Synthetic flavonoids as potential antiviral agents against SARS-CoV-2 main protease

References

• Ancy, I., Sivanandam, M., & Kumaradhas, P. (2020). Possibility of HIV-1 protease inhibitors-clinical trial drugs as repurposed drugs for SARS-CoV-2 main protease: A molecular docking, molecular dynamics and binding free energy simulation study. Journal of Biomolecular Structure and Dynamics, 1–8. https://doi.org/10.1080/07391102.2020.1786459
   Web of Science ®Google Scholar
• Chae, S. C., Lee, J. H., & Park, S. U. (2013). Recent studies on flavonoids and their antioxidant activities. EXCLI Journal, 12, 226–230.
   PubMed Web of Science ®Google Scholar
• Ciliberto, G., Mancini, R., & Paggi, M. G. (2020). Drug repurposing against COVID-19: Focus on anticancer agents. Journal of Experimental & Clinical Cancer Research: Cr, 39(1), 86. https://doi.org/10.1186/s13046-020-01590-2
   PubMed Web of Science ®Google Scholar
• Dai, W., Zhang, B., Jiang, X.-M., Su, H., Li, J., Zhao, Y., Xie, X., Jin, Z., Peng, J., Liu, F., Li, C., Li, Y., Bai, F., Wang, H., Cheng, X., Cen, X., Hu, S., Yang, X., Wang, J., … Liu, H. (2020). Structure-based design of antiviral drug candidates targeting the SARS-CoV-2 main protease. Science (New York, N.Y.).), 368(6497), 1331–1335. https://doi.org/10.1126/science.abb4489
   PubMed Web of Science ®Google Scholar
• Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7, 42717. https://doi.org/10.1038/srep42717
   PubMed Web of Science ®Google Scholar
• Ertekin, S. S., Morgado-Carrasco, D., Forns, X., & Mascaro, J. M. Jr. (2020). Complete remission of hypertrophic discoid cutaneous lupus erythematosus after treatment of chronic hepatitis C with direct-acting antivirals. JAMA Dermatology, 156(4), 471–472. https://doi.org/10.1001/jamadermatol.2020.0013
   PubMed Web of Science ®Google Scholar
• Ghosh, R., Chakraborty, A., Biswas, A., & Chowdhuri, S. (2020). Evaluation of green tea polyphenols as novel corona virus (SARS CoV-2) main protease (Mpro) inhibitors - An in silico docking and molecular dynamics simulation study. Journal of Biomolecular Structure and Dynamics, 1–13. https://doi.org/10.1080/07391102.2020.1779818
   Google Scholar
• Gupta, S., Singh, A. K., Kushwaha, P. P., Prajapati, K. S., Shuaib, M., Senapati, S., & Kumar, S. (2020). Identification of potential natural inhibitors of SARS-CoV2 main protease by molecular docking and simulation studies. Journal of Biomolecular Structure and Dynamics, 1–12. https://doi.org/10.1080/07391102.2020.1776157
   PubMedGoogle Scholar
• Gurung, A. B., Ali, M. A., Lee, J., Farah, M. A., & Al-Anazi, K. M. (2020). Unravelling lead antiviral phytochemicals for the inhibition of SARS-CoV-2 Mpro enzyme through in silico approach. Life Sciences, 255, 117831. https://doi.org/10.1016/j.lfs.2020.117831
   PubMed Web of Science ®Google Scholar
• Hage-Melim, L. I. d. S., Federico, L. B., de Oliveira, N. K. S., Francisco, V. C. C., Correia, L. C., de Lima, H. B., Gomes, S. Q., Barcelos, M. P., Francischini, I. A. G., & da Silva, C. H. T. d. P. (2020a). Virtual screening, ADME/Tox predictions and the drug repurposing concept for future use of old drugs against the COVID-19. Life Sciences, 256, 117963. https://doi.org/10.1016/j.lfs.2020.117963
   PubMed Web of Science ®Google Scholar
• Holmes, J. A., & Chung, R. T. (2020). Shortening treatment with direct-acting antivirals in HCV-positive organ transplantation. The Lancet. Gastroenterology & Hepatology, 5(7), 626–627. https://doi.org/10.1016/S2468-1253(20)30154-0
   PubMed Web of Science ®Google Scholar
• Ibrahim, M. A. A., Abdeljawaad, K. A. A., Abdelrahman, A. H. M., & Hegazy, M. F. (2020). Natural-like products as potential SARS-CoV-2 M(pro) inhibitors: In-silico drug discovery. Journal of Biomolecular Structure and Dynamics, 1–13. https://doi.org/10.1080/07391102.2020.1790037
   Google Scholar
• Jimenez-Alberto, A., Ribas-Aparicio, R. M., Aparicio-Ozores, G., & Castelan-Vega, J. A. (2020). Virtual screening of approved drugs as potential SARS-CoV-2 main protease inhibitors. Comput Biol Chem, 88, 107325. https://doi.org/10.1016/j.compbiolchem.2020.107325
   PubMed Web of Science ®Google Scholar
• Jin, Z., Du, X., Xu, Y., Deng, Y., Liu, M., Zhao, Y., Zhang, B., Li, X., Zhang, L., Peng, C., Duan, Y., Yu, J., Wang, L., Yang, K., Liu, F., Jiang, R., Yang, X., You, T., Liu, X., … Yang, H. (2020). Structure of Mpro from SARS-CoV-2 and discovery of its inhibitors. Nature, 582(7811), 289–293. https://doi.org/10.1038/s41586-020-2223-y
   PubMed Web of Science ®Google Scholar
• Joshi, T., 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(8), 4529–4536. https://doi.org/10.26355/eurrev_202004_21036
   PubMed Web of Science ®Google Scholar
• Khan, S. A., Zia, K., Ashraf, S., Uddin, R., & Ul-Haq, Z. (2020). Identification of chymotrypsin-like protease inhibitors of SARS-CoV-2 via integrated computational approach. Journal of Biomolecular Structure and Dynamics, 1–10. https://doi.org/10.1080/07391102.2020.1751298
   Web of Science ®Google Scholar
• King, A. R., Lodola, A., Carmi, C., Fu, J., Mor, M., & Piomelli, D. (2009). A critical cysteine residue in monoacylglycerol lipase is targeted by a new class of isothiazolinone-based enzyme inhibitors. British Journal of Pharmacology, 157(6), 974–983. https://doi.org/10.1111/j.1476-5381.2009.00276.x
   PubMed Web of Science ®Google Scholar
• Kumar, Y., Singh, H., & Patel, C. N. (2020). In silico prediction of potential inhibitors for the main protease of SARS-CoV-2 using molecular docking and dynamics simulation based drug-repurposing. Journal of Infection and Public Health, 13(9), 1210–1223. https://doi.org/10.1016/j.jiph.2020.06.016
   PubMed Web of Science ®Google Scholar
• Lalani, S., & Poh, C. L. (2020). Flavonoids as antiviral agents for enterovirus A71 (EV-A71). Viruses, 12(2), 184. https://doi.org/10.3390/v12020184
   PubMed Web of Science ®Google Scholar
• Mahase, E. (2020). Covid-19: WHO declares pandemic because of "alarming levels" of spread, severity, and inaction. BMJ (Clinical Research ed.).), 368, m1036. https://doi.org/10.1136/bmj.m1036
   PubMed Web of Science ®Google Scholar
• Marinho, E. M., Batista de Andrade Neto, J., Silva, J., Rocha da Silva, C., Cavalcanti, B. C., Marinho, E. S., & Nobre Junior, H. V. (2020). Virtual screening based on molecular docking of possible inhibitors of Covid-19 main protease. Microbial Pathogenesis, 148, 104365. https://doi.org/10.1016/j.micpath.2020.104365
   PubMed Web of Science ®Google Scholar
• Mengist, H. M., Fan, X., & Jin, T. (2020). Designing of improved drugs for COVID-19: Crystal structure of SARS-CoV-2 main protease Mpro). Signal Transduction and Target Therapy, 5(1), 67. https://doi.org/10.1038/s41392-020-0178-y
   PubMed Web of Science ®Google Scholar
• Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). Autodock4 and AutodockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. https://doi.org/10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• Mughal, E. U., Javid, A., Sadiq, A., Murtaza, S., Zafar, M. N., Khan, B. A., … Khan, K. M. (2018). Synthesis, structure-activity relationship and molecular docking studies of 3-O-flavonol glycosides as cholinesterase inhibitors. Bioorg Med Chem, 26(12), 3696–3706. https://doi.org/10.1016/j.bmc.2018.05.050
   PubMed Web of Science ®Google Scholar
• Mughal, E. U., Sadiq, A., Ashraf, J., Zafar, M. N., Sumrra, S. H., Tariq, R., Mumtaz, A., Javid, A., Khan, B. A., Ali, A., & Javed, C. O. (2019). Flavonols and 4-thioflavonols as potential acetylcholinesterase and butyrylcholinesterase inhibitors: Synthesis, structure-activity relationship and molecular docking studies. Bioorganic Chemistry, 91, 103124. https://doi.org/10.1016/j.bioorg.2019.103124
   PubMed Web of Science ®Google Scholar
• Mughal, E. U., Sadiq, A., Murtaza, S., Rafique, H., Zafar, M. N., Riaz, T., Khan, B. A., Hameed, A., & Khan, K. M. (2017). Synthesis, structure-activity relationship and molecular docking of 3-oxoaurones and 3-thioaurones as acetylcholinesterase and butyrylcholinesterase inhibitors. Bioorg Med Chem, 25(1), 100–106. https://doi.org/10.1016/j.bmc.2016.10.016
   PubMed Web of Science ®Google Scholar
• Muralidharan, N., Sakthivel, R., Velmurugan, D., & Gromiha, M. M. (2020). Computational studies of drug repurposing and synergism of lopinavir, oseltamivir and ritonavir binding with SARS-CoV-2 protease against COVID-19. Journal of Biomolecular Structure and Dynamics., 1–6. https://doi.org/10.1080/07391102.2020.1752802
   Web of Science ®Google Scholar
• Narkhede, R. R., Pise, A. V., Cheke, R. S., & Shinde, S. D. (2020). Recognition of natural products as potential inhibitors of COVID-19 main protease (Mpro): In-silico evidences. Natural Products and Bioprospecting, 10(5), 297–306. https://doi.org/10.1007/s13659-020-00253-1
   PubMed Web of Science ®Google Scholar
• Niu, C., Yin, J., Zhang, J., Vederas, J. C., & James, M. N. (2008). Molecular docking identifies the binding of 3-chloropyridine moieties specifically to the S1 pocket of SARS-CoV Mpro. Bioorganic & Medicinal Chemistry, 16(1), 293–302. https://doi.org/10.1016/j.bmc.2007.09.034
   PubMed Web of Science ®Google Scholar
• Panche, A. N., Diwan, A. D., & Chandra, S. R. (2016). Flavonoids: An overview. Journal of Nutritional Science, 5, e47. https://doi.org/10.1017/jns.2016.41
   PubMed Web of Science ®Google Scholar
• Pietta, P. G. (2000). Flavonoids as antioxidants. Journal of Natural Products, 63(7), 1035–1042. https://doi.org/10.1021/np9904509
   PubMed Web of Science ®Google Scholar
• Sepay, N., Sepay, N., Al Hoque, A., Mondal, R., Halder, U. C., & Muddassir, M. (2020). In silico fight against novel coronavirus by finding chromone derivatives as inhibitor of coronavirus main proteases enzyme. Structural Chemistry, 31(5), 1831–1840. https://doi.org/10.1007/s11224-020-01537-5
   PubMed Web of Science ®Google Scholar
• Shah, B., Modi, P., & Sagar, S. R. (2020). In silico studies on therapeutic agents for COVID-19: Drug repurposing approach. Life Sciences, 252, 117652. https://doi.org/10.1016/j.lfs.2020.117652
   PubMed Web of Science ®Google Scholar
• Sies, H., & Parnham, M. J. (2020). Potential therapeutic use of ebselen for COVID-19 and other respiratory viral infections. Free Radical Bioloogy and Medicine, 156, 107–112. https://doi.org/10.1016/j.freeradbiomed.2020.06.032
   PubMed Web of Science ®Google Scholar
• Song, F., Shi, N., Shan, F., Zhang, Z., Shen, J., Lu, H., Ling, Y., Jiang, Y., & Shi, Y. (2020). Emerging 2019 novel coronavirus (2019-nCoV) pneumonia. Radiology, 295(1), 210–217. https://doi.org/10.1148/radiol.2020200274
   PubMed Web of Science ®Google Scholar
• Standing, J. F. (2020). Quantitative clinical pharmacology input to SARS-CoV-2 therapeutics should be based on robust data. Clinical Pharmacology and Therapeutics, 108(2), 187. https://doi.org/10.1002/cpt.1872
   PubMed Web of Science ®Google Scholar
• Ton, A. T., Gentile, F., Hsing, M., Ban, F., & Cherkasov, A. (2020). Rapid identification of potential inhibitors of SARS-CoV-2 main protease by deep docking of 1.3 billion compounds. Molecular Informatics, 39(8), e2000028. https://doi.org/10.1002/minf.202000028
   PubMed Web of Science ®Google Scholar
• Tripathi, M. K., Singh, P., Sharma, S., Singh, T. P., Ethayathulla, A. S., & Kaur, P. (2020). Identification of bioactive molecule from Withania somnifera (Ashwagandha) as SARS-CoV-2 main protease inhibitor. Journal of Biomolecular Structure and Dynamics, 1–14. https://doi.org/10.1080/07391102.2020.1790425
   Web of Science ®Google Scholar
• Viani, F., Rossi, B., Panzeri, W., Merlini, L., Martorana, A. M., Polissi, A., & Galante, Y. M. (2017). Synthesis and anti-bacterial activity of a library of 1,2-benzisothiazol-3(2H)-one (BIT) derivatives amenable of crosslinking to polysaccharides. Tetrahedron, 73(13), 1745–1761. https://doi.org/10.1016/j.tet.2017.02.025
   Web of Science ®Google Scholar
• Villoutreix, B. O., Beaune, P. H., Tamouza, R., Krishnamoorthy, R., & Leboyer, M. (2020). Prevention of COVID-19 by drug repurposing: Rationale from drugs prescribed for mental disorders. Drug Discov Today, 25(8), 1287–1290. https://doi.org/10.1016/j.drudis.2020.06.022
   PubMed Web of Science ®Google Scholar
• Wang, C., Horby, P. W., Hayden, F. G., & Gao, G. F. (2020). A novel coronavirus outbreak of global health concern. Lancet (London, England), 395(10223), 470–473. https://doi.org/10.1016/S0140-6736(20)30185-9
   PubMed Web of Science ®Google Scholar
• Wang, L., Bao, B.-B., Song, G.-Q., Chen, C., Zhang, X.-M., Lu, W., Wang, Z., Cai, Y., Li, S., Fu, S., Song, F.-H., Yang, H., & Wang, J.-G. (2017). Discovery of unsymmetrical aromatic disulfides as novel inhibitors of SARS-CoV main protease: Chemical synthesis, biological evaluation, molecular docking and 3D-QSAR study. European Journal of Medicinal Chemistry, 137, 450–461. https://doi.org/10.1016/j.ejmech.2017.05.045
   PubMed Web of Science ®Google Scholar
• Wang, Y., Xing, J., Xu, Y., Zhou, N., Peng, J., Xiong, Z., Liu, X., Luo, X., Luo, C., Chen, K., Zheng, M., & Jiang, H. (2015). In silico ADME/T modelling for rational drug design. Quarterly Reviews of Biophysics, 48(4), 488–515. https://doi.org/10.1017/S0033583515000190
   PubMed Web of Science ®Google Scholar
• Whitworth, J. (2020). COVID-19: A fast evolving pandemic. Transactions of the Royal Society of Tropical Medicine and Hygiene, 114(4), 241–248. https://doi.org/10.1093/trstmh/traa025
   PubMed Web of Science ®Google Scholar
• WHO (2020, October 11). Coronavirus disease (COVID-19). https://www.who.int/docs/default-source/coronaviruse/situation-reports/20201012-weekly-epi-update-9.pdf
   Google Scholar
• Wu, F., Zhao, S., Yu, B., Chen, Y.-M., Wang, W., Song, Z.-G., Hu, Y., Tao, Z.-W., Tian, J.-H., Pei, Y.-Y., Yuan, M.-L., Zhang, Y.-L., Dai, F.-H., Liu, Y., Wang, Q.-M., Zheng, J.-J., Xu, L., Holmes, E. C., & Zhang, Y.-Z. (2020). A new coronavirus associated with human respiratory disease in China. Nature, 579(7798), 265–269. https://doi.org/10.1038/s41586-020-2008-3
   PubMed Web of Science ®Google Scholar
• Zakaryan, H., Arabyan, E., Oo, A., & Zandi, K. (2017). Flavonoids: Promising natural compounds against viral infections. Archives of Virology, 162(9), 2539–2551. https://doi.org/10.1007/s00705-017-3417-y
   PubMed Web of Science ®Google Scholar
• Zhang, L., Lin, D., Sun, X., Curth, U., Drosten, C., Sauerhering, L., Becker, S., Rox, K., & Hilgenfeld, R. (2020). Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved α-ketoamide inhibitors. Science (New York, N.Y.).), 368(6489), 409–412. https://doi.org/10.1126/science.abb3405
   PubMed Web of Science ®Google Scholar
• Zhou, P., Yang, X.-L., Wang, X.-G., Hu, B., Zhang, L., Zhang, W., Si, H.-R., Zhu, Y., Li, B., Huang, C.-L., Chen, H.-D., Chen, J., Luo, Y., Guo, H., Jiang, R.-D., Liu, M.-Q., Chen, Y., Shen, X.-R., Wang, X., … Shi, Z.-L. (2020). A pneumonia outbreak associated with a new coronavirus of probable bat origin. Nature, 579(7798), 270–273. https://doi.org/10.1038/s41586-020-2012-7
   PubMed Web of Science ®Google Scholar
• Zhu, N., Zhang, D., Wang, W., Li, X., Yang, B., Song, J., Zhao, X., Huang, B., Shi, W., Lu, R., Niu, P., Zhan, F., Ma, X., Wang, D., Xu, W., Wu, G., Gao, G. F., & Tan, W.; China Novel Coronavirus Investigating and Research Team. (2020). A novel coronavirus from patients with pneumonia in China, 2019. The New England Journal of Medicine, 382(8), 727–733. https://doi.org/10.1056/NEJMoa2001017
   PubMed Web of Science ®Google Scholar
• Zou, L., Ruan, F., Huang, M., Liang, L., Huang, H., Hong, Z., Yu, J., Kang, M., Song, Y., Xia, J., Guo, Q., Song, T., He, J., Yen, H.-L., Peiris, M., & Wu, J. (2020). SARS-CoV-2 viral load in upper respiratory specimens of infected patients. The New England Journal of Medicine, 382(12), 1177–1179. https://doi.org/10.1056/NEJMc2001737
   PubMed Web of Science ®Google Scholar