Recent development of 3C and 3CL protease inhibitors for anti-coronavirus and anti-picornavirus drug discovery

Biochemical Society Transactions

Volumn 39, Issue 5, 2011, Pages 1371-1375

  Ramajayam, R ^a   Tan, Kian Pin ^a   Liang, Po Huang ^a  

^a INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

3C protease; 3CL protease; Coronavirus; Picornavirus; Severe acute respiratory syndrome (SARS)

Indexed keywords

ANILIDE; BENZOTRIAZOLE DERIVATIVE; BIPHENYL SULFONE; DIOL DERIVATIVE; ESTER DERIVATIVE; LIGNIN; N PHENYL 2 (2 PYRIMIDINYLTHIO)ACETAMIDE; POLYPHENOL DERIVATIVE; PROTEINASE INHIBITOR; PYRAZOLE DERIVATIVE; PYRIMIDINONE DERIVATIVE; RUPINTRIVIR; TERPENOID DERIVATIVE; TG 0204998; TRIFLUOROMETHYLKETONE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ANTIVIRAL ACTIVITY; CONFERENCE PAPER; CORONAVIRUS; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PICORNAVIRUS; PRIORITY JOURNAL; SEVERE ACUTE RESPIRATORY SYNDROME;

CYSTEINE ENDOPEPTIDASES; DRUG DISCOVERY; HUMANS; MOLECULAR STRUCTURE; PICORNAVIRIDAE; PICORNAVIRIDAE INFECTIONS; PROTEASE INHIBITORS; VIRAL PROTEINS; VIRUS REPLICATION;

CORONAVIRUS; COXSACKIEVIRUS; ENTEROVIRUS; PICORNAVIRIDAE; RHINOVIRUS; SARS CORONAVIRUS;

EID: 80053372160     PISSN: 03005127     EISSN: 14708752     Source Type: Journal    
DOI: 10.1042/BST0391371     Document Type: Conference Paper

References (32)

1. Lessler, J., Reich, N.G., Brookmeyer, R., Perl, T.M., Nelson, K.E. and Cummings, D.A.T. (2009) Incubation periods of acute respiratory viral infections: a systematic review. Lancet Infect. Dis. 9, 291-300
2. Monto, A.S. (1989) Acute respiratory infection in children of developing countries: challenge of the 1990s. Rev. Infect. Dis. 11, 498-505
3. Melnick, J.L. (1996) Enteroviruses, polioviruses, coxsackieviruses, echoviruses and newer enteroviruses. In Fields Virology (Fields, B.N. and Knipe, D.M., eds), 3rd edn, pp. 655-712, Lippincott Williams and Wilkins, New York
4. Siddell, S.G., Ziebuhr, J. and Snijder, E.J. (2005) Coronaviruses, toroviruses and arteriviruses. In Topley and Wilson's Microbiology and Microbial Infections (Mahy, B.W. and Ter Meulen, V., eds), vol. 1, pp. 823-856, Hodder Arnold, London
5. Ksiazek, T.G., Erdman, D., Goldsmith, C.S., Zaki, S.R., Peret, T., Emery, S., Tong, S., Urbani, C., Comer, J.A., Lim, W. et al. (2003) A novel coronavirus associated with severe acute respiratory syndrome. N. Engl. J. Med. 348, 1953-1966 (Pubitemid 36569984)
6. Peiris, J.S.M., Lai, S.T., Poon, L.L.M., Guan, Y., Yam, L.Y.C., Lim, W., Nicholls, J., Yee, W.K.S., Yan, W.W., Cheung, M.T. et al. (2003) Coronavirus as a possible cause of severe acute respiratory syndrome. Lancet 361, 1319-1325 (Pubitemid 36514862)
7. Rota, P.A., Oberste, M.S., Monroe, S.S., Nix, W.A., Campagnoli, R., Icenogle, J.P., Penaranda, S., Bankamp, B., Maher, K., Chen, M.H. et al. (2003) Characterization of a novel coronavirus associated with severe acute respiratory syndrome. Science 300, 1394-1399 (Pubitemid 36638152)
8. He, J.F., Peng, G.W., Min, J., Yu, D.W., Liang, W.L., Zhang, S.Y., Xu, R.H., Zheng, H.Y., Wu, X.W., Xu, J. et al. (2004) Molecular evolution of the SARS coronavirus during the course of the SARS epidemic in China. Science 303, 1666-1669 (Pubitemid 38338324)
9. Baker, S.C. (2008) Coronaviruses: molecular biology. In Encyclopedia of Virology (Mahy, B.W.J. and van Regenmortel, M.H.V., eds), 3rd edn, vol. 1, pp. 554-562, Academic Press, New York
10. Liang, P.H. (2006) Characterization and inhibition of SARS-CoV 3CL protease. Curr. Top. Med. Chem. 6, 361-376
11. Racaniello, V.R. (2007) Picornaviridae: the viruses and their replication. In Fields Virology (Knipe, D.M., Howley, P.M., Griffin, D.E., Lamb, R.A., Martin, M.A., Roizman, B. and Straus, S.E., eds), 5th edn, vol. 1, pp. 795-838, Wolters Kluwer Health and Lippincott Williams and Wilkins, New York
12. Porter, A.G. (1993) Picornavirus nonstructural proteins: emerging roles in virus replication and inhibition of host cell functions. J. Virol. 67, 6917-6921
13. Kuo, C.J., Chi, Y.H., Hsu, T.A. and Liang, P.H. (2004) Characterization of SARS main protease and inhibitor assay using a fluorogenic substrate. Biochem. Biophys. Res. Commun. 318, 862-867
14. Hsu, M.F., Kuo, C.J., Chang, K.T., Chang, H.C., Chou, C.C., Ko, T.P., Shr, H.L., Chang, G.G., Wang, A.H. and Liang, P.H. (2005) Mechanism of the maturation process of SARS-CoV 3CL protease. J. Biol. Chem. 280, 31257-31266 (Pubitemid 41291863)
15. Hsu, J.T.-A., Kuo, C.J., Hsieh, S.P., Wang, Y.C., Huang, K.K., Lin, C.P.-C., Huang, P.F. and Liang, P.H. (2004) Evaluation of metal-conjugated compounds as inhibitors of SARS 3CL protease of SARS-CoV. FEBS Lett. 574, 116-120 (Pubitemid 39200905)
16. Lee, C.C., Kuo, C.J., Hsu, M.F., Liang, P.H., Fang, J.M., Shie, J.J. and Wang, A.H. (2007) Structural basis of mercury- and zinc-conjugated complexes as SARS-CoV 3C-like protease inhibitors. FEBS Lett. 581, 5454-5458
17. Wu, C.Y., Jan, J.T., Ma, H.H., Kuo, C.J., Juan, H.F., Cheng, Y.S., Hsu, H.H., Wu, D., Brik, A., Liu, R.S. et al. (2004) Small molecules targeting severe acute respiratory syndrome (SARS) human coronavirus. Proc. Natl. Acad. Sci. U.S.A. 101, 10012-10017 (Pubitemid 38898719)
18. Shao, Y.M., Yang, W.B., Peng, H.P., Hsu, M.F., Tsai, K.C., Kuo, T.H., Wang, A.H., Liang, P.H., Lin, C.H., Yang, A.S. and Wong, C.H. (2007) Structure-based design and synthesis of highly potent SARS-CoV 3CL protease inhibitors. ChemBioChem 8, 1654-1657 (Pubitemid 47523666)
19. Shie, J.J., Fang, J.M., Kuo, T.H., Kuo, C.J., Liang, P.H., Huang, H.J., Wu, Y.T., Jan, J.T., Cheng, Y.S. and Wong, C.H. (2005) Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic á,β- unsaturated esters. Bioorg. Med. Chem. 13, 5240-5252
20. Shie, J.J., Fang, J.M., Kuo, T.H., Kuo, C.J., Liang, P.H., Huang, H.J., Yang, W.B., Lin, C.H., Chen, J.L., Wu, Y.T. and Wong, C.H. (2005) Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease. J. Med. Chem. 48, 4469-4473
21. Wu, C.Y., King, K.Y., Kuo, C.J., Fang, J.M., Wu, Y.T., Ho, M.Y., Liao, C.L., Shie, J.J., Liang, P.H. and Wong, C.H. (2006) Stable benzotriazole esters as mechanism-based inactivators of the severe acute respiratory syndrome 3CL protease. Chem. Biol. 13, 261-268
22. Tsai, K.C., Chen, S.Y., Liang, P.H., Luo, I.L., Mahindroo, N., Hsieh, S.P., Chao, Y.S., Lien, W., Lin, T.H. and Wu, S.Y. (2006) Discovery of a novel family of SARS-CoV protease inhibitors by virtual screening and 3D-QSAR studies. J. Med. Chem. 49, 3485-3495 (Pubitemid 43902455)
23. Lu, I.L., Mahindroo, N., Liang, P.H., Kuo, C.J., Hsieh, H.P., Chao, Y.S. and Wu, S.Y. (2006) Structure-based drug design and structural biology study of novel nonpeptide inhibitors of SARS-CoV main protease. J. Med. Chem. 49, 5154-5161 (Pubitemid 44260211)
24. Chen, C.N., Lin, C.P.-C., Huang, K.K., Chen, W.C., Jiang, W.T., Hsieh, H.P., Liang, P.H. and Hsu, J.T.-A. (2005) Inhibition of SARS-CoV 3C-Like protease activity by natural products. Evidence-based Complementary Altern. Med. 2, 209-215
25. Wen, C.C., Kuo, Y.H., Jan, J.T., Liang, P.H., Wang, S.Y., Liu, H.G., Lee, C.K., Chang, S.T., Kuo, C.J., Lee, S.S. et al. (2006) Specific plant terpenoids and lignins possess potent antiviral activities against severe acute respiratory syndrome coronavirus. J. Med. Chem. 50, 4087-4095
26. Shao, Y.M., Yang, W.B., Kuo, T.H., Tsai, K.C., Lin, C.H., Yang, A.S., Liang, P.H. and Wong, C.H. (2008) Design, synthesis, and evaluation of trifluoromethyl ketones as inhibitors of SARS-CoV 3CL protease. Bioorg. Med. Chem. 16, 4652-4660
27. Ramajayam, R., Tan, K.P., Liu, H.G. and Liang, P.H. (2010) Synthesis, docking studies, and evaluation of pyrimidines as inhibitors of SARS-CoV 3CL protease. Bioorg. Med. Chem. Lett. 20, 3569-3572
28. Kuo, C.J., Liu, H.G., Lo, Y.K., Seong, C.M., Lee, K.I., Jung, Y.S. and Liang, P.H. (2009) Individual and common inhibitors of coronavirus and piconorvirus main proteases. FEBS Lett. 583, 549-555
29. Ramajayam, R., Tan, K.P., Liu, H.G. and Liang, P.H. (2010) Synthesis and evaluation of pyrazolone compounds as SARS coronavirus 3C-like protease inhibitors. Bioorg. Med. Chem. 18, 7849-7854
30. Lee, C.C., Kuo, C.J., Ko, T.P., Hsu, M.F., Tsui, Y.C., Chang, S.C., Yang, S., Chen, S.J., Chen, H.C., Hsu, M.C. et al. (2009) Structural basis of inhibition specificities of 3C and 3C-like proteases by Zn-coordinating and peptidomimetic compounds. J. Biol. Chem. 284, 7646-7655
31. Yang, S., Chen, S.J., Hsu, M.F., Wu, J.D., Tseng, C.T., Liu, Y.F., Chen, S.C., Kuo, C.W., Wu, C.S., Chang, L.W. et al. (2006) Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor. J. Med. Chem. 49, 4971-4980 (Pubitemid 44201055)
32. Binford, S.L., Maldonado, F., Brothers, M.A., Weady, P.T., Zalman, L.S., Meador, J.W., Matthews, D.A. and Patick, A.K (2005) Conservation of amino acids in human rhinovirus 3C protease correlates with broad-spectrum antiviral activity of rupintrivir, a novel human rhinovirus 3C protease inhibitor. Antimicrob. Agents Chemother. 49, 619-626 (Pubitemid 40175671)