Computational and experimental insights on the interaction of artemisinin, dihydroartemisinin and chloroquine with SARS-CoV-2 spike protein receptor-binding domain (RBD)

References

• Al Adem K, Shanti A, Stefanini C, Lee S. 2020. Inhibition of SARS-CoV-2 entry into host cells using small molecules. Pharmaceuticals (Basel). 13(12):447.
   PubMedGoogle Scholar
• Alexpandi R, De Mesquita JF, Pandian SK, Ravi AV. 2020. Quinolines-based SARS-CoV-2 3CLpro and RdRp inhibitors and spike-RBD-ACE2 inhibitor for drug-repurposing against COVID-19: an in silico. Anal Front Microbiol. 11(1796). PMID: 32793181 PMCID: PMC7390959 DOI: 10.3389/fmicb.2020.01796
   Google Scholar
• Aweeka FT, German PI. 2008. Clinical pharmacology of artemisinin-based combination therapies. Clin Pharmacokinet. 47(2):91–102.
   PubMed Web of Science ®Google Scholar
• Badraoui R, Adnan M, Bardakci F, Alreshidi MM. 2021. Chloroquine and hydroxychloroquine interact differently with ACE2 domains reported to bind with the coronavirus spike protein: mediation by ACE2 polymorphism. Molecules. 26(3):673.
   PubMed Web of Science ®Google Scholar
• Basu A, Sarkar A, Maulik U. 2020. Molecular docking study of potential phytochemicals and their effects on the complex of SARS-CoV2 spike protein and human ACE2. Sci Rep. 10(1):17699.
   PubMed Web of Science ®Google Scholar
• Bourgonje AR, Abdulle AE, Timens W, Hillebrands JL, Navis GJ, Gordijn SJ, Bolling MC, Dijkstra G, Voors AA, Osterhaus AD, et al. 2020. Angiotensin-converting enzyme 2 (ACE2), SARS-CoV-2 and the pathophysiology of coronavirus disease 2019 (COVID-19). J Pathol. 251(3):228–248.
   PubMed Web of Science ®Google Scholar
• Brown GD. 2010. The biosynthesis of Artemisinin (Qinghaosu) and the phytochemistry of Artemisia annua L. (Qinghao). Molecules. 15(11):7603–7698.
   PubMed Web of Science ®Google Scholar
• Cao R, Hu H, Li Y, Wang X, Xu M, Liu J, Zhang H, Yan Y, Zhao L, Li W, et al. 2020. Anti-SARS-CoV-2 Potential of Artemisinins in vitro. ACS Infect Dis. 6(9):2524–2531.
   PubMed Web of Science ®Google Scholar
• Chen RH, Yang LJ, Hamdoun S, Chung SK, Lam CW, Zhang KX, Guo X, Xia C, Law BYK, Wong VKW. 2021. 1,2,3,4,6-Pentagalloyl glucose, a RBD-ACE2 binding inhibitor to prevent SARS-CoV-2 infection. Front Pharmacol. 12:634176.
   PubMed Web of Science ®Google Scholar
• Coghi P, Yaremenko IA, Prommana P, Radulov PS, Syroeshkin MA, Wu YJ, Gao JY, Gordillo FM, Mok S, Wong VKW, et al. 2018. Novel peroxides as promising anticancer agents with unexpected depressed antimalarial Activity. ChemMedChem. 13(9):902–908.
   PubMed Web of Science ®Google Scholar
• Doerr S, Harvey MJ, Noé F, De Fabritiis G. 2016. HTMD: high-throughput molecular dynamics for molecular discovery. J Chem Theory Comput. 12(4):1845–1852.
   PubMed Web of Science ®Google Scholar
• Fantini J, Di Scala C, Chahinian H, Yahi N. 2020. Structural and molecular modelling studies reveal a new mechanism of action of chloroquine and hydroxychloroquine against SARS-CoV-2 infection. Int J Antimicrob Agents. 55(5):105960.
   PubMed Web of Science ®Google Scholar
• Gendrot M, Andreani J, Boxberger M, Jardot P, Fonta I, Le Bideau M, Duflot I, Mosnier J, Rolland C, Bogreau H, et al. 2020. Antimalarial drugs inhibit the replication of SARS-CoV-2: An in vitro evaluation. Travel Med Infect Dis. 37:101873.
   PubMed Web of Science ®Google Scholar
• Gianoncelli A, Ongaro A, Zagotto G, Memo M, Ribaudo G. 2020. 2020. 2-(3,4-Dihydroxyphenyl)-4-(2-(4-nitrophenyl)hydrazono)-4H-chromene-3,5,7-triol. Molbank. 2020(3):M1144.
   Web of Science ®Google Scholar
• Ho WE, Peh HY, Chan TK, Wong WSF. 2014. Artemisinins: pharmacological actions beyond anti-malarial. Pharmacol Ther. 142(1):126–139.
   PubMed Web of Science ®Google Scholar
• Kavak E, Mutlu D, Ozok O, Arslan S, Kivrak A. 2021. Design, synthesis and pharmacological evaluation of novel Artemisinin-thymol. Nat Prod Res. PMID: 33416016. doi:10.1080/14786419.2020.1865954.
   PubMed Web of Science ®Google Scholar
• Krishna S, Augustin Y, Wang J, Xu C, Staines HM, Platteeuw H, Kamarulzaman A, Sall A, Kremsner P. 2021. Repurposing antimalarials to tackle the COVID-19 pandemic. Trends Parasitol. 37(1):8–11.
   PubMed Web of Science ®Google Scholar
• Kshirsagar SG, Rao RV. 2021. Antiviral and immunomodulation effects of Artemisia. Medicina (Kaunas. ). 57(3):217.
   PubMed Web of Science ®Google Scholar
• Mauthe M, Orhon I, Rocchi C, Zhou X, Luhr M, Hijlkema KJ, Coppes RP, Engedal N, Mari M, Reggiori F. 2018. Chloroquine inhibits autophagic flux by decreasing autophagosome-lysosome fusion. Autophagy. 14(8):1435–1455.
   PubMed Web of Science ®Google Scholar
• Nahar L, Guo M, Sarker SD. 2020. A review on the latest advances in extraction and analysis of artemisinin. Phytochem Anal. 31(1):5–14.
   PubMed Web of Science ®Google Scholar
• Prashantha CN, Gouthami K, Lavanya L, Bhavanam S, Jakhar A, Shakthiraju RG, Suraj V, Sahana KV, Sujana HS, Guruprasad NM, et al. 2021. Molecular screening of antimalarial, antiviral, anti-inflammatory and HIV protease inhibitors against spike glycoprotein of coronavirus. J Mol Graph Model. 102:107769.
   PubMed Web of Science ®Google Scholar
• Rathod SB, Prajapati PB, Punjabi LB, Prajapati KN, Chauhan N, Mansuri MF. 2020. Peptide modelling and screening against human ACE2 and spike glycoprotein RBD of SARS-CoV-2. In Silico Pharmacol. 8(1):3.
   PubMedGoogle Scholar
• Tai W, He L, Zhang X, Pu J, Voronin D, Jiang S, Zhou Y, Du L. 2020. Characterization of the receptor-binding domain (RBD) of 2019 novel coronavirus: implication for development of RBD protein as a viral attachment inhibitor and vaccine. Cell Mol Immunol. 17(6):613–620.
   PubMed Web of Science ®Google Scholar
• Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG, Seidah NG, Nichol ST. 2005. Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virol J. 2:69.
   PubMed Web of Science ®Google Scholar
• Wang N, Han S, Liu R, Meng L, He H, Zhang Y, Wang C, Lv Y, Wang J, Li X, et al. 2020. Chloroquine and hydroxychloroquine as ACE2 blockers to inhibit viropexis of 2019-nCoV Spike pseudotyped virus. Phytomedicine. 79:153333.
   PubMed Web of Science ®Google Scholar
• Wrapp D, Wang N, Corbett KS, Goldsmith JA, Hsieh CL, Abiona O, Graham BS, McLellan JS. 2020. Cryo-EM structure of the 2019-nCoV spike in the prefusion conformation. Science. 367(6483):1260–1263.
   PubMed Web of Science ®Google Scholar
• Xiu S, Dick A, Ju H, Mirzaie S, Abdi F, Cocklin S, Zhan P, Liu X. 2020. Inhibitors of SARS-CoV-2 entry: current and future opportunities. J Med Chem. 63(21):12256–12274.
   PubMed Web of Science ®Google Scholar