Antimalarial phytochemicals as inhibitors against COVID-19 ACE2 receptor: Computational screening
Quinine, artemisinin, febrifugine, brusatol, chaparrin tehranolide, glaucarubin, sergeoliden, and yingzhaosu A, nine antimalarial phytochemicals, were the focus of an in-silico analysis aimed at discovering new therapeutic molecules against COVID-19 infection. The screening of these molecules included a molecular docking approach within the Angiotensin-converting enzyme-2 (ACE2) receptor. In addition, drug-likeness, ADMET analysis and pharmacophore mapping have been performed. The result of the docking process was based on the energy binding values as well as the number and type of interactions established with the receptor active site residues, which were compared with those of co-crystallized ligand and chloroquine. Febrifugine showed the most interesting energetic and interactive activities that were closer to the reference molecule and better than those of chloroquine. Whereas artemisinin has produced results that are the closest to those of chloroquine. Similarly, drug-likeness and ADMET analysis have shown that febrifugine and artemisinin check most of the filters and pharmacokinetic properties required for the choice of an effective therapeutic molecule. A pharmacophore model was designed on the basis of a training set consisting of the most relevant molecules; it has one metal ligator cum hydrophobic region cum hydrogen bond acceptor, one hydrogen bond acceptor cum metal ligator and one hydrophobic aromatic ring. This model is proposed to be used for the in-silico discovery of new therapeutic molecules against coronavirus.
Aanouz I, Belhassan A, Khatabi KE, Lakhlifi T, Idrissi ME, Bouachrine M (2020). Moroccan medicinal plants as inhibitors of COVID-19: Computational investigations. Journal of Biomolecular Structure and Dynamics 2020:1-12. https://doi.org/10.1080/07391102.2020.1758790
Abdelli I, Hassani F, Bekkel Brikci D, Ghalem S (2020). In silico study the inhibition of angiotensin converting enzyme 2 receptor of COVID-19 by Ammoides verticillata components harvested from Western Algeria. Journal of Biomolecular Structure and Dynamics 2020:1-17. https://doi.org/10.1080/07391102.2020.1763199
Bruce-Chwatt LJ (1981). Chemotherapy of malaria. WHO (2nd ed), Geneva, Switzerland.
Cecchelli R, Berezowski V, Lundquist S, Culot M, Renftel M, Dehouck MP, Fenart L (2007). Modelling of the blood-brain barrier in drug discovery and development. Nature Reviews Drug Discovery 6(8):650-661. https://doi.org/10.1038/nrd2368
Di Trani L, Savarino A, Campitelli L, Norelli S, Puzelli S, D’Ostilio D, … Cassone A (2007). Different pH requirements are associated with divergent inhibitory effects of chloroquine on human and avian influenza A viruses. Virology Journal 4:39. https://doi.org/10.1186/1743-422X-4-39
Dong E, Du H, Gardner L (2020). An interactive web-based dashboard to track COVID-19 in 447 real time. The Lancet Infectious Disease 20(5):P533-534. https://doi.org/10.1016/S1473-448 3099(20)30120-1
Foley M, Tilley L (1998). Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents. Pharmacology & Therapeutics 79(1):55-87. https://doi.org/10.1016/s0163-7258(98)00012-6
Gautreta P, Lagiera J-C, Parolaa P, Hoang VT, Meddeb L, Mailhe M, … Raoult D (2000). Hydroxychloroquine and azithromycin as a treatment of COVID-19: results of an openlabel non-randomized clinical trial. International Journal of Antimicrobial Agents 56(1):105949. https://doi.org/10.1016/j.ijantimicag.2020.105949
Ghose AK, Viswanadhan VN, Wendoloski JJ (1999). A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. Journal of Combinatorial Chemistry 1:55. https://doi.org/10.1021/cc9800071
Gorbalenya AE, Baker SC, Baric RS, de Groot RJ, Drosten C, Gulyaeva AA, … Ziebuhr J (2020). Severe acute respiratory syndrome-related coronavirus: the species and its viruses-a 4 statement of the Coronavirus Study Group. Nature Microbiology. https://doi.org/10.1101/2020.02.07.937862
Huang J, Chen H, Shang Y, Zhu H, Chen G, Chen Y, … Xia J (2020). Efficacy of chloroquine and Lopinavir/ Ritonavir in mild/general novel coronavirus (CoVID-19) infections: a prospective, open-label, multicenter randomized controlled clinical study. Trials 21:1. https://doi.org/10.21203/rs.3.rs-16392/v1
Joshi T, Sharma P, Mathpal S, Pundir H, Bhatt V, Chandra S (2020). In silico screening of natural compounds against COVID-19 by targeting Mpro and ACE2 using molecular docking. European Review for Medical and Pharmacological Sciences 24:4529-4536. https://doi.org/10.26355/eurrev_202004_21036
Krafts K, Hempelmann E, Skórska-Stania A (2010). From methylene blue to chloroquine: a brief review of the development of an antimalarial therapy. Parasitology Research 111:1-6. https://doi.org/10.1007/s00436-012-2886-x
Kumar A, Choudhir G, Shukla SK, Sharma M, Tyagi P, Bhushan A, Rathore M (2020). Identification of phytochemical inhibitors against main protease of COVID-19 using molecular modeling approaches. Journal of Biomolecular Structure and Dynamics https://doi.org/10.1080/07391102.2020.1772112
Kuznik A, Bencina M, Svajger U, Jeras M, Rozman B, Jerala R (2011). Mechanism of endosomal TLR Inhibition by Antimalarial drugs and imidazoquinolines. Journal of Immunology 186:4794-804. https://doi.org/10.4049/jimmunol.1000702
Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997). Experimental and computational approaches to estimate solubility and permeabilityin drug discovery and development settings. Advanced Drug Delivery Reviews 46(1-3):3-26. https://doi.org/10.1016/S0169-409X(96)00423-1
Macfarlane DE, Manzel L (1998). Antagonism of immunostimulatory CpG-oligodeoxynucleotides by quinacrine, chloroquine, and structurally related compounds. Journal of Immunology 160(3):1122-31.
Marmor MF, Kellner U, Lai TY, Melles RB, Mieler WF (2016). Recommendations on screening for chloroquine and hydroxychloroquine retinopathy (2016 Revision). American Academy of Ophthalmology 123(6):1386-94. https://doi.org/10.1016/j.ophtha.2016.01.058
Meng X-Y, Zhang H-X, Mezei Z, Cui M (2011). Molecular docking: A powerful approach for structure-based drug discovery. Current Computer-Aided Drug Design 7(2):146-157. https://doi.org/10.2174/157340911795677602
Mojab F (2012). Antimalarial natural products: a review. Avicenna Journal of Phytomedicine 2(2):52-62.
Sanguinetti MC, Tristani-Firouzi M (2006). hERG potassium channels and cardiac arrhythmia. Nature 440:463-469. https://doi.org/10.1038/nature04710
Savarino A, Gennero L, Sperber K, Boelaert JR (2001). The anti-HIV-1 activity of chloroquine. Journal of Clinical Virology 20:131-5. https://doi.org/10.1016/s1386-6532(00)00139-6
Sim DSM (2015). Drug Absorption and Bioavailability. In: Chan Y, Ng K, Sim D (Eds). Pharmacological Basis of Acute Care. Springer, Cham. pp 17-26. https://doi.org/10.1007/978-3-319-10386-0_3
Tai W, Lu T, Yuan H, Wang F, Liu H, Lu S, … Chen Y (2012). Pharmacophore modeling and virtual screening studies to identify new c-Met inhibitors. Journal of Molecular Modeling 18(7):3087-3100. https://doi.org/10.1007/s00894-011-1328-5
Tillement JP, Duché JD, Barré J (2006). Liaisons des médicaments aux protéines circulantes: caractéristiques, rôles et modifications physio-pathologiques [Drug binding to blood proteins: characteristics, roles and pathophysiological changes]. Bulletin de l'Académie Nationale de Médecine 190(4-5):935-947.
Toropov AA, Toropova AP, Raska Jr I, Leszczynska D, Leszczynski J (2014). Comprehension of drug toxicity: Software and databases. Computers in Biology and Medicine 45:20-25. https://doi.org/10.1016/j.compbiomed.2013.11.013
Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD (2002). Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry 45(12):2615-2623. https://doi.org/10.1021/jm020017n
Vermeulen NPE (2003). Prediction of drug metabolism: the case of cytochrome P450 2D6. Current Topics in Medicinal Chemistry 3(11):1227-1239. https://doi.org/10.2174/1568026033451998
Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG, … Nichol ST (2005). Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virology Journal 2:69. https://doi.org/10.1186/1743- 422X- 2- 69
Vincent MJ, Bergeron E, Benjannet S, Erickson BR, Rollin PE, Ksiazek TG (2005). Chloroquine is a potent inhibitor of SARS coronavirus infection and spread. Virology Journal 2:69. https://doi.org/10.1186/1743-422X-2-69
Wang M, Cao R, Zhang L, Yang X, Liu J, Xu X, … Xiao G (2020). Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro. Cell Research 30:269-271. https://doi.org/10.1038/s41422-020-0282-0
Yao X, Ye F, Zhang M, Cui C, Huang B, Niu P, … Liu D (2020). Hydroxychloroquine for the Treatment of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). Clinical Infectious Diseases 71(15):732-739. https://doi.org/10.1093/cid/ciaa237
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