66 nM, respectively. Artesunate shows higher affinity than oseltamivir with interactions between artesunate and amino acids at position 246 had important influences on artesunate affinity toward NA from H5N1.
Conclusion: In silico molecular docking results indicated that artesunate could be considered as NA inhibitor and should be potential to be developed as anti-influenza particularly to H5N1 with oseltamivir resistance.
2. Maurer-Stroh S, Li Y, Bastien N, Gunalan V, Lee RT, Eisenhaber F, et al. Potential human adaptation mutation of influenza A(H5N1) virus, Canada. Emerg Infect Dis 2014;20(9):1580-2.
3. Aiki-Raji CO, Aguilar PV, Kwon YK, Goetz S, Suarez DL, Jethra AI, et al. Phylogenetics and pathogenesis of early avian influenza viruses (H5N1), Nigeria. Emerg Infect Dis 2008;14(11):1753-5.
4. Eyer L, Hruska K. Antiviral agents targeting the influenza virus: A review and publication analysis. Vet Med 2013;58(3):113-85.
5. Moscona A. Neuraminidase inhibitors for influenza. N Engl J Med 2005;353(13):1363-73.
6. McKimm-Breschkin JL. Influenza neuraminidase inhibitors: Antiviral action and mechanisms of resistance. Influenza Other Respir Viruses 2012;7 Suppl 1:25-36.
7. Abed Y, Baz M, Boivin G. Impact of neuraminidase mutations conferring influenza resistance to neuraminidase inhibitors in the N1 and N2 genetic backgrounds. Antivir Ther 2006;11(8):971-6.
8. von Itzstein M. The war against influenza: Discovery and development of sialidase inhibitors. Nat Rev Drug Discov 2007;6(12):967-74.
9. Nguyen HT, Fry AM, Gubareva LV. Review: Neuraminidase inhibitor resistance in influenza viruses and laboratory testing methods. Antiviral Ther 2012;17:159-73.
10. Nitsch-Osuch A, Brydak LB. Influenza viruses resistant to neuraminidase inhibitors. Acta Biochim Pol 2014;61(3):505-8.
11. Hudson JB. Review: The use of herbal extracts in the control of influenza. J Med Plant Res 2009;3(13):1189-95.
12. Efferth T, Romero MR, Wolf DG, Stamminger T, Marin JJ, Marschall M. The antiviral activities of artemisinin and artesunate. Clin Infect Dis 2008;47(6):804-11.
13. Karamoddini MK, Emami SA, Ghannad MS, Sani EA, Sahebkar A. Antiviral activities of aerial subsets of Artemisia species against herpes simplex virus Type 1 (HSV1) in vitro. Asian Biomed 2011;5(1):63-8.
14. Cosconati S, Forli S, Perryman AL, Harris R, Goodsell DS, Olson AJ. Virtual screening with autodock: Theory and practice. Expert Opin Drug Discov 2010;5(6):597-607.
15. Oâ€™Boyle NM, Banck M, James CA, Morley C, Vandermeersch T, Hutchison GR. Open Babel: An open chemical toolbox. J Cheminform 2011;3:33.
16. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, et al. AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 2009;30(16):2785-91.
17. Russell RJ, Haire LF, Stevens DJ, Collins PJ, Lin YP, Blackburn GM, et al. The structure of H5N1 avian influenza neuraminidase suggests new opportunities for drug design. Nature 2006;443(7107):45-9.
18. Miladiyah I, Jumina J, Haryana SM, Mustofa M. In Silico molecular docking of xanthone derivatives as cyclooxygenase-2 inhibitor agents. Int J Pharm Pharm Sci 2017;9(3):98-104.
19. Kontoyianni M, McClellan LM, Sokol GS. Evaluation of docking performance: Comparative data on docking algorithms. J Med Chem 2004;47(3):558-65.
20. Bissantz C, Folkers G, Rognan D. Protein-based virtual screening of chemical databases 1. Evaluation of different docking/scoring combinations. J Med Chem 2000;43(25):4759-67.
21. Umashankar V, Gurunathan S. Drug discovery: An appraisal. Int J Pharm Pharm Sci 2015;7(4):59-66.
22. Kim R, Skolnick J. Assessment of programs for ligand binding affinity prediction. J Comput Chem 2008;29(8):1316-31.
23. Munusami P, Indu AG, Vasavi CS, Diyva G. Molecular docking studies on flavonoid compound: An insight into aromatase inhibitors. Int J Pharm Pharm Sci 2014;6(10):141-8.
24. Thangathirupathi A, Naushad A, Natarajan P, Ramesh KD. Molecular docking studies of andrographolide with xanthine oxidase. Asian J Pharm Clin Res 2013;6(2):300-2.
25. Okomo-Adhiambo M, Sleeman K, Ballenger K, Nguyen HT, Mishin VP, Sheu TG, et al. Neuraminidase inhibitor susceptibility testing in human influenza viruses: A laboratory surveillance perspective. Viruses 2010;2(10):2269-89.
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